Tretinoin
Identification
- Summary
Tretinoin is a vitamin A derivative used to treat acne vulgaris and certain types of promyelocytic leukemia, as well as various skin conditions in over-the-counter medications.
- Brand Names
- Altreno, Atralin, Biacna, Refissa, Renova, Retin-A, Stieva-A, Tri-luma, Twyneo, Veltin, Vesanoid, Ziana
- Generic Name
- Tretinoin
- DrugBank Accession Number
- DB00755
- Background
Tretinoin, also known as all-trans-retinoic acid (ATRA), is a naturally occurring derivative of vitamin A (retinol).1 It is an oxidation product in the physiological pathway of vitamin A metabolism.5 In human circulation, tretinoin is normally found at very low concentrations, approximately 4 to 14 nmol/L.5 Tretinoin exhibits anti-inflammatory, antineoplastic, antioxidant, and free radical-scavenging activities.5 It has been used in dermatology for many years to treat various skin conditions ranging from acne to wrinkles 1,11 and activates nuclear receptors to regulate epithelial cell growth and differentiation.1,2,3 Tretinoin is given orally to treat acute promyelocytic leukemia 13 and topically to treat skin conditions such as acne.15,12,14
- Type
- Small Molecule
- Groups
- Approved, Investigational, Nutraceutical
- Structure
- Weight
- Average: 300.442
Monoisotopic: 300.208930142 - Chemical Formula
- C20H28O2
- Synonyms
- (all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid
- 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoic acid (ECL)
- Acide retinoique
- all trans Retinoic acid
- all trans-Retinoic acid
- all-(E)-Retinoic acid
- all-trans-beta-Retinoic acid
- all-trans-Retinoic acid
- all-trans-Tretinoin
- all-trans-Vitamin A acid
- all-trans-Vitamin A1 acid
- ATRA
- beta-Retinoic acid
- Retinoic acid
- Retionic acid
- trans-Retinoic acid
- Tretin M
- Tretinoin
- Tretinoina
- Trétinoïne
- Tretinoinum
- Vitamin A acid
- External IDs
- AGN 100335
- NSC-122758
- Ro 1-5488
Pharmacology
- Indication
Oral tretinoin is indicated for induction of remission in adults and pediatric patients one year of age and older with acute promyelocytic leukemia (APL), characterized by the presence of t(15;17) translocation or presence of PML/RARα gene expression and who are refractory to or who have relapsed from anthracycline chemotherapy or for whom anthracycline-based chemotherapy is contraindicated.13
Topical tretinoin is also indicated alone 15 or in combination with benzoyl peroxide 12 or clindamycin 14 for the treatment of acne vulgaris. It is also used in prescription and over-the-counter for treating various skin conditions such as melasma,16 hyperpigmentation,1 and photoaging 10 alone or in combination with other drugs.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Acne vulgaris •••••••••••• Used in combination to treat Acne vulgaris Combination Product in combination with: Benzoyl peroxide (DB09096) •••••••••••• ••••• Used in combination to treat Acne vulgaris Combination Product in combination with: Clindamycin (DB01190) •••••••••••• Used in combination to treat Alopecia Combination Product in combination with: Minoxidil (DB00350) •••••••••••• •••••••• Used in combination to treat Cornification and dystrophic skin disorders Combination Product in combination with: Urea (DB03904) •••••••••••• ••••• - Contraindications & Blackbox Warnings
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- Pharmacodynamics
Tretinoin is a vitamin A derivative that promotes cell production, proliferation, and differentiation. When used topically, tretinoin regulates epidermal cell turnover and collagen production. It also prevents collagen loss, reduces inflammation, and blocks the induction of matrix metalloproteinase (MMP), which are enzymes that disrupt collagen and elastic fibres.1,2,3,10 In short-term and long-term studies, topical application of tretinoin at doses ranging from 0.001% to 0.1% was associated with improvements in clinical signs of photoaging and fine wrinkles, increased epidermal thickness, compaction of the stratum corneum, and decreased melanin content.4,10,11,7 It also improved melanocyte differentiation and distribution, promotion of epidermal hyperplasia, and angiogenesis.7
Tretinoin exhibits antineoplastic activities when given orally.13 Tretinoin was shown to induce differentiation in tumour cells.6 It induced cytodifferentiation and decreased acute promyelocytic leukemia (APL) cell proliferation in culture and in vivo. In patients with APL, tretinoin promoted the initial maturation of the primitive promyelocytes derived from the leukemic clone, followed by a repopulation of the bone marrow and peripheral blood by normal, polyclonal hematopoietic cells in patients achieving complete remission.13
- Mechanism of action
The exact mechanism of action of tretinoin in skin conditions and acute promyelocytic leukemia (APL) has not been fully elucidated; however, several proposed mechanisms exist. Tretinoin is believed to exert its pharmacological actions by binding to and activating two types of nuclear receptors - retinoic acid receptors (RARs) alpha, beta, and gamma and retinoid X receptors (RXRs). In the human skin, RARs (especially RAR-alpha) form heterodimers with RXR to act as inducible transcription regulators of genes involved in cell differentiation by binding to retinoic acid response elements.9,11 Tretinoin binds to RXRs to promote epidermal proliferation. It also blocks the actions of inflammatory mediators, enhancing procollagen production and collagen type I and III formations.1,2,3,7 Some animal and human studies suggest that tretinoin induces the expression of transforming growth factor beta (TGF-β), which stimulates the transcription of several types of collagen messenger RNA. Collagen formation curtails further solar UV-induced skin damage and aging processes.7
Acne is associated with abnormal follicular formation from excessive keratinization of epithelial cells. Tretinoin promotes cornified cell detachment and enhances keratinocyte shedding. It also stimulates mitotic activity and loosely-adherent corneocyte turnover to expel comedo contents, reducing microcomedo precursor lesions of acne vulgaris.1,12 Tretinoin may reduce epidermal melanin and pigmentation by increasing keratinocyte turnover and reducing tyrosinase activity.3,10
RAR-alpha and -beta have also been implicated in APL.9 APL is characterized by a t(15;17) chromosomal translocation, which fuses the promyelocytic myeloid leukemia (PML) gene with the RAR-alpha gene.5,6 The resulting PML-RAR-alpha fusion protein plays a role in the pathogenesis of APL by aberrating promyelocyte differentiation. The PML-RAR-alpha fusion protein is found to be predominant in leukemic cells, exerting a dominant negative effect on RAR, RXR and PML function.5 Tretinoin induces terminal differentiation in hemopoietic precursor cell lines and APL cells.6 Tretinoin is believed to promote caspase-mediated cleavage and proteasome-dependent degradation to cause apoptosis and degradation of the PML-RAR-alpha fusion protein.1 It may also convert the fusion protein from a transcription repressor to an activator.1
Target Actions Organism ARetinoic acid receptor alpha agonistHumans ARetinoic acid receptor beta agonistHumans ARetinoic acid receptor gamma agonistHumans URetinoic acid receptor RXR-alpha agonistHumans ARetinoic acid receptor RXR-beta agonistHumans ARetinoic acid receptor RXR-gamma agonistHumans UCellular retinoic acid-binding protein 1 binderHumans URetinoic acid receptor responder protein 1 agonistHumans URetinal dehydrogenase 1 substrateHumans URetinal dehydrogenase 2 substrateHumans URetinoic acid-induced protein 3 regulatorHumans ULipocalin-1 binderHumans UOdorant-binding protein 2a binderHumans URetinol-binding protein 4 binderHumans U[Pyruvate dehydrogenase [lipoamide]] kinase isozyme 4, mitochondrial upregulatorHumans UCarcinoembryonic antigen downregulatorHumans - Absorption
Tretinoin applied topically is expected to remain on the stratum corneum and undergo minimal systemic absorption.4,7 In one study, the topical application of radiolabelled tretinoin for 28 days was associated with a total percutaneous absorption of 2%.4
The extent of absorption was examined after a once-daily application of 1.9 g of the combination product with benzoyl peroxide for 14 days. On Day 14, at steady-state, the mean Cmax was 0.15-0.19 ng/mL for tretinoin, 0.27-0.34 ng/mL for the metabolite 4-keto 13-cis retinoic acid, and 0.13-0.28 ng/mL for 13-cis retinoic acid, respectively. The Cmax varied across different age groups (children, adolescents, and adults). The corresponding ranges for the mean AUC0-24 were 0.63-2.06, 2.39-2.89, and 0.96-1.99 ng*h/mL.12
Following oral administration, the absolute bioavailability of tretinoin was approximately 50%.13 While the effect of food on tretinoin is unclear, food increases the oral absorption of retinoids, as a class.13,18 When the oral dose of 22.5 mg/m2 tretinoin was administered twice daily, the mean ± SD Cmax was 394 ± 89 ng/mL after the first dose and 138 ± 139 ng/mL after one week of continuous treatment. The area under the curve (AUC) was 537 ± 191 ng·h/mL after the first dose and 249 ± 185 ng·h/mL after one week of continuous treatment. The Tmax was between one and two hours.13
- Volume of distribution
Tretinoin is rapidly and extensively distributed to tissues following oral administration but does not cross the blood-brain barrier. The apparent volume of distribution (Vd) of intravenous tretinoin is dose-dependent and significantly greater at low doses. The Vd was 0.52 ± 0.12 L/kg after 0.0125 mg/kg and 0.21 ± 0.05 L/kg after 0.25 mg/kg.5
- Protein binding
Protein binding of tretinoin is greater than 95%, predominately to albumin.5,13 Plasma protein binding remains constant over the 10 to 500 ng/mL concentration range.13
- Metabolism
Tretinoin is rapidly metabolized to form various oxidized and conjugated metabolites. It forms several metabolites stereoisomerization derivatives (9-cis-retinoic acid or alitretinoin and 13-cis-retinoic acid or isotretinoin), oxidation derivatives (4-hydroxy-retinoic acid, 4-oxo-retinoic acid, 18-hydroxy-retinoic acid, 5,6-epoxy-retinoic acid, 3,4-didehydro-retinoic acid and retinotaurine), stereoisomerization and oxidation derivatives (13-cis-4-oxo-retinoic acid), glucuronidation derivatives (retinoyl beta-glucuronide, 13-cis-retinoyl beta-glucuronide, 4-oxo-retinoyl beta-glucuronide, 5,6-epoxyretinoyl beta-glucuronide and 13-cis-4-oxo-retinoyl beta-glucuronide), nonpolar metabolites of retinoic acid, and retinoic acid esters.5
Tretinoin is metabolized by several CYP enzymes, including CYP3A4, CYP2C8, and CYP2E. It also undergoes glucuronidation by UGT2B7. The metabolites 4-oxo retinoic acid and 4-oxo trans retinoic acid glucuronide have one-third of the pharmacological activity of the parent compound.8,13 When the plasma concentrations decreased to one-third of their day-one concentrations after one week of continuous therapy, tretinoin induced its own metabolism.5,13
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- Route of elimination
Tretinoin metabolites are excreted in bile and urine.18 Following administration of radiolabeled tretinoin at doses of 2.75 mg and 50 mg - which are 0.53 to 9.6 times the approved recommended dosage based on 1.7 m2, respectively - approximately 63% of the radioactivity was recovered in the urine within 72 hours, and 31% appeared in the feces within six days.13
- Half-life
The terminal elimination half-life of tretinoin following initial dosing is 0.5 to 2 hours in patients with APL.13
- Clearance
No information is available.
- Adverse Effects
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- Toxicity
The oral LD50 in rats is 2000 mg/kg. The dermal LD50 in rabbits is >2500 mg/kg.17
Reversible signs of hypervitaminosis A, such as headache, nausea, vomiting, and mucocutaneous symptoms, are expected to appear in tretinoin overdose. Overdosage with other retinoids has been associated with transient headache, facial flushing, cheilosis, abdominal pain, dizziness and ataxia: these symptoms have quickly resolved without apparent residual effects. here is no specific treatment in the case of an overdose and it is advised to treat patients experiencing tretinoin overdose in a special hematological unit.13
- Pathways
Pathway Category Retinol Metabolism Metabolic Vitamin A Deficiency Disease - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Tretinoin can be increased when it is combined with Abametapir. Abatacept The metabolism of Tretinoin can be increased when combined with Abatacept. Acalabrutinib The metabolism of Tretinoin can be decreased when combined with Acalabrutinib. Acebutolol Tretinoin may decrease the antihypertensive activities of Acebutolol. Aceclofenac The risk or severity of elevated intracranial pressure can be increased when Aceclofenac is combined with Tretinoin. - Food Interactions
- Take with food. Effect of food on tretinoin absorption is unclear, but food increases the bioavailability of retinoids drug class.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Images
- International/Other Brands
- Aberel (Janssen) / Aberela (Janssen) / Airol (Pierre Fabre Dermo) / Dermairol (Roche) / Eudyna (Zydus) / Kétrel (Bailleul) / Sotret (Ranbaxy Laboratories Inc.) / Stieva-A (Stiefel) / Vitinoin
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Altreno Lotion 0.05 % w/w Topical Bausch Health, Canada Inc. Not applicable Not applicable Canada Altreno Lotion 0.5 mg/1g Topical Bausch Health US, LLC 2018-08-24 Not applicable US Atralin Gel 0.05 g/100g Topical Bausch Health US, LLC 2007-07-26 Not applicable US Avita Cream 0.25 mg/1g Topical Mylan Bertek Pharmaceuticals 2015-11-01 2015-11-19 US Avita Gel 0.25 mg/1g Topical Mylan Pharmaceuticals Inc. 1998-03-18 2023-05-31 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Jamp Tretinoin Capsule 10 mg Oral Jamp Pharma Corporation 2022-08-29 Not applicable Canada Obagi Cream 0.5 mg/1g Topical YS PLUS CORPORATION 2014-10-01 2015-12-31 US Obagi Cream 1 mg/1g Topical YS PLUS CORPORATION 2014-10-01 2015-12-31 US Refissa Cream 0.5 mg/1g Topical Obagi Medical Products, Inc. 2010-02-22 2016-05-01 US Refissa Cream 0.5 mg/1g Topical Suneva Medical, Inc. 2009-06-17 Not applicable US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image ทีนา - เอ ครีม Cream 0.05 %w/w Topical บริษัท 2 เอ็ม.(เมด-เมเกอร์) จำกัด จำกัด 1990-01-30 Not applicable Thailand เรติน - เอ Cream 0.025 %w/w Topical บริษัท โอลิค (ประเทศไทย) จำกัด 1990-10-05 Not applicable Thailand - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ACNATAC Tretinoin (0.025 %) + Clindamycin (1 %) Gel Topical Farmed S.R.L. 2023-12-28 Not applicable Italy Acnatac 10 mg/g + 0,25 mg/g Gel Tretinoin (0.25 mg/g) + Clindamycin (10 mg/g) Gel Topical Mylan österreich Gmb H 2013-03-26 Not applicable Austria AKNEMYCIN PLUS SOLUTION Tretinoin (0.025 g/100g) + Erythromycin (4 g/100g) Solution Topical ZUELLIG PHARMA PTE. LTD. 2000-02-04 Not applicable Singapore ALBAVANCE F Tretinoin (0.01 %) + Fluocinolone acetonide (4 %) + Hydroquinone (0.05 %) Cream Immortal Pharmaceutical Laboratories 2017-09-18 2027-04-19 Indonesia BALISA VAS Tretinoin (0.3 mg/g) + Urea (120 mg/g) Cream Topical 2006-04-01 Not applicable Germany - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 011010 Niacinamide 4% / Tretinoin 0.025% Tretinoin (0.025 g/100g) + Nicotinamide (4 g/100g) Gel Topical Sincerus Florida, LLC 2020-07-02 Not applicable US 011013 Niacinamide 4% / Tretinoin 0.025% Tretinoin (0.025 g/100g) + Nicotinamide (4 g/100g) Cream Topical Sincerus Florida, LLC 2020-07-02 Not applicable US 011020 Niacinamide 4% / Tretinoin 0.05% Tretinoin (0.05 g/100g) + Nicotinamide (4 g/100g) Gel Topical Sincerus Florida, LLC 2020-07-02 Not applicable US 011021 Niacinamide 4% / Tretinoin 0.05% Tretinoin (0.05 g/100g) + Nicotinamide (4 g/100g) Cream Topical Sincerus Florida, LLC 2020-07-02 Not applicable US 011218 Niacinamide 2% / Spironolactone 5% / Tretinoin 0.025% Tretinoin (0.025 g/100g) + Nicotinamide (2 g/100g) + Spironolactone (5 g/100g) Gel Topical Sincerus Florida, LLC 2020-07-02 Not applicable US
Categories
- ATC Codes
- L01XF01 — Tretinoin
- L01XF — Retinoids for cancer treatment
- L01X — OTHER ANTINEOPLASTIC AGENTS
- L01 — ANTINEOPLASTIC AGENTS
- L — ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
- D10AD — Retinoids for topical use in acne
- D10A — ANTI-ACNE PREPARATIONS FOR TOPICAL USE
- D10 — ANTI-ACNE PREPARATIONS
- D — DERMATOLOGICALS
- Drug Categories
- Agents that produce hypertension
- Alkenes
- Anti-Acne Preparations
- Anti-Acne Preparations for Topical Use
- Antineoplastic Agents
- Antineoplastic and Immunomodulating Agents
- Biological Factors
- Cardiotoxic antineoplastic agents
- Carotenoids
- Cell Stimulants and Proliferants
- Cyclohexanes
- Cyclohexenes
- Cycloparaffins
- Cytochrome P-450 CYP2A6 Substrates
- Cytochrome P-450 CYP2B6 Substrates
- Cytochrome P-450 CYP2C18 Substrates
- Cytochrome P-450 CYP2C8 Substrates
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP2E1 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 CYP3A7 Substrates
- Cytochrome P-450 Substrates
- Dermatologicals
- Diterpenes
- Hydrocarbons, Acyclic
- Hypotensive Agents
- Immunosuppressive Agents
- Keratolytic Agents
- Pigments, Biological
- Polyenes
- Retinoids
- Retinoids for cancer treatment
- Retinoids for Topical Use in Acne
- Terpenes
- UGT2B7 substrates
- Vitamin A
- Vitamins
- Vitamins (Fat Soluble)
- Classification
- Not classified
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 5688UTC01R
- CAS number
- 302-79-4
- InChI Key
- SHGAZHPCJJPHSC-YCNIQYBTSA-N
- InChI
- InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+
- IUPAC Name
- (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
- SMILES
- C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)=O
References
- General References
- Yoham AL, Casadesus D: Tretinoin. . [Article]
- Kang S: The mechanism of action of topical retinoids. Cutis. 2005 Feb;75(2 Suppl):10-3; discussion 13. [Article]
- Baldwin HE, Nighland M, Kendall C, Mays DA, Grossman R, Newburger J: 40 years of topical tretinoin use in review. J Drugs Dermatol. 2013 Jun 1;12(6):638-42. [Article]
- Thorne EG: Long-term clinical experience with a topical retinoid. Br J Dermatol. 1992 Sep;127 Suppl 41:31-6. doi: 10.1111/j.1365-2133.1992.tb16985.x. [Article]
- Regazzi MB, Iacona I, Gervasutti C, Lazzarino M, Toma S: Clinical pharmacokinetics of tretinoin. Clin Pharmacokinet. 1997 May;32(5):382-402. doi: 10.2165/00003088-199732050-00004. [Article]
- Gillis JC, Goa KL: Tretinoin. A review of its pharmacodynamic and pharmacokinetic properties and use in the management of acute promyelocytic leukaemia. Drugs. 1995 Nov;50(5):897-923. doi: 10.2165/00003495-199550050-00008. [Article]
- Noble S, Wagstaff AJ: Tretinoin. A review of its pharmacological properties and clinical efficacy in the topical treatment of photodamaged skin. Drugs Aging. 1995 Jun;6(6):479-96. doi: 10.2165/00002512-199506060-00008. [Article]
- Marill J, Cresteil T, Lanotte M, Chabot GG: Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol. 2000 Dec;58(6):1341-8. [Article]
- Marill J, Idres N, Capron CC, Nguyen E, Chabot GG: Retinoic acid metabolism and mechanism of action: a review. Curr Drug Metab. 2003 Feb;4(1):1-10. doi: 10.2174/1389200033336900. [Article]
- Sitohang IBS, Makes WI, Sandora N, Suryanegara J: Topical tretinoin for treating photoaging: A systematic review of randomized controlled trials. Int J Womens Dermatol. 2022 Mar 25;8(1):e003. doi: 10.1097/JW9.0000000000000003. eCollection 2022 Mar. [Article]
- Mukherjee S, Date A, Patravale V, Korting HC, Roeder A, Weindl G: Retinoids in the treatment of skin aging: an overview of clinical efficacy and safety. Clin Interv Aging. 2006;1(4):327-48. doi: 10.2147/ciia.2006.1.4.327. [Article]
- DailyMed Label: TWYNEO (tretinoin and benzoyl peroxide) topical cream [Link]
- FDA Approved Drug Products: VESANOID (tretinoin) capsules, for oral use [Link]
- DailyMed Label: CLINDAMYCIN PHOSPHATE and TRETINOIN Gel 1.2% / 0.025%, for topical use only [Link]
- DailyMed Label: Tretinoin Topical Cream or Gel [Link]
- DailyMed Label: TRIDERMA (hydroquinone, tretinoin, fluocinolone acetonide) topical cream [Link]
- Medisca: TRETINOIN, USP (Retinoic Acid) MSDS [Link]
- Cancer Care Ontario Tretinoin Monograph [Link]
- External Links
- Human Metabolome Database
- HMDB0001852
- KEGG Drug
- D00094
- KEGG Compound
- C00777
- PubChem Compound
- 5538
- PubChem Substance
- 46504843
- ChemSpider
- 392618
- BindingDB
- 31883
- 10753
- ChEBI
- 15367
- ChEMBL
- CHEMBL38
- ZINC
- ZINC000012358651
- Therapeutic Targets Database
- DNC000117
- PharmGKB
- PA164746900
- PDBe Ligand
- REA
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Tretinoin
- PDB Entries
- 1cbr / 1cbs / 1fem / 1g5y / 1gx9 / 1n4h / 1rlb / 2acl / 2fr3 / 2g78 … show 12 more
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Photodamaged Skin / Solar Elastosis 1 4 Completed Other Acne / Healthy Subjects (HS) 1 4 Completed Prevention Acne 1 4 Completed Treatment Acne 2 4 Completed Treatment Acne Vulgaris 9
Pharmacoeconomics
- Manufacturers
- Hoffmann la roche inc
- Genpharm inc
- Barr laboratories inc
- Ranbaxy pharmaceuticals inc
- Ranbaxy laboratories ltd
- Mylan bertek pharmaceuticals inc
- Ortho dermatologics
- Johnson and johnson consumer companies inc
- Spear pharmaceuticals inc
- Triax pharmaceuticals llc
- Dow pharmaceutical sciences inc
- Mylan pharmaceuticals inc
- Teva pharmaceuticals usa
- Wockhardt eu operations (swiss) ag
- Ranbaxy Pharmaceuticals Inc.
- Packagers
- Actavis Group
- Ameri-Pac Inc.
- A-S Medication Solutions LLC
- Barr Pharmaceuticals
- Cardinal Health
- Catalent Pharma Solutions
- Contract Pharm
- Coria Laboratories
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- DPT Laboratories Ltd.
- Draxis Specialty Pharmaceuticals Inc.
- F Hoffmann-La Roche Ltd.
- Galderma Laboratories
- Genesis Pharmaceutical Inc.
- Hill Laboratories Inc.
- Medicis Pharmaceutical Co.
- Medisca Inc.
- Murfreesboro Pharmaceutical Nursing Supply
- Mylan
- Obagi Medical Products Inc.
- Ortho Mcneil Janssen Pharmaceutical Inc.
- Ortho-McNeil-Janssen Pharmaceuticals Inc.
- Perrigo Co.
- Pharmedix
- Physicians Total Care Inc.
- Ranbaxy Laboratories
- Rebel Distributors Corp.
- Rouses Point Pharmaceuticals LLC
- Sandoz
- Spear Dermatology Products Inc.
- Stiefel Labs
- Triax Pharmaceuticals LLC
- Valeant Ltd.
- Wockhardt Ltd.
- Dosage Forms
Form Route Strength Lotion Topical 50 mg Solution Topical 0.05 g Gel Topical 0.025 % Cream Topical 0.04 g Cream Topical 0.1 % Capsule Oral 10.000 mg Cream Topical 0.5 MG/G Solution Topical 0.5 MG/ML Solution Topical 4 g/100g Gel Topical 0.05 g Lotion Topical 0.05 % w/w Lotion Topical 0.5 mg/1g Capsule Oral 10.0000 mg Solution Topical 0.025 g Gel Topical 0.025 g Lotion Topical Lotion Topical 0.05 g Kit Topical Cream Topical Emulsion Topical Cream Cream Topical 0.05 g/100g Cream Topical 0.2 mg/1g Cream Topical 0.05 g Cream Topical 0.025 g Lotion Topical Cream Topical 0.1 mg/1g Gel Topical 0.01 % w/w Gel Topical 0.0100 g Gel Topical 0.025 % w/w Liquid Topical 0.5 mg/1mL Gel Cutaneous Gel Topical 0.04 % w/w Gel Topical 0.1 % w/w Gel Topical 0.4 mg/1g Gel Topical 0.6 mg/1g Gel Topical 1 mL/1g Gel Topical 400 mL/1g Cream Topical 0.01 % Cream Topical 0.050 g Gel Topical Solution Topical Liquid Topical .05 % Cream Topical 0.01 % w/w Cream Topical 0.025 % w/w Cream Topical 0.05 % w/w Cream Topical 0.1 % w/w Solution Topical 0.025 % Gel Topical .01 % Cream Topical 0.1 g Cream Cutaneous 0.050 g Cream Topical Cream Topical 0.375 mg/1g Gel Topical 0.1 mg/1g Gel Topical 0.25 mg/1g Cream Topical 0.75 mg/1g Capsule Oral 10 mg/1 Cream Topical 0.025 mg/1g Cream Topical 0.05 mg/1g Cream Topical 0.25 mg/1g Cream Topical 0.5 mg/1g Cream Topical 1 mg/1g Cream Topical 1.0 mg/1g Gel Topical 0.01 mg/1g Gel Topical 0.025 mg/1g Gel Topical 0.04 mg/1g Gel Topical 0.05 g/100g Gel Topical 0.5 mg/1g Gel Topical 0.8 mg/1g Powder Not applicable 1 g/1g Gel Topical 1 mg/1g Cream; kit; lotion Topical Kit Topical 0.25 mg/1g Kit Topical 0.5 mg/1g Kit Topical 1 mg/1g Cream Cutaneous Cream Topical 0.1 mg/g Gel Topical Capsule Oral 10 mg Capsule, liquid filled Oral 10 mg/1 Capsule, gelatin coated Oral Capsule Oral Capsule, liquid filled Oral 10 mg Cream Topical 0.025 % Cream Topical 0.05 % Gel Topical 0.025 % Solution Topical Gel Topical 0.01 % Gel Topical 0.05 % Cream Topical .025 % Cream Topical .05 % Cream Topical .1 % Gel Topical .025 % Gel Topical 0.1 %w/w Gel Topical 0.05 %w/w Cream Topical 0.025 %w/w Cream Topical 0.05 %w/w - Prices
Unit description Cost Unit Tretinoin (Emollient) 0.05% Cream 60 gm Tube 200.07USD tube Tri-Luma 0.01-4-0.05% Cream 30 gm Tube 199.99USD tube Solage 2-0.01% Solution 30ml Bottle 168.67USD bottle Tretinoin (Emollient) 0.05% Cream 40 gm Tube 135.99USD tube Tretinoin 0.1% Cream 45 gm Tube 114.16USD tube Tretinoin 0.025% Gel 45 gm Tube 99.64USD tube Tretinoin 0.01% Gel 45 gm Tube 98.85USD tube Tretinoin 0.05% Cream 45 gm Tube 97.94USD tube Tretinoin 0.025% Cream 45 gm Tube 83.97USD tube Tretinoin acid powder 74.21USD g Tretinoin 0.1% Cream 20 gm Tube 60.96USD tube Tretinoin 0.05% Cream 20 gm Tube 52.23USD tube Tretinoin 0.025% Cream 20 gm Tube 44.36USD tube Tretinoin 0.025% Gel 15 gm Tube 42.26USD tube Tretinoin 0.01% Gel 15 gm Tube 35.99USD tube Vesanoid 10 mg capsule 30.32USD capsule Accutane 40 mg capsule 27.62USD capsule Tretinoin 10 mg capsule 27.29USD capsule Accutane 20 mg capsule 23.77USD capsule Amnesteem 40 mg capsule 22.6USD capsule Claravis 40 mg capsule 21.73USD capsule Accutane 10 mg capsule 20.05USD capsule Amnesteem 20 mg capsule 19.45USD capsule Claravis 20 mg capsule 18.7USD capsule Claravis 30 mg capsule 16.78USD capsule Amnesteem 10 mg capsule 16.4USD capsule Claravis 10 mg capsule 15.77USD capsule Sotret 40 mg capsule 10.08USD capsule Sotret 20 mg capsule 8.67USD capsule Sotret 30 mg capsule 8.44USD capsule Sotret 10 mg capsule 7.31USD capsule Tri-luma cream 6.4USD g Retin-a micro 0.04% gel 5.65USD g Retin-a micro 0.1% gel 5.65USD g Solage topical solution 5.59USD ml Retin-a micro pump 0.04% gel 4.74USD g Retin-a micro pump 0.1% gel 4.74USD g Retin-a 0.05% cream 4.64USD g Retin-a 0.1% cream 4.51USD g Renova 0.02% cream 4.46USD g Renova pump 0.02% cream 4.28USD g Retin-a 0.025% cream 4.14USD g Refissa 0.05% cream 3.6USD g Tretinoin 0.05% emollient crm 3.38USD g Avita 0.025% cream 3.19USD g Tretinoin 0.1% cream 2.36USD g Tretinoin 0.025% cream 2.17USD g Tretinoin 0.05% cream 2.02USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5470567 No 1995-11-28 2010-03-19 US US5955109 No 1999-09-21 2016-09-21 US US6353029 No 2002-03-05 2020-08-24 US US6531141 No 2003-03-11 2020-03-07 US US8247395 No 2012-08-21 2022-10-22 US US8653053 No 2014-02-18 2022-10-25 US US7939516 No 2011-05-10 2025-05-04 US US7915243 No 2011-03-29 2026-03-22 US US6387383 No 2002-05-14 2020-08-03 US US6517847 No 2003-02-11 2020-08-03 US US10653656 No 2020-05-19 2038-08-22 US US9868103 No 2018-01-16 2028-08-08 US US11071878 No 2021-07-27 2030-12-30 US US10420743 No 2019-09-24 2038-07-12 US US10653899 No 2020-05-19 2030-12-30 US US8617580 No 2013-12-31 2028-02-03 US US11324710 No 2018-08-22 2038-08-22 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 178-184 https://www.medisca.com/NDC_SPECS/MUS/0001/MSDS/0001.pdf logP 6.3 https://www.medisca.com/NDC_SPECS/MUS/0001/MSDS/0001.pdf - Predicted Properties
Property Value Source Water Solubility 0.00477 mg/mL ALOGPS logP 5.66 ALOGPS logP 5.01 Chemaxon logS -4.8 ALOGPS pKa (Strongest Acidic) 4.76 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 37.3 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 97.79 m3·mol-1 Chemaxon Polarizability 36.85 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9925 Blood Brain Barrier + 0.9311 Caco-2 permeable + 0.7603 P-glycoprotein substrate Non-substrate 0.6144 P-glycoprotein inhibitor I Non-inhibitor 0.8912 P-glycoprotein inhibitor II Non-inhibitor 0.8088 Renal organic cation transporter Non-inhibitor 0.8639 CYP450 2C9 substrate Non-substrate 0.8221 CYP450 2D6 substrate Non-substrate 0.9115 CYP450 3A4 substrate Substrate 0.6025 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.8831 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.9301 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9252 Ames test Non AMES toxic 0.8944 Carcinogenicity Non-carcinogens 0.7081 Biodegradation Ready biodegradable 0.5554 Rat acute toxicity 2.1455 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9562 hERG inhibition (predictor II) Non-inhibitor 0.9538
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 202.3292981 predictedDarkChem Lite v0.1.0 [M-H]- 204.5572981 predictedDarkChem Lite v0.1.0 [M-H]- 192.63275 predictedDeepCCS 1.0 (2019) [M-H]- 202.3292981 predictedDarkChem Lite v0.1.0 [M-H]- 204.5572981 predictedDarkChem Lite v0.1.0 [M-H]- 202.3292981 predictedDarkChem Lite v0.1.0 [M-H]- 204.5572981 predictedDarkChem Lite v0.1.0 [M-H]- 192.63275 predictedDeepCCS 1.0 (2019) [M-H]- 192.63275 predictedDeepCCS 1.0 (2019) [M+H]+ 194.99077 predictedDeepCCS 1.0 (2019) [M+H]+ 194.99077 predictedDeepCCS 1.0 (2019) [M+H]+ 194.99077 predictedDeepCCS 1.0 (2019) [M+Na]+ 202.33412 predictedDeepCCS 1.0 (2019) [M+Na]+ 202.33412 predictedDeepCCS 1.0 (2019) [M+Na]+ 202.33412 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific Function
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
- Gene Name
- RARA
- Uniprot ID
- P10276
- Uniprot Name
- Retinoic acid receptor alpha
- Molecular Weight
- 50770.805 Da
References
- Vollberg TM Sr, Nervi C, George MD, Fujimoto W, Krust A, Jetten AM: Retinoic acid receptors as regulators of human epidermal keratinocyte differentiation. Mol Endocrinol. 1992 May;6(5):667-76. [Article]
- Regazzi MB, Iacona I, Gervasutti C, Lazzarino M, Toma S: Clinical pharmacokinetics of tretinoin. Clin Pharmacokinet. 1997 May;32(5):382-402. doi: 10.2165/00003088-199732050-00004. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific Function
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
- Gene Name
- RARB
- Uniprot ID
- P10826
- Uniprot Name
- Retinoic acid receptor beta
- Molecular Weight
- 50488.63 Da
References
- Steidl U, Schroeder T, Steidl C, Kobbe G, Graef T, Bork S, Pechtel S, Kliszewski S, Kuendgen A, Rohr UP, Fenk R, Schroeder M, Haase D, Haas R, Kronenwett R: Distinct gene expression pattern of malignant hematopoietic stem and progenitor cells in polycythemia vera. Ann N Y Acad Sci. 2005 Jun;1044:94-108. [Article]
- Regazzi MB, Iacona I, Gervasutti C, Lazzarino M, Toma S: Clinical pharmacokinetics of tretinoin. Clin Pharmacokinet. 1997 May;32(5):382-402. doi: 10.2165/00003088-199732050-00004. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific Function
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
- Gene Name
- RARG
- Uniprot ID
- P13631
- Uniprot Name
- Retinoic acid receptor gamma
- Molecular Weight
- 50341.405 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Reddy AP, Chen JY, Zacharewski T, Gronemeyer H, Voorhees JJ, Fisher GJ: Characterization and purification of human retinoic acid receptor-gamma 1 overexpressed in the baculovirus-insect cell system. Biochem J. 1992 Nov 1;287 ( Pt 3):833-40. [Article]
- Kamei Y, Kawada T, Kazuki R, Sugimoto E: Retinoic acid receptor gamma 2 gene expression is up-regulated by retinoic acid in 3T3-L1 preadipocytes. Biochem J. 1993 Aug 1;293 ( Pt 3):807-12. [Article]
- Borger DR, Mi Y, Geslani G, Zyzak LL, Batova A, Engin TS, Pirisi L, Creek KE: Retinoic acid resistance at late stages of human papillomavirus type 16-mediated transformation of human keratinocytes arises despite intact retinoid signaling and is due to a loss of sensitivity to transforming growth factor-beta. Virology. 2000 May 10;270(2):397-407. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Regazzi MB, Iacona I, Gervasutti C, Lazzarino M, Toma S: Clinical pharmacokinetics of tretinoin. Clin Pharmacokinet. 1997 May;32(5):382-402. doi: 10.2165/00003088-199732050-00004. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- Curator comments
- Tretinoin interacts 40-fold less efficiently with RXR-alpha than with RAR-alpha.
- General Function
- Zinc ion binding
- Specific Function
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
- Gene Name
- RXRA
- Uniprot ID
- P19793
- Uniprot Name
- Retinoic acid receptor RXR-alpha
- Molecular Weight
- 50810.835 Da
References
- Mizuguchi Y, Wada A, Nakagawa K, Ito M, Okano T: Antitumoral activity of 13-demethyl or 13-substituted analogues of all-trans retinoic acid and 9-cis retinoic acid in the human myeloid leukemia cell line HL-60. Biol Pharm Bull. 2006 Sep;29(9):1803-9. [Article]
- Regazzi MB, Iacona I, Gervasutti C, Lazzarino M, Toma S: Clinical pharmacokinetics of tretinoin. Clin Pharmacokinet. 1997 May;32(5):382-402. doi: 10.2165/00003088-199732050-00004. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific Function
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
- Gene Name
- RXRB
- Uniprot ID
- P28702
- Uniprot Name
- Retinoic acid receptor RXR-beta
- Molecular Weight
- 56921.38 Da
References
- Stafslien DK, Vedvik KL, De Rosier T, Ozers MS: Analysis of ligand-dependent recruitment of coactivator peptides to RXRbeta in a time-resolved fluorescence resonance energy transfer assay. Mol Cell Endocrinol. 2007 Jan 29;264(1-2):82-9. Epub 2006 Dec 20. [Article]
- Redfern CP: Enhancing enhancers: new complexities in the retinoid regulation of gene expression. Biochem J. 2004 Oct 1;383(Pt 1):e1-2. [Article]
- Nagasawa H, Takahashi S, Kobayashi A, Tazawa H, Tashima Y, Sato K: Effect of retinoic acid on murine preosteoblastic MC3T3-E1 cells. J Nutr Sci Vitaminol (Tokyo). 2005 Oct;51(5):311-8. [Article]
- Schrage K, Koopmans G, Joosten EA, Mey J: Macrophages and neurons are targets of retinoic acid signaling after spinal cord contusion injury. Eur J Neurosci. 2006 Jan;23(2):285-95. [Article]
- Hoegberg P, Schmidt CK, Fletcher N, Nilsson CB, Trossvik C, Gerlienke Schuur A, Brouwer A, Nau H, Ghyselinck NB, Chambon P, Hakansson H: Retinoid status and responsiveness to 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in mice lacking retinoid binding protein or retinoid receptor forms. Chem Biol Interact. 2005 Sep 10;156(1):25-39. [Article]
- Regazzi MB, Iacona I, Gervasutti C, Lazzarino M, Toma S: Clinical pharmacokinetics of tretinoin. Clin Pharmacokinet. 1997 May;32(5):382-402. doi: 10.2165/00003088-199732050-00004. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific Function
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
- Gene Name
- RXRG
- Uniprot ID
- P48443
- Uniprot Name
- Retinoic acid receptor RXR-gamma
- Molecular Weight
- 50870.72 Da
References
- Koda T, Imai H, Morita M: Antiestrogenic activity of vitamin A in in vivo uterotrophic assay. Life Sci. 2007 Feb 13;80(10):945-9. Epub 2006 Nov 22. [Article]
- He JC, Lu TC, Fleet M, Sunamoto M, Husain M, Fang W, Neves S, Chen Y, Shankland S, Iyengar R, Klotman PE: Retinoic acid inhibits HIV-1-induced podocyte proliferation through the cAMP pathway. J Am Soc Nephrol. 2007 Jan;18(1):93-102. Epub 2006 Dec 20. [Article]
- Day RM, Lee YH, Park AM, Suzuki YJ: Retinoic acid inhibits airway smooth muscle cell migration. Am J Respir Cell Mol Biol. 2006 Jun;34(6):695-703. Epub 2006 Feb 2. [Article]
- Schrage K, Koopmans G, Joosten EA, Mey J: Macrophages and neurons are targets of retinoic acid signaling after spinal cord contusion injury. Eur J Neurosci. 2006 Jan;23(2):285-95. [Article]
- Wang J, Yen A: A novel retinoic acid-responsive element regulates retinoic acid-induced BLR1 expression. Mol Cell Biol. 2004 Mar;24(6):2423-43. [Article]
- Regazzi MB, Iacona I, Gervasutti C, Lazzarino M, Toma S: Clinical pharmacokinetics of tretinoin. Clin Pharmacokinet. 1997 May;32(5):382-402. doi: 10.2165/00003088-199732050-00004. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Transporter activity
- Specific Function
- Cytosolic CRABPs may regulate the access of retinoic acid to the nuclear retinoic acid receptors.
- Gene Name
- CRABP1
- Uniprot ID
- P29762
- Uniprot Name
- Cellular retinoic acid-binding protein 1
- Molecular Weight
- 15565.45 Da
References
- Regazzi MB, Iacona I, Gervasutti C, Lazzarino M, Toma S: Clinical pharmacokinetics of tretinoin. Clin Pharmacokinet. 1997 May;32(5):382-402. doi: 10.2165/00003088-199732050-00004. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Not Available
- Specific Function
- Inhibitor of the cytoplasmic carboxypeptidase AGBL2, may regulate the alpha-tubulin tyrosination cycle.
- Gene Name
- RARRES1
- Uniprot ID
- P49788
- Uniprot Name
- Retinoic acid receptor responder protein 1
- Molecular Weight
- 33284.865 Da
References
- Youssef EM, Chen XQ, Higuchi E, Kondo Y, Garcia-Manero G, Lotan R, Issa JP: Hypermethylation and silencing of the putative tumor suppressor Tazarotene-induced gene 1 in human cancers. Cancer Res. 2004 Apr 1;64(7):2411-7. [Article]
- Zirn B, Samans B, Spangenberg C, Graf N, Eilers M, Gessler M: All-trans retinoic acid treatment of Wilms tumor cells reverses expression of genes associated with high risk and relapse in vivo. Oncogene. 2005 Aug 4;24(33):5246-51. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Retinal dehydrogenase activity
- Specific Function
- Binds free retinal and cellular retinol-binding protein-bound retinal. Can convert/oxidize retinaldehyde to retinoic acid (By similarity).
- Gene Name
- ALDH1A1
- Uniprot ID
- P00352
- Uniprot Name
- Retinal dehydrogenase 1
- Molecular Weight
- 54861.44 Da
References
- Mic FA, Molotkov A, Molotkova N, Duester G: Raldh2 expression in optic vesicle generates a retinoic acid signal needed for invagination of retina during optic cup formation. Dev Dyn. 2004 Oct;231(2):270-7. [Article]
- Everts HB, King LE Jr, Sundberg JP, Ong DE: Hair cycle-specific immunolocalization of retinoic acid synthesizing enzymes Aldh1a2 and Aldh1a3 indicate complex regulation. J Invest Dermatol. 2004 Aug;123(2):258-63. [Article]
- Gidlof AC, Ocaya P, Olofsson PS, Torma H, Sirsjo A: Differences in retinol metabolism and proliferative response between neointimal and medial smooth muscle cells. J Vasc Res. 2006;43(4):392-8. Epub 2006 Jul 6. [Article]
- Matt N, Dupe V, Garnier JM, Dennefeld C, Chambon P, Mark M, Ghyselinck NB: Retinoic acid-dependent eye morphogenesis is orchestrated by neural crest cells. Development. 2005 Nov;132(21):4789-800. Epub 2005 Oct 5. [Article]
- Kim H, Lapointe J, Kaygusuz G, Ong DE, Li C, van de Rijn M, Brooks JD, Pollack JR: The retinoic acid synthesis gene ALDH1a2 is a candidate tumor suppressor in prostate cancer. Cancer Res. 2005 Sep 15;65(18):8118-24. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Retinal dehydrogenase activity
- Specific Function
- Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Does metabolize octanal and decanal but does not metabolize citral, benzaldehyde, acetaldehyde and propanal...
- Gene Name
- ALDH1A2
- Uniprot ID
- O94788
- Uniprot Name
- Retinal dehydrogenase 2
- Molecular Weight
- 56723.495 Da
References
- Mic FA, Sirbu IO, Duester G: Retinoic acid synthesis controlled by Raldh2 is required early for limb bud initiation and then later as a proximodistal signal during apical ectodermal ridge formation. J Biol Chem. 2004 Jun 18;279(25):26698-706. Epub 2004 Apr 6. [Article]
- Bordelon T, Montegudo SK, Pakhomova S, Oldham ML, Newcomer ME: A disorder to order transition accompanies catalysis in retinaldehyde dehydrogenase type II. J Biol Chem. 2004 Oct 8;279(41):43085-91. Epub 2004 Aug 7. [Article]
- Mic FA, Molotkov A, Molotkova N, Duester G: Raldh2 expression in optic vesicle generates a retinoic acid signal needed for invagination of retina during optic cup formation. Dev Dyn. 2004 Oct;231(2):270-7. [Article]
- Doxakis E, Davies AM: Retinoic acid negatively regulates GDNF and neurturin receptor expression and responsiveness in embryonic chicken sympathetic neurons. Mol Cell Neurosci. 2005 Aug;29(4):617-27. [Article]
- Everts HB, Sundberg JP, Ong DE: Immunolocalization of retinoic acid biosynthesis systems in selected sites in rat. Exp Cell Res. 2005 Aug 15;308(2):309-19. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Regulator
- General Function
- G-protein coupled receptor activity
- Specific Function
- Orphan receptor. Could be involved in modulating differentiation and maintaining homeostasis of epithelial cells. This retinoic acid-inducible GPCR provide evidence for a possible interaction betwe...
- Gene Name
- GPRC5A
- Uniprot ID
- Q8NFJ5
- Uniprot Name
- Retinoic acid-induced protein 3
- Molecular Weight
- 40250.69 Da
References
- Xu J, Tian J, Shapiro SD: Normal lung development in RAIG1-deficient mice despite unique lung epithelium-specific expression. Am J Respir Cell Mol Biol. 2005 May;32(5):381-7. Epub 2005 Jan 27. [Article]
- Inoue S, Nambu T, Shimomura T: The RAIG family member, GPRC5D, is associated with hard-keratinized structures. J Invest Dermatol. 2004 Mar;122(3):565-73. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Cysteine-type endopeptidase inhibitor activity
- Specific Function
- Could play a role in taste reception. Could be necessary for the concentration and delivery of sapid molecules in the gustatory system. Can bind various ligands, with chemical structures ranging fr...
- Gene Name
- LCN1
- Uniprot ID
- P31025
- Uniprot Name
- Lipocalin-1
- Molecular Weight
- 19249.845 Da
References
- Breustedt DA, Schonfeld DL, Skerra A: Comparative ligand-binding analysis of ten human lipocalins. Biochim Biophys Acta. 2006 Feb;1764(2):161-73. Epub 2006 Jan 6. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Odorant binding
- Specific Function
- Probably binds and transports small hydrophobic volatile molecules with a higher affinity for aldehydes and large fatty acids.
- Gene Name
- OBP2A
- Uniprot ID
- Q9NY56
- Uniprot Name
- Odorant-binding protein 2a
- Molecular Weight
- 19318.245 Da
References
- Breustedt DA, Schonfeld DL, Skerra A: Comparative ligand-binding analysis of ten human lipocalins. Biochim Biophys Acta. 2006 Feb;1764(2):161-73. Epub 2006 Jan 6. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Retinol transporter activity
- Specific Function
- Delivers retinol from the liver stores to the peripheral tissues. In plasma, the RBP-retinol complex interacts with transthyretin, this prevents its loss by filtration through the kidney glomeruli.
- Gene Name
- RBP4
- Uniprot ID
- P02753
- Uniprot Name
- Retinol-binding protein 4
- Molecular Weight
- 23009.8 Da
References
- Breustedt DA, Schonfeld DL, Skerra A: Comparative ligand-binding analysis of ten human lipocalins. Biochim Biophys Acta. 2006 Feb;1764(2):161-73. Epub 2006 Jan 6. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Upregulator
- General Function
- Pyruvate dehydrogenase (acetyl-transferring) kinase activity
- Specific Function
- Kinase that plays a key role in regulation of glucose and fatty acid metabolism and homeostasis via phosphorylation of the pyruvate dehydrogenase subunits PDHA1 and PDHA2. This inhibits pyruvate de...
- Gene Name
- PDK4
- Uniprot ID
- Q16654
- Uniprot Name
- [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 4, mitochondrial
- Molecular Weight
- 46468.79 Da
References
- Kwon HS, Huang B, Ho Jeoung N, Wu P, Steussy CN, Harris RA: Retinoic acids and trichostatin A (TSA), a histone deacetylase inhibitor, induce human pyruvate dehydrogenase kinase 4 (PDK4) gene expression. Biochim Biophys Acta. 2006 Mar-Apr;1759(3-4):141-51. Epub 2006 Apr 27. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Downregulator
- General Function
- Not Available
- Specific Function
- Not Available
- Gene Name
- Not Available
- Uniprot ID
- Q14081
- Uniprot Name
- Carcinoembryonic antigen
- Molecular Weight
- 4903.595 Da
References
- Friedman J, Seger M, Levinsky H, Allalouf D: Modulation of carcinoembryonic antigen release by HT-29 colon carcinoma line in the presence of different agents. Experientia. 1987 Oct 15;43(10):1121-2. doi: 10.1007/BF01956058. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A7
- Uniprot ID
- P24462
- Uniprot Name
- Cytochrome P450 3A7
- Molecular Weight
- 57525.03 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Marill J, Cresteil T, Lanotte M, Chabot GG: Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol. 2000 Dec;58(6):1341-8. [Article]
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
- FDA Approved Drug Products: VESANOID (tretinoin) capsules, for oral use [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Marill J, Cresteil T, Lanotte M, Chabot GG: Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol. 2000 Dec;58(6):1341-8. [Article]
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
- Gene Name
- CYP2A6
- Uniprot ID
- P11509
- Uniprot Name
- Cytochrome P450 2A6
- Molecular Weight
- 56501.005 Da
References
- Marill J, Cresteil T, Lanotte M, Chabot GG: Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol. 2000 Dec;58(6):1341-8. [Article]
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C18
- Uniprot ID
- P33260
- Uniprot Name
- Cytochrome P450 2C18
- Molecular Weight
- 55710.075 Da
References
- Marill J, Cresteil T, Lanotte M, Chabot GG: Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol. 2000 Dec;58(6):1341-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d 24-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A1
- Uniprot ID
- P04798
- Uniprot Name
- Cytochrome P450 1A1
- Molecular Weight
- 58164.815 Da
References
- Marill J, Cresteil T, Lanotte M, Chabot GG: Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol. 2000 Dec;58(6):1341-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Leukotriene-b4 20-monooxygenase activity
- Specific Function
- Catalyzes the omega- and (omega-1)-hydroxylation of various fatty acids such as laurate, myristate and palmitate. Has little activity toward prostaglandins A1 and E1. Oxidizes arachidonic acid to 2...
- Gene Name
- CYP4A11
- Uniprot ID
- Q02928
- Uniprot Name
- Cytochrome P450 4A11
- Molecular Weight
- 59347.31 Da
References
- Marill J, Cresteil T, Lanotte M, Chabot GG: Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol. 2000 Dec;58(6):1341-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Glucuronosyltransferase activity
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
- Gene Name
- UGT2B7
- Uniprot ID
- P16662
- Uniprot Name
- UDP-glucuronosyltransferase 2B7
- Molecular Weight
- 60694.12 Da
References
- FDA Approved Drug Products: VESANOID (tretinoin) capsules, for oral use [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
- Gene Name
- CYP2E1
- Uniprot ID
- P05181
- Uniprot Name
- Cytochrome P450 2E1
- Molecular Weight
- 56848.42 Da
References
- FDA Approved Drug Products: VESANOID (tretinoin) capsules, for oral use [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Retinoic acid binding
- Specific Function
- Plays a key role in retinoic acid metabolism. Acts on retinoids, including all-trans-retinoic acid (RA) and its stereoisomer 9-cis-RA. Capable of both 4-hydroxylation and 18-hydroxylation. Responsi...
- Gene Name
- CYP26A1
- Uniprot ID
- O43174
- Uniprot Name
- Cytochrome P450 26A1
- Molecular Weight
- 56198.11 Da
References
- Heise R, Mey J, Neis MM, Marquardt Y, Joussen S, Ott H, Wiederholt T, Kurschat P, Megahed M, Bickers DR, Merk HF, Baron JM: Skin retinoid concentrations are modulated by CYP26AI expression restricted to basal keratinocytes in normal human skin and differentiated 3D skin models. J Invest Dermatol. 2006 Nov;126(11):2473-80. doi: 10.1038/sj.jid.5700432. Epub 2006 Jun 15. [Article]
- Lee SJ, Perera L, Coulter SJ, Mohrenweiser HW, Jetten A, Goldstein JA: The discovery of new coding alleles of human CYP26A1 that are potentially defective in the metabolism of all-trans retinoic acid and their assessment in a recombinant cDNA expression system. Pharmacogenet Genomics. 2007 Mar;17(3):169-80. doi: 10.1097/FPC.0b013e32801152d6. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Maiti TK, Ghosh KS, Debnath J, Dasgupta S: Binding of all-trans retinoic acid to human serum albumin: fluorescence, FT-IR and circular dichroism studies. Int J Biol Macromol. 2006 May 30;38(3-5):197-202. Epub 2006 Mar 6. [Article]
- N'soukpoe-Kossi CN, Sedaghat-Herati R, Ragi C, Hotchandani S, Tajmir-Riahi HA: Retinol and retinoic acid bind human serum albumin: stability and structural features. Int J Biol Macromol. 2007 Apr 10;40(5):484-90. Epub 2006 Nov 24. [Article]
- Karnaukhova E: Interactions of human serum albumin with retinoic acid, retinal and retinyl acetate. Biochem Pharmacol. 2007 Mar 15;73(6):901-10. Epub 2006 Dec 2. [Article]
- Regazzi MB, Iacona I, Gervasutti C, Lazzarino M, Toma S: Clinical pharmacokinetics of tretinoin. Clin Pharmacokinet. 1997 May;32(5):382-402. doi: 10.2165/00003088-199732050-00004. [Article]
- FDA Approved Drug Products: VESANOID (tretinoin) capsules, for oral use [Link]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Transporter activity
- Specific Function
- Cytosolic CRABPs may regulate the access of retinoic acid to the nuclear retinoic acid receptors.
- Gene Name
- CRABP1
- Uniprot ID
- P29762
- Uniprot Name
- Cellular retinoic acid-binding protein 1
- Molecular Weight
- 15565.45 Da
References
- Hoegberg P, Schmidt CK, Fletcher N, Nilsson CB, Trossvik C, Gerlienke Schuur A, Brouwer A, Nau H, Ghyselinck NB, Chambon P, Hakansson H: Retinoid status and responsiveness to 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in mice lacking retinoid binding protein or retinoid receptor forms. Chem Biol Interact. 2005 Sep 10;156(1):25-39. [Article]
- Donato LJ, Noy N: Fluorescence-based technique for analyzing retinoic acid. Methods Mol Biol. 2010;652:177-87. doi: 10.1007/978-1-60327-325-1_10. [Article]
- Napoli JL: Functions of Intracellular Retinoid Binding-Proteins. Subcell Biochem. 2016;81:21-76. doi: 10.1007/978-94-024-0945-1_2. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Transporter activity
- Specific Function
- Transports retinoic acid to the nucleus. Regulates the access of retinoic acid to the nuclear retinoic acid receptors.
- Gene Name
- CRABP2
- Uniprot ID
- P29373
- Uniprot Name
- Cellular retinoic acid-binding protein 2
- Molecular Weight
- 15692.925 Da
References
- Hoegberg P, Schmidt CK, Fletcher N, Nilsson CB, Trossvik C, Gerlienke Schuur A, Brouwer A, Nau H, Ghyselinck NB, Chambon P, Hakansson H: Retinoid status and responsiveness to 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in mice lacking retinoid binding protein or retinoid receptor forms. Chem Biol Interact. 2005 Sep 10;156(1):25-39. [Article]
- Ohnishi K: PML-RARalpha inhibitors (ATRA, tamibaroten, arsenic troxide) for acute promyelocytic leukemia. Int J Clin Oncol. 2007 Oct;12(5):313-7. Epub 2007 Oct 22. [Article]
- Donato LJ, Noy N: Fluorescence-based technique for analyzing retinoic acid. Methods Mol Biol. 2010;652:177-87. doi: 10.1007/978-1-60327-325-1_10. [Article]
- Napoli JL: Functions of Intracellular Retinoid Binding-Proteins. Subcell Biochem. 2016;81:21-76. doi: 10.1007/978-94-024-0945-1_2. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54