Isotretinoin
Identification
- Summary
Isotretinoin is a retinoid used to treat severe recalcitrant acne.
- Brand Names
- Absorica, Accutane, Amnesteem, Claravis, Clarus, Epuris, Myorisan, Sotret, Zenatane
- Generic Name
- Isotretinoin
- DrugBank Accession Number
- DB00982
- Background
Isotretinoin is a retinoid derivative of vitamin A used in the treatment of severe recalcitrant acne.Label It was most widely marketed under the brand name Accutane, which has since been discontinued.10 Isotretinoin is associated with major risks in pregnancy and is therefore only available under the iPLEDGE program in the United States.12 The first isotretinoin-containing product was FDA approved on 7 May 1982.10
- Type
- Small Molecule
- Groups
- Approved
- Structure
- Weight
- Average: 300.4351
Monoisotopic: 300.20893014 - Chemical Formula
- C20H28O2
- Synonyms
- (7E,9E,11E,13Z)-retinoic acid
- 13-cis-retinoic acid
- 13-cis-Vitamin A acid
- 13-RA
- cis-RA
- Isotretinoin
- Isotretinoína
- Isotrétinoine
- Isotretinoino
- Isotretinoinum
- Neovitamin A acid
- External IDs
- RO 4-3780
- RO-4-3780
Pharmacology
- Indication
Isotretinoin is indicated to treat severe recalcitrant nodular acne and patients ≥12 years enrolled in the iPLEDGE program.Label,12
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Acne conglobata •••••••••••• ••••••• Treatment of Neuroblastoma ••• ••••• Treatment of Rosacea ••• ••••• Treatment of Sezary syndrome ••• ••••• Treatment of Early mycosis fungoides (mf) ••• ••••• - Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
The pharmacodynamics of isotretinoin are poorly understood.Label
- Mechanism of action
Isotretinoin produces its effects through altering progress through the cell cycle, cell differentiation, survival, and apoptosis.4 These actions reduce sebum production, preventing the blockage of pores, and growth of acne causing bacteria.4 Isotretinoin and 4-oxo-isotretinoin both significantly reduce the production of sebum.4,Label Isotretinoin has little to no affinity for retinol binding proteins (RBPs) and retinoic acid nuclear receptors (RARs).4 Tretinoin and 4-oxo-tretinion bind to the RAR-γ receptor, which is suspected to be part of the action of acne treatment by isotretinoin.4 Isotretinoin induces apoptosis in sebocytes, leading to a decrease in sebum production.4 Isotretinoin also reduces the formation of comedones by reducing hyperkeratinization through an unknown mechanism.4 Isotretinoin does not directly kill bacteria but it does reduce the size of sebum ducts and makes the microenvironment less hospitable to acne causing bacteria.4 It may also increase immune mechanisms and alter chemotaxis of monocytes to reduce inflammation.4
There is preliminary evidence suggesting isotretinoin may interact with FoxO1, which may explain a substantial number of isotretinoin's unexplained actions.9
Target Actions Organism URetinoic acid receptor gamma Not Available Humans URetinoic acid receptor alpha other/unknownHumans - Absorption
Patients reach a maximum concentration of 74-511ng/mL after 1-4 hours following a 100mg oral dose.1 Isotretinoin is better absorbed with a high fat meal and bioavailability may change from one brand to another.Label
Following a 40mg oral dose, fasted subjects reached a maximum concentration of 314ng/mL in 2.9 hours with an area under the curve of 4055ng/mL*hr.Label Subjects given a high fat meal and a 40mg oral doses reached a maximum concentration of 395ng/mL in 6.4 hours with an area under the curve of 6095ng/mL*mL.Label
- Volume of distribution
The volume of distribution in humans is unknown because there is no intravenous preparation.13 In a study of pediatric patients with neuroblastoma the volume of distribution was found to be 85L.6 The volume of distribution was also found to be 2432mL/kg in guinea pigs and 1716mL/kg in obese rats.5
- Protein binding
Isotretinoin is >99.9% protein bound, mainly to serum albumin.Label
- Metabolism
Isotretinoin, or 13-cis-retinoic acid can undergo reversible cis-trans isomerization to all-trans-retinoic acid.8 Isotretinoin undergoes 4-hydroxylation to 4-hydroxy-13-cis-retinoic acid, which is oxidized to the main metabolite 4-oxo-13-cis-retinoic acid.8,3. All-trans-retinoic acid undergoes 4-hydroxylation to 4-hydroxy-all-trans-retinoic acid, which is oxidized to 4-oxo-all-trans-retinoic acid.8 4-oxo-13-cis-retinoic acid can undergo reversible cis-trans isomerization to 4-oxo-all-trans-retinoic acid.8
Hover over products below to view reaction partners
- Route of elimination
Isotretinoin and its metabolites are conjugated and excreted in the urine and feces in similar amounts.Label 53-74% of an oral dose is eliminated as unchanged isotretinoin in the feces.1
- Half-life
The half life ranges from 7-39 hours13 with a mean elimination half life of 20 hours.1 The half life of 4-oxo-13-cis-retinoic acid ranges from 17-50 hours with a mean elimination half life of 25 hours.13
- Clearance
The clearance of isotretinoin is 15.9L/h in pediatric patients with neuroblastoma.6 Clearance is also 21.3mL/min/kg in guinea pigs and 7.2mL/min/kg in obese rats.5
- Adverse Effects
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- Toxicity
Patients experiencing an overdose may present with vomiting, facial flushing, cheilosis, abdominal pain, headache, dizziness, and ataxia.Label These symptoms may rapidly resolve.Label Generally no treatment is required for these overdoses.7
The oral lowest dose causing toxic effect (TDLO) for children is 30mg/kg/21W, oral TDLO for men is 24mg/kg/4W, oral TDLO for women is 56mg/kg/8W.14 The intraperitoneal LD50 for rats is 901mg/kg, oral LD50 for mice is 3389mg/kg, oral LD50 for rats is >4000mg/kg.14
Isotretinoin is associated with major congenital malformations, spontaneous abortion, and premature birth.Label It is unknown if isotretinoin is expressed in breast milk but due to the associated hazards a decision should be made to either stop nursing or stop taking isotretinoin.Label
In animal studies, isotretinoin was associated with an increased risk of pheochromocytoma and adrenal medullary hyperplasia at doses above the recommended clinical dose.Label Isotretinoin was negative for the Ames test of mutagenicity once and weakly positive a second time.Label It has not been shown to be clastogenic.Label A study in dogs noted testicular atrophy after doses of 10-30 times the recommended clinical dose for 30 weeks.Label In trials with men there were no effects seen on sperm count, motility, morphology, ejaculate volume, and seminal plasma fructose.Label
- Pathways
- Not Available
- 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 softwareAbacavir Isotretinoin may decrease the excretion rate of Abacavir which could result in a higher serum level. Abametapir The serum concentration of Isotretinoin can be increased when it is combined with Abametapir. Aceclofenac Aceclofenac may decrease the excretion rate of Isotretinoin which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Isotretinoin which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of Isotretinoin which could result in a higher serum level. - Food Interactions
- Avoid alcohol. Alcohol with isotretinoin can lead to inflammation of the liver.
- Avoid vitamin A supplements.
- Take with food. High-fat food increases drug absorption.
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
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Absorica Capsule 20 mg/1 Oral Sun Pharmaceutical Industries, Inc. 2012-06-08 Not applicable US Absorica Capsule 40 mg/1 Oral Sun Pharmaceutical Industries, Inc. 2012-06-08 Not applicable US Absorica Capsule 10 mg/1 Oral Sun Pharmaceutical Industries, Inc. 2012-06-08 Not applicable US Absorica Capsule 35 mg/1 Oral Sun Pharmaceutical Industries, Inc. 2015-02-17 Not applicable US Absorica Capsule 30 mg/1 Oral Sun Pharmaceutical Industries, Inc. 2012-06-08 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Accutane Capsule, gelatin coated 40 mg/1 Oral Jg Pharma Inc. 2022-08-01 Not applicable US Accutane Capsule, gelatin coated 20 mg/1 Oral Jg Pharma Inc. 2021-01-11 2023-11-30 US Accutane Capsule, gelatin coated 20 mg/1 Oral Jg Pharma Inc. 2022-08-01 Not applicable US Accutane Capsule, gelatin coated 30 mg/1 Oral Jg Pharma Inc. 2021-01-11 2024-01-31 US Accutane Capsule, gelatin coated 10 mg/1 Oral Jg Pharma Inc. 2021-01-11 2023-12-31 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ETREXİN % 2 + % 0.05 JEL Isotretinoin (0.05 %) + Erythromycin (2 %) Gel Topical VEM İLAÇ SAN. VE TİC. A.Ş. 2014-04-07 Not applicable Turkey ISOTREXIN JEL, 30 G Isotretinoin (0.05 %) + Erythromycin (2 %) Gel Topical GLAXOSMİTHKLİNE İLAÇLARI SAN. VE TİC. A.Ş. 2010-07-06 2020-05-28 Turkey MUNDERM JEL , 30 GRAM Isotretinoin (0.5 mg) + Erythromycin (20 mg) Gel Topical HELBA İLAÇ İÇ VE DIŞ SAN. TİC. A.Ş. 2014-11-14 Not applicable Turkey
Categories
- ATC Codes
- D10AD04 — Isotretinoin
- D10AD — Retinoids for topical use in acne
- D10A — ANTI-ACNE PREPARATIONS FOR TOPICAL USE
- D10 — ANTI-ACNE PREPARATIONS
- D — DERMATOLOGICALS
- D10AD — Retinoids for topical use in acne
- D10A — ANTI-ACNE PREPARATIONS FOR TOPICAL USE
- D10 — ANTI-ACNE PREPARATIONS
- D — DERMATOLOGICALS
- Drug Categories
- Agents Causing Muscle Toxicity
- Alkenes
- Anti-Acne Preparations
- Anti-Acne Preparations for Systemic Use
- Anti-Acne Preparations for Topical Use
- Biological Factors
- Carotenoids
- Cyclohexanes
- Cyclohexenes
- Cycloparaffins
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Dermatologicals
- Drugs causing inadvertant photosensitivity
- Drugs that are Mainly Renally Excreted
- Hydrocarbons, Acyclic
- Misc. Skin and Mucous Membrane Agents
- Noxae
- Photosensitizing Agents
- Pigments, Biological
- Polyenes
- Retinoids
- Retinoids for Topical Use in Acne
- Retinoids for Treatment of Acne
- Teratogens
- Terpenes
- Toxic Actions
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Prenol lipids
- Sub Class
- Retinoids
- Direct Parent
- Retinoids
- Alternative Parents
- Diterpenoids / Medium-chain fatty acids / Methyl-branched fatty acids / Unsaturated fatty acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Aliphatic homomonocyclic compound / Branched fatty acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Diterpenoid / Fatty acid / Fatty acyl / Hydrocarbon derivative / Medium-chain fatty acid
- Molecular Framework
- Aliphatic homomonocyclic compounds
- External Descriptors
- retinoic acid (CHEBI:6067) / Retinoids (LMPR01090021)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- EH28UP18IF
- CAS number
- 4759-48-2
- InChI Key
- SHGAZHPCJJPHSC-XFYACQKRSA-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
- (2Z,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
- Synthesis Reference
Ashok Kumar, Dharmendra Singh, Ganesh Devidas Mahale, Ragnesh Kumar Rana, Mahesh Kharade, "PROCESS FOR PREPARATION OF HIGHLY PURE ISOTRETINOIN." U.S. Patent US20080207946, issued August 28, 2008.
US20080207946- General References
- Khoo KC, Reik D, Colburn WA: Pharmacokinetics of isotretinoin following a single oral dose. J Clin Pharmacol. 1982 Aug-Sep;22(8-9):395-402. [Article]
- Miastkowska M, Sikora E, Ogonowski J, Zielina M, Łudzik A: The kinetic study of isotretinoin release from nanoemulsion Colloids and Surfaces A: Physicochemical and Engineering Aspects. 2016 Dec 5;510:63-68. [Article]
- Vane FM, Bugge CJ: Identification of 4-oxo-13-cis-retinoic acid as the major metabolite of 13-cis-retinoic acid in human blood. Drug Metab Dispos. 1981 Nov-Dec;9(6):515-20. [Article]
- Layton A: The use of isotretinoin in acne. Dermatoendocrinol. 2009 May;1(3):162-9. doi: 10.4161/derm.1.3.9364. [Article]
- Chien DS, Sandri RB, Tang-Liu DS: Systemic pharmacokinetics of acitretin, etretinate, isotretinoin, and acetylenic retinoids in guinea pigs and obese rats. Drug Metab Dispos. 1992 Mar-Apr;20(2):211-7. [Article]
- Veal GJ, Cole M, Errington J, Pearson AD, Foot AB, Whyman G, Boddy AV: Pharmacokinetics and metabolism of 13-cis-retinoic acid (isotretinoin) in children with high-risk neuroblastoma - a study of the United Kingdom Children's Cancer Study Group. Br J Cancer. 2007 Feb 12;96(3):424-31. doi: 10.1038/sj.bjc.6603554. Epub 2007 Jan 16. [Article]
- Aubin S, Lorette G, Muller C, Vaillant L: Massive isotretinoin intoxication. Clin Exp Dermatol. 1995 Jul;20(4):348-50. [Article]
- Brazzell RK, Colburn WA: Pharmacokinetics of the retinoids isotretinoin and etretinate. A comparative review. J Am Acad Dermatol. 1982 Apr;6(4 Pt 2 Suppl):643-51. [Article]
- Melnik BC: Isotretinoin and FoxO1: A scientific hypothesis. Dermatoendocrinol. 2011 Jul;3(3):141-65. doi: 10.4161/derm.3.3.15331. Epub 2011 Jul 1. [Article]
- FDA Approved Drug Products: Accutane Oral Capsule [Link]
- FDA Approved Drug Products: Absorica [Link]
- iPLEDGE Program Home Page [Link]
- New Zealand Drug Data Sheet: Oratane [Link]
- Isotretinoin MSDS [Link]
- Health Canada Product Monograph: Accutane Roche (isotretinoin) capsules for oral administration [Link]
- External Links
- Human Metabolome Database
- HMDB0006219
- KEGG Drug
- D00348
- PubChem Compound
- 5282379
- PubChem Substance
- 46508729
- ChemSpider
- 4445539
- BindingDB
- 50031459
- 6064
- ChEBI
- 6067
- ChEMBL
- CHEMBL547
- ZINC
- ZINC000003792789
- Therapeutic Targets Database
- DAP000009
- PharmGKB
- PA450128
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Isotretinoin
- FDA label
- Download (175 KB)
- MSDS
- Download (37.3 KB)
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 Diagnostic Acne Vulgaris 1 4 Completed Basic Science Adverse Drug Reaction (ADR) 1 4 Completed Diagnostic Acne Vulgaris 1 4 Completed Other CYP2D6 Polymorphism 1 4 Completed Prevention Proliferative Vitreoretinopathy 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Barr Pharmaceuticals
- Catalent Pharma Solutions
- F Hoffmann-La Roche Ltd.
- Mylan
- Pharmaceutical Utilization Management Program VA Inc.
- Physicians Total Care Inc.
- Ranbaxy Laboratories
- Dosage Forms
Form Route Strength Capsule Oral 25 mg/1 Capsule Oral 35 mg/1 Capsule Oral 16 mg Capsule Oral 16 mg/1 Capsule Oral 24 mg Capsule Oral 24 mg/1 Capsule Oral 28 mg/1 Capsule Oral 32 mg/1 Capsule Oral 32 mg Capsule Oral 8 mg Capsule Oral 8 mg/1 Capsule, liquid filled Oral 10 mg/1 Capsule, liquid filled Oral 40 mg/1 Capsule Oral 40 mg Capsule, gelatin coated Oral 10 mg Capsule, gelatin coated Oral 20 mg Capsule Oral 10 mg/1 Capsule Oral 20 mg/1 Capsule Oral 40 mg/1 Capsule Oral Capsule Oral 30 mg/1 Capsule, liquid filled Oral 30 mg/1 Capsule, liquid filled Oral 0.21 mg Capsule Oral 30 mg Gel Topical Capsule Oral 10.00 mg Capsule, liquid filled Oral 10 mg Capsule, liquid filled Oral 20 mg Capsule, liquid filled Oral 30 mg Capsule, liquid filled Oral 40 mg Capsule, liquid filled Oral 4000000 mg Capsule, liquid filled Oral 5 mg Gel Topical 50 mg Gel Topical 0.05 g Capsule, liquid filled Oral 1000000 mg Capsule, liquid filled Oral 2000000 mg Cream Topical Gel Topical 0.05 % Gel Topical Capsule Oral 20.0000 mg Capsule Oral 5.0000 mg Capsule Oral 20.00 mg Capsule Oral 5 MG Capsule Oral 20.000 mg Capsule, gelatin coated Oral 10 mg/1 Capsule, gelatin coated Oral 30 mg/1 Capsule, gelatin coated Oral 40 mg/1 Capsule, liquid filled Oral 20 mg/1 Capsule Oral 20 mg Capsule Oral 10.000 mg Capsule Oral 10.0000 mg Capsule, gelatin coated Oral 20 mg/1 Capsule Oral 10 mg - Prices
Unit description Cost Unit Accutane 20 mg capsule 23.77USD capsule Amnesteem 40 mg capsule 22.6USD capsule Claravis 40 mg capsule 22.6USD capsule Amnesteem 20 mg capsule 19.45USD capsule Claravis 20 mg capsule 18.7USD capsule Claravis 30 mg capsule 16.45USD capsule Amnesteem 10 mg capsule 16.4USD capsule Claravis 10 mg capsule 15.77USD capsule Accutane 40 mg capsule 14.88USD capsule Accutane 10 mg capsule 10.55USD 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 Clarus 40 mg Capsule 2.14USD capsule Clarus 10 mg Capsule 1.05USD capsule DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US8367102 No 2013-02-05 2021-09-21 US US9089534 No 2015-07-28 2021-09-21 US US7435427 No 2008-10-14 2021-09-21 US US9078925 No 2015-07-14 2021-09-21 US US8952064 No 2015-02-10 2021-09-21 US US9750711 No 2017-09-05 2035-05-29 US US9700535 No 2017-07-11 2035-08-04 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 189-190 MSDS boiling point (°C) 462.8 http://www.chemspider.com/Chemical-Structure.4445539.html water solubility 0.00477mg/mL https://www.sciencedirect.com/science/article/pii/S0927775716305817 logP 5.66 https://www.sciencedirect.com/science/article/pii/S0927775716305817 pKa ~4 https://www.rochecanada.com/content/dam/rochexx/roche-ca/products/ConsumerInformation/MonographsandPublicAdvisories/Accutane/Accutane_PM_E.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 36.15 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]- 202.7295981 predictedDarkChem Lite v0.1.0 [M-H]- 203.3218981 predictedDarkChem Lite v0.1.0 [M-H]- 189.60449 predictedDeepCCS 1.0 (2019) [M+H]+ 191.9625 predictedDeepCCS 1.0 (2019) [M+Na]+ 199.03537 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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
- Layton A: The use of isotretinoin in acne. Dermatoendocrinol. 2009 May;1(3):162-9. doi: 10.4161/derm.1.3.9364. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Other/unknown
- 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
- Dahl AR, Grossi IM, Houchens DP, Scovell LJ, Placke ME, Imondi AR, Stoner GD, De Luca LM, Wang D, Mulshine JL: Inhaled isotretinoin (13-cis retinoic acid) is an effective lung cancer chemopreventive agent in A/J mice at low doses: a pilot study. Clin Cancer Res. 2000 Aug;6(8):3015-24. [Article]
- Zouboulis CC: Isotretinoin revisited: pluripotent effects on human sebaceous gland cells. J Invest Dermatol. 2006 Oct;126(10):2154-6. [Article]
- Vu-Dac N, Gervois P, Torra IP, Fruchart JC, Kosykh V, Kooistra T, Princen HM, Dallongeville J, Staels B: Retinoids increase human apo C-III expression at the transcriptional level via the retinoid X receptor. Contribution to the hypertriglyceridemic action of retinoids. J Clin Invest. 1998 Aug 1;102(3):625-32. [Article]
- Taylor LE, Bennett GD, Finnell RH: Altered gene expression in murine branchial arches following in utero exposure to retinoic acid. J Craniofac Genet Dev Biol. 1995 Jan-Mar;15(1):13-25. [Article]
- Shroot B, Michel S: Pharmacology and chemistry of adapalene. J Am Acad Dermatol. 1997 Jun;36(6 Pt 2):S96-103. [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
- Hendrix CW, Jackson KA, Whitmore E, Guidos A, Kretzer R, Liss CM, Shah LP, Khoo KC, McLane J, Trapnell CB: The effect of isotretinoin on the pharmacokinetics and pharmacodynamics of ethinyl estradiol and norethindrone. Clin Pharmacol Ther. 2004 May;75(5):464-75. doi: 10.1016/j.clpt.2004.01.003. [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
- Layton A: The use of isotretinoin in acne. Dermatoendocrinol. 2009 May;1(3):162-9. doi: 10.4161/derm.1.3.9364. [Article]
- Tsukada M, Schroder M, Seltmann H, Orfanos CE, Zouboulis CC: High albumin levels restrict the kinetics of 13-cis retinoic acid uptake and intracellular isomerization to all-trans retinoic acid and inhibit its anti-proliferative effect on SZ95 sebocytes. J Invest Dermatol. 2002 Jul;119(1):182-5. doi: 10.1046/j.1523-1747.2002.01816.x. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55