Identification
- Summary
Alitretinoin is a vitamin A derivative used to treat Kaposi's sarcoma and used off label to treat chronic hand eczema and psoriasis.
- Brand Names
- Panretin
- Generic Name
- Alitretinoin
- DrugBank Accession Number
- DB00523
- Background
An important regulator of gene expression during growth and development, and in neoplasms. Tretinoin, also known as retinoic acid and derived from maternal vitamin A, is essential for normal growth; and embryonic development. An excess of tretinoin can be teratogenic. It is used in the treatment of psoriasis; acne vulgaris; and several other skin diseases. It has also been approved for use in promyelocytic leukemia (leukemia, promyelocytic, acute).
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Alitretinoin (DB00523)
- Weight
- Average: 300.4351
Monoisotopic: 300.20893014 - Chemical Formula
- C20H28O2
- Synonyms
- (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid
- (7E,9Z,11E,13E)-retinoic acid
- 9-cis-retinoic acid
- 9-cis-Tretinoin
- 9(Z)-Retinoic acid
- Alitretinoin
- Alitretinoína
- Alitrétinoïne
- Alitretinoinum
- External IDs
- AGN 192013
- AGN-192013
- ALRT-1057
- ALRT1057
- BAL-4079
- BAL4079
- CCRIS 7098
- LG100057
- LGD1057
- NSC-659772
Pharmacology
- Indication
For topical treatment of cutaneous lesions in patients with AIDS-related Kaposi's sarcoma.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Chronic eczema of the hand •••••••••••• Treatment of Cutaneous lesions •••••••••••• Treatment of Refractory eczema of the hand •••••••••••• Treatment of Severe eczema of the hand •••••••••••• - 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
Alitretinoin (9-cis-retinoic acid) is a naturally-occurring endogenous retinoid indicated for topical treatment of cutaneous lesions in patients with AIDS-related Kaposi's sarcoma. Alitretinoin inhibits the growth of Kaposi's sarcoma (KS) cells in vitro.
- Mechanism of action
Alitretinoin binds to and activates all known intracellular retinoid receptor subtypes (RARa, RARb, RARg, RXRa, RXRb and RXRg). Once activated these receptors function as transcription factors that regulate the expression of genes that control the process of cellular differentiation and proliferation in both normal and neoplastic cells.
Target Actions Organism ARetinoic acid receptor alpha agonistHumans ARetinoic acid receptor RXR-alpha agonistHumans ARetinoic acid receptor beta agonistHumans ARetinoic acid receptor RXR-beta agonistHumans ARetinoic acid receptor gamma agonistHumans ARetinoic acid receptor RXR-gamma agonistHumans UInsulin-like growth factor-binding protein 3 Not Available Humans UPregnancy-specific beta-1-glycoprotein 5 Not Available Humans UCytochrome P450 26C1 Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- 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 softwareAmbroxol The risk or severity of methemoglobinemia can be increased when Alitretinoin is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Alitretinoin is combined with Articaine. Benzocaine The risk or severity of methemoglobinemia can be increased when Alitretinoin is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Alitretinoin is combined with Benzyl alcohol. Bupivacaine The risk or severity of methemoglobinemia can be increased when Alitretinoin is combined with Bupivacaine. - Food Interactions
- Take at the same time every day.
- Take with food. Food increases the bioavailability of alitretinoin capsules.
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.- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Hanzema Capsule 30 mg Oral Dr Reddy's Laboratories Inc 2021-06-09 Not applicable Canada 
Hanzema Capsule 10 mg Oral Dr Reddy's Laboratories Inc 2021-06-09 Not applicable Canada Panretin Gel 60 mg/60g Topical Concordia Pharmaceuticals Inc. 2019-09-10 Not applicable US 
Panretin Gel 60 mg/60g Topical Eisai Inc. 2009-02-03 2021-10-31 US Panretin Gel 1 mg/1g Topical Ligand Pharmaceuticals Incorporated 2006-10-06 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Clindamycin 1% / Niacinamide 4% / Tretinoin 0.05% Alitretinoin (0.05 g/100g) + Clindamycin phosphate (1 g/100g) + Nicotinamide (4 g/100g) Cream Topical Sincerus Florida, LLC 2019-05-04 Not applicable US
Categories
- ATC Codes
- L01XF02 — Alitretinoin
- L01XF — Retinoids for cancer treatment
- L01X — OTHER ANTINEOPLASTIC AGENTS
- L01 — ANTINEOPLASTIC AGENTS
- L — ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
- Drug Categories
- Agents for Dermatitis, Excluding Corticosteroids
- Alkenes
- Antineoplastic Agents
- Antineoplastic and Immunomodulating Agents
- Biological Factors
- Carotenoids
- Cyclohexanes
- Cyclohexenes
- Cycloparaffins
- Dermatologicals
- Diterpenes
- Hydrocarbons, Acyclic
- Misc. Skin and Mucous Membrane Agents
- P-glycoprotein substrates
- Pigments, Biological
- Polyenes
- Retinoids
- Retinoids for cancer treatment
- Terpenes
- Vitamin A
- Vitamins
- Vitamins (Fat Soluble)
- 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:50648) / Retinoids (C15493) / Retinoids (LMPR01090022)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 1UA8E65KDZ
- CAS number
- 5300-03-8
- InChI Key
- SHGAZHPCJJPHSC-ZVCIMWCZSA-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,6Z,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
Hector F. DeLuca, Praveen K. Tadikonda, "Method of synthesis of retinoic acid." U.S. Patent US5808120, issued December, 1975.
US5808120- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0002369
- KEGG Drug
- D02815
- KEGG Compound
- C15493
- PubChem Compound
- 449171
- PubChem Substance
- 46507356
- ChemSpider
- 395778
- BindingDB
- 31892
- 81864
- ChEBI
- 50648
- ChEMBL
- CHEMBL705
- ZINC
- ZINC000012661824
- Therapeutic Targets Database
- DAP000275
- PharmGKB
- PA164746900
- PDBe Ligand
- 9CR
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Alitretinoin
- PDB Entries
- 1epb / 1fby / 1fm6 / 1fm9 / 1k74 / 1tyr / 1xdk / 1xiu / 1xls / 2nnh … show 14 more
- FDA label
- Download (21.8 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 Terminated Treatment Atopic Dermatitis 1 3 Completed Other Hand Dermatosis 1 3 Completed Treatment Atopic Dermatitis 2 3 Completed Treatment Chronic Hand Eczema (CHE) 1 3 Completed Treatment Hand Dermatosis 2
Pharmacoeconomics
- Manufacturers
- Eisai inc
- Packagers
- Basilea Pharmaceuticals Corp.
- Contract Pharm
- Eisai Inc.
- Ortho-McNeil-Janssen Pharmaceuticals Inc.
- Dosage Forms
Form Route Strength Capsule Oral Cream Topical Gel Cutaneous Gel Cutaneous 0.1 % Gel Topical 0.1 % Gel Topical 1 mg/1g Gel Topical 60 mg/60g Capsule Oral 10 mg Capsule Oral 30 mg - Prices
Unit description Cost Unit Retin-A Micro Pump 0.04% Gel 50 gm Bottle 246.73USD bottle Retin-A Micro Pump 0.1% Gel 50 gm Bottle 246.73USD bottle Retin-A Micro 0.04% Gel 45 gm Tube 212.3USD tube Retin-A Micro 0.1% Gel 45 gm Tube 212.3USD tube Retin-A 0.1% Cream 45 gm Tube 211.1USD tube Retin-A 0.05% Cream 45 gm Tube 181.16USD tube Retin-A 0.025% Cream 45 gm Tube 163.07USD tube Retin-A 0.025% Gel 45 gm Tube 162.79USD tube Retin-A 0.01% Gel 45 gm Tube 161.48USD tube Retin-A Micro 0.04% Gel 20 gm Tube 123.7USD tube Retin-A Micro 0.1% Gel 20 gm Tube 117.51USD tube Retin-A 0.1% Cream 20 gm Tube 112.51USD tube Retin-A 0.05% Cream 20 gm Tube 97.85USD tube Retin-A 0.025% Cream 20 gm Tube 85.59USD tube Retin-A 0.01% Gel 15 gm Tube 75.83USD tube Retin-A 0.025% Gel 15 gm Tube 69.01USD tube Panretin 0.1% gel 41.0USD g Vesanoid 10 mg capsule 31.54USD capsule Retin-a micro 0.04% gel 5.65USD g Retin-a micro 0.1% gel 5.65USD g 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 DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region CA2301907 No 2009-02-10 2018-08-18 Canada US5932622 No 1999-08-03 2016-08-03 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 189-190 °C Not Available water solubility 0.6 mg/L Not Available logP 4.2 Not Available - Predicted Properties
Property Value Source logP 5.01 Chemaxon 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 35.91 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
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-000i-2190000000-86aaab132a5b092ebf10 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-0390000000-af1a6974c2a7872f36c7 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0090000000-82a486e1feafa5cf4f1b Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00lu-2970000000-05e8c3f4df3fed93b093 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0190000000-08192331c8e265ce508b Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-2890000000-2b136364b4a3a972b85b Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-052f-4910000000-f6c3b4ffdf3dc3f695a2 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 199.0770981 predictedDarkChem Lite v0.1.0 [M-H]- 191.2097689 predictedDarkChem Standard v0.1.0 [M-H]- 195.2712981 predictedDarkChem Lite v0.1.0 [M-H]- 198.9717981 predictedDarkChem Lite v0.1.0 [M-H]- 190.23927 predictedDeepCCS 1.0 (2019) [M+H]+ 192.59727 predictedDeepCCS 1.0 (2019) [M+Na]+ 200.62029 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- 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
- Baumann L, Vujevich J, Halem M, Martin LK, Kerdel F, Lazarus M, Pacheco H, Black L, Bryde J: Open-label pilot study of alitretinoin gel 0.1% in the treatment of photoaging. Cutis. 2005 Jul;76(1):69-73. [Article]
- Milliano MT, Luxon BA: Rat hepatic stellate cells become retinoid unresponsive during activation. Hepatol Res. 2005 Nov;33(3):225-33. Epub 2005 Oct 25. [Article]
- Rasooly R, Schuster GU, Gregg JP, Xiao JH, Chandraratna RA, Stephensen CB: Retinoid x receptor agonists increase bcl2a1 expression and decrease apoptosis of naive T lymphocytes. J Immunol. 2005 Dec 15;175(12):7916-29. [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]
- Ritter M, Kattmann D, Teichler S, Hartmann O, Samuelsson MK, Burchert A, Bach JP, Kim TD, Berwanger B, Thiede C, Jager R, Ehninger G, Schafer H, Ueki N, Hayman MJ, Eilers M, Neubauer A: Inhibition of retinoic acid receptor signaling by Ski in acute myeloid leukemia. Leukemia. 2006 Mar;20(3):437-43. [Article]
- Cheng C, Michaels J, Scheinfeld N: Alitretinoin: a comprehensive review. Expert Opin Investig Drugs. 2008 Mar;17(3):437-43. doi: 10.1517/13543784.17.3.437 . [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [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
- RXRA
- Uniprot ID
- P19793
- Uniprot Name
- Retinoic acid receptor RXR-alpha
- Molecular Weight
- 50810.835 Da
References
- Bartholin L, Powers SE, Melhuish TA, Lasse S, Weinstein M, Wotton D: TGIF inhibits retinoid signaling. Mol Cell Biol. 2006 Feb;26(3):990-1001. [Article]
- Calleja C, Messaddeq N, Chapellier B, Yang H, Krezel W, Li M, Metzger D, Mascrez B, Ohta K, Kagechika H, Endo Y, Mark M, Ghyselinck NB, Chambon P: Genetic and pharmacological evidence that a retinoic acid cannot be the RXR-activating ligand in mouse epidermis keratinocytes. Genes Dev. 2006 Jun 1;20(11):1525-38. [Article]
- Zhelyaznik N, Mey J: Regulation of retinoic acid receptors alpha, beta and retinoid X receptor alpha after sciatic nerve injury. Neuroscience. 2006 Sep 15;141(4):1761-74. Epub 2006 Jun 19. [Article]
- Fukasawa H, Kagechika H, Shudo K: [Retinoid therapy for autoimmune diseases]. Nihon Rinsho Meneki Gakkai Kaishi. 2006 Jun;29(3):114-26. [Article]
- 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]
- Cheng C, Michaels J, Scheinfeld N: Alitretinoin: a comprehensive review. Expert Opin Investig Drugs. 2008 Mar;17(3):437-43. doi: 10.1517/13543784.17.3.437 . [Article]
- Garnock-Jones KP, Perry CM: Alitretinoin: in severe chronic hand eczema. Drugs. 2009 Aug 20;69(12):1625-34. doi: 10.2165/11202200-000000000-00000. [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
- Mizuiri H, Yoshida K, Toge T, Oue N, Aung PP, Noguchi T, Yasui W: DNA methylation of genes linked to retinoid signaling in squamous cell carcinoma of the esophagus: DNA methylation of CRBP1 and TIG1 is associated with tumor stage. Cancer Sci. 2005 Sep;96(9):571-7. [Article]
- Milliano MT, Luxon BA: Rat hepatic stellate cells become retinoid unresponsive during activation. Hepatol Res. 2005 Nov;33(3):225-33. Epub 2005 Oct 25. [Article]
- Liu Z, Zhang L, Ding F, Li J, Guo M, Li W, Wang Y, Yu Z, Zhan Q, Wu M, Liu Z: 5-Aza-2'-deoxycytidine induces retinoic acid receptor-beta(2) demethylation and growth inhibition in esophageal squamous carcinoma cells. Cancer Lett. 2005 Dec 18;230(2):271-83. [Article]
- Nalbandian A, Pang AL, Rennert OM, Chan WY, Ravindranath N, Djakiew D: A novel function of differentiation revealed by cDNA microarray profiling of p75NTR-regulated gene expression. Differentiation. 2005 Oct;73(8):385-96. [Article]
- Husson M, Enderlin V, Delacourte A, Ghenimi N, Alfos S, Pallet V, Higueret P: Retinoic acid normalizes nuclear receptor mediated hypo-expression of proteins involved in beta-amyloid deposits in the cerebral cortex of vitamin A deprived rats. Neurobiol Dis. 2006 Jul;23(1):1-10. Epub 2006 Mar 10. [Article]
- Garnock-Jones KP, Perry CM: Alitretinoin: in severe chronic hand eczema. Drugs. 2009 Aug 20;69(12):1625-34. doi: 10.2165/11202200-000000000-00000. [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
- Brtko J: Role of retinoids and their cognate nuclear receptors in breast cancer chemoprevention. Cent Eur J Public Health. 2007 Mar;15(1):3-6. [Article]
- Germain P, Chambon P, Eichele G, Evans RM, Lazar MA, Leid M, De Lera AR, Lotan R, Mangelsdorf DJ, Gronemeyer H: International Union of Pharmacology. LXIII. Retinoid X receptors. Pharmacol Rev. 2006 Dec;58(4):760-72. [Article]
- Bergheim I, Wolfgarten E, Bollschweiler E, Holscher AH, Bode CH, Parlesak A: Role of retinoic acid receptors in squamous-cell carcinoma in human esophagus. J Carcinog. 2005 Nov 8;4:20. [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]
- Cheng C, Michaels J, Scheinfeld N: Alitretinoin: a comprehensive review. Expert Opin Investig Drugs. 2008 Mar;17(3):437-43. doi: 10.1517/13543784.17.3.437 . [Article]
- Garnock-Jones KP, Perry CM: Alitretinoin: in severe chronic hand eczema. Drugs. 2009 Aug 20;69(12):1625-34. doi: 10.2165/11202200-000000000-00000. [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
- Dzhagalov I, Chambon P, He YW: Regulation of CD8+ T lymphocyte effector function and macrophage inflammatory cytokine production by retinoic acid receptor gamma. J Immunol. 2007 Feb 15;178(4):2113-21. [Article]
- Parrella E, Gianni M, Fratelli M, Barzago MM, Raska I Jr, Diomede L, Kurosaki M, Pisano C, Carminati P, Merlini L, Dallavalle S, Tavecchio M, Rochette-Egly C, Terao M, Garattini E: Antitumor activity of the retinoid-related molecules (E)-3-(4'-hydroxy-3'-adamantylbiphenyl-4-yl)acrylic acid (ST1926) and 6-[3-(1-adamantyl)-4-hydroxyphenyl]-2-naphthalene carboxylic acid (CD437) in F9 teratocarcinoma: Role of retinoic acid receptor gamma and retinoid-independent pathways. Mol Pharmacol. 2006 Sep;70(3):909-24. Epub 2006 Jun 20. [Article]
- Li M, Hener P, Zhang Z, Kato S, Metzger D, Chambon P: Topical vitamin D3 and low-calcemic analogs induce thymic stromal lymphopoietin in mouse keratinocytes and trigger an atopic dermatitis. Proc Natl Acad Sci U S A. 2006 Aug 1;103(31):11736-41. Epub 2006 Jul 31. [Article]
- Garnock-Jones KP, Perry CM: Alitretinoin: in severe chronic hand eczema. Drugs. 2009 Aug 20;69(12):1625-34. doi: 10.2165/11202200-000000000-00000. [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]
- 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
- Adamczewski Z, Makarewicz J, Mikosinski S, Knapska-Kucharska M, Gunerska-Szadkowska A, Oszukowska L, Karwowska A, Lewinski A: [Application of 13-cis-retinoic acid in patients with 131I scintigraphically-negative metastases of differentiated thyroid carcinoma]. Endokrynol Pol. 2006 Jul-Aug;57(4):403-6. [Article]
- Brtko J: Role of retinoids and their cognate nuclear receptors in breast cancer chemoprevention. Cent Eur J Public Health. 2007 Mar;15(1):3-6. [Article]
- Germain P, Chambon P, Eichele G, Evans RM, Lazar MA, Leid M, De Lera AR, Lotan R, Mangelsdorf DJ, Gronemeyer H: International Union of Pharmacology. LXIII. Retinoid X receptors. Pharmacol Rev. 2006 Dec;58(4):760-72. [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]
- Garnock-Jones KP, Perry CM: Alitretinoin: in severe chronic hand eczema. Drugs. 2009 Aug 20;69(12):1625-34. doi: 10.2165/11202200-000000000-00000. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Protein tyrosine phosphatase activator activity
- Specific Function
- IGF-binding proteins prolong the half-life of the IGFs and have been shown to either inhibit or stimulate the growth promoting effects of the IGFs on cell culture. They alter the interaction of IGF...
- Gene Name
- IGFBP3
- Uniprot ID
- P17936
- Uniprot Name
- Insulin-like growth factor-binding protein 3
- Molecular Weight
- 31673.87 Da
References
- Chang YS, Cho JY, Cho HA, Kim HJ, Chang J, Ahn CM, Kim SK, Kim SK: 9-cis retinoic acid induces insulin-like growth factor binding protein-3 through DR-8 retinoic acid responsive elements. Cancer Biol Ther. 2006 Jun;5(6):586-92. Epub 2006 Jun 5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- Not Available
- Gene Name
- PSG5
- Uniprot ID
- Q15238
- Uniprot Name
- Pregnancy-specific beta-1-glycoprotein 5
- Molecular Weight
- 37712.79 Da
References
- Lopez-Diaz F, Nores R, Panzetta-Dutari G, Slavin D, Prieto C, Koritschoner NP, Bocco JL: RXRalpha regulates the pregnancy-specific glycoprotein 5 gene transcription through a functional retinoic acid responsive element. Placenta. 2007 Aug-Sep;28(8-9):898-906. Epub 2007 May 2. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Plays a role in retinoic acid metabolism. Acts on retinoids, including all-trans-retinoic acid (RA) and its stereoisomer 9-cis-RA (preferred substrate).
- Specific Function
- Heme binding
- Gene Name
- CYP26C1
- Uniprot ID
- Q6V0L0
- Uniprot Name
- Cytochrome P450 26C1
- Molecular Weight
- 57110.385 Da
References
- Helvig C, Taimi M, Cameron D, Jones G, Petkovich M: Functional properties and substrate characterization of human CYP26A1, CYP26B1, and CYP26C1 expressed by recombinant baculovirus in insect cells. J Pharmacol Toxicol Methods. 2011 Nov-Dec;64(3):258-63. doi: 10.1016/j.vascn.2011.08.005. Epub 2011 Aug 31. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- 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]
- Donato LJ, Noy N: Suppression of mammary carcinoma growth by retinoic acid: proapoptotic genes are targets for retinoic acid receptor and cellular retinoic acid-binding protein II signaling. Cancer Res. 2005 Sep 15;65(18):8193-9. [Article]
- Bry K, Lappalainen U: Pathogenesis of bronchopulmonary dysplasia: the role of interleukin 1beta in the regulation of inflammation-mediated pulmonary retinoic acid pathways in transgenic mice. Semin Perinatol. 2006 Jun;30(3):121-8. [Article]
- Wei T, Geiser AG, Qian HR, Su C, Helvering LM, Kulkarini NH, Shou J, N'Cho M, Bryant HU, Onyia JE: DNA microarray data integration by ortholog gene analysis reveals potential molecular mechanisms of estrogen-dependent growth of human uterine fibroids. BMC Womens Health. 2007 Apr 2;7:5. [Article]
- Boorjian SA, Milowsky MI, Kaplan J, Albert M, Cobham MV, Coll DM, Mongan NP, Shelton G, Petrylak D, Gudas LJ, Nanus DM: Phase 1/2 clinical trial of interferon alpha2b and weekly liposome-encapsulated all-trans retinoic acid in patients with advanced renal cell carcinoma. J Immunother. 2007 Sep;30(6):655-62. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- 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]
- Goelden U, Pfoertner S, Hansen W, Toepfer T, von Knobloch R, Hofmann R, Buer J, Schrader AJ: Expression and functional influence of cellular retinoic acid-binding protein II in renal cell carcinoma. Urol Int. 2005;75(3):269-76. [Article]
- Levadoux-Martin M, Li Y, Blackburn A, Chabanon H, Hesketh JE: Perinuclear localisation of cellular retinoic acid binding protein I mRNA. Biochem Biophys Res Commun. 2006 Feb 3;340(1):326-31. [Article]
- Jetten AM: Multi-stage program of differentiation in human epidermal keratinocytes: regulation by retinoids. J Invest Dermatol. 1990 Nov;95(5 Suppl):44S-46S. [Article]
- Bry K, Lappalainen U: Pathogenesis of bronchopulmonary dysplasia: the role of interleukin 1beta in the regulation of inflammation-mediated pulmonary retinoic acid pathways in transgenic mice. Semin Perinatol. 2006 Jun;30(3):121-8. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Schuetz EG, Yasuda K, Arimori K, Schuetz JD: Human MDR1 and mouse mdr1a P-glycoprotein alter the cellular retention and disposition of erythromycin, but not of retinoic acid or benzo(a)pyrene. Arch Biochem Biophys. 1998 Feb 15;350(2):340-7. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55