U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C20H28O2
Molecular Weight 300.4351
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 4
Charge 0

SHOW SMILES / InChI
Structure of ISOTRETINOIN

SMILES

CC(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(C)=C\C(O)=O

InChI

InChIKey=SHGAZHPCJJPHSC-XFYACQKRSA-N
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-

HIDE SMILES / InChI

Description

Alitretinoin, or 9-cis-retinoic acid, is a form of vitamin A. It is also used in medicine as an antineoplastic (anti-cancer) agent developed by Ligand Pharmaceuticals. 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. 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. In the United States, topical alitretinoin (in the form of a gel; trade name Panretin) is indicated for the treatment of skin lesions in AIDS-related Kaposi's sarcoma.

Approval Year

PubMed

PubMed

TitleDatePubMed
Effects of xenobiotics and peroxisome proliferator-activated receptor-alpha on the human UDPglucose dehydrogenase gene expression.
2005
The detection of differentiation-inducing chemicals by using green fluorescent protein expression in genetically engineered teratocarcinoma cells.
2005 Apr
[Receptor-related mechanism of proliferation inhibilion and apoptosis induetion of human tongue squamous cell line Tca8113 by retinoids].
2005 Aug
Retinoic acid induces VEGF gene expression in human retinal pigment epithelial cells (ARPE-19).
2005 Dec
Coactivation of liver receptor homologue-1 by peroxisome proliferator-activated receptor gamma coactivator-1alpha on aromatase promoter II and its inhibition by activated retinoid X receptor suggest a novel target for breast-specific antiestrogen therapy.
2005 Dec 15
Retinoid x receptor agonists increase bcl2a1 expression and decrease apoptosis of naive T lymphocytes.
2005 Dec 15
Nuclear import of the retinoid X receptor, the vitamin D receptor, and their mutual heterodimer.
2005 Dec 2
Open-label pilot study of alitretinoin gel 0.1% in the treatment of photoaging.
2005 Jul
A new retinoid-like compound that activates peroxisome proliferator-activated receptors and lowers blood glucose in diabetic mice.
2005 Jul
Effects of 9-cis-retinoic acid on the insulin-like growth factor axis in former smokers.
2005 Jul 1
Specificity of receptor-ligand interactions and their effect on dimerisation as observed by electrospray mass spectrometry: bile acids form stable adducts to the RXRalpha.
2005 Nov
Effect of retinoic acid on murine preosteoblastic MC3T3-E1 cells.
2005 Oct
Regulation of a highly specific retinoic acid-4-hydroxylase (CYP26A1) enzyme and all-trans-retinoic acid metabolism in human intestinal, liver, endothelial, and acute promyelocytic leukemia cells.
2005 Oct
Hepatocyte growth factor receptor signaling mediates the anti-fibrotic action of 9-cis-retinoic acid in glomerular mesangial cells.
2005 Oct
Arsenic trioxide inhibits nuclear receptor function via SEK1/JNK-mediated RXRalpha phosphorylation.
2005 Oct
Liver X receptor and retinoic X receptor agonists modulate the expression of genes involved in lipid metabolism in human endothelial cells.
2005 Oct
The human ABCG1 gene: identification of LXR response elements that modulate expression in macrophages and liver.
2005 Oct
Physiological and receptor-selective retinoids modulate interferon gamma signaling by increasing the expression, nuclear localization, and functional activity of interferon regulatory factor-1.
2005 Oct 28
VPAC1 expression is regulated by FXR agonists in the human gallbladder epithelium.
2005 Sep
Regulation of adiponectin receptor 1 in human hepatocytes by agonists of nuclear receptors.
2005 Sep 2
The human tumor antigen PRAME is a dominant repressor of retinoic acid receptor signaling.
2005 Sep 23
Regression of NMU-induced mammary tumors with the combination of melatonin and 9-cis-retinoic acid.
2005 Sep 8
Organ-specific expression profiles of rat mammary gland, liver, and lung tissues treated with targretin, 9-cis retinoic acid, and 4-hydroxyphenylretinamide.
2006 Apr
Effects of PPAR and RXR ligands in semaphorin 6B gene expression of human MCF-7 breast cancer cells.
2006 Apr
Organotin compounds enhance 17beta-hydroxysteroid dehydrogenase type I activity in human choriocarcinoma JAr cells: potential promotion of 17beta-estradiol biosynthesis in human placenta.
2006 Apr 28
TGIF inhibits retinoid signaling.
2006 Feb
9-Cis-retinoic acid suppresses inflammatory responses of microglia and astrocytes.
2006 Feb
Nonclassical action of retinoic acid on the activation of the cAMP response element-binding protein in normal human bronchial epithelial cells.
2006 Feb
Prostate cancer cell type-specific involvement of the VDR and RXR in regulation of the human PTHrP gene via a negative VDRE.
2006 Feb
Retinoid-mediated stimulation of steroid sulfatase activity in myeloid leukemic cell lines requires RARalpha and RXR and involves the phosphoinositide 3-kinase and ERK-MAP kinase pathways.
2006 Feb 1
Analysis of ligand binding and protein dynamics of human retinoid X receptor alpha ligand-binding domain by nuclear magnetic resonance.
2006 Feb 14
Investigation of the mechanisms by which EB1089 abrogates apoptosis induced by 9-cis retinoic acid in pancreatic cancer cells.
2006 Jan
Vitamin A inhibits pancreatic stellate cell activation: implications for treatment of pancreatic fibrosis.
2006 Jan
Retinoic acid receptors and tissue-transglutaminase mediate short-term effect of retinoic acid on migration and invasion of neuroblastoma SH-SY5Y cells.
2006 Jan 12
Effects of 9-cis retinoic acid on human homeobox gene NKX3.1 expression in prostate cancer cell line LNCaP.
2006 Jul
Retinoic acids increase P2X2 receptor expression through the 5'-flanking region of P2rx2 gene in rat phaeochromocytoma PC-12 cells.
2006 Jul
Retinoids activate the RXR/SXR-mediated pathway and induce the endogenous CYP3A4 activity in Huh7 human hepatoma cells.
2006 Jul
Peroxisome proliferator-activated receptor-gamma and retinoic acid X receptor alpha represses the TGFbeta1 gene via PTEN-mediated p70 ribosomal S6 kinase-1 inhibition: role for Zf9 dephosphorylation.
2006 Jul
A novel cytochrome P450, zebrafish Cyp26D1, is involved in metabolism of all-trans retinoic acid.
2006 Jul
Thiazolidinediones and rexinoids induce peroxisome proliferator-activated receptor-coactivator (PGC)-1alpha gene transcription: an autoregulatory loop controls PGC-1alpha expression in adipocytes via peroxisome proliferator-activated receptor-gamma coactivation.
2006 Jun
Efficacy of new retinoids in the prevention of mammary cancers and correlations with short-term biomarkers.
2006 Jun
CYP4A11 is repressed by retinoic acid in human liver cells.
2006 Jun 12
Co-resistance to retinoic acid and TRAIL by insertion mutagenesis into RAM.
2006 Jun 22
Effects of rexinoids on thyrotrope function and the hypothalamic-pituitary-thyroid axis.
2006 Mar
Receptor-selective retinoids inhibit the growth of normal and malignant breast cells by inducing G1 cell cycle blockade.
2006 Mar
The phosphoinositide 3-kinase/Akt pathway is essential for the retinoic acid-induced differentiation of F9 cells.
2006 Mar 30
Retinoic acid exerts dual regulatory actions on the expression and nuclear localization of interferon regulatory factor-1.
2006 May
9-cis-Retinoic acid inhibition of lung carcinogenesis in the A/J mouse model is accompanied by increased expression of RAR-beta but no change in cyclooxygenase-2.
2006 Nov 28
Molecular cloning of the rat beta-carotene 15,15'-monooxygenase gene and its regulation by retinoic acid.
2006 Sep
Unsaturated fatty acids suppress the expression of the ATP-binding cassette transporter G1 (ABCG1) and ABCA1 genes via an LXR/RXR responsive element.
2007 Mar
Patents

Sample Use Guides

In Vivo Use Guide
Panretin (Alitretinoin) gel should initially be applied two (2) times a day to cutaneous KS lesions. The application frequency can be gradually increased to three (3) or four (4) times a day according to individual lesion tolerance.
Route of Administration: Topical
In Vitro Use Guide
The addition of 5 nM Alitretinoin to the maturation medium was beneficial for parthenogenetic pig embryo production.
Name Type Language
ISOTRETINOIN
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
RO 4-3780
Code English
ISOTRETINOIN [ORANGE BOOK]
Common Name English
ISOTRETINOIN [MI]
Common Name English
VITAMIN A ACID, 13-CIS
Common Name English
ACCUTANE
Brand Name English
SOTRET
Brand Name English
RETINOIC ACID, 13-CIS-
Common Name English
ISOTRETINOIN [USP-RS]
Common Name English
RO-4-3780
Code English
RO-43780
Code English
ISOTRETINOIN [INN]
Common Name English
TRETINOIN IMPURITY A [EP]
Common Name English
ISOTRETINOIN [WHO-DD]
Common Name English
CLARAVIS
Brand Name English
PAT-001
Code English
ISOTRETINOIN [USP]
Common Name English
13-CIS-RETINOIC ACID
Common Name English
ISOTRETINOIN [HSDB]
Common Name English
ABSORICA
Brand Name English
RETINOIC ACID 13-CIS-FORM [MI]
Common Name English
3,7-DIMETHYL-9-(2,6,6-TRIMETHYL-1-CYCLOHEXEN-1-YL)2-CIS-4-TRANS-6-TRANS-8-TRANS-NONATETRAENOIC ACID
Common Name English
ISOTRETINOIN [EP]
Common Name English
AMNESTEEM
Brand Name English
ISOTRETINOIN [USAN]
Common Name English
ISOTRETINOIN [VANDF]
Common Name English
ISOTRETINOIN [MART.]
Common Name English
Classification Tree Code System Code
WHO-ATC D10AD54
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
WHO-VATC QD10AD04
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
LIVERTOX 523
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
WHO-ATC D10BA01
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
NDF-RT N0000007700
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
WHO-ATC D10AD04
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
NDF-RT N0000007700
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
NDF-RT N0000007700
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
WHO-VATC QD10BA01
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
NDF-RT N0000175607
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
FDA ORPHAN DRUG 424614
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
NDF-RT N0000007700
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
NDF-RT N0000007700
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
NCI_THESAURUS C804
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
WHO-VATC QD10AD54
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
Code System Code Type Description
RXCUI
6064
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
PRIMARY RxNorm
HSDB
4759-48-2
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
PRIMARY
EVMPD
SUB08341MIG
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
PRIMARY
PUBCHEM
5282379
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
PRIMARY
ChEMBL
CHEMBL547
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
PRIMARY
ECHA (EC/EINECS)
225-296-0
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
PRIMARY
CAS
4759-48-2
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
PRIMARY
LactMed
4759-48-2
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
PRIMARY
DRUG BANK
DB00982
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
PRIMARY
MERCK INDEX
M6544
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
PRIMARY Merck Index
INN
4617
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
PRIMARY
MESH
D015474
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
PRIMARY
IUPHAR
7600
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
PRIMARY
MERCK INDEX
M9558
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
PRIMARY
WIKIPEDIA
ISOTRETINOIN
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
PRIMARY
EPA CompTox
4759-48-2
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
PRIMARY
NCI_THESAURUS
C603
Created by admin on Mon Oct 21 19:53:26 UTC 2019 , Edited by admin on Mon Oct 21 19:53:26 UTC 2019
PRIMARY