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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
Generation of radical oxygen species by neural crest cells treated in vitro with isotretinoin and 4-oxo-isotretinoin.
1990
Taste and olfactory disturbances after treatment for acne with isotretinoin, a 13-cis-isomer of retinoic acid.
1990
Acute depression from isotretinoin.
1990 Jun
[Acne fulminans triggered by isotretinoin therapy].
1991
Acute depression from isotretinoin.
1991 Jul
Improvement of scleromyxedema associated with isotretinoin therapy.
1991 May
Fatty liver following isotretinoin therapy.
1991 May
Acne, isotretinoin treatment and acute depression.
2001 Jul
A phase II study of 13-cis retinoic acid plus interferon alpha-2a in advanced stage penile carcinoma: an Eastern Cooperative Oncology Group study (E3893).
2003
Two new adverse effects of isotretinoin.
2003 Mar
Taking advantage of a side effect of isotretinoin.
2003 Mar
Isotretinoin and antidepressant pharmacotherapy: a prescription sequence symmetry analysis.
2003 Sep
13-cis Retinoic acid ameliorates benzoyl peroxide-induced oxidative stress and hyperproliferative response in murine skin: a chemopreventive study.
2004
Isotretinoin-associated intracranial hypertension.
2004 Jun
Isotretinoin therapy induces DNA oxidative damage.
2005
Isotretinoin (Ro-Accutane) teratogenesis. A case report.
2005
The detection of differentiation-inducing chemicals by using green fluorescent protein expression in genetically engineered teratocarcinoma cells.
2005 Apr
Isotretinoin therapy and mood changes in adolescents with moderate to severe acne: a cohort study.
2005 May
Inhibitors of the arachidonic acid pathway and peroxisome proliferator-activated receptor ligands have superadditive effects on lung cancer growth inhibition.
2005 May 15
Apoptotic events induced by naturally occurring retinoids ATRA and 13-cis retinoic acid on human hepatoma cell lines Hep3B and HepG2.
2005 Nov 18
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
Matrix metalloproteinases of epithelial origin in facial sebum of patients with acne and their regulation by isotretinoin.
2005 Oct
Mechanism of retinoid receptors in inhibiting proliferation and inducing apoptosis of human melanoma cell line A375.
2005 Sep 5
Differential regulation of Toll-like receptor and CD14 pathways by retinoids and corticosteroids in human sebocytes.
2006
Increased use of mental health services related to isotretinoin treatment: a 5-year analysis.
2006 Aug
Incidence of depression related to isotretinoin treatment in 100 acne vulgaris patients.
2006 Dec
The results and side effects of systemic isotretinoin treatment in 100 patients with acne vulgaris.
2006 Dec
[Panic attacks in a patient treated with isotretinoin for acne. Report of one case].
2006 Dec
Nonclassical action of retinoic acid on the activation of the cAMP response element-binding protein in normal human bronchial epithelial cells.
2006 Feb
Angioedema and urticaria due to isotretinoin therapy.
2006 Jan
Small molecule RPE65 antagonists limit the visual cycle and prevent lipofuscin formation.
2006 Jan 24
13 Cis-retinoic acid mediates apoptosis in Dalton's lymphoma ascites cells by regulating gene expression.
2007
Cytodifferentiation by retinoids, a novel therapeutic option in oncology: rational combinations with other therapeutic agents.
2007
Atrial tachycardia associated with isotretinoin use.
2007 Aug
Isotretinoin, pregnancies, abortions and birth defects: a population-based perspective.
2007 Feb
Antitumor effect of the histone deacetylase inhibitor LAQ824 in combination with 13-cis-retinoic acid in human malignant melanoma.
2007 Jan
Cerebral ischemia probably related to isotretinoin.
2007 Jun
Molecular targeting of retinoic acid metabolism in neuroblastoma: the role of the CYP26 inhibitor R116010 in vitro and in vivo.
2007 Jun 4
Acneiform eruptions associated with epidermal growth factor receptor-targeted chemotherapy.
2007 Mar
CD69 on CD56+ NK cells and response to chemoimmunotherapy in metastatic melanoma.
2007 Nov
No association found between patients receiving isotretinoin for acne and the development of depression in a Canadian prospective cohort.
2007 Summer
13-cis-retinoic acid induces apoptosis by modulating caspase-3, bcl-2, and p53 gene expression and regulates the activation of transcription factors in B16F-10 melanoma cells.
2008
Use of oral isotretinoin in photoaging therapy.
2008 Jan-Feb
Enhanced ocular isotretinoin toxicity in mitochondrial disorder.
2008 Jun
A cerebellar demyelinating lesion following treatment of acne with isotretinoin.
2008 Mar
Temporal changes in gene expression in the skin of patients treated with isotretinoin provide insight into its mechanism of action.
2009 May
The use of isotretinoin in acne.
2009 May
The effect of isotretinoin treatment on plasma homocysteine levels in acne vulgaris.
2010 Aug
Antagonism of cytotoxic chemotherapy in neuroblastoma cell lines by 13-cis-retinoic acid is mediated by the antiapoptotic Bcl-2 family proteins.
2010 Dec
Chemical genomics profiling of environmental chemical modulation of human nuclear receptors.
2011 Aug
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