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Details

Stereochemistry ACHIRAL
Molecular Formula C20H28O2
Molecular Weight 300.4359
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 4
Charge 0

SHOW SMILES / InChI
Structure of ISOTRETINOIN

SMILES

C/C(=C(/[H])\C(\[H])=C(/[H])\C(=C(\[H])/C(=O)O)\C)/C(/[H])=C(\[H])/C1=C(C)CCCC1(C)C

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

Molecular Formula C20H28O2
Molecular Weight 300.4359
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 4
Optical Activity NONE

Description
Curator's Comment:: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20886lbl.pdf

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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ACCUTANE

Approved Use

Accutane is indicated for the treatment of severe recalcitrant nodular acne. Nodules are inflammatory lesions with a diameter of 5 mm or greater. The nodules may become suppurative or hemorrhagic. “Severe,” by definition, means “many” as opposed to “few or several” nodules. Because of significant adverse effects associated with its use, Accutane should be reserved for patients with severe nodular acne who are unresponsive to conventional therapy, including systemic antibiotics. In addition, Accutane is indicated only for those female patients who are not pregnant, because Accutane can cause severe birth defects.

Launch Date

3.89491196E11
PubMed

PubMed

TitleDatePubMed
Generation of radical oxygen species by neural crest cells treated in vitro with isotretinoin and 4-oxo-isotretinoin.
1990
[Acne fulminans triggered by isotretinoin therapy].
1991
Improvement of scleromyxedema associated with isotretinoin therapy.
1991 May
Fatty liver following isotretinoin therapy.
1991 May
Isotretinoin therapy induces DNA oxidative damage.
2005
The detection of differentiation-inducing chemicals by using green fluorescent protein expression in genetically engineered teratocarcinoma cells.
2005 Apr
Treatment of photoaged skin with a cream containing 0.05% isotretinoin and sunscreens.
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
All-trans-retinoic acid accelerates the differentiation of human B lymphocytes maturing into plasma cells.
2005 Dec
Retinoic acid and its 4-oxo metabolites are functionally active in human skin cells in vitro.
2005 Jul
Apoptotic events induced by naturally occurring retinoids ATRA and 13-cis retinoic acid on human hepatoma cell lines Hep3B and HepG2.
2005 Nov 18
[Erectile dysfunction during isotretinoin therapy].
2005 Nov-Dec
Serum levels of albumin, triglycerides, total protein and glucose in rats are altered after oral treatment with low doses of 13-cis-retinoic acid or all-trans-retinoic acid.
2005 Nov-Dec
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
Low-dose isotretinoin in the treatment of acne vulgaris.
2006 Apr
Increased use of mental health services related to isotretinoin treatment: a 5-year analysis.
2006 Aug
[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
[From the Cochrane Library: Improvement of photodamaged skin with retinoid creams and not with other local treatments].
2006 Jan 21
Small molecule RPE65 antagonists limit the visual cycle and prevent lipofuscin formation.
2006 Jan 24
[Mechanism of receptor for retinoids inducing apoptosis of human melanoma cell line A375].
2006 Jul
Retinoids activate the RXR/SXR-mediated pathway and induce the endogenous CYP3A4 activity in Huh7 human hepatoma cells.
2006 Jul
A novel cytochrome P450, zebrafish Cyp26D1, is involved in metabolism of all-trans retinoic acid.
2006 Jul
A rare side-effect of systemic isotretinoin treatment: hoarseness.
2006 Nov
13-cis Retinoic acid induces apoptosis and cell cycle arrest in human SEB-1 sebocytes.
2006 Oct
Chronic administration of 13-cis-retinoic acid increases depression-related behavior in mice.
2006 Sep
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
Isotretinoin-induced pleuritic chest pain.
2007 Feb
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
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
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
Isotretinoin and the risk of depression in patients with acne vulgaris: a case-crossover study.
2008 Apr
Hypercalcemia induced by 13 cis-retinoic acid in patients with neuroblastoma.
2008 Apr
Enhanced ocular isotretinoin toxicity in mitochondrial disorder.
2008 Jun
Sacroiliitis and polyneuropathy during isotretinoin treatment.
2008 Mar
Gene microarray analysis of human renal cell carcinoma: the effects of HDAC inhibition and retinoid treatment.
2008 Oct
Different mRNA expression profiling of nuclear retinoid, thyroid, estrogen and PPARgamma receptors, their coregulators and selected genes in rat liver and spleen in response to short-term in vivo administration of 13-cis retinoic acid.
2009 Jan 30
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
Hypercalcemia and osteoblastic lesions induced by 13-Cis-retinoic acid mimicking relapsed neuroblastoma.
2009 Oct
Retinoids activate RXR/CAR-mediated pathway and induce CYP3A.
2010 Jan 15
Chemical genomics profiling of environmental chemical modulation of human nuclear receptors.
2011 Aug
Patents

Sample Use Guides

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
The addition of 5 nM Alitretinoin to the maturation medium was beneficial for parthenogenetic pig embryo production.
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:02:41 UTC 2021
Edited
by admin
on Fri Jun 25 21:02:41 UTC 2021
Record UNII
EH28UP18IF
Record Status Validated (UNII)
Record Version
  • Download
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
ISOTRETINOIN [EP MONOGRAPH]
Common Name English
RO-43780
Code English
ABSORICA LD
Brand Name 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
13-CIS-RETINOIC ACID
Common Name English
ISOTRETINOIN [HSDB]
Common Name English
NSC-758156
Code 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
AMNESTEEM
Brand Name English
ISOTRETINOIN [USAN]
Common Name English
ISOTRETINOIN [VANDF]
Common Name English
ISOTRETINOIN [USP MONOGRAPH]
Common Name English
ISOTRETINOIN [MART.]
Common Name English
Classification Tree Code System Code
WHO-ATC D10AD54
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
WHO-VATC QD10AD04
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
LIVERTOX 523
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
WHO-ATC D10BA01
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
NDF-RT N0000007700
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
WHO-ATC D10AD04
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
NDF-RT N0000007700
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
NDF-RT N0000007700
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
WHO-VATC QD10BA01
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
NDF-RT N0000175607
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
FDA ORPHAN DRUG 424614
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
NDF-RT N0000007700
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
NDF-RT N0000007700
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
NCI_THESAURUS C804
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
WHO-VATC QD10AD54
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
Code System Code Type Description
RXCUI
6064
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
PRIMARY RxNorm
HSDB
3929
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
PRIMARY
EVMPD
SUB08341MIG
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
PRIMARY
PUBCHEM
5282379
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
PRIMARY
FDA UNII
EH28UP18IF
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
PRIMARY
ChEMBL
CHEMBL547
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
PRIMARY
ECHA (EC/EINECS)
225-296-0
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
PRIMARY
CAS
4759-48-2
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
PRIMARY
DRUG BANK
DB00982
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
PRIMARY
MERCK INDEX
M6544
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
PRIMARY Merck Index
DRUG CENTRAL
1508
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
PRIMARY
INN
4617
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
PRIMARY
MESH
D015474
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
PRIMARY
IUPHAR
7600
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
PRIMARY
MERCK INDEX
M9558
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
PRIMARY
LACTMED
Isotretinoin
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
PRIMARY
WIKIPEDIA
ISOTRETINOIN
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
PRIMARY
USP_CATALOG
1353500
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
PRIMARY USP-RS
EPA CompTox
4759-48-2
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
PRIMARY
NCI_THESAURUS
C603
Created by admin on Fri Jun 25 21:02:41 UTC 2021 , Edited by admin on Fri Jun 25 21:02:41 UTC 2021
PRIMARY
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