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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 ALITRETINOIN

SMILES

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

InChI

InChIKey=SHGAZHPCJJPHSC-ZVCIMWCZSA-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 300.4351
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 4
Optical Activity NONE

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
Post-isotretinoin vasculitis.
1990 Feb 10
Acute depression from isotretinoin.
1990 Jun
Improvement of scleromyxedema associated with isotretinoin therapy.
1991 May
Fatty liver following isotretinoin therapy.
1991 May
Activation of peroxisome proliferator-activated receptor alpha increases the expression and activity of microsomal triglyceride transfer protein in the liver.
2005 Jan 14
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
Isotretinoin (13-cis-retinoic acid)-associated premature ventricular contractions.
2009 Jul-Aug
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
Giant cobblestone-like papillae during isotretinoin therapy.
2009 Sep-Oct
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
Retinoids activate RXR/CAR-mediated pathway and induce CYP3A.
2010 Jan 15
Onset of Kleine-Levin Syndrome in association with isotretinoin treatment.
2010 Jun
Psychiatric reactions to isotretinoin in patients with bipolar disorder.
2010 May
Sacroiliitis and severe disability due to isotretinoin therapy.
2010 May
Isotretinoin-induced encephalopathy.
2010 Nov
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.
Substance Class Chemical
Created
by admin
on Mon Oct 21 19:53:24 UTC 2019
Edited
by admin
on Mon Oct 21 19:53:24 UTC 2019
Record UNII
1UA8E65KDZ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALITRETINOIN
EMA EPAR   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
PANRETIN
Brand Name English
RETINOIC ACID 9-CIS-FORM [MI]
Common Name English
LG-100057
Code English
ALITRETINOIN [MART.]
Common Name English
9-CIS-RETINOIC ACID
Common Name English
ALITRETINOIN [USAN]
Common Name English
ALRT-1057
Code English
ALITRETINOIN [ORANGE BOOK]
Common Name English
ALRT1057
Code English
LGD-1057
Code English
LGD1057
Code English
ALITRETINOIN [MI]
Common Name English
ALITRETINOIN [WHO-DD]
Common Name English
ALITRETINOIN [VANDF]
Common Name English
ALITRETINOIN [INN]
Common Name English
LG100057
Code English
(2E,4E,6Z,8E)-3,7-DIMETHYL-9-(2,6,6-TRIMETHYL-1-CYCLOHEXEN-1-YL)-2,4,6,8-NONATETRAENOIC ACID
Systematic Name English
TRETINOIN IMPURITY D [EP]
Common Name English
ALITRETINOIN [HSDB]
Common Name English
9-CIS RETINOIC ACID
Common Name English
AGN 192013
Code English
NSC-659772
Code English
AGN-192013
Code English
ALITRETINOIN [EMA EPAR]
Common Name English
BAL-4079
Code English
Classification Tree Code System Code
WHO-ATC D11AX19
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
WHO-VATC QL01XX22
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
WHO-VATC QD11AH04
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
NDF-RT N0000007700
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
NCI_THESAURUS C804
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
NDF-RT N0000007700
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
FDA ORPHAN DRUG 101296
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
WHO-ATC D11AH04
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
EMA ASSESSMENT REPORTS PANRETIN (AUTHORIZED: SARCOMA, KAPOSI)
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
NDF-RT N0000007700
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
NDF-RT N0000007700
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
FDA ORPHAN DRUG 110998
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
WHO-ATC L01XX22
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
NDF-RT N0000175607
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
FDA ORPHAN DRUG 66592
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
NDF-RT N0000007700
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
Code System Code Type Description
NCI_THESAURUS
C1574
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY
INN
7781
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY
HSDB
5300-03-8
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY
ChEMBL
CHEMBL705
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY
MERCK INDEX
M1511
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY Merck Index
MERCK INDEX
M9558
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY
MESH
C103303
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY
EPA CompTox
5300-03-8
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY
CAS
5300-03-8
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY
DRUG BANK
DB00523
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY
RXCUI
81864
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY RxNorm
IUPHAR
2645
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY
WIKIPEDIA
ALITRETINOIN
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY
EVMPD
SUB00344MIG
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY
PUBCHEM
449171
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY