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 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

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.

Originator

Approval Year

1982
61
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2314
Sarcoma, Kaposi
 10.0 nM [EC50]
Agonist
2314
Sarcoma, Kaposi
 3.0 nM [EC50]
Agonist
2314
Sarcoma, Kaposi
 195.0 nM [EC50]
Agonist
2314
Sarcoma, Kaposi
 50.0 nM [EC50]
Agonist
2314
Sarcoma, Kaposi
 140.0 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
7777
ACCUTANE
Primary
Retinoic acid receptor beta
Retinoid X receptor gamma
Retinoid X receptor alpha
Retinoic acid receptor gamma
Retinoid X receptor alpha
Approved
7777
Panretin gel
Approved (off-label)
7
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
Improvement of scleromyxedema associated with isotretinoin therapy.
1991 May
Fatty liver following isotretinoin therapy.
1991 May
Vitamin A status in mice affects the histone code of the phosphoenolpyruvate carboxykinase gene in liver.
2005 Dec
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
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

Patents

JP2000327577A
3
JP2002511398A
8
JP2003506349A
5
JP2005527487A
2
JP2006519264A
49
JP2007513165A
42
JP2009513567A
58
JP2009526755A
382
JP2010526091A
20
JP2011528275A
409
JP2011529067A
22
JP4571408B2
2
JP4658037B2
30
JPH01275532A
3
JPH04244058A
2
JPH0899826A
2
JPH0899830A
2
JPH0899831A
2
JPH0959207A
2
JPH1072345A
2
JPH11199478A
2
JPH11302194A
2

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
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
ACTIVE MOIETY
Structure of ALITRETINOIN
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966