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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 ALITRETINOIN

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-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
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.

Originator

Approval Year

1982
95
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2470
 10.0 nM [EC50]
Agonist
2470
 50.0 nM [EC50]
Agonist
2470
 195.0 nM [EC50]
Agonist
2470
 3.0 nM [EC50]
Agonist
2470
 140.0 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8043
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
Primary
Approved
8043
Panretin gel

Approved Use

Panretin gel is indicated for topical treatment of cutaneous lesions in patients with AIDS-related Kaposi’s sarcoma.

Launch Date

9.1782722E11
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
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
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
[Erectile dysfunction during isotretinoin therapy].
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
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
[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
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-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
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
Hypercalcemia induced by 13 cis-retinoic acid in patients with neuroblastoma.
2008 Apr
Use of oral isotretinoin in photoaging therapy.
2008 Jan-Feb
Sacroiliitis and polyneuropathy during isotretinoin treatment.
2008 Mar
A cerebellar demyelinating lesion following treatment of acne with isotretinoin.
2008 Mar
Isotretinoin (13-cis-retinoic acid)-associated premature ventricular contractions.
2009 Jul-Aug
Giant cobblestone-like papillae during isotretinoin therapy.
2009 Sep-Oct
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
Isotretinoin-induced encephalopathy.
2010 Nov
Chemical genomics profiling of environmental chemical modulation of human nuclear receptors.
2011 Aug
Patents

Patents

JP2000327577A
5
JP2002511398A
9
JP2003506349A
7
JP2005527487A
3
JP2006519264A
52
JP2007513165A
51
JP2009513567A
59
JP2009526755A
410
JP2010526091A
21
JP2011528275A
417
JP2011529067A
25
JP4571408B2
3
JP4658037B2
33
JPH01275532A
4
JPH04244058A
3
JPH0899826A
3
JPH0899830A
3
JPH0899831A
3
JPH0959207A
3
JPH1072345A
3
JPH11199478A
3
JPH11302194A
3

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 Fri Jun 25 21:31:44 UTC 2021 , Edited by admin on Fri Jun 25 21:31:44 UTC 2021
WHO-VATC QL01XX22
Created by admin on Fri Jun 25 21:31:45 UTC 2021 , Edited by admin on Fri Jun 25 21:31:45 UTC 2021
WHO-VATC QD11AH04
Created by admin on Fri Jun 25 21:31:45 UTC 2021 , Edited by admin on Fri Jun 25 21:31:45 UTC 2021
NDF-RT N0000007700
Created by admin on Fri Jun 25 21:31:44 UTC 2021 , Edited by admin on Fri Jun 25 21:31:44 UTC 2021
NCI_THESAURUS C804
Created by admin on Fri Jun 25 21:31:44 UTC 2021 , Edited by admin on Fri Jun 25 21:31:44 UTC 2021
NDF-RT N0000007700
Created by admin on Fri Jun 25 21:31:44 UTC 2021 , Edited by admin on Fri Jun 25 21:31:44 UTC 2021
FDA ORPHAN DRUG 101296
Created by admin on Fri Jun 25 21:31:44 UTC 2021 , Edited by admin on Fri Jun 25 21:31:44 UTC 2021
WHO-ATC D11AH04
Created by admin on Fri Jun 25 21:31:44 UTC 2021 , Edited by admin on Fri Jun 25 21:31:44 UTC 2021
EMA ASSESSMENT REPORTS PANRETIN (AUTHORIZED: SARCOMA, KAPOSI)
Created by admin on Fri Jun 25 21:31:44 UTC 2021 , Edited by admin on Fri Jun 25 21:31:44 UTC 2021
NDF-RT N0000007700
Created by admin on Fri Jun 25 21:31:44 UTC 2021 , Edited by admin on Fri Jun 25 21:31:44 UTC 2021
NDF-RT N0000007700
Created by admin on Fri Jun 25 21:31:44 UTC 2021 , Edited by admin on Fri Jun 25 21:31:44 UTC 2021
FDA ORPHAN DRUG 110998
Created by admin on Fri Jun 25 21:31:44 UTC 2021 , Edited by admin on Fri Jun 25 21:31:44 UTC 2021
WHO-ATC L01XX22
Created by admin on Fri Jun 25 21:31:44 UTC 2021 , Edited by admin on Fri Jun 25 21:31:44 UTC 2021
NDF-RT N0000175607
Created by admin on Fri Jun 25 21:31:45 UTC 2021 , Edited by admin on Fri Jun 25 21:31:45 UTC 2021
FDA ORPHAN DRUG 66592
Created by admin on Fri Jun 25 21:31:44 UTC 2021 , Edited by admin on Fri Jun 25 21:31:44 UTC 2021
NDF-RT N0000007700
Created by admin on Fri Jun 25 21:31:44 UTC 2021 , Edited by admin on Fri Jun 25 21:31:44 UTC 2021
FDA ORPHAN DRUG 708819
Created by admin on Fri Jun 25 21:31:44 UTC 2021 , Edited by admin on Fri Jun 25 21:31:44 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C1574
Created by admin on Fri Jun 25 21:31:44 UTC 2021 , Edited by admin on Fri Jun 25 21:31:44 UTC 2021
PRIMARY
INN
7781
Created by admin on Fri Jun 25 21:31:44 UTC 2021 , Edited by admin on Fri Jun 25 21:31:44 UTC 2021
PRIMARY
HSDB
7186
Created by admin on Fri Jun 25 21:31:44 UTC 2021 , Edited by admin on Fri Jun 25 21:31:44 UTC 2021
PRIMARY
ChEMBL
CHEMBL705
Created by admin on Fri Jun 25 21:31:44 UTC 2021 , Edited by admin on Fri Jun 25 21:31:44 UTC 2021
PRIMARY
MERCK INDEX
M1511
Created by admin on Fri Jun 25 21:31:44 UTC 2021 , Edited by admin on Fri Jun 25 21:31:44 UTC 2021
PRIMARY Merck Index
DRUG CENTRAL
3862
Created by admin on Fri Jun 25 21:31:44 UTC 2021 , Edited by admin on Fri Jun 25 21:31:44 UTC 2021
PRIMARY
MERCK INDEX
M9558
Created by admin on Fri Jun 25 21:31:44 UTC 2021 , Edited by admin on Fri Jun 25 21:31:44 UTC 2021
PRIMARY
MESH
C103303
Created by admin on Fri Jun 25 21:31:44 UTC 2021 , Edited by admin on Fri Jun 25 21:31:44 UTC 2021
PRIMARY
EPA CompTox
5300-03-8
Created by admin on Fri Jun 25 21:31:44 UTC 2021 , Edited by admin on Fri Jun 25 21:31:44 UTC 2021
PRIMARY
CAS
5300-03-8
Created by admin on Fri Jun 25 21:31:44 UTC 2021 , Edited by admin on Fri Jun 25 21:31:44 UTC 2021
PRIMARY
DRUG BANK
DB00523
Created by admin on Fri Jun 25 21:31:44 UTC 2021 , Edited by admin on Fri Jun 25 21:31:44 UTC 2021
PRIMARY
RXCUI
81864
Created by admin on Fri Jun 25 21:31:45 UTC 2021 , Edited by admin on Fri Jun 25 21:31:45 UTC 2021
PRIMARY RxNorm
IUPHAR
2645
Created by admin on Fri Jun 25 21:31:44 UTC 2021 , Edited by admin on Fri Jun 25 21:31:44 UTC 2021
PRIMARY
WIKIPEDIA
ALITRETINOIN
Created by admin on Fri Jun 25 21:31:45 UTC 2021 , Edited by admin on Fri Jun 25 21:31:45 UTC 2021
PRIMARY
EVMPD
SUB00344MIG
Created by admin on Fri Jun 25 21:31:44 UTC 2021 , Edited by admin on Fri Jun 25 21:31:44 UTC 2021
PRIMARY
PUBCHEM
449171
Created by admin on Fri Jun 25 21:31:45 UTC 2021 , Edited by admin on Fri Jun 25 21:31:45 UTC 2021
PRIMARY
FDA UNII
1UA8E65KDZ
Created by admin on Fri Jun 25 21:31:44 UTC 2021 , Edited by admin on Fri Jun 25 21:31:44 UTC 2021
PRIMARY
ACTIVE MOIETY
Structure of ALITRETINOIN
NIH
NCATS
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ACCESSIBILITY
DISCLAIMER
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