U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C21H26O3
Molecular Weight 326.4293
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 4
Charge 0

SHOW SMILES / InChI
Structure of ACITRETIN

SMILES

COC1=C(C)C(C)=C(\C=C\C(C)=C\C=C\C(C)=C\C(O)=O)C(C)=C1

InChI

InChIKey=IHUNBGSDBOWDMA-AQFIFDHZSA-N
InChI=1S/C21H26O3/c1-14(8-7-9-15(2)12-21(22)23)10-11-19-16(3)13-20(24-6)18(5)17(19)4/h7-13H,1-6H3,(H,22,23)/b9-7+,11-10+,14-8+,15-12+

HIDE SMILES / InChI

Molecular Formula C21H26O3
Molecular Weight 326.4293
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 https://www.ncbi.nlm.nih.gov/pubmed/21720660

Acitretin is all-Trans-9-(4-methoxy-2, 3, 6¬ trimethylphenyl)-three, 7-dimethyl-2, 4, 6, 8-nonatetraenoic acid. It is a metabolite of exterminate and is related to both retinoic acid and retinol (vitamin A). It is taken orally, and is typically used for psoriasis. The mechanism of action of is unknown. However it is believed to work by targeting specific receptors (retinoid receptors such as RXR and RAR) in the skin, which help normalize the growth cycle of skin cells. Studies on nuclear retinoic acid receptors have shown that acitretin activates all 3 receptor subtypes (RAR-alpha, -beta, and -gamma) without measurable receptor binding; this paradox remains unexplained.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
SORIATANE

Approved Use

Acitretin Capsules USP are indicated for the treatment of severe psoriasis in adults. Because of significant adverse effects associated with their use, Acitretin Capsules USP should be prescribed only by those knowledgeable in the systemic use of retinoids. In females of reproductive potential, Acitretin Capsules USP should be reserved for non-pregnant patients who are unresponsive to other therapies or whose clinical condition contraindicates the use of other treatments (see boxed CONTRAINDICATIONS AND WARNINGS — Acitretin Capsules USP can cause severe birth defects). Most patients experience relapse of psoriasis after discontinuing therapy. Subsequent courses, when clinically indicated, have produced efficacy results similar to the initial course of therapy.

Launch Date

8.4646081E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
416 ng/mL
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ACITRETIN plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: MALE
food status: FED
416 ng/mL
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ACITRETIN plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
2249 ng × h/mL
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ACITRETIN plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.8 h
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ACITRETIN plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: MALE
food status: FED
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Determination of the aromatic retinoids (etretin and isoetretin) in biological fluids by high-performance liquid chromatography.
1987 Oct 9
Identification of etretinate metabolites in human blood.
1989 May-Jun
Identification of etretinate metabolites in human bile.
1989 May-Jun
High-performance liquid chromatographic determination of etretinate and all-trans- and 13-cis-acitretin in human plasma.
1990 Feb 2
Acitretin-associated thrombotic stroke.
2002 Dec
Effects of ATRA, acitretin and tazarotene on growth and apoptosis of Tca8113 cells.
2005
[Effects of all-trans-retinoic acid, acitretin and tazarotene on apoptosis and Bax/Bcl-2 expressions of human melanoma cells A375 and the significance].
2005 Aug
Papillon-Lefèvre syndrome treated with acitretin.
2005 Aug
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Recurrent dysphonia and acitretin.
2006 Dec
[Acitretin induces apoptosis and changes of relative signaling pathway in epidermoid carcinoma cell line A431].
2006 Mar
Acitretin induces apoptosis through CD95 signalling pathway in human cutaneous squamous cell carcinoma cell line SCL-1.
2009 Sep
A correlation between the in vitro drug toxicity of drugs to cell lines that express human P450s and their propensity to cause liver injury in humans.
2014 Jan
Patents

Sample Use Guides

SORIATANE (acitretin capsules) should be initiated at 25 to 50 mg per day, given as a single dose with the main meal. Maintenance doses of 25 to 50 mg per day may be given dependent upon an individual patient’s response to initial treatment. Relapses may be treated as outlined for initial therapy.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: Acitretin plays an inhibitory role in the tumor cell growth and induces the cell apoptosis in A431 cells. The regulation of the Jak/STAT3 signaling pathway may play an important role in inducing growth inhibition and apoptosis by Acitretin in A431 cells.
A431 (epidermoid carcinoma cell lines) were treated with Acitretin at the concentration of 10(-5)mol/L in different time intervals
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:02:54 UTC 2023
Edited
by admin
on Fri Dec 15 15:02:54 UTC 2023
Record UNII
LCH760E9T7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ACITRETIN
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
ACITRETINE
Common Name English
ACITRETIN [EP MONOGRAPH]
Common Name English
ACITRETIN [MI]
Common Name English
ACITRETIN [USP-RS]
Common Name English
ACITRETIN [USAN]
Common Name English
ACITRETIN [USP IMPURITY]
Common Name English
NEOTIGASON
Common Name English
ETRETIN
Common Name English
9-(4-METHOXY-2,3,6-TRIMETHYLPHENYL)-3,7-DIMETHYL-2,4,6,8-NONATETRAENOIC ACID
Systematic Name English
acitretin [INN]
Common Name English
ACITRETIN [USP MONOGRAPH]
Common Name English
ACITRETIN [ORANGE BOOK]
Common Name English
RO 10-1670
Code English
ACITRETIN [MART.]
Common Name English
2,4,6,8-NONATETRAENOIC ACID, 9-(4-METHOXY-2,3,6-TRIMETHYLPHENYL)-3,7-DIMETHYL-, (ALL-E)-
Common Name English
RO-10-1670/000
Code English
SORIATANE
Brand Name English
RO 10-1670/000
Code English
ACITRETIN [VANDF]
Common Name English
ACITRETIN [HSDB]
Common Name English
Acitretin [WHO-DD]
Common Name English
(all-E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid
Common Name English
Classification Tree Code System Code
NDF-RT N0000007700
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
NDF-RT N0000175607
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
NDF-RT N0000007700
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
WHO-ATC D05BB02
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
NDF-RT N0000007700
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
WHO-VATC QD05BB02
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
NDF-RT N0000007700
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
NCI_THESAURUS C804
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
LIVERTOX NBK548784
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
NDF-RT N0000007700
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
Code System Code Type Description
CHEBI
50173
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
PRIMARY
RS_ITEM_NUM
1011007
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
PRIMARY
PUBCHEM
5284513
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
PRIMARY
DRUG BANK
DB00459
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
PRIMARY
RXCUI
16818
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
PRIMARY RxNorm
LACTMED
Acitretin
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
PRIMARY
USAN
X-94
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
PRIMARY
ChEMBL
CHEMBL1131
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
PRIMARY
INN
5530
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
PRIMARY
MESH
D017255
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
PRIMARY
SMS_ID
100000084604
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
PRIMARY
MERCK INDEX
m1373
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID6022553
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
PRIMARY
DRUG CENTRAL
78
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
PRIMARY
WIKIPEDIA
ACITRETIN
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
PRIMARY
FDA UNII
LCH760E9T7
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
PRIMARY
ECHA (EC/EINECS)
259-474-4
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
PRIMARY
HSDB
7187
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
PRIMARY
NCI_THESAURUS
C985
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
PRIMARY
DAILYMED
LCH760E9T7
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
PRIMARY
IUPHAR
7598
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
PRIMARY
EVMPD
SUB05240MIG
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
PRIMARY
CAS
55079-83-9
Created by admin on Fri Dec 15 15:02:54 UTC 2023 , Edited by admin on Fri Dec 15 15:02:54 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
TARGET -> INHIBITOR
BINDER->LIGAND
BINDING
TARGET -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
PRODRUG -> METABOLITE ACTIVE
URINE
METABOLITE -> PARENT
Clinical evidence has shown that etretinate (a retinoid with a much longer half-life, see below) can be formed with concurrent ingestion of acitretin and ethanol.
METABOLITE -> PARENT
METABOLITE -> PARENT
MAJOR
METABOLITE -> PARENT
METABOLITE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC