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 ISOACITRETIN

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-UGOGCBOOSA-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
Severe hepatotoxic reaction with progression to cirrhosis after use of a novel retinoid (acitretin).
1990 Sep
Severe cholestatic hepatitis in a patient taking acitretin.
2002 Mar
Peripheral sensory neuropathy associated with short-term oral acitretin therapy.
2003 Jan-Feb
Acitretin embryopathy: a case report.
2004 Oct
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
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 Sat Dec 16 10:50:05 UTC 2023
Edited
by admin
on Sat Dec 16 10:50:05 UTC 2023
Record UNII
BK59Y5A02O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ISOACITRETIN
Common Name English
RO-13-7652
Code English
ACITRETIN RELATED COMPOUND A [USP-RS]
Common Name English
ISOETRETIN
Common Name English
ACITRETIN IMPURITY A [EP IMPURITY]
Common Name English
13-CIS-ACITRETIN
Common Name English
13-CIS-ETRETIN
Common Name English
ACITRETIN RELATED COMPOUND A [USP IMPURITY]
USP-RS  
Common Name English
2,4,6,8-NONATETRAENOIC ACID, 9-(4-METHOXY-2,3,6-TRIMETHYLPHENYL)-3,7-DIMETHYL-, (2Z,4E,6E,8E)-
Systematic Name English
Code System Code Type Description
FDA UNII
BK59Y5A02O
Created by admin on Sat Dec 16 10:50:05 UTC 2023 , Edited by admin on Sat Dec 16 10:50:05 UTC 2023
PRIMARY
RS_ITEM_NUM
1011018
Created by admin on Sat Dec 16 10:50:05 UTC 2023 , Edited by admin on Sat Dec 16 10:50:05 UTC 2023
PRIMARY
PUBCHEM
6437841
Created by admin on Sat Dec 16 10:50:05 UTC 2023 , Edited by admin on Sat Dec 16 10:50:05 UTC 2023
PRIMARY
CAS
69427-46-9
Created by admin on Sat Dec 16 10:50:05 UTC 2023 , Edited by admin on Sat Dec 16 10:50:05 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> METABOLITE
MAJOR
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Tmax PHARMACOKINETIC