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Details

Stereochemistry ACHIRAL
Molecular Formula C21H26O3
Molecular Weight 326.4301
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 4
Charge 0

SHOW SMILES / InChI
Structure of ACITRETIN

SMILES

C/C(=C(/[H])\C(\[H])=C(/[H])\C(=C(/[H])\C(=O)O)\C)/C(/[H])=C(\[H])/c1c(C)cc(c(C)c1C)OC

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 326.4301
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
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
Oral acitretin in psoriasis: drug and vitamin A concentrations in plasma, skin and adipose tissue.
1992
Acitretin-induced myopathy.
1996 May
Peripheral sensory neuropathy associated with short-term oral acitretin therapy.
2003 Jan-Feb
Papillon-Lefèvre syndrome treated with acitretin.
2005 Aug
Low-dose acitretin is associated with fewer adverse events than high-dose acitretin in the treatment of psoriasis.
2006 Aug
Acitretin induces capillary leak syndrome in a patient with pustular psoriasis.
2007 Feb
Acitretin and sixth nerve palsy.
2007 Oct
Acitretin affects bioenergetics of liver mitochondria and promotes mitochondrial permeability transition: potential mechanisms of hepatotoxicity.
2013 Apr 5
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 Jun 25 20:54:37 UTC 2021
Edited
by admin
on Fri Jun 25 20:54:37 UTC 2021
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
NEOTIGASON
Common Name English
ETRETIN
Common Name English
ACITRETIN [USP]
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 [WHO-DD]
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
(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 Jun 25 20:54:37 UTC 2021 , Edited by admin on Fri Jun 25 20:54:37 UTC 2021
NDF-RT N0000175607
Created by admin on Fri Jun 25 20:54:37 UTC 2021 , Edited by admin on Fri Jun 25 20:54:37 UTC 2021
NDF-RT N0000007700
Created by admin on Fri Jun 25 20:54:37 UTC 2021 , Edited by admin on Fri Jun 25 20:54:37 UTC 2021
WHO-ATC D05BB02
Created by admin on Fri Jun 25 20:54:37 UTC 2021 , Edited by admin on Fri Jun 25 20:54:37 UTC 2021
NDF-RT N0000007700
Created by admin on Fri Jun 25 20:54:37 UTC 2021 , Edited by admin on Fri Jun 25 20:54:37 UTC 2021
WHO-VATC QD05BB02
Created by admin on Fri Jun 25 20:54:37 UTC 2021 , Edited by admin on Fri Jun 25 20:54:37 UTC 2021
NDF-RT N0000007700
Created by admin on Fri Jun 25 20:54:37 UTC 2021 , Edited by admin on Fri Jun 25 20:54:37 UTC 2021
NCI_THESAURUS C804
Created by admin on Fri Jun 25 20:54:37 UTC 2021 , Edited by admin on Fri Jun 25 20:54:37 UTC 2021
LIVERTOX 12
Created by admin on Fri Jun 25 20:54:37 UTC 2021 , Edited by admin on Fri Jun 25 20:54:37 UTC 2021
NDF-RT N0000007700
Created by admin on Fri Jun 25 20:54:37 UTC 2021 , Edited by admin on Fri Jun 25 20:54:37 UTC 2021
Code System Code Type Description
PUBCHEM
5284513
Created by admin on Fri Jun 25 20:54:37 UTC 2021 , Edited by admin on Fri Jun 25 20:54:37 UTC 2021
PRIMARY
DRUG BANK
DB00459
Created by admin on Fri Jun 25 20:54:37 UTC 2021 , Edited by admin on Fri Jun 25 20:54:37 UTC 2021
PRIMARY
RXCUI
16818
Created by admin on Fri Jun 25 20:54:37 UTC 2021 , Edited by admin on Fri Jun 25 20:54:37 UTC 2021
PRIMARY RxNorm
LACTMED
Acitretin
Created by admin on Fri Jun 25 20:54:37 UTC 2021 , Edited by admin on Fri Jun 25 20:54:37 UTC 2021
PRIMARY
ChEMBL
CHEMBL1131
Created by admin on Fri Jun 25 20:54:37 UTC 2021 , Edited by admin on Fri Jun 25 20:54:37 UTC 2021
PRIMARY
INN
5530
Created by admin on Fri Jun 25 20:54:37 UTC 2021 , Edited by admin on Fri Jun 25 20:54:37 UTC 2021
PRIMARY
MESH
D017255
Created by admin on Fri Jun 25 20:54:37 UTC 2021 , Edited by admin on Fri Jun 25 20:54:37 UTC 2021
PRIMARY
MERCK INDEX
M1373
Created by admin on Fri Jun 25 20:54:37 UTC 2021 , Edited by admin on Fri Jun 25 20:54:37 UTC 2021
PRIMARY Merck Index
EPA CompTox
55079-83-9
Created by admin on Fri Jun 25 20:54:37 UTC 2021 , Edited by admin on Fri Jun 25 20:54:37 UTC 2021
PRIMARY
USP_CATALOG
1011007
Created by admin on Fri Jun 25 20:54:37 UTC 2021 , Edited by admin on Fri Jun 25 20:54:37 UTC 2021
PRIMARY USP-RS
DRUG CENTRAL
78
Created by admin on Fri Jun 25 20:54:37 UTC 2021 , Edited by admin on Fri Jun 25 20:54:37 UTC 2021
PRIMARY
WIKIPEDIA
ACITRETIN
Created by admin on Fri Jun 25 20:54:37 UTC 2021 , Edited by admin on Fri Jun 25 20:54:37 UTC 2021
PRIMARY
FDA UNII
LCH760E9T7
Created by admin on Fri Jun 25 20:54:37 UTC 2021 , Edited by admin on Fri Jun 25 20:54:37 UTC 2021
PRIMARY
ECHA (EC/EINECS)
259-474-4
Created by admin on Fri Jun 25 20:54:37 UTC 2021 , Edited by admin on Fri Jun 25 20:54:37 UTC 2021
PRIMARY
HSDB
7187
Created by admin on Fri Jun 25 20:54:37 UTC 2021 , Edited by admin on Fri Jun 25 20:54:37 UTC 2021
PRIMARY
NCI_THESAURUS
C985
Created by admin on Fri Jun 25 20:54:37 UTC 2021 , Edited by admin on Fri Jun 25 20:54:37 UTC 2021
PRIMARY
IUPHAR
7598
Created by admin on Fri Jun 25 20:54:37 UTC 2021 , Edited by admin on Fri Jun 25 20:54:37 UTC 2021
PRIMARY
EVMPD
SUB05240MIG
Created by admin on Fri Jun 25 20:54:37 UTC 2021 , Edited by admin on Fri Jun 25 20:54:37 UTC 2021
PRIMARY
CAS
55079-83-9
Created by admin on Fri Jun 25 20:54:37 UTC 2021 , Edited by admin on Fri Jun 25 20:54:37 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
TARGET -> INHIBITOR
BINDER->LIGAND
BINDING
TARGET -> INHIBITOR
CONSTITUENT ALWAYS PRESENT -> PARENT
IDENTIFIED AS IMPURITY A For impurity A, not more than the area of the peak due to acitretin in the chromatogram obtained with reference solution (c) (0.3 per cent)
Related Record Type Details
METABOLITE -> PARENT
PRODRUG -> METABOLITE ACTIVE
URINE
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)
EP
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