ACITRETIN

First approved in 1996

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 Search

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

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/019821s027lbl.pdf
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Retinoid X receptor gamma/retinoic acid receptor alpha 2 Target ID: CHEMBL2363072 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=10459139	Agonist 2637

Conditions

Condition	Modality	Targets	Highest Phase	Product
Psoriasis 83 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/019821s027lbl.pdf	Palliative		Approved 8307	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

C_max

Value	Dose	Co-administered	Analyte	Population
416 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2977392	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/019821s024lbl.pdf	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

Value	Dose	Co-administered	Analyte	Population
2249 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2977392	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.8 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2977392	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

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-0185	http://www.3bsc.com/index/pro_info.php?id=19541
3B Scientific (Wuhan) Corp	3B1-00387	http://www.3bsc.com/index/pro_info.php?id=20599
AA Blocks	AA0038XM	https://www.aablocks.com/goods/Goods/detail?id=AA0038XM
AHH Chemical co.,ltd	API-1171	http://www.ahhchemical.com/product/API-1171.html
AK Scientific, Inc. (AKSCI)	70814	http://www.aksci.com/item_detail.php?cat=70814
Aaron Chemicals	AR0039PE	http://www.aaronchem.com/55079-83-9
AbMole Bioscience	M1961	http://www.abmole.com/products/acitretin.html
Achemo Scientific Limited	AC-13570	http://www.achemo.com/product_view.asp?ID=3460
Achemtek	0104-022959	http://www.achemtek.com/55079-83-9
Acorn PharmaTech	ACN-038108	http://www.acornpharmatech.com/
Active Biopharma	ABP000589	http://www.activebiopharma.com/55079-83-9
Adooq BioScience	A10035	https://www.adooq.com/acitretin.html
Alfa Chemistry	AP55079839-A	https://reagents.alfa-chemistry.com/product/acitretin-cas-55079-83-9-12993.html
Alfa Chemistry	AP55079839-B	https://reagents.alfa-chemistry.com/product/acitretin-cas-55079-83-9-12994.html
Alsachim	2192	http://www.alsachim.com/product-C3175-glo.bal-view.html
Ambinter	Amb16231686	http://www.ambinter.com/reference/16231686
ApexBio Technology	A2415	http://www.apexbt.com/acitretin-22433.html
Aurora Fine Chemicals LLC	A17.901.689	http://online.aurorafinechemicals.com/info?ID=A17.901.689
AvaChem Scientific	1685	http://www.avachem.com/productSearch.asp?1685
BLD Pharm	BD21403	http://www.bldpharm.com/products/55079-83-9.html
BioCrick	BCC1189	http://www.biocrick.com/Acitretin-BCC1189.html
Boerchem	BC209054	http://www.boerchem.com/?product_35413.html
CSNpharm	CSN12772	https://www.csnpharm.com/products/acitretin.html
Capot Chemical	25112	http://www.capotchem.com/en/25112.htm
Chem Scene	CS-1855	http://www.chemscene.com/55079-83-9.html
ChemFaces	CFN93053	http://www.chemfaces.com/natural/Acitretin-CFN93053.html
ChemMol	30104568	http://www.chemmol.com/chemmol/30104568.html
ChemMol	44003483	http://www.chemmol.com/chemmol/44003483.html
ChemMol	49401249	http://www.chemmol.com/chemmol/49401249.html
ChemMol	99105225	http://www.chemmol.com/chemmol/99105225.html
Chemspace	CSSB00020587494	https://chem-space.com/CSSB00020587494
Glentham Life Sciences	GP9248	http://www.glentham.com/products/product/GP9248/
Hairui	HR23837	http://www.hairuichem.com/en/product/55079-83-9.html
Hefei Hirisun Pharmatech Co., Ltd	HR130526	http://www.hirisunpharm.com/55079-83-9.html
LGC Standards	DRE-A10032000AA-100	https://www.lgcstandards.com/US/en/p/DRE-A10032000AA-100
LGC Standards	DRE-C10032000	https://www.lgcstandards.com/US/en/p/DRE-C10032000
LGC Standards	LGCFOR3427.00	https://www.lgcstandards.com/US/en/p/LGCFOR3427.00
LGC Standards	MM3427.00	https://www.lgcstandards.com/US/en/p/MM3427.00
Lab Network	LN01263888	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01263888
MedChem Express	HY-B0107	https://www.medchemexpress.com/acitretin.html
OChem	80	http://www.ocheminc.com/index.php?act=psearch&pid=079A839
Renno Tech	RP17661	http://www.rennotech.com/product_show.asp?id=23539
Selleck Chemicals	S1368	http://www.selleckchem.com/products/Acitretin.html
Sigma-Aldrich	A0225000_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/a0225000?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	BP827_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/bp827?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	PHR1523_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/phr1523?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	44707_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/44707?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1011007_USP	https://www.sigmaaldrich.com/catalog/product/usp/1011007?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S800522	https://www.smolecule.com/products/s800522
Synblock Inc	AB07538	http://www.synblock.com/product/55079-83-9.html
TCI (Tokyo Chemical Industry)	A3097	http://www.tcichemicals.com/eshop/en/us/commodity/A3097/index.html
THE BioTek	bt-463378	https://www.thebiotek.com/product/others/bt-463378
Yuhao Chemical	LX3192	http://www.chemyuhao.com/55079-83-9.html
abcr GmbH	AB505807	http://www.abcr.com/shop/en/AB505807

PubMed

Title	Date	PubMed
Determination of the aromatic retinoids (etretin and isoetretin) in biological fluids by high-performance liquid chromatography.	1987 Oct 9	2963014
Identification of etretinate metabolites in human bile.	1989 May-Jun	2568908
High-performance liquid chromatographic determination of etretinate and all-trans- and 13-cis-acitretin in human plasma.	1990 Feb 2	2139439
Severe hepatotoxic reaction with progression to cirrhosis after use of a novel retinoid (acitretin).	1990 Sep	2147707
Oral acitretin in psoriasis: drug and vitamin A concentrations in plasma, skin and adipose tissue.	1992	1350412
Severe limb defects and craniofacial anomalies in a fetus conceived during acitretin therapy.	1995 Oct	8838291
Acitretin-induced myopathy.	1996 May	8736360
Acitretin-associated thrombotic stroke.	2002 Dec	12452748
Severe cholestatic hepatitis in a patient taking acitretin.	2002 Mar	11922592
Sensorimotor polyneuropathy after a three-month oral acitretin therapy.	2002 Nov-Dec	12469004
Peripheral sensory neuropathy associated with short-term oral acitretin therapy.	2003 Jan-Feb	12566828
Capillary leak syndrome induced by acitretin.	2004 Jan	14746632
Effects of ATRA, acitretin and tazarotene on growth and apoptosis of Tca8113 cells.	2005	16196285
A woman with sudden bilateral sensorineural hearing loss after treatment psoriasis with acitretin.	2005 Jun	16858938
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Recurrent dysphonia and acitretin.	2006 Dec	16274958
Interaction between genetic control of vascular endothelial growth factor production and retinoid responsiveness in psoriasis.	2006 Feb	16385345
Acitretin induces capillary leak syndrome in a patient with pustular psoriasis.	2007 Feb	17097361
Acitretin and sixth nerve palsy.	2007 Oct	17894719
Acitretin induces apoptosis through CD95 signalling pathway in human cutaneous squamous cell carcinoma cell line SCL-1.	2009 Sep	18624760
Acitretin affects bioenergetics of liver mitochondria and promotes mitochondrial permeability transition: potential mechanisms of hepatotoxicity.	2013 Apr 5	23384448
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	24085192

Patents

Sample Use Guides

In Vivo Use Guide

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

A431 (epidermoid carcinoma cell lines) were treated with Acitretin at the concentration of 10(-5)mol/L in different time intervals

Name

Type

Language

ACITRETIN

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