Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR5099)
Drug Name
Acitretin
Synonyms
Acitretina; Acitretine; Acitretinum; Etretin; Isoacitretin; Isoetretin; Neotigason; Soriatane; TMMP; Acitretina [Spanish]; Acitretine [French]; Acitretinum [Latin]; Retinoid etretin; U0279; Ro 10-1670; Ro 13-7652; Soriatane (TN); Soriatane, Acitretin; Acitretin (USAN/INN); Acitretin [USAN:INN:BAN]; All-trans-Acitretin; Ro 10-1670/000; Ro-10-1670; Ro-13-7652; Ro-10-1670/000; All-trans-3,7-Dimethyl-9-(4-methoxy-2,3,6-trimethylphenyl)-2,4,6,8-nonatetraenoic acid; (2E,4E,6E,8E)-3,7-dimethyl-9-[2,3,6-trimethyl-4-(methyloxy)phenyl]nona-2,4,6,8-tetraenoic acid; (2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid; (all-E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid; 13-cis-Acitretin; 9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid; 9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
Indication Psoriasis vulgaris [ICD11: EA90] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 326.4 Topological Polar Surface Area 46.5
Heavy Atom Count 24 Rotatable Bond Count 6
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
5284513
ChEBI ID
CHEBI:50173
CAS Number
55079-83-9
TTD Drug ID
D05QDC
Formula
C21H26O3
Canonical SMILES
CC1=CC(=C(C(=C1/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C)C)C)OC
InChI
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+
InChIKey
IHUNBGSDBOWDMA-AQFIFDHZSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
13-cis-Acitretin(Ro 13-7652) DM000958
6437841
Unclear - Unclear 1 [2]
15-O-glucuronide DM018750 N. A. Unclear - Unclear 1 [2]
Ro 12-7310 DM015491
6438583
Unclear - Unclear 1 [2]
Ro 23-4293 DM015608
10064368
Unclear - Unclear 1 [2]
Ro 23-4293 Metabolite M1 DM018748 N. A. Unclear - Unclear 1 [2]
Tol-CoA DM018289 N. A. Unclear - Unclear 1 [3]
Tol-GlcU DM018291 N. A. Unclear - Unclear 1 [3]
Tol-OH DM016856
162623572
Unclear - Unclear 1 [3]
3-O-glucuronide DM018749 N. A. Unclear - Unclear 2 [2]
MED5 DM015187
135911
Unclear - Unclear 2 [3]
Ro 23-3571 DM015678
10425018
Unclear - Unclear 2 [2]
Ro 23-4293 Metabolite M1 DM018748 N. A. Unclear - Unclear 2 [2]
Ro 23-4750 DM016774
154731619
Unclear - Unclear 2 [2]
Tol-COOH DM015250
193897
Unclear - Unclear 2 [3]
Tol-O-SO3H DM018290 N. A. Unclear - Unclear 2 [3]
Tol-Tau DM016077
44251089
Unclear - Unclear 2 [3]
⏷ Show the Full List of 16  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR010221 Acitretin 13-cis-Acitretin Unclear - Unclear Unclear [2]
MR010223 Acitretin Ro 23-4293 Unclear - Unclear Unclear [2]
MR010225 Acitretin Ro 12-7310 Unclear - Unclear Unclear [2]
MR011044 Acitretin 15-O-glucuronide Unclear - Unclear Unclear [2]
MR011045 Acitretin Ro 23-4293 Metabolite M1 Unclear - Unclear Unclear [2]
MR011055 Acitretin Tol-CoA Unclear - Unclear Unclear [3]
MR011058 Acitretin Tol-OH Unclear - Unclear Unclear [3]
MR011061 Acitretin TOL-GlcU Unclear - Unclear Unclear [3]
MR013997 Acitretin 13-cis-Acitretin(Ro 13-7652) Unclear - Unclear Unclear [2]
MR010222 13-cis-Acitretin Ro 23-4750 Unclear - Unclear Unclear [2]
MR013998 13-cis-Acitretin(Ro 13-7652) Ro-23-4750 Unclear - Unclear Unclear [2]
MR011043 Ro 12-7310 3-O-glucuronide Unclear - Unclear Unclear [2]
MR010224 Ro 23-4293 Ro 23-3571 Unclear - Unclear Unclear [2]
MR011042 Ro 23-4293 Ro 23-4293 Metabolite M1 Unclear - Unclear Unclear [2]
MR011056 Tol-CoA Tol-Tau Unclear - Unclear Unclear [3]
MR011057 Tol-CoA Tol-Gly Unclear - Unclear Unclear [3]
MR011059 Tol-OH Tol-O-SO3H Unclear - Unclear Unclear [3]
MR011060 Tol-OH Tol-COOH Unclear - Unclear Unclear [3]
⏷ Show the Full List of 18 MR(s)
References
1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7598).
2 Acitretin. A review of its pharmacology and therapeutic use
3 Identification of coenzyme A-related tolmetin metabolites in rats: relationship with reactive drug metabolites

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