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

General Information of Drug (ID: DR0672)
Drug Name
Etretinate
Synonyms
Ethyl etrinoate; Etretinato; Etretinato [INN-Spanish]; Etretinatum; Etretinatum [INN-Latin]; Retinoid; Ro 10-9359; Ro-10-9359; Tegison; Tigason; etretinate; 54350-48-0; 65M2UDR9AG; C23H30O3; CCRIS 3615; CHEBI:4913; EINECS 259-119-3; Ethyl (all-E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate; Ethyl all-trans-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate; HSDB 7185; NSC 297936; UNII-65M2UDR9AG
Indication Keratosis pilaris [ICD11: ED56] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 354.5 Topological Polar Surface Area 35.5
Heavy Atom Count 26 Rotatable Bond Count 8
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
5282375
PubChem SID
147405 ; 7847382 ; 7979209 ; 8617028 ; 12013448 ; 14754444 ; 24702109 ; 39315832 ; 48415995 ; 49997871 ; 50112753 ; 50140619 ; 56352872 ; 57358640 ; 71821675 ; 92309122 ; 92716748 ; 92729647 ; 93304521 ; 103167534 ; 103825409 ; 113857080 ; 117577847 ; 126622714 ; 126663123 ; 127324001 ; 127324002 ; 131318257 ; 135002908 ; 137005793 ; 137128958 ; 138097872 ; 139221756 ; 144206054 ; 152029411 ; 162173068 ; 164827405 ; 170465372 ; 175611923 ; 176262082 ; 176484353 ; 177749313 ; 179116679 ; 179225741 ; 184546000 ; 198959792 ; 198992373 ; 223365934 ; 223673365 ; 225039591
ChEBI ID
CHEBI:4913
CAS Number
54350-48-0
TTD Drug ID
D0B1IP
Formula
C23H30O3
Canonical SMILES
CCOC(=O)C=C(C)C=CC=C(C)C=CC1=C(C(=C(C=C1C)OC)C)C
InChI
1S/C23H30O3/c1-8-26-23(24)14-17(3)11-9-10-16(2)12-13-21-18(4)15-22(25-7)20(6)19(21)5/h9-15H,8H2,1-7H3/b11-9+,13-12+,16-10+,17-14+
InChIKey
HQMNCQVAMBCHCO-DJRRULDNSA-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
Acitretin DM000957
5284513
Oxidation - Oxidation 1 [3]
13-cis-Acitretin(Ro 13-7652) DM000958
6437841
Unclear 2 [4]
Acitretin-CoA DM000960
155489088
Other reaction - Ethyl Esterification 2 [3]
13-cis-Etretinate DM000959
6439657
Other reaction - Ethyl Esterification 3 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000994 Etretinate Acitretin Oxidation - Oxidation Unclear [3]
MR000991 Acitretin 13-cis-Acitretin Unclear Unclear [4]
MR000992 Acitretin Acitretin-CoA Other reaction - Ethyl Esterification Unclear [3]
MR000993 13-cis-Acitretin 13-cis-Etretinate Other reaction - Ethyl Esterification Unclear [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Retinoic acid 4-hydroxylase 26B1 (CYP26B1) DME0032 Homo sapiens
CP26B_HUMAN
1.14.13.-
[2]
References
1 Etretinate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Lipopolysaccharide opposes the induction of CYP26A1 and CYP26B1 gene expression by retinoic acid in the rat liver in vivo. Am J Physiol Gastrointest Liver Physiol. 2007 Apr;292(4):G1029-36.
3 In vitro metabolism of acitretin by human liver microsomes: evidence of an acitretinoyl-coenzyme A thioester conjugate in the transesterification to etretinate Biochem Pharmacol. 2000 Aug 15;60(4):507-16. doi: 10.1016/s0006-2952(00)00339-7.
4 A potentially new metabolic pathway: ethyl esterification of acitretin Xenobiotica. 1992 Aug;22(8):993-1002. doi: 10.3109/00498259209049905.

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.