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

General Information of Drug (ID: DR0675)
Drug Name
Exemestane
Synonyms
Exemestane [USAN:INN:BAN]; Exemestano; Exemestano [INN-Spanish]; Exemestanum; Exemestanum [INN-Latin]; NY22HMQ4BX; PNU-155971; Aromasin; Aromasine; EXEMESTANE; 107868-30-4; 6-Methylenandrosta-1,4-diene-3,17-dione; 6-Methylene-androsta-1,4-diene-3,17-dione; 6-Methyleneandrosta-1,4-diene-3,17-dione; Androsta-1,4-diene-3,17-dione, 6-methylene-; CHEBI:4953; FCE-24304; FCE24304; Fce 24304; HSDB 7463; UNII-NY22HMQ4BX
Indication Breast cancer [ICD11: 2C60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 296.4 Topological Polar Surface Area 34.1
Heavy Atom Count 22 Rotatable Bond Count 0
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
60198
PubChem SID
10362 ; 532118 ; 7848026 ; 7978495 ; 8186720 ; 11528610 ; 12014009 ; 14898201 ; 14922734 ; 26719821 ; 43117629 ; 46386592 ; 46508243 ; 47734117 ; 48415996 ; 49681613 ; 53787997 ; 57313998 ; 71825450 ; 76229105 ; 92308414 ; 92712532 ; 99436932 ; 99437373 ; 103770357 ; 104320132 ; 117585772 ; 118043418 ; 119525530 ; 124658984 ; 124757072 ; 125163876 ; 126608810 ; 126630089 ; 126666059 ; 127510064 ; 134337915 ; 135260226 ; 135724569 ; 136367947 ; 136903807 ; 136946607 ; 137005560 ; 137230761 ; 141857635 ; 144115969 ; 144205052 ; 151979532 ; 152034580 ; 152164568
ChEBI ID
CHEBI:4953
CAS Number
107868-30-4
TTD Drug ID
D0D2VS
Formula
C20H24O2
Canonical SMILES
CC12CCC3C(C1CCC2=O)CC(=C)C4=CC(=O)C=CC34C
InChI
1S/C20H24O2/c1-12-10-14-15-4-5-18(22)20(15,3)9-7-16(14)19(2)8-6-13(21)11-17(12)19/h6,8,11,14-16H,1,4-5,7,9-10H2,2-3H3/t14-,15-,16-,19+,20-/m0/s1
InChIKey
BFYIZQONLCFLEV-DAELLWKTSA-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
17beta-DHE conjugation with glucuronic acid DM000131 N. A. Conjugation - Conjugation 1 [3] , [4]
17beta-dihydroexemestane DM000129
11392371
Reduction - Reduction 1 [3] , [4] , [5]
6-hydroxymethylandrosta-1,4,6-triene-3,17-dione DM000130 N. A. Oxidation - Deamination 1 [3]
Unclear DM009999 N. A. Oxidation - Oxidation 1 [3] , [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000999 Exemestane 17beta-dihydroexemestane Reduction - Reduction CYP1A2 ... [3], [4], [5]
MR001000 Exemestane 6-hydroxymethylandrosta-1,4,6-triene-3,17-dione Oxidation - Deamination CYP2B6 ... [3]
MR001001 Exemestane 17beta-DHE conjugation with glucuronic acid Conjugation - Conjugation Unclear [3], [4]
MR001002 Exemestane . Oxidation - Oxidation CYP3A4 [3], [6]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Lauric acid omega-hydroxylase (CYP4A11) DME0029 Homo sapiens
CP4AB_HUMAN
1.14.15.3
[2]
References
1 Exemestane was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 In vitro metabolism of exemestane by hepatic cytochrome P450s: impact of nonsynonymous polymorphisms on formation of the active metabolite 17-dihydroexemestane Pharmacol Res Perspect. 2017 Apr 27;5(3):e00314. doi: 10.1002/prp2.314.
3 In vitro metabolism of exemestane by hepatic cytochrome P450s: impact of nonsynonymous polymorphisms on formation of the active metabolite 17beta-dihydroexemestane. Pharmacol Res Perspect. 2017 Apr 27;5(3):e00314.
4 Inhibition of the aromatase enzyme by exemestane cysteine conjugates. Mol Pharmacol. 2022 Aug 11;102(5):216-22. doi: 10.1124/molpharm.122.000545.
5 Influence of Glutathione-S-Transferase A1*B Allele on the Metabolism of the Aromatase Inhibitor, Exemestane, in Human Liver Cytosols and in Patients Treated With Exemestane. J Pharmacol Exp Ther. 2022 Sep;382(3):327-334. doi: 10.1124/jpet.122.001232.
6 LABEL:EXEMESTANE tablet

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