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

General Information of Drug (ID: DR0113)
Drug Name
Anastrozole
Synonyms
Anastrozol; Anastrozole, 98%; Arimidex; YBBLVLTVTVSKRW-UHFFFAOYSA-N; ZD 1033; ZD-1033; ZD1033; anastrazole; anastrozole; 120511-73-1; 2,2'-(5-((1H-1,2,4-triazol-1-yl)methyl)-1,3-phenylene)bis(2-methylpropanenitrile); 2-[3-(2-cyanopropan-2-yl)-5-(1,2,4-triazol-1-ylmethyl)phenyl]-2-methylpropanenitrile; 2Z07MYW1AZ; C17H19N5; CHEBI:2704; CHEMBL1399; HSDB 7462; ICI D1033; ICI-D 1033; ICI-D1033; NSC719344; UNII-2Z07MYW1AZ; alpha,alpha,alpha',alpha'-Tetramethyl-5-(1H-1,2,4-triazol-1-ylmethyl)-m-benzenediacetonitrile
Indication Breast cancer [ICD11: 2C60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 293.4 Topological Polar Surface Area 78.3
Heavy Atom Count 22 Rotatable Bond Count 4
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
2187
PubChem SID
10359 ; 535026 ; 5128740 ; 7848023 ; 7978492 ; 8151486 ; 11528617 ; 12014321 ; 14751420 ; 26719808 ; 26758041 ; 29221365 ; 46386543 ; 46504987 ; 46510669 ; 48415567 ; 49681575 ; 53007586 ; 53789173 ; 56311273 ; 56313558 ; 56313576 ; 57321190 ; 58106884 ; 81040864 ; 87351875 ; 92308653 ; 92308946 ; 92712142 ; 99436928 ; 103478231 ; 104299862 ; 117672710 ; 118313740 ; 124659088 ; 124757065 ; 124801312 ; 125163869 ; 125311691 ; 125339200 ; 126630179 ; 126657740 ; 126667645 ; 129769972 ; 131296284 ; 134337917 ; 135018130 ; 135698190 ; 135727309 ; 136348802
ChEBI ID
CHEBI:2704
CAS Number
120511-73-1
TTD Drug ID
D0W0BF
Formula
C17H19N5
Canonical SMILES
CC(C)(C#N)C1=CC(=CC(=C1)CN2C=NC=N2)C(C)(C)C#N
InChI
1S/C17H19N5/c1-16(2,9-18)14-5-13(8-22-12-20-11-21-22)6-15(7-14)17(3,4)10-19/h5-7,11-12H,8H2,1-4H3
InChIKey
YBBLVLTVTVSKRW-UHFFFAOYSA-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
3,5-Bis-(2-methylpropiononitrile)-benzoic acid DM001375
57540772
Oxidation - N-Dealkylation 1 [2]
Anastrozole glucuronide metabolite DM001373 N. A. Unclear 1 [4] , [5]
Hydroxyanastrozole DM001371
118753629
Oxidation - Hydroxylation 1 [2]
Triazole DM001374
67516
Oxidation - N-Dealkylation 1 [2]
Hydroxyanastrozole glucuronide metabolite DM001372
118753630
Conjugation - O-Glucuronidation 2 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000237 Anastrozole Hydroxyanastrozole Oxidation - Hydroxylation CYP3A4 ... [2]
MR000238 Anastrozole Anastrozole glucuronide metabolite Unclear Unclear [4], [5]
MR000239 Anastrozole Triazole Oxidation - N-Dealkylation Unclear [2]
MR000240 Anastrozole 3,5-Bis-(2-methylpropiononitrile)-benzoic acid Oxidation - N-Dealkylation Unclear [2]
MR000236 Hydroxyanastrozole Hydroxyanastrozole glucuronide metabolite Conjugation - O-Glucuronidation UGT [6]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[2]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A4 (UGT1A4) DME0048 Homo sapiens
UD14_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[2]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [3]
⏷ Show the Full List of 9  DME(s)
References
1 Anastrozole was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 In vitro and in vivo oxidative metabolism and glucuronidation of anastrozole. Br J Clin Pharmacol. 2010 Dec;70(6):854-69.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 Oxidative metabolism of amprenavir in the human liver. Effect of the CYP3A maturation. Drug Metab Dispos. 2003 Mar;31(3):275-81.
5 Anastrozole and related glucuronic acid conjugate are electrophilic species. Xenobiotica. 2022 Apr;52(4):380-388. doi: 10.1080/00498254.2022.2086503.
6 DrugBank(Pharmacology-Metabolism)Anastrozole

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