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

General Information of Drug (ID: DR1749)
Drug Name
Aspirin
Synonyms
Acetophen; Acetosal; Acetosalin; Acetylin; Acetylsalicylate; Acidum acetylsalicylicum; Acylpyrin; Aspergum; Aspirdrops; Benaspir; ACETYLSALICYLIC ACID; Aceticyl; Acetonyl; Colfarit; Easprin; Ecolen; Ecotrin; Empirin; Endydol; Enterosarein; Globentyl; Micristin; O-Acetylsalicylic acid; Pharmacin; Polopiryna; Premaspin; Rheumintabletten; Rhodine; Salcetogen; Saletin; Salicylic acid acetate; Solprin acid; Temperal; aspirin; o-Acetoxybenzoic acid; o-Carboxyphenyl acetate; 2-(Acetyloxy)benzoic acid; 2-Acetoxybenzoic acid; 50-78-2; Acenterine
Indication Myocardial infarction [ICD11: BA41] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 180.16 Topological Polar Surface Area 63.6
Heavy Atom Count 13 Rotatable Bond Count 3
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
2244
PubChem SID
4594 ; 87798 ; 476106 ; 602429 ; 829042 ; 832958 ; 840714 ; 3135921 ; 5261264 ; 7847177 ; 7885805 ; 7978731 ; 8143164 ; 8149208 ; 8151516 ; 10524572 ; 11110749 ; 11335730 ; 11360969 ; 11364139 ; 11364685 ; 11366701 ; 11367247 ; 11369263 ; 11369809 ; 11372248 ; 11372850 ; 11373537 ; 11375409 ; 11377425 ; 11377972 ; 11406615 ; 11461941 ; 11485574 ; 11489715 ; 11491110 ; 11491914 ; 11495059 ; 15195166 ; 17389202 ; 17390036 ; 17404602 ; 24278218 ; 24714725 ; 24890623 ; 24890723 ; 24891140 ; 26611613 ; 26679412 ; 26717767
ChEBI ID
ChEBI:15365
CAS Number
50-78-2
TTD Drug ID
D0GY5Z
Formula
C9H8O4
Canonical SMILES
CC(=O)OC1=CC=CC=C1C(=O)O
InChI
1S/C9H8O4/c1-6(10)13-8-5-3-2-4-7(8)9(11)12/h2-5H,1H3,(H,11,12)
InChIKey
BSYNRYMUTXBXSQ-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
Salicylic acid DM001773
338
Unclear - Unclear 1 [2]
Gentistic acid DM001774
3469
Unclear - Unclear 2 [2]
Phenolic glucuronide DM001771 N. A. Conjugation - Glucuronidation 2 [2]
Salicylic acid acyl glucuronide DM001772 N. A. Conjugation - Glucuronidation 2 [2]
Salicyluric acid DM001775
10253
Unclear - Unclear 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002992 Aspirin Salicylic acid Unclear - Unclear CES2 [2]
MR002993 Salicylic acid Phenolic glucuronide Conjugation - Glucuronidation UGT1A6 [2]
MR002994 Salicylic acid Salicylic acid acyl glucuronide Conjugation - Glucuronidation UGT1A6 [2]
MR002995 Salicylic acid Gentistic acid Unclear - Unclear CYP2C9 [2]
MR002996 Salicylic acid Salicyluric acid Unclear - Unclear Unclear [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Carboxylesterase 2 (CES2) DME0057 Homo sapiens
EST2_HUMAN
3.1.1.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
N-acetyltransferase 2 (NAT2) DME0051 Homo sapiens
ARY2_HUMAN
2.3.1.5
[4]
Sulfotransferase 1A1 (SULT1A1) DME0008 Homo sapiens
ST1A1_HUMAN
2.8.2.1
[5]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[6]
UDP-glucuronosyltransferase 1A6 (UGT1A6) DME0072 Homo sapiens
UD16_HUMAN
2.4.1.17
[2]
Unclear metabolic mechanism (DME-unclear) DME1429 Helicobacter apodemus Not Available Not Available [7]
Unclear metabolic mechanism (DME-unclear) DME1433 Jeotgalicoccus psychrophilus Not Available Not Available [7]
Unclear metabolic mechanism (DME-unclear) DME1449 Prevotella copri Not Available Not Available [7]
Unclear metabolic mechanism (DME-unclear) DME1457 Ruminococcus albus Not Available Not Available [7]
⏷ Show the Full List of 11  DME(s)
References
1 Aspirin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Effect of common single-nucleotide polymorphisms in acetylsalicylic acid metabolic pathway genes on platelet reactivity in patients with diabetes Med Sci Monit. 2013 May 27;19:394-408. doi: 10.12659/MSM.883922.
3 Isozyme-specific induction of low-dose aspirin on cytochrome P450 in healthy subjects. Clin Pharmacol Ther. 2003 Mar;73(3):264-71.
4 Polymorphisms of Aspirin-Metabolizing Enzymes CYP2C9, NAT2 and UGT1A6 in Aspirin-Intolerant Urticaria. Allergy Asthma Immunol Res. 2011 Oct;3(4):273-6.
5 Inhibition of human phenol and estrogen sulfotransferase by certain non-steroidal anti-inflammatory agents. Curr Drug Metab. 2006 Oct;7(7):745-53.
6 Pharmacogenomics in aspirin intolerance. Curr Drug Metab. 2009 Nov;10(9):998-1008.
7 Gut microbiota-mediated drug-drug interaction between amoxicillin and aspirin. Sci Rep. 2019 Nov 7;9(1):16194.

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