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

General Information of Drug (ID: DR1648)
Drug Name
Trimethoprim
Synonyms
Trimanyl; Trimethioprim; Trimethoprime; Trimethoprimum; Trimetoprim; Trimetoprima; Trimopan; Trimpex; Triprim; Trisulcom; Trisulfam; Uretrim; Apo-Sulfatrim; Bacticel; Bactramin; Chemotrin; Cotrimel; Espectrin; Fermagex; Lagatrim; Monoprim; Monotrim; Monotrimin; NIH 204; Novotrimel; Pancidim; Proloprim; Sinotrim; Sugaprim; Sulfamar; Sulfamethoprim; Sulfoxaprim; Syraprim; Urobactrim; Wellcoprim; Wellcoprin; Zamboprim; trimethoprim; 2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine; 5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine; 738-70-5; Abaprim
Indication Infectious cystitis [ICD11: GC00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 290.32 Topological Polar Surface Area 106
Heavy Atom Count 21 Rotatable Bond Count 5
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
5578
PubChem SID
5066 ; 406777 ; 604810 ; 837167 ; 857743 ; 3146445 ; 4752045 ; 7847213 ; 7890832 ; 7980835 ; 8027414 ; 8149571 ; 8153433 ; 10321479 ; 10534335 ; 11111923 ; 11111924 ; 11113621 ; 11335764 ; 11361003 ; 11363061 ; 11365623 ; 11368185 ; 11371565 ; 11374002 ; 11376347 ; 11461975 ; 11466236 ; 11467356 ; 11484610 ; 11485852 ; 11488753 ; 11490459 ; 11492187 ; 11493981 ; 14824824 ; 17389524 ; 17405825 ; 22391545 ; 24278201 ; 24870616 ; 24889615 ; 25623645 ; 26611964 ; 26680042 ; 26697109 ; 26704777 ; 26747124 ; 26747125 ; 26751820
ChEBI ID
ChEBI:45924
CAS Number
738-70-5
TTD Drug ID
D0AO5H
Formula
C14H18N4O3
Canonical SMILES
COC1=CC(=CC(=C1OC)OC)CC2=CN=C(N=C2N)N
InChI
1S/C14H18N4O3/c1-19-10-5-8(6-11(20-2)12(10)21-3)4-9-7-17-14(16)18-13(9)15/h5-7H,4H2,1-3H3,(H4,15,16,17,18)
InChIKey
IEDVJHCEMCRBQM-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
1-NO-TMP DM002396
23278278
Oxidation - N-Oxidation 1 [2]
3-Desmethyl-TMP DM002397
12849769
Oxidation - O-Demethylation 1 [2]
3-NO-TMP DM002395
5244071
Oxidation - N-Oxidation 1 [2]
4-Desmethyl-TMP DM002398
10423570
Oxidation - O-Demethylation 1 [2]
Calpha-NAC-TMP DM002400 N. A. Oxidation - C-Oxidation 1 [2]
Calpha-OH-TMP DM002399
44362947
Oxidation - C-Oxidation 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002456 Trimethoprim 3-NO-TMP Oxidation - N-Oxidation CYP1A2 [2]
MR002457 Trimethoprim 1-NO-TMP Oxidation - N-Oxidation CYP3A4 [2]
MR002458 Trimethoprim 3-Desmethyl-TMP Oxidation - O-Demethylation CYP2C9 [2]
MR002459 Trimethoprim 4-Desmethyl-TMP Oxidation - O-Demethylation CYP3A4 [2]
MR002460 Trimethoprim Calpha-OH-TMP Oxidation - C-Oxidation CYP3A4 ... [2]
MR002461 Trimethoprim Calpha-NAC-TMP Oxidation - C-Oxidation CYP3A4 [2]
⏷ Show the Full List of 6 MR(s)
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 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[5]
References
1 Trimethoprim was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 In Vitro Hepatic Oxidative Biotransformation of Trimethoprim Drug Metab Dispos. 2015 Sep;43(9):1372-80. doi: 10.1124/dmd.115.065193.
3 Pioglitazone is metabolised by CYP2C8 and CYP3A4 in vitro: potential for interactions with CYP2C8 inhibitors. Basic Clin Pharmacol Toxicol. 2006 Jul;99(1):44-51.
4 Trimethoprim and sulfamethoxazole are selective inhibitors of CYP2C8 and CYP2C9, respectively. Drug Metab Dispos. 2002 Jun;30(6):631-5.
5 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.

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