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TRIMETHOPRIM

Created:1999-07-08
Last modified:  2011-06-04

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Chemical Details

Formal Charge0
Atom Count39
Chiral Atom Count0
Bond Count40
Aromatic Bond Count12
2D diagram of TOP
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Chemical Component Summary

NameTRIMETHOPRIM
Systematic Name (OpenEye OEToolkits)5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine
FormulaC14 H18 N4 O3
Molecular Weight290.318
TypeNON-POLYMER

Chemical Descriptors

TypeProgramVersionDescriptor
SMILESACDLabs10.04n1c(N)c(cnc1N)Cc2cc(OC)c(OC)c(OC)c2
SMILESCACTVS3.341COc1cc(Cc2cnc(N)nc2N)cc(OC)c1OC
SMILESOpenEye OEToolkits1.5.0COc1cc(cc(c1OC)OC)Cc2cnc(nc2N)N
Canonical SMILESCACTVS3.341 COc1cc(Cc2cnc(N)nc2N)cc(OC)c1OC
Canonical SMILESOpenEye OEToolkits1.5.0 COc1cc(cc(c1OC)OC)Cc2cnc(nc2N)N
InChIInChI1.03 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)
InChIKeyInChI1.03 IEDVJHCEMCRBQM-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
DrugBank IDDB00440 
NameTrimethoprim
Groups
  • vet_approved
  • approved
DescriptionTrimethoprim is an antifolate antibacterial agent that inhibits bacterial dihydrofolate reductase (DHFR), a critical enzyme that catalyzes the formation of tetrahydrofolic acid (THF) - in doing so, it prevents the synthesis of bacterial DNA and ultimately continued bacterial survival.[L11893] Trimethoprim is often used in combination with [sulfamethoxazole] due to their complementary and synergistic mechanisms but may be used as a monotherapy in the treatment and/or prophylaxis of urinary tract infections.[L11893,L11830] It is structurally and chemically related to [pyrimethamine], another antifolate antimicrobial used in the treatment of plasmodial infections.[T707]
Synonyms
  • 5-[(3,4,5-trimethoxyphenyl)methyl]-2,4-pyrimidinediamine
  • Trimethoprimum
  • Triméthoprime
  • Trimethoprim
  • 2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine
Brand Names
  • Protrin Tab
  • Sandoz Polytrimethoprim
  • Sulfatrim Pediatric
  • Roubac Tab 160/800
  • Bactrim Roche Suspension Paediatric
IndicationAs a monotherapy, trimethoprim is indicated for the treatment of acute episodes of uncomplicated urinary tract infections caused by susceptible bacteria, including _E. coli._, _K. pneumoniae_, _Enterobacter spp._, _P. mirabilis_, and coagulase-negative _Staphylococcus_ species.[L11893,L11890] In various formulations in combination with [sulfamethoxazole], trimethoprim is indicated for the following infections caused by bacteria with documented susceptibility: urinary tract infections, acute otitis media in pediatric patients (when clinically indicated), acute exacerbations of chronic bronchitis in adults, enteritis caused by susceptible _Shigella_, prophylaxis and treatment of _Pneumocystis jiroveci_ pneumonia, and travelers' diarrhea caused by enterotoxigenic _E. coli_.[L11830,L11863] Trimethoprim is available as an ophthalmic solution in combination with [polymyxin B] for the treatment of acute bacterial conjunctivitis, blepharitis, and blepharoconjunctivitis caused by susceptible bacteria.[L11887]
Categories
  • Agents causing hyperkalemia
  • Agents Causing Muscle Toxicity
  • Anti-Infective Agents
  • Anti-Infective Agents, Urinary
  • Antibacterials for Systemic Use
ATC-Code
  • J01EE03
  • J01EA01
  • J04AM08
  • J01EE01
  • J01EE04
CAS number738-70-5

Drug Targets

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
NameTarget SequencePharmacological ActionActions
Dihydrofolate reductaseMVGSLNCIVAVSQNMGIGKNGDLPWPPLRNEFRYFQRMTTTSSVEGKQNL...unknownmodulator
Dihydrofolate reductaseMISLIAALAVDRVIGMENAMPWNLPADLAWFKRNTLNKPVIMGRHTWESI...unknowninhibitor
Cytochrome P450 2C9MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...unknownsubstrate
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate
Cytochrome P450 1A2MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...unknownsubstrate
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL22
PubChem 5578
ChEMBL CHEMBL22
ChEBI CHEBI:45924
CCDC/CSD AMXBPM13, AMXBPM12, AMXBPM10, AMXBPM11, QASHEX, GIGQIX, BEXVOP
COD 4512814, 4512813, 2019772