TOP

TRIMETHOPRIM

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

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Chemical Details
Formal Charge	0
Atom Count	39
Chiral Atom Count	0
Bond Count	40
Aromatic Bond Count	12

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Chemical Component Summary
Name	TRIMETHOPRIM
Systematic Name (OpenEye OEToolkits)	5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine
Formula	C₁₄ H₁₈ N₄ O₃
Molecular Weight	290.318
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	n1c(N)c(cnc1N)Cc2cc(OC)c(OC)c(OC)c2
SMILES	CACTVS	3.341	COc1cc(Cc2cnc(N)nc2N)cc(OC)c1OC
SMILES	OpenEye OEToolkits	1.5.0	COc1cc(cc(c1OC)OC)Cc2cnc(nc2N)N
Canonical SMILES	CACTVS	3.341	COc1cc(Cc2cnc(N)nc2N)cc(OC)c1OC
Canonical SMILES	OpenEye OEToolkits	1.5.0	COc1cc(cc(c1OC)OC)Cc2cnc(nc2N)N
InChI	InChI	1.03	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)
InChIKey	InChI	1.03	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 ID	DB00440 ?
Name	Trimethoprim
Groups	approved vet_approved
Description	Trimethoprim 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	Trimethoprim sulfate 5-[(3,4,5-trimethoxyphenyl)methyl]-2,4-pyrimidinediamine Trimethoprim hydrochloride Trimethoprim Triméthoprime 2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine Trimethoprimum Trimetoprima
Brand Names	Sulfamethoxazole and Trimethoprim (Double Strength) Sulfatrim DS Sulfatrim Pediatric PMS-polytrimethoprim Polytrim Ophthalmic Solution Coptin Tab Roubac Tab 80/400 Sulfamethoxazole and Trimethoprim Injection, BP Roubac Tab 160/800 TRIMPEX trimethoprim hydrochloride Septra Injection Nu-cotrimox Sus 40/8mg/ml Protrin Df Tab Polytrim Proloprim Tab 100mg Protrin Tab Coptin Oral Suspension Sulfamethoxazole and Trimethoprim DS Teva-trimel DS Trisulfa Tab Sulfamethox-TMP DS SULFAMETHOXAZOLE AND TRIMETHOPRIM double strength Apo-sulfatrim Oral Suspension Septra Grape Teva-trimel Bactrim Roche Suspension Paediatric Polymyxin B Sulfate and Trimethoprim Sulfate Proloprim 200 Tab 200mg sulfamethoxazole-trimethoprim (SMZ) Bactrim Trisulfa S Suspension Septra Sulfamethoxazole and Trimethoprim Double Strength Bactrim DS Roche Tab Bactrim Roche Tab Bactrim Roche Inj POLYMYXIN B SULFATE and TRIMETHOPRIM SULFATE Septra DS Sulfamethoxazole and Trimethoprim for Injection, USP Polymyxin B Sulfate and Trimethoprim Proloprim Primsol Septra Pediatric Suspension Sulfatrim Trimethoprim Septra DS Tablets Trisulfa DS Tab Sulfamethoxazole and Trimethoprim Tablets Trimethoprim Tablets Trimethoprim sulfate and Polymyxin B sulfate Sulfameth/Trimeth-DS SULFAMETHOXAZOLE and TRIMETHOPRIM Sulfamethoxazole and Trimethoprim Bactrim DS Sandoz Polytrimethoprim SulfatrimTM Pediatric Suspension Riva-sep DS PrimSol Nu-cotrimox Tab 400/80mg Nu-cotrimox-DS Tab 800/160mg
Indication	As 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 Antibiotics for Pneumocystis Pneumonia Antiinfectives for Systemic Use Antimycobacterials Cytochrome P-450 CYP1A2 Substrates Cytochrome P-450 CYP2C8 Inhibitors Cytochrome P-450 CYP2C8 Inhibitors (moderate) Cytochrome P-450 CYP2C8 Substrates Cytochrome P-450 CYP2C9 Substrates Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Drugs causing inadvertant photosensitivity Drugs that are Mainly Renally Excreted Enzyme Inhibitors Folic Acid Antagonists MATE 1 Inhibitors MATE 1 Substrates MATE 2 Inhibitors MATE 2 Substrates MATE inhibitors MATE substrates P-glycoprotein inducers P-glycoprotein inhibitors P-glycoprotein substrates Photosensitizing Agents Pyrimidines Renal Agents Sulfonamides and trimethoprim Trimethoprim and Derivatives
ATC-Code	J01EE03 J01EA01 J04AM08 J01EE01 J01EE04 J01EE02 J01EE05 J01EE07
CAS number	738-70-5

Drug Targets

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License

Name	Target Sequence	Pharmacological Action	Actions
Dihydrofolate reductase	MVGSLNCIVAVSQNMGIGKNGDLPWPPLRNEFRYFQRMTTTSSVEGKQNL...	unknown	modulator
Dihydrofolate reductase	MISLIAALAVDRVIGMENAMPWNLPADLAWFKRNTLNKPVIMGRHTWESI...	unknown	inhibitor
Cytochrome P450 2C9	MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...	unknown	substrate
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate
Cytochrome P450 1A2	MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...	unknown	substrate
Cytochrome P450 2C8	MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI...	unknown	substrate,inhibitor
ATP-dependent translocase ABCB1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate
Multidrug and toxin extrusion protein 1	MEAPEEPAPVRGGPEATLEVRGSRCLRLSAFREELRALLVLAGPAFLVQL...	unknown	substrate,inhibitor
Multidrug and toxin extrusion protein 2	MDSLQDTVALDHGGCCPALSRLVPRGFGTEMWTLFALSGPLFLFQVLTFM...	unknown	substrate,inhibitor
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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 Name	Reference
Pharos	CHEMBL22
PubChem	5578
ChEMBL	CHEMBL22
ChEBI	CHEBI:45924
CCDC/CSD	AMXBPM13, AMXBPM12, AMXBPM10, AMXBPM11, QASHEX, GIGQIX, BEXVOP
COD	4512814, 4512813, 2019772