General
Preferred name
TRIMETHOPRIM
Synonyms
BW-72U ()
BW 56-72 ()
NIH 204 ()
NSC-106568 ()
Trimethoprim ()
Trimethoprim (lactate) ()
BW 56-72, NIH 204, NSC-106568 ()
Trimethoprim-d3 ()
Trimpex 200 ()
Primsol ()
Trimogal ()
Infectotrimet ()
Polytrim ()
Proloprim ()
Proloprin ()
TCMDC-125538 ()
Trimethoprimum ()
Trimpex ()
Wellcoprim ()
BW-56-72 ()
Ipral ()
Ledatrim ()
Monotrim ()
Trimopan ()
Triprimix 200 ()
Tiempe ()
NIH-204 ()
Syraprim ()
Trimethoprim hcl ()
TRIMETHOPRIM HYDROCHLORIDE ()
Trimethoprim sulphate ()
BW 72U ()
TRIMETHOPRIM SULFATE ()
2,4-Diamino-5-(3,4,5-Trimethoxy-Benzyl)-Pyrimidin-1-Ium ()
P&D ID
PD002101
CAS
738-70-5
23256-42-0
60834-30-2
8064-90-2
56585-33-2
1189923-38-3
Tags
natural product
drug
drug candidate
available
Approved by
FDA
First approval
1973
1988
1995
Drug indication
Urinary tract infection
Antibacterial
Drug Status
vet_approved
approved
experimental
Max Phase
4.0
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
MOA Trimethoprim inhibits dihydrofolate reductase. This inhibition prevents the conversion of dihydrofolic acid (DHF) to tetrahydrofolic acid (THF) in the thymidine synthesis pathway. Trimethoprim acts on bacterial dihydrofolate reductase with thousands of times the affinity of human dihydrofolate reductase.; ; Sulfamethoxazole inhibits dihydrofolate synthetase (aka dihydropteroate synthetase), an enzyme involved further upstream in the same pathway. Trimethoprim and sulfamethoxazole are commonly used in combination due to their synergistic effects. This drug combination also reduces the development of resistance that is seen when either drug is used alone.
ROE Ten to twenty percent of trimethoprim is metabolized, primarily in the liver; the remainder is excreted unchanged in the urine.; After oral administration, 50% to 60% of trimethoprim is excreted in the urine within 24 hours, approximately 80% of this being unmetabolized trimethoprim. Trimethoprim also passes the placental barrier and is excreted in human milk.
DESCRIPTION Trimethoprim is a synthetic diaminopyrimidine molecule with antibacterial and antiprotozoal activities. Mechanistically, it inhibits bacterial dihydrofolate reductase and disrupts the conversion of dihydrofolic acid to tetrahydrofolic acid which ultimately inhibits bacterial DNA synthesis. Sulfonamide drugs potentiate trimethoprim's activity. (GtoPdb)
DESCRIPTION Potent inhibitor of bacterial and protozoal dihydrofolate reductase (LOPAC library)
Cell lines
0
Organisms
8
Compound Sets
28
Cayman Chemical Bioactives
16473
26119
CeMM library of unique drugs (CLOUD)
ChEMBL Approved Drugs
CHEMBL22
CHEMBL1201080
CHEMBL2110367
ChEMBL Drugs
CHEMBL22
CHEMBL1201080
CHEMBL2110367
CZ-OPENSCREEN Bioactive Library
Drug Repurposing Hub
DrugBank
DB00440
DB03125
DrugBank Approved Drugs
DB00440
DrugCentral
2755
DrugCentral Approved Drugs
2755
DrugMAP
DMM7CHK
DrugMAP Approved Drugs
DMM7CHK
DrugMatrix
Enamine BioReference Compounds
EU-OPENSCREEN Bioactive Compound Library
EOS100345
Guide to Pharmacology
10931
LOPAC library
MedChem Express Bioactive Compound Library
HY-B0510
HY-B0510C
NCATS Inxight Approved Drugs
AN164J8Y0X
NIH Clinical Collections (NCC)
NPC Screening Collection
Other bioactive compounds
Pandemic Response Box
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
trimethoprim
TargetMol Bioactive Compound Library
T1153
The Spectrum Collection
External IDs
97
Properties
(calculated by RDKit )
Molecular Weight
290.14
Hydrogen Bond Acceptors
7
Hydrogen Bond Donors
2
Rotatable Bonds
5
Ring Count
2
Aromatic Ring Count
2
cLogP
1.26
TPSA
105.51
Fraction CSP3
0.29
Chiral centers
0.0
Largest ring
6.0
QED
0.85
Structural alerts
2
aggregator (Aggregator Advisor)
Aggregators
aggregator (ZINC)
Aggregators
Related compounds
Custom attributes
(extracted from source data)
Selectivity
Dihydrofolate reductase
MOA
bacterial dihydrofolate reductase inhibitor
dihydrofolate reductase inhibitor
Target
Bacterial dihydrofolate reductase
DHFR
Thymidylate Synthase
DHFR, TYMS
antibiotic
Antifolate
Bacterial
Influenza Virus
Antibiotics,Bacterial,DHFR
Pathway
DNA Damage/DNA Repair
Metabolism
Cell Cycle/Checkpoint
Anti-infection
Cell Cycle/DNA Damage
Indication
urinary tract infections, ear infections, diarrhea
Disease Area
infectious disease, gastroenterology
Therapeutic Class
Antiinfective Agents
Source data