Trimethoprim hydrochlorideProduct ingredient for Trimethoprim

Name
Trimethoprim hydrochloride
Drug Entry
Trimethoprim

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.14 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.14,16 It is structurally and chemically related to pyrimethamine, another antifolate antimicrobial used in the treatment of plasmodial infections.11

Accession Number
DBSALT001480
Structure
Thumb
Synonyms
Trimethoprim HCl
UNII
9XE000OU9B
CAS Number
60834-30-2
Weight
Average: 326.78
Monoisotopic: 326.1145682
Chemical Formula
C14H19ClN4O3
InChI Key
YLCCEQZHUHUYPA-UHFFFAOYSA-N
InChI
InChI=1S/C14H18N4O3.ClH/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);1H
IUPAC Name
5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine hydrochloride
SMILES
Cl.COC1=CC(CC2=CN=C(N)N=C2N)=CC(OC)=C1OC
External Links
ChemSpider
151659
ChEMBL
CHEMBL1201080
Wikipedia
Trimethoprim
Predicted Properties
PropertyValueSource
Water Solubility0.615 mg/mLALOGPS
logP1.26ALOGPS
logP1.28ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)17.33ChemAxon
pKa (Strongest Basic)7.16ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area105.51 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity81.51 m3·mol-1ChemAxon
Polarizability29.71 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon