2-hydroxypropanoic acid; 5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine

• ChemBase ID: 133985
• Molecular Formular: C17H24N4O6
• Molecular Mass: 380.39566
• Monoisotopic Mass: 380.16958451
• SMILES: CC(C(=O)O)O.COc1cc(cc(c1OC)OC)Cc1cnc(nc1N)N
• Canonical SMILES: OC(=O)C(O)C.COc1cc(Cc2cnc(nc2N)N)cc(c1OC)OC
• InChI: InChI=1S/C14H18N4O3.C3H6O3/c1-19-10-5-8(6-11(20-2)12(10)21-3)4-9-7-17-14(16)18-13(9)15;1-2(4)3(5)6/h5-7H,4H2,1-3H3,(H4,15,16,17,18);2,4H,1H3,(H,5,6)
• InChIKey: IIZVTUWSIKTFKO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxypropanoic acid; 5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine
• IUPAC Traditional name: lactic acid; trimethoprim
• Synonyms: Trimethoprim lactate salt; 2,4-二氨基-5-(3,4,5-三甲氧基苄基)嘧啶 乳酸盐; 甲氧苄啶 乳酸盐

Database IDs

• CAS Number: 23256-42-0
• EC Number: 245-533-1
• MDL Number: MFCD00171722
• PubChem SID: 162228262
• PubChem CID: 3084396

CALCULATED PROPERTIES

• Acid pKa: 17.334406
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 0.020083463
• LogD (pH = 7.4): 1.0960962
• Log P: 1.2839073
• Molar Refractivity: 81.5094 cm^3
• Polarizability: 29.759577 Å^3
• Polar Surface Area: 105.51 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98%

DETAILS

Sigma Aldrich - T0667

Application
Trimethoprim is primarily used as an antibacterial agent. It has dihydrofolate reductase inhibitor activity with selectivity for the prokaryote enzyme. It is used clinically to treat urinary tract infections, mild acute prostatitis, recurrent cystitis, asymptomatic bacteriuria during pregnancy and respiratory tract infections1. Trimethoprim lactate salt is used as a selection agent2.
Biochem/physiol Actions
The combination of trimethoprim and sulfamethoxazole interferes with the cellular metabolism of folic acid in the bacterial cell by blocking the biosynthesis of nucleotides. Trimethoprim binds to prokaryote-specific dihydrofolate reductase (DHFR) and inhibits the reduction of dihydrofolic acid (DHF) to tetrahydrofolic acid (THF). THF is an essential precursor in the thymidine synthesis pathway and interference with this pathway inhibits bacterial DNA synthesis1.