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Substance Name: Trimethoprim [USAN:USP:INN:BAN:JAN]
RN: 738-70-5
UNII: AN164J8Y0X
InChIKey: IEDVJHCEMCRBQM-UHFFFAOYSA-N

Note

  • A pyrimidine inhibitor of dihydrofolate reductase, it is an antibacterial related to PYRIMETHAMINE. It is potentiated by SULFONAMIDES and the TRIMETHOPRIM, SULFAMETHOXAZOLE DRUG COMBINATION is the form most often used. It is sometimes used alone as an antimalarial. TRIMETHOPRIM RESISTANCE has been reported.

Molecular Formula

  • C14-H18-N4-O3

Molecular Weight

  • 290.3212
 

Classification Codes

  • Anti-Infective Agents
  • Anti-Infective Agents, Urinary
  • Antibacterial
  • Antimalarials
  • Antiparasitic Agents
  • Antiprotozoal Agents
  • Cytochrome P-450 CYP2C8 Inhibitors
  • Cytochrome P-450 Enzyme Inhibitors
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Folic Acid Antagonists
  • Human Data
  • Metabolic Side Effects of Drugs and Substances
  • Mutation Data
  • Renal Agents
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Trimethoprim
  • Trimethoprim [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Trimethoprim

Synonyms

  • 2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine
  • 2,4-Pyrimidinediamine, 5-((3,4,5-trimethoxyphenyl)-methyl)-
  • 2,4-Pyrimidinediamine, 5-((3,4,5-trimethoxyphenyl)methyl)-
  • 5-((3,4,5-Trimethoxyphenyl)methyl)-2,4-pyrimidinediamine
  • 5-(3,4,5-Trimethoxybenzyl)-2,4-diaminopyrimidine
  • 5-25-13-00429 (Beilstein Handbook Reference)
  • Abaprim
  • Acuco
  • AI3-52594
  • Alcorim-F
  • Anitrim
  • Antrima
  • Antrimox
  • Apo-Sulfatrim
  • Bacdan
  • Bacidal
  • Bacide
  • Bacin
  • Bacta
  • Bacterial [Antibiotic]
  • Bacticel
  • Bactifor
  • Bactoprim
  • Bactramin
  • Bencole
  • Bethaprim
  • Biosulten
  • Briscotrim
  • BRN 0625127
  • BW 56-72
  • CCRIS 2410
  • Centrim
  • Chemotrin
  • Cidal
  • Co-Trimoxizole
  • Colizole
  • Colizole DS
  • component of Bactrim
  • component of Septra
  • Conprim
  • Cotrimel
  • Deprim
  • Diseptyl
  • Dosulfin
  • Duocide
  • EINECS 212-006-2
  • Esbesul
  • Espectrin
  • Euctrim
  • Exbesul
  • Fermagex
  • Fortrim
  • Futin
  • HSDB 6781
  • Ikaprim
  • Kombinax
  • Lagatrim
  • Lagatrim Forte
  • Lastrim
  • Lescot
  • Metoprim
  • Monoprim
  • Monotrim
  • Monotrimin
  • NIH 204
  • NIH 204 (VAN)
  • Novotrimel
  • NSC 106568
  • NSC-106568
  • Omstat
  • Pancidim
  • Proloprim
  • Protrin
  • Purbal
  • Pyrimidine, 2,4-diamino-5-(3,4,5-trimethoxybenzyl)-
  • Resprim
  • Resprim Forte
  • Roubac
  • Roubal
  • Salvatrim
  • Septrin DS
  • Septrin Forte
  • Septrin S
  • Setprin
  • Sinotrim
  • Smz-Tmp
  • Stopan
  • Streptoplus
  • Sugaprim
  • Sulfamar
  • Sulfamethoprim
  • Sulfoxaprim
  • Sulmeprim
  • Sulthrim
  • Sultrex
  • Syraprim
  • TMP
  • Tmp Smx
  • Toprim
  • Trimanyl
  • Trimeth/Sulfa
  • Trimethoprim
  • Trimethoprime
  • Trimethoprime [INN-French]
  • Trimethoprimum
  • Trimethoprimum [INN-Latin]
  • Trimetoprim
  • Trimetoprim [DCIT]
  • Trimetoprim [Polish]
  • Trimetoprima
  • Trimetoprima [INN-Spanish]
  • Trimexol
  • Trimez-IFSA
  • Trimezol
  • Trimono
  • Trimopan
  • Trimpex
  • Trimpex 200
  • Triprim
  • Trisul
  • Trisulcom
  • Trisulfam
  • Trisural
  • U-Prin
  • UNII-AN164J8Y0X
  • Uretrim
  • Uro-D S
  • Urobactrim
  • Utetrin
  • Velaten
  • Veltrim
  • Wellcoprim
  • Wellcoprin
  • WR 5949
  • Xeroprim
  • Zamboprim

Systematic Names

  • 2,4-Pyrimidinediamine, 5-((3,4,5-trimethoxyphenyl)methyl)-
  • Pyrimidine, 2,4-diamino-5-(3,4,5-trimethoxybenzyl)-
  • Trimethoprim

Mixture Names

  • Bactrim
  • Cotrim
  • Septra
  • SMZ/TMP
  • Sulfatrim

Registry Numbers

CAS Registry Number

  • 738-70-5

FDA UNII

  • AN164J8Y0X

System Generated Number

  • 0000738705

Structure Descriptors

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

IEDVJHCEMCRBQM-UHFFFAOYSA-N

Smiles

COc1cc(cc(c1OC)OC)Cc2cnc(nc2N)N

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 90mg/kg (90mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION Chemotherapy Vol. 14, Pg. 37, 1969.
mouse LD50 intraperitoneal 400mg/kg (400mg/kg)   Toksikologicheskii Vestnik. Vol. (2), Pg. 34, 1998.
mouse LD50 intravenous 132mg/kg (132mg/kg)   Journal of Chemotherapy. Vol. 5, Pg. 400, 1993.
mouse LD50 oral 2764mg/kg (2764mg/kg)   United States Patent Document. Vol. #4180578,
mouse LD50 subcutaneous > 5gm/kg (5000mg/kg)   Chemotherapy Vol. 21, Pg. 175, 1973.
rat LD50 intraperitoneal 500mg/kg (500mg/kg)   Toksikologicheskii Vestnik. Vol. (2), Pg. 34, 1998.
rat LD50 oral > 5300mg/kg (5300mg/kg)   Toksikologicheskii Vestnik. Vol. (2), Pg. 34, 1998.
rat LD50 subcutaneous > 5gm/kg (5000mg/kg)   Chemotherapy Vol. 21, Pg. 175, 1973.
women TDLo oral 56mg/kg/7D-I (56mg/kg) MUSCULOSKELETAL: JOINTS

BLOOD: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: HEMATURIA		 Postgraduate Medical Journal. Vol. 68, Pg. 391, 1992.
women TDLo oral 60mg/kg/10D-I (60mg/kg) BLOOD: THROMBOCYTOPENIA New Zealand Medical Journal. Vol. 106, Pg. 251, 1993.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 199-203 deg C   EXP
pKa Dissociation Constant 7.12 (none) 20 EXP
log P (octanol-water) 0.91 (none)   EXP
Water Solubility 400 mg/L 25 EXP
Vapor Pressure 9.88E-09 mm Hg 25 EST
Henry's Law Constant 2.39E-14 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.03E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.