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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
- All
- Classifications
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- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
- Anti-Dyskinesia Agents
- Anti-Infective Agents
- Anti-Infective Agents, Urinary
- Antibacterial
- Antimalarials
- Antiparasitic Agents
- Antiprotozoal Agents
- Central Nervous System 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
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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
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-NSmiles
COc1cc(Cc2cnc(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.