Basic information
- Name:
TRIMETHOPRIM and SULPHAMETHOXAZOLE
- CAS No.:
8064-90-2
- Molecular Structure:
- Formula:
- C14H18N4O3•C10H11N3O3S
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Chemistry
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IUPAC Name: 5-[(3,4,5-Trimethoxyphenyl)methyl]pyrimidine-2,4-diamine
Molecular Formula: C14H18N4O3
Molecular Weight: 290.32 g/mol
Canonical SMILES: COC1=CC(=CC(=C1OC)OC)CC2=CN=C(N=C2N)N
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)
Classification Code: Anti-infective agents; Anti-infective agents, urinary; Antimalarials; Antiparasitic Agents; Antiprotozoal Agents; Drug / Therapeutic Agent; Human Data; Renal Agents
Index of Refraction: 1.608
Molar Refractivity: 80.25 cm3
Molar Volume: 231.8 cm3
Surface Tension: 53.9 dyne/cm
Density: 1.252 g/cm3
Flash Point: 271.9 °C
Enthalpy of Vaporization: 80.02 kJ/mol
Boiling Point: 526 °C at 760 mmHg
Vapour Pressure of Trimethoprim (CAS NO.8064-90-2): 3.74E-11 mmHg at 25 °C
Uses
Trimethoprim (CAS NO.8064-90-2) is a bacteriostatic antibiotic mainly used in the prophylaxis and treatment of urinary tract infections and was commonly used in a 1:5 combination with sulfamethoxazole, a sulfonamide antibiotic, which inhibits an earlier step in the folate synthesis pathway. It is used as monotherapy and indicated for the prophylaxis and treatment of urinary tract infections.
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| child | TDLo | oral | 432mg/kg/9D-I (432mg/kg) | BLOOD: THROMBOCYTOPENIA | Southern Medical Journal. Vol. 76, Pg. 503, 1983. |
| human | LDLo | oral | 274mg/kg/10D- (274mg/kg) | CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP LUNGS, THORAX, OR RESPIRATION: CYANOSIS KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED | Lancet. Vol. 1, Pg. 831, 1978. |
| man | TDLo | intravenous | 80mg/kg/4D-I (80mg/kg) | Annals of Internal Medicine. Vol. 103, Pg. 161, 1985. | |
| man | TDLo | oral | 457mg/kg/5D-I (457mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD ENDOCRINE: HYPOGLYCEMIA | New York State Journal of Medicine. Vol. 84, Pg. 30, 1984. |
| man | TDLo | unreported | 576mg/kg/1W-I (576mg/kg) | GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF ENDOCRINE PANCREAS | Annals of Internal Medicine. Vol. 104, Pg. 363, 1986.
|
| mouse | LD50 | intraperitoneal | 2010mg/kg (2010mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA | Chemotherapy Vol. 21, Pg. 175, 1973. |
| mouse | LD50 | oral | 3740mg/kg (3740mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION BEHAVIORAL: ATAXIA | Kiso to Rinsho. Clinical Report. Vol. 12, Pg. 2716, 1978. |
| mouse | LD50 | subcutaneous | > 3gm/kg (3000mg/kg) | Chemotherapy Vol. 21, Pg. 175, 1973. | |
| rat | LD50 | intraperitoneal | 1840mg/kg (1840mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Chemotherapy Vol. 21, Pg. 175, 1973. |
| rat | LD50 | oral | 5350mg/kg (5350mg/kg) | SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Kiso to Rinsho. Clinical Report. Vol. 12, Pg. 2716, 1978. |
| rat | LD50 | subcutaneous | > 3gm/kg (3000mg/kg) | Chemotherapy Vol. 21, Pg. 175, 1973. | |
| women | TDLo | oral | 19mg/kg (19mg/kg) | LUNGS, THORAX, OR RESPIRATION: DYSPNEA LUNGS, THORAX, OR RESPIRATION: CYANOSIS | Annals of Internal Medicine. Vol. 106, Pg. 331, 1987. |
| women | TDLo | oral | 22400ug/kg/7D (22.4mg/kg) | LIVER: "JAUNDICE, CHOLESTATIC" SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | Postgraduate Medical Journal. Vol. 56, Pg. 202, 1980. |
Safety Profile
Human poison by ingestion. Moderately toxic experimentally by ingestion and intraperitoneal routes. Human systemic effects by ingestion and intravenous routes: decreased urine volume or anuria, skin dermatitis, fever and other metabolic changes. When heated to decomposition it emits very toxic fumes of NOx and SOx.
Specification
Trimethoprim (CAS NO.8064-90-2), its Synonyms are Chemitrim ; Septrim ; SMZ/TMP ; Sulfamethoxazole/Trimethoprim ; Trimethoprim-Sulfamethoxazole Combination .
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