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8064-90-2

Basic Information
CAS No.: 8064-90-2
Name: SMZ/TMP
Molecular Structure:
Molecular Structure of 8064-90-2 (SMZ/TMP)
Formula: C14H18N4O3•C10H11N3O3S
Molecular Weight: 543.66
Synonyms: Sulfamethoxazole/Trimethoprim;TRIMETHOPRIM/SULPHAMETHOXAZOLE;Chemitrim;SMZ/TMP;Trimethoprim-Sulfamethoxazole Combination;Septrim;
Boiling Point: 526°C at 760 mmHg
Flash Point: 271.9°C
Safety: 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.
PSA: 212.11000
LogP: 5.52100
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Chemistry


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 .