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738-70-5

738-70-5 structure
738-70-5 structure
  • Name: Trimethoprim
  • Chemical Name: trimethoprim
  • CAS Number: 738-70-5
  • Molecular Formula: C14H18N4O3
  • Molecular Weight: 290.318
  • Catalog: API Synthetic anti-infective drugs Sulfonamides and synergists
  • Create Date: 2018-02-08 08:00:00
  • Modify Date: 2024-01-02 18:26:49
  • Trimethoprim is a bacteriostatic antibiotic used mainly in the prophylaxis and treatment of urinary tract infections.Target: DHFRTrimethoprim (TMP), an inhibitor of dihydrofolate reductase, decreases the level of tetrahydrofolate supplying one-carbon units for biosynthesis of nucleotides, proteins, and panthotenate. TMP caused induction of DnaK, DnaJ, GroEL, ClpB, and IbpA/B Hsps. Among these Hsps, IbpA/B were most efficiently induced by TMP and coaggregated with the insoluble proteins [1]. Trimethoprim binds to dihydrofolate reductase 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 synthesis. Trimethoprim's affinity for bacterial dihydrofolate reductase is several thousand times greater than its affinity for human dihydrofolate reductase. Sulfamethoxazole inhibits dihydropteroate synthetase, an enzyme involved further upstream in the same pathway. Trimethoprim and sulfamethoxazole are commonly used in combination due to their synergistic effects. This drug combination also reduces the development of resistance that is seen when either drug is used alone [2].
Name trimethoprim
Synonyms EINECS 212-006-2
Trimanyl
Triprim
Instalac
Trimethoprim
Monotrimin
MFCD00036761
5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine
Trimogal
5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine
WELLCOPRIM
Proloprim
2,4-Pyrimidinediamine, 5-[(3,4,5-trimethoxyphenyl)methyl]-
Trimpex
Monotrim
TCMDC-125538
Uretrim
Bactramin
5-(3,4,5-Trimethoxybenzyl)-2,4-pyrimidinediamine
5-{[3,4,5-tris(methyloxy)phenyl]methyl}pyrimidine-2,4-diamine
Trimopan
Syraprim
Tiempe
UNII-AN164J8Y0X
Description Trimethoprim is a bacteriostatic antibiotic used mainly in the prophylaxis and treatment of urinary tract infections.Target: DHFRTrimethoprim (TMP), an inhibitor of dihydrofolate reductase, decreases the level of tetrahydrofolate supplying one-carbon units for biosynthesis of nucleotides, proteins, and panthotenate. TMP caused induction of DnaK, DnaJ, GroEL, ClpB, and IbpA/B Hsps. Among these Hsps, IbpA/B were most efficiently induced by TMP and coaggregated with the insoluble proteins [1]. Trimethoprim binds to dihydrofolate reductase 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 synthesis. Trimethoprim's affinity for bacterial dihydrofolate reductase is several thousand times greater than its affinity for human dihydrofolate reductase. Sulfamethoxazole inhibits dihydropteroate synthetase, an enzyme involved further upstream in the same pathway. Trimethoprim and sulfamethoxazole are commonly used in combination due to their synergistic effects. This drug combination also reduces the development of resistance that is seen when either drug is used alone [2].
Related Catalog
References

[1]. Laskowska, E., et al., Trimethoprim induces heat shock proteins and protein aggregation in E. coli cells. Curr Microbiol, 2003. 47(4): p. 286-9.

[2]. Brogden, R.N., et al., Trimethoprim: a review of its antibacterial activity, pharmacokinetics and therapeutic use in urinary tract infections. Drugs, 1982. 23(6): p. 405-30.
Density 1.3±0.1 g/cm3
Boiling Point 405.2±55.0 °C at 760 mmHg
Melting Point 199-203 °C
Molecular Formula C14H18N4O3
Molecular Weight 290.318
Flash Point 198.8±31.5 °C
Exact Mass 290.137878
PSA 105.51000
LogP 0.38
Vapour Pressure 0.0±0.9 mmHg at 25°C
Index of Refraction 1.600
Storage condition 2-8°C
Stability Stable. Incompatible with strong oxidizing agents, acids.
Water Solubility DMSO: soluble | <0.1 g/100 mL at 24 ºC

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UV8225000
CHEMICAL NAME :
Pyrimidine, 2,4-diamino-5-(3,4,5-trimethoxybenzyl)-
CAS REGISTRY NUMBER :
738-70-5
BEILSTEIN REFERENCE NO. :
0625127
LAST UPDATED :
199703
DATA ITEMS CITED :
24
MOLECULAR FORMULA :
C14-H18-N4-O3
MOLECULAR WEIGHT :
290.36
WISWESSER LINE NOTATION :
T6N CNJ BZ DZ E1R CO1 DO1 EO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
56 mg/kg/7D-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - hematuria Blood - other changes Musculoskeletal - joints
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
60 mg/kg/10D-I
TOXIC EFFECTS :
Blood - thrombocytopenia
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1460 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - acute pulmonary edema Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2764 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1870 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - acute pulmonary edema Lungs, Thorax, or Respiration - dyspnea
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
132 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
90 mg/kg
TOXIC EFFECTS :
Vascular - BP lowering not characterized in autonomic section
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
31800 mg/kg/30D-I
TOXIC EFFECTS :
Blood - changes in bone marrow (not otherwise specified)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
27300 mg/kg/13W-I
TOXIC EFFECTS :
Brain and Coverings - recordings from specific areas of CNS Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
31800 mg/kg/30D-I
TOXIC EFFECTS :
Blood - changes in bone marrow (not otherwise specified) Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
2250 mg/kg
SEX/DURATION :
female 11-13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

MUTATION DATA

TEST SYSTEM :
Rodent - rat
DOSE/DURATION :
800 mg/kg/8D
REFERENCE :
JOURAA Journal of Urology. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1917- Volume(issue)/page/year: 112,348,1974 *** REVIEWS *** TOXICOLOGY REVIEW HFHBAG Hartford Hospital Bulletin. (Hartford Hospital, 80 Seymour St., Hartford, CT 06115) V.1- 1938/39- Volume(issue)/page/year: 29,364,1974 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4630 No. of Facilities: 918 (estimated) No. of Industries: 4 No. of Occupations: 9 No. of Employees: 21309 (estimated) No. of Female Employees: 16105 (estimated)
Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes T: Toxic;
Risk Phrases R25
Safety Phrases S45
RIDADR 3249
WGK Germany 3
RTECS UV8225000
Packaging Group III
Hazard Class 6.1(b)
HS Code 2933599090
HS Code 2933599090
Summary 2933599090. other compounds containing a pyrimidine ring (whether or not hydrogenated) or piperazine ring in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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