Trimethoprim

Modify Date: 2024-01-02 18:26:49

Trimethoprim structure	Common Name	Trimethoprim
	CAS Number	738-70-5	Molecular Weight	290.318
	Density	1.3±0.1 g/cm3	Boiling Point	405.2±55.0 °C at 760 mmHg
	Molecular Formula	C₁₄H₁₈N₄O₃	Melting Point	199-203 °C
	MSDS	Chinese USA	Flash Point	198.8±31.5 °C

Use of Trimethoprim

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
Synonym	More Synonyms

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	Signaling Pathways >> Cell Cycle/DNA Damage >> Antifolate Research Areas >> Inflammation/Immunology
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.

Description

Related Catalog

Signaling Pathways >> Cell Cycle/DNA Damage >> Antifolate

Research Areas >> Inflammation/Immunology

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

Trimethoprim MSDS(Chinese)

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

Precursor 7
CAS#:55694-05-8 2,4-Dichloro-5-... CAS#:74-88-4 methyl iodide CAS#:30078-48-9 3-Anilino-2-(3,... CAS#:506-93-4 Guanidine nitrate
CAS#:86-81-7 3,4,5-Trimethox... CAS#:30077-81-7 3-Morpholino-2-... CAS#:113-00-8 guanidine
DownStream 4
CAS#:30806-86-1 (2,4-diaminopyr... CAS#:554-68-7 Triethylammoniu... CAS#:68496-29-7 N-[4-amino-5-(3... CAS#:66093-35-4 Talmetoprim

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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EINECS 212-006-2

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5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

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5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine

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Trimpex

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TCMDC-125538

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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

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Trimethoprim

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