Trimethoprim

TRIMETOPRIM · Trimethopim(TMP) · Trimethorim · Trimpex · Proloprim · TRIMETHORPIM · TRIMETHOPRIMUM · TRIMETHOPRIM USP

Identifikatoren & physikalische Daten

CAS No.	738-70-5
Summenformel	C14H18N4O3
Durchschnittliche Molmasse	290,32 g/mol
Monoisotopische Masse	290,13789044 g/mol
SMILES	COc1cc(Cc2cnc(N)nc2N)cc(OC)c1OC
InChIKey	IEDVJHCEMCRBQM-UHFFFAOYSA-N
PubChem CID	5578
ChEMBL	CHEMBL22
ChEBI	CHEBI:45924
EC No.	212-006-2
DTXSID	DTXSID3023712
Lokaler Name	Trimethoprim

Chemische & physikalische Eigenschaften

XLogP	0,9
Polarare Oberfläche (TPSA)	106
H-Brücken-Donoren	2
H-Brücken-Akzeptoren	7
Frei drehbare Bindungen	5
Schwere Atome	21
Formalladung	0
Komplexität	307
Stoffklassen	Pharmaceutical
Arzneimittel	Pharmaceuticals -> Listed in ZINC15Pharmaceuticals -> AntibioticsPharmaceuticals -> Antibiotics (Bacteriostatic)Pharmaceuticals -> Used in Switzerland
LogP (Verteilungskoeffizient)	log Kow = 0.910.60.92
Geruch	Odorless
Geschmack	Bitter
Color/Form	White to cream, crystalline powder
Löslichkeit	less than 1 mg/mL at 75 °F (NTP, 1992)... Very slightly soluble in water and slightly soluble in alcohol.Soluble in N,N-dimethylacetamide (DMAC) at 13.86benzyl alcohol at 7.29propylene glycol at 2.57chloroform at 1.82methanol at 1.21ether at 0.003benzene at 0.002 g/100 ml at 25 °C.In water, 400 mg/l @ 25 °C6.15e-01 g/LDMSO: soluble<0.1 g/100 mL at 24 ºC
Human Drugs	Breast FeedingLactationMilk, HumanAnti-Infective Agents, UrinaryAntibacterial AgentsFolic Acid AntagonistsFDA approved drugs -> Active ingredientAccess group antibiotics
Animal Drugs	Active Ingredients (Trimethoprim) -> FDA GreenbookPharmaceuticals -> UK Veterinary Medicines Directorate ListPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Decomposition	When heated to decomposition it emits toxic fumes of /nitrogen oxide/.
Schmelzpunkt	390 to 397 °F (NTP, 1992)199-203 °C199 - 203 °C
Physical Description	Trimethoprim is an odorless white powder. Bitter taste. (NTP, 1992)Solid
Siedepunkt	432.41°C (rough estimate)
Dichte	1.1648 (rough estimate)
Brechungsindex	1.6000 (estimate)
Lagerbedingungen	2-8°C
Aggregatzustand	white powder
pKa (Säurekonstante)	6.6(at 25℃)
Farbe	colorless or white
Biologische Quelle	synthetic
Merck	14,9709
BRN	625127
Henry-Konstante	4.1×108 mol/(m3Pa) at 25℃, HSDB (2015)
BCS Class	2
Stabilität	Stable. Incompatible with strong oxidizing agents, acids.
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-N
SMILES	COc1cc(Cc2cnc(N)nc2N)cc(OC)c1OC
CAS Datenbank	738-70-5(CAS DataBase Reference)
NIST chemische Informationen	Trimethoprim(738-70-5)
EPA chemische Informationen	Trimethoprim (738-70-5)

Sicherheit & Vorschriften

GHS-Einstufung	This chemical does not meet GHS hazard criteria for 7.9% (11 of 140) of reports.DangerH302 (85%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P260, P264, P270, P273, P280, P301+P317, P318, P319, P330, P391, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 140 reports by companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Regulatorische Informationen	Chemical: 2,4-Pyrimidinediamine, 5-[(3,4,5-trimethoxyphenyl)methyl]-Trimethoprim: Does not have an individual approval but may be used under an appropriate group standard
DOT-Kennzeichnung	Poison
Brandgefahren	Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
Gesundheitsgefahren	SYMPTOMS: Symptoms of exposure to this compound may include rash, pruritis, dermatitis, epigastric distress, nausea, and vomiting.
FDA-Anforderungen	Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended21 U.S.C. 321-392).Trimethoprim and sulfadiazine tablets. (a) Each tablet contains 30 mg (5 mg of trimethoprim and 25 mg of sulfadiazine), 120 mg (20 mg of trimethoprim and 100 mg of sulfadiazine), 480 mg (80 mg of trimethoprim and 400 mg of sulfadiazine) or 960 mg (160 mg of trimethoprim and 800 mg of sulfadiazine) ... (c) Conditions of use: (1) The drug is used in dogs where systemic antibacterial action against sensitive organisms is required, either alone or as an adjunct to surgery or debridement with associated infection. The drug is indicated where control of bacterial infection is required during the treatment of acute urinary tract infections, acute bacterial complications of distemper, acute respiratory tract infections, acute alimentary tract infections, wound infections, and abscesses. ... (6) The drug should not be used in patients showing marked liver parenchymal damage or blood dyscrasia, nor in those with a history of sulfonamide sensitivity. (7) Federal law restricts this drug to use by or on the order of a licensed veterinarian. /Trimethoprim and sulfadiazine/

Anwendungen & Verwendung

Beschreibung

Trimethoprim selectivity between bacterial and mammalian dihydrofolate reductases results from the subtle but significant architectural differences between these enzyme systems. Whereas the bacterial enzyme and the mammalian enzyme both efficiently catalyze the conversion of dihydrofolic acid to tetrahydrofolic acid, the bacterial enzyme is sensitive to inhibition by trimethoprim by up to 40,000-fold lower concentrations than the mouse enzyme is. This difference explains the useful selective toxicity of trimethoprim.

Verwenden

An antibacterial and inhibitor of formylation. Dihydrofolate reductase inhibitor with selectivity for the prokaryote enzyme.Trimethoprim is an antibiotic involved in the treatment of urinary tract infections, middle ear infections and travelers diarrhea. It is associated with sulfamethoxazole and interferes with the cellular metabolism of folic acid in the bacterial cell by blocking the biosynthesis of nucleotides. Furthermore, It is also used to treat and prevent Pneumocystis jiroveci pneumonia.