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Trimethoprim

Pyrimethamine class antibacterial agents Side effects Chemical Properties Uses Production methods
Trimethoprim
Trimethoprim structure
CAS No.
738-70-5
Chemical Name:
Trimethoprim
Synonyms
Ipral;Baktar;Tiempe;wr5949;5-(3,4;bw56-72;NIH 204;Trimpex;Uretrim;Veltrim
CBNumber:
CB2745185
Molecular Formula:
C14H18N4O3
Formula Weight:
290.32
MOL File:
738-70-5.mol

Trimethoprim Properties

Melting point:
199-203 °C
Boiling point:
432.41°C (rough estimate)
Density 
1.1648 (rough estimate)
refractive index 
1.6000 (estimate)
storage temp. 
2-8°C
solubility 
DMSO: soluble
form 
white powder
pka
6.6(at 25℃)
color 
colorless or white
Water Solubility 
<0.1 g/100 mL at 24 ºC
Merck 
14,9709
BRN 
625127
Stability:
Stable. Incompatible with strong oxidizing agents, acids.
CAS DataBase Reference
738-70-5(CAS DataBase Reference)
NIST Chemistry Reference
Trimethoprim(738-70-5)
EPA Substance Registry System
2,4-Pyrimidinediamine, 5-[(3,4,5-trimethoxyphenyl) methyl]-(738-70-5)
SAFETY
  • Risk and Safety Statements
Hazard statements  H227
Precautionary statements  P210e-P280a-P370+P378a-P403+P235-P501a
Hazard Codes  T
Risk Statements  25
Safety Statements  45-24/25
RIDADR  3249
WGK Germany  3
RTECS  UV8225000
8-10-21
HazardClass  6.1(b)
PackingGroup  III
HS Code  29335995
Toxicity LD50 orally in mice: 7000 mg/kg (Yamamoto)

Trimethoprim price More Price(22)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 1692505 Trimethoprim United States Pharmacopeia (USP) Reference Standard 738-70-5 300mg $348 2018-11-13 Buy
Sigma-Aldrich 16967 Trimethoprim certified reference material, TraceCERT 738-70-5 100mg $141 2018-11-13 Buy
TCI Chemical T2286 Trimethoprim >98.0%(HPLC)(T) 738-70-5 25g $119 2018-11-22 Buy
Alfa Aesar J63053 Trimethoprim 738-70-5 5g $70.4 2018-11-13 Buy
Alfa Aesar J63053 Trimethoprim 738-70-5 1g $26.3 2018-11-13 Buy

Trimethoprim Chemical Properties,Uses,Production

Pyrimethamine class antibacterial agents

Trimethoprim is a lipophilic and weak alkaline pyrimethamine class bacteriostatic agent. It is a white or almost white crystalline powder, odorless, bitter, and slightly soluble in chloroform, ethanol or and acetone, but almost insoluble in water and highly soluble in glacial acetic acid solution. It has an antibacterial spectrum which is similar with sulfa drugs, but with a strong antibacterial effect. It has a good effect on treating Escherichia coli, Proteus mirabilis, Klebsiella pneumoniae, Staphylococcus saprophyticus, and a variety of other gram-positive and negative bacteria. But it is ineffective against Pseudomonas aeruginosa infection. Its minimum inhibitory concentration is often less than 10 mg/L with using alone being easy to cause bacterial resistance, and thus it is generally not used alone, and mainly combined with sulfa drug to form compound preparation for clinical treatment of urinary tract infections, intestinal infections, respiratory infections, dysentery, enteritis, typhoid fever, meningitis, otitis media, meningitis, sepsis and soft tissue infections. It has an effect on treating typhoid and paratyphoid effect which is not less than ampicillin; It can also be combined with long-acting sulfa drugs for prevention and treatment of drug-resistant falciparum malaria.
The basic principle of anti-bacterial of trimethoprim is to interfere with folate metabolism in bacteria. The main mechanism of action is the selective inhibition of the activity of dihydrofolate reductase in bacteria so that dihydrofolate can’t be reduced to tetrahydrofolate. Since the synthesis of folic acid is the main part of a nucleic acid biosynthesis, and therefore the product prevents bacterial nucleic acids and proteins synthesis. Moreover, the binding affinity of trimethoprim (TMP) to bacterial dihydrofolate reductase enzyme is five times as strong as that to the mammalian dihydrofolate reductase. The combination between it with sulfa drugs can cause dual blockage to the folic acid biosynthesis metabolism of bacteria so that there is a synergistic effect which will enhance the antibacterial activity of sulfa drugs, and can turn antibacterial effect to bactericidal effect which reduce the drug-resistant strains. In addition, the product can also enhance the antibacterial effects of a variety of other antibiotics (such as tetracycline, gentamicin).

Side effects

Trimethoprim (referred to as the TMP) has a low toxicity with commonly used dose causing rare cases of adverse reactions. Since the product can interfere with folate metabolism which may cause patients’ suffer from some adverse reactions of blood systems such as anemia, leukopenia and thrombocytopenia. This is commonly observed in cases of overdose or long duration of application. Therefore, during the treatment, it is necessary to regularly check blood condition. This product has the maximum daily dosage being lower than 0.5g with continuous medication time being less than one week. Upon blood system adverse reaction, the patient can orally administrate folic acid preparation for treatment. This product is not suitable to be simultaneously combined with anticancer drugs, antiepileptic drugs and other folic acid antagonists used; the combination between TMP and SMZ or SD even can cause crystallization of urine. Other adverse reactions also include mild skin rash and gastrointestinal reactions.

Chemical Properties

White crystalline powder, odorless, bitter taste. Melting point: 199-203 °C. It is insoluble in water, ether, benzene, and slightly soluble in chloroform, methanol, highly soluble in acetic acid.

Uses

1. It can be used as a synergistic antimicrobial drugs; it can also be used for treating bacterial infections and coccidiosis in poultry.
2. It is a novel orally administrated broad-spectrum antibiotics. It has a similar antibacterial spectrum with sulfa drugs but with a stronger potency. It is effective in treating a variety of Gram positive and negative bacteria. Since the bacteria is easy to evolve drug resistance to this product, it is not suitable to be used alone as an antimicrobial drug. The combination between trimethoprim and sulfa drugs can enhance the antibacterial activity by several times to several dozens of times. The product is mainly used for being as the synergistic drugs for sulfonamide drugs with a general ratio of 1: 5 for usage. It can also be used as a veterinary drug for treatment of avian sepsis caused by Escherichia coli, salmonellosis, fowl typhoid, cholera, and respiratory system secondary bacterial infections. It can also be used for the treatment of coccidiosis.
3. Application: used as antibacterial synergistic drugs; treat respiratory tract infections, urinary tract infections and intestinal infections when being used alone.
The above information is edited by the chemicalbook of Dai xiongfeng.

Production methods

Use Trimethoxybenzaldehyde as raw material; first condense with methoxypropionitrile to produce 3'4'5'-trimethoxy-2-cyano-3-methoxy-propene; and cyclized together with guanidine nitrate in the presence of methanol/sodium methoxide.

Chemical Properties

Crystalline

Uses

anti-inflammatory

Uses

An antibacterial agent which selectively inhibits dihydrofolate reductase.

brand name

Proloprim (Monarch); Trimpex (Roche).

General Description

Odorless white powder. Bitter taste.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Trimethoprim readily forms salts with acids. .

Fire Hazard

Flash point data for Trimethoprim are not available. Trimethoprim is probably combustible.

Clinical Use

Trimethoprim (5-[(3,4,5-trimethoxyphenyl)methyl]-2,4-pyrimidinediamine or 2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine) is closely related to several antimalarialsbut does not have good antimalarial activity by itself; it is,however, a potent antibacterial. Originally introduced incombination with sulfamethoxazole, it is now available as asingle agent.
Approved by the FDA in 1980, trimethoprim as a singleagent is used only for the treatment of uncomplicatedurinary tract infections. The argument for trimethoprim asa single agent was summarized in 1979 by Wormser andDeutsch. They point out that several studies comparingtrimethoprim with TMP–SMX for the treatment ofchronic urinary tract infections found no statistically relevantdifference between the two courses of therapy.The concern is that when used as a single agent, bacterianow susceptible to trimethoprim will rapidly developresistance. In combination with a sulfonamide, however,the bacteria will be less likely to do so. That is, they willnot survive long enough to easily develop resistance toboth drugs.

Trimethoprim Preparation Products And Raw materials

Raw materials

Preparation Products


Trimethoprim Suppliers

Global( 347)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Shenzhen Sendi Biotechnology Co.Ltd.
0755-23311925 18102838259
0755-23311925 Abel@chembj.com CHINA 3194 55
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 20672 55
Mainchem Co., Ltd.
+86-0592-6210733
+86-0592-6210733 sales@mainchem.com CHINA 32447 55
PI & PI BIOTECH INC.
020-81716320
020-81716319 Sales@pipitech.com CHINA 2543 55
Hubei XinRunde Chemical Co., Ltd.
+8615102730682; +8618874586545
02783214688 bruce@xrdchem.cn CHINA 535 55
Hefei TNJ Chemical Industry Co.,Ltd.
86-0551-65418684 18949823763
86-0551-65418684 info@tnjchem.com China 1861 55
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 30002 58
Hebei Ruishun Trade Co.,LTD
17052563120
Mike@rsbiology.com CHINA 302 58
Chemwill Asia Co.,Ltd.
86-21-51086038
86-21-51861608 chemwill_asia@126.com;sales@chemwill.com;chemwill@hotmail.com;chemwill@gmail.com CHINA 23976 58
Hubei Jusheng Technology Co.,Ltd.
86-18871470254
027-59599243 sales@jushengtech.com CHINA 28236 58

View Lastest Price from Trimethoprim manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2019-04-03 Trimethoprim in stock GMP Factory
738-70-5
US $1.00 / KG 1KG GMP Factory in China 1000 metric tons Chemwill Asia Co.,Ltd.
2019-07-22 Trimethoprim
738-70-5
US $1.00 / g 1g 99% 1000 Kilogram/Kilograms per Month Cangzhou Wanyou New Material Technology Co.,Ltd
2018-08-20 Trimethoprim
738-70-5
US $1.00 / KG 1G 98% 100KG career henan chemical co

Trimethoprim Spectrum


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