ChemicalBook
Chinese Japanese Germany Korea

(2S,5R,6S)-6-[(3-Hydroxy-3-oxo-2-thiophen-3-ylpropanoyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

(2S,5R,6S)-6-[(3-Hydroxy-3-oxo-2-thiophen-3-ylpropanoyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(2S,5R,6S)-6-[(3-Hydroxy-3-oxo-2-thiophen-3-ylpropanoyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid structure
CAS No.
66148-78-5
Chemical Name:
(2S,5R,6S)-6-[(3-Hydroxy-3-oxo-2-thiophen-3-ylpropanoyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Synonyms
Temopen;BRL-17421;Temocillin;TEMOCILLIN SODIUM;(6S)-6-[(Carboxy-3-thienylacetyl)amino]-6-methoxypenicillanic acid;(6S)-6-[2-Carboxy-2-(3-thienyl)acetamido]-6-methoxypenicillanic acid;(2S,5R,6S)-6-[(3-Hydroxy-3-oxo-2-thiophen-3-ylpropanoyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1;N-((2S,5R,6S)-2-Carboxy-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-6-yl)-3-thiophenemalonamic acid;(2S,5R,6S)-6-{[Carboxy(3-thienyl)acetyl]amino}-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;(2S,5R,6S)-6-[(3-Hydroxy-3-oxo-2-thiophen-3-ylpropanoyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
CBNumber:
CB9284654
Molecular Formula:
C16H16N2Na2O7S2
Formula Weight:
458.42
MOL File:
66148-78-5.mol

(2S,5R,6S)-6-[(3-Hydroxy-3-oxo-2-thiophen-3-ylpropanoyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Properties

SAFETY

(2S,5R,6S)-6-[(3-Hydroxy-3-oxo-2-thiophen-3-ylpropanoyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid price

Manufacturer Product number Product description CAS number Packaging Price Updated Buy

(2S,5R,6S)-6-[(3-Hydroxy-3-oxo-2-thiophen-3-ylpropanoyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical Properties,Uses,Production

Uses

Antibacterial.

Antimicrobial activity

The introduction of the 6-α-methoxy group has resulted in loss of activity against Gram-positive cocci and anaerobic Gram-negative bacilli, but it is active against enterobacteria (MIC 1–8 mg/L), H. influenzae and Mor. catarrhalis, with somewhat elevated MICs against carbapenemase- producing isolates of K. pneumoniae (MIC 16–64 mg/L) and Esch. coli (modal MICs 8–16 mg/L). In most cases, β-lactamase-positive and negative strains are equally susceptible. In contrast to the structurally related ticarcillin, it is inactive against Ps. aeruginosa, but Burkholderia cepacia, Ps. acidovorans and Aeromonas spp. are susceptible (MIC 4 mg/L). Most Acinetobacter spp. are resistant, and Ser. marcescens exhibits variable susceptibility.
It is bactericidal at concentrations 2–4 times the MIC; filaments formed at lower concentrations slowly lyse at higher drug levels. Temocillin consists of diastereoisomers. The naturally predominant R epimer is more rapidly bactericidal than the S epimer. It is highly resistant to most bacterial β-lactamases, including those that confer resistance to extended-spectrum cephalosporins. It is hydrolyzed by β-lactamases produced by Flavobacterium spp. and by those of Bacteroides spp.

Pharmacokinetics

Oral absorption: Negligible
Cmax 1 g intramuscular injection: 70 mg/L
1 g rapid intravenous infusion: 172 mg/L after 5 min
Plasma half-life: 4.3–5.4 h
Plasma protein binding: 85%
Absorption and distribution
It is not absorbed when given orally and must be administered parenterally. Relatively high protein binding, together with its distribution in a volume less than the extracellular fluid, accounts for its relatively low renal clearance and subsequent high urinary concentrations that may be effective against some Enterobacteriaceae resistant to other β-lactam antibiotics. In artificial blister fluid and peritoneal fluid, concentrations reach 50% of the peak plasma level; in lymph, concentrations reach 25–60% of the simultaneous plasma level, with a similar half-life. The R epimer differs from the S epimer in lower protein binding, a 25% greater volume of distribution and a 60% shorter half-life.
Metabolism and excretion
Elimination is principally in the glomerular filtrate, with 80% of the dose appearing in the urine in the first 24 h. A small amount is disposed of in the bile and by degradation. Elimination declines in parallel with renal function, the half-life reaching 30 h in patients with creatinine clearance below 5%.

Clinical Use

Severe infection with susceptible bacteria, including urinary and respiratory tract infections, peritonitis and septicemia.

Side effects

As with all penicillins, hypersensitivity reactions, including serious anaphylactic responses, may occur. It is generally well tolerated and administration of 4 g intravenously every 12 h produced no significant effect on template bleeding time, prothrombin time or ADP-induced platelet aggregation.

(2S,5R,6S)-6-[(3-Hydroxy-3-oxo-2-thiophen-3-ylpropanoyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Preparation Products And Raw materials

Raw materials

Preparation Products


(2S,5R,6S)-6-[(3-Hydroxy-3-oxo-2-thiophen-3-ylpropanoyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Suppliers

Global( 15)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Shanghai T&W Pharmaceutical Co., Ltd. +86 21 61551611
+86 21 50676805 contact@trustwe.com China 9924 58
Henan Jiuhua Biological Technology Co., Ltd. 15738884691 15324876487qq:2949584887 237654463
0371-55320919 jiuhuabiochem@163.com China 2768 58
Wuhan Wsem Biological Co., Ltd. 027-83778876 13667159345
027-83778876 3369551489@qq.com China 4863 55
Aikon International Limited qq:2885670560;13813800073
(6)02557626880 cfding@aikonchem.com China 13938 58
Nanjing crow LuNing pharmaceutical technology co., LTD 13382066392
sales@croteau-lab.com CHINA 4893 58

66148-78-5((2S,5R,6S)-6-[(3-Hydroxy-3-oxo-2-thiophen-3-ylpropanoyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)Related Search:


  • (2S,5R,6S)-6-[(3-Hydroxy-3-oxo-2-thiophen-3-ylpropanoyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • N-((2S,5R,6S)-2-Carboxy-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-6-yl)-3-thiophenemalonamic acid
  • Temocillin
  • (6S)-6-[2-Carboxy-2-(3-thienyl)acetamido]-6-methoxypenicillanic acid
  • BRL-17421
  • Temopen
  • (6S)-6-[(Carboxy-3-thienylacetyl)amino]-6-methoxypenicillanic acid
  • TEMOCILLIN SODIUM
  • 66148-78-5
  • (2S,5R,6S)-6-[(3-Hydroxy-3-oxo-2-thiophen-3-ylpropanoyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1
  • (2S,5R,6S)-6-{[Carboxy(3-thienyl)acetyl]amino}-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Copyright 2017 © ChemicalBook. All rights reserved