(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 C화학적 특성, 용도, 생산

용도

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
C_max 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.

부작용

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 준비 용품 및 원자재

원자재

준비 용품

(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 공급 업체

공급자	전화	이메일	국가	제품 수	이점
CONIER CHEM AND PHARMA LIMITED	+8618523575427	sales@conier.com	China	47465	58
Shaanxi Dideu Medichem Co. Ltd	+86-029-81138252 +86-18789408387	1057@dideu.com	China	3783	58
Shaanxi Dideu Medichem Co. Ltd	+86-029-89586680 +86-18192503167	1026@dideu.com	China	9553	58
Dideu Industries Group Limited	+86-29-89586680 +86-15129568250	1026@dideu.com	China	29474	58
AFINE CHEMICALS LIMITED	0571-85134551	info@afinechem.com	CHINA	15377	58
BOC Sciences	+16314854226	inquiry@bocsci.com	United States	19743	58
Hefei Hirisun Pharmatech Co., Ltd	+8615056975894	shawn@hirisunpharm.com	CHINA	9923	58
Alfa Chemistry	+1-5166625404	Info@alfa-chemistry.com	United States	21317	58
Amadis Chemical Company Limited	571-89925085	sales@amadischem.com	China	131981	58
Shanghai T&W Pharmaceutical Co., Ltd.	+86 21 61551611		China	9901	58

(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 관련 검색: