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| | (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 Basic information |
| Product 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: | TEMOCILLIN SODIUM;(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;(6S)-6-[(Carboxy-3-thienylacetyl)amino]-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;(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;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 | | CAS: | 66148-78-5 | | MF: | C16H18N2O7S2 | | MW: | 414.45 | | EINECS: | 266-184-1 | | Product Categories: | | | 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 Structure](CAS/GIF/66148-78-5.gif) |
| | (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 |
| Boiling point | 761.9±60.0 °C(Predicted) | | density | 1.60±0.1 g/cm3(Predicted) | | pka | 2.46±0.50(Predicted) |
| | (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 Usage And Synthesis |
| Uses | Antibacterial. | | Definition | ChEBI: Temocillin is a penicillin compound having a 6alpha-methoxy and 6beta-[2-carboxy(thiophen-3-yl)acetamido side-groups. It is a conjugate acid of a temocillin(2-). | | 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. | | Drug interactions | Potentially hazardous interactions with other drugs
Temocillin can reduce the excretion of methotrexate
(increased risk of toxicity). | | Metabolism | Temocillin is excreted unchanged mainly in the kidney. |
| | (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 |
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