 Home > Encyclopedia > Temocillin

Temocillin

Temocillin structure

CAS No:
66148-78-5
Formula:
C16H18N2O7S2
Chemical Name:
Temocillin
Synonyms:
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[2-carboxy-2-(3-thienyl)acetyl]amino]-6-methoxy-3,3-dimethyl-7-oxo-,(2S,5R,6S)-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[(carboxy-3-thienylacetyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-,[2S-(2α,5α,6α)]-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[(carboxy-3-thienylacetyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-,(2S,5R,6S)-;(2S,5R,6S)-6-[[2-Carboxy-2-(3-thienyl)acetyl]amino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;AB 17421;Temocillin;Negaban
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

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-).|Temocillin has been investigated in Infection, Liver Dysfunction, and Urinary Tract Infection.

Temocillin Basic Attributes

Molecular Weight：

458.42

Exact Mass：

414.45

EC Number：

266-184-1

ATC Code：

J01CA17|J - Antiinfectives for systemic use

Characteristics

PSA：

187

XLogP3：

0.85090

Density：

1.6 g/cm3

Boiling Point：

761.9ºC at 760 mmHg

Refractive Index：

1.675

Drug Information

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

MeSH Entry Terms：

BRL 17421

Temocillin Use and Manufacturing

Methods of Manufacturing

Method 1: The benzyl ester of 6-APA reacts with formic acid to form formamide at position 6, then convert it to isocyanate group with phosgene, and then react with disulfide to introduce methylthio group at position 6 to acidly decompose isocyanate Make it into a free amino group. Under the action of mercury dichloride, replace the methylthio group at the 6-position with a methoxy group, and then react with 2-(thiophen-3-yl)-2-benzyloxycarbonyl acetyl chloride. The guillotine chain is introduced to the ammonia at the position, and finally the benzyl protecting group is removed by catalytic hydrogenolysis to obtain temoxilin. Method 2: After the following compounds are chlorinated to form a diene, the 6-position methoxy group is introduced, and the phosphorous acid is used for addition reduction, followed by catalytic hydrogenation to remove the protective group, and hydrolysis into a salt to obtain temocillin sodium.

Uses

Semi-synthetic penicillin, stable to many p-lactamases. It has a strong antibacterial effect against Escherichia coli, Salmonella, Shigella, Pneumoniae, Proteus, Enterobacter. It is highly effective against third-generation cephalosporins, including ceftazidime, ceftazidime-resistant intestinal bacteria, and citric acid bacteria. However, it is ineffective against Gram-positive bacteria and Pseudomonas aeruginosa. Used for sepsis, respiratory tract infection, peritonitis, urinary tract infection, biliary tract infection, gonorrhea caused by sensitive bacteria.

Computed Properties

Molecular Weight:414.5
XLogP3:1.1
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:6
Exact Mass:414.05554326
Monoisotopic Mass:414.05554326
Topological Polar Surface Area:187
Heavy Atom Count:27
Complexity:700
Defined Atom Stereocenter Count:3
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes