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Cefamandole

Cefamandole structure

CAS No:
34444-01-4
Formula:
C18H18N6O5S2
Chemical Name:
Cefamandole
Synonyms:
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(2R)-2-hydroxy-2-phenylacetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-,(6R,7R)-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[(hydroxyphenylacetyl)amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-,[6R-[6α,7β(R*)]]-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(2R)-hydroxyphenylacetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-,(6R,7R)-;(6R,7R)-7-[[(2R)-2-Hydroxy-2-phenylacetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;Cefadole;Cefamandole;Cephamandole;3-(1-Methyltetrazol-5-ylthiomethyl)-7-D-mandelamido-3-cephem-4-carboxylic acid;Cephadole;L-Cefamandole;Cefamandol;CMT
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Cefamandole is a second-generation broad-spectrum cephalosporin antibiotic. As the antibiotic is broken down in the body, it releases free NMTT, which can cause hypoprothrombinemia.

Solid

Cefamandole is a cephalosporin compound having (R)-mandelamido and N-methylthiotetrazole side-groups. It has a role as an antibacterial drug. It is a cephalosporin and a semisynthetic derivative. It is a conjugate acid of a cefamandole(1-).|Cefamandole is also known as cephamandole. It is a parenterally administered broad-spectrum cephalosporin antibiotic. It is generally formulated as a formate ester[cefamandole nafate]. It is no longer marketed in the United States.|Cefamandole is a second-generation cephalosporin antibiotic with bactericidal activity. Cefamandole is active against Haemophilus and gram-negative bacilli susceptible to other cephalosporins. It is also active against many strains resistant to other cephalosporins, such as Enterobacter species and indole-positive Proteus species.|Semisynthetic wide-spectrum cephalosporin with prolonged action, probably due to beta-lactamase resistance. It is used also as the nafate.

Cefamandole Basic Attributes

Molecular Weight：

462.5

Exact Mass：

462.50

EC Number：

252-030-0

UNII：

5CKP8C2LLI

DSSTox ID：

DTXSID7022750

NCI Thesaurus Code：

C353

ATC Code：

J - Antiinfectives for systemic use

Characteristics

PSA：

201.14000

XLogP3：

0.10320

Density：

1.75 g/cm3

Melting Point：

182-184

Water Solubility：

5.81e-01 g/L

Flammability characteristics：

Thermal decomposition emits toxic nitrogen oxides and sulfur oxide fumes

Collision Cross Section：

197.9 Å² [M+Na]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]

Safety Information

Storage features：

The warehouse is low-temperature, ventilated and dry

Precautionary statement(s)：

P261, P264, P271, P272, P280, P285, P302+P352, P304+P340, P304+P341, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P403+P233, P405, P501

Hazard Statements：

H315

GHS Classification：

|Danger|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P272, P280, P285, P302+P352, P304+P340, P304+P341, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity Summary：

Symptoms of overdose include blood in the urine, diarrhea, nausea, upper abdominal pain, and vomiting.

Protein Binding：

75%

Drug Information

Drug Indication：

For the treatment of serious infections caused by susceptible strains of microorganisms.

Pharmacology：

The parenteral prodrug formate ester cefamandole nafate is a broad-spectrum cephalosporin antibiotic. The bactericidal action of cefamandole results from inhibition of cell-wall synthesis. Cephalosporins have in vitro activity against a wide range of gram-positive and gram-negative organisms.

MeSH：

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

Biological Half-Life：

The half-life after an intravenous dose is 32 minutes; after intramuscular administration, the half-life is 60 minutes.

Mechanism of Action：

Like all beta-lactam antibiotics, cefamandole binds to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, causing the inhibition of the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefamandole interferes with an autolysin inhibitor.

MeSH Entry Terms：

Cefamandole

Cefamandole Use and Manufacturing

Intermediate for the oreparation of Phenylephrine Glucuronide.

Computed Properties

Molecular Weight:462.5
XLogP3:-0.9
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:10
Rotatable Bond Count:7
Exact Mass:462.07801004
Monoisotopic Mass:462.07801004
Topological Polar Surface Area:201
Heavy Atom Count:31
Complexity:777
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes