Basic information
- CAS
61622-34-2- Standard SMILES
CN(C)CCn1nnnc1SCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)Cc3csc(N)n3)[C@H]2SC1- InChIKey
QYQDKDWGWDOFFU-IUODEOHRSA-N- Molecular formula
- C18H23N9O4S3
- Average molar mass
- 525.6 g/mol
- Monoisotopic mass
- 525.10351377
Overview
Cefotiam is a cephalosporin with ({1-[2-(dimethylamino)ethyl]-1H-tetrazol-5-yl}sulfanyl)methyl and (2-amino-1,3-thiazol-4-yl)acetamido substituents at positions 3 and 7, respectively, of the cephem skeleton. A third generation beta-lactam cephalosporin antibiotic, it is active against a broad spectrum of both Gram positive and Gram negative bacteria. It has a role as an antibacterial drug. It is a cephalosporin, a semisynthetic derivative and a beta-lactam antibiotic allergen.
Names & identifiers
- Preferred name
- Cefotiam
- IUPAC
- (6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)acetyl]amino]-3-[[1-[2-(dimethylamino)ethyl]tetrazol-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- English name
- Cefotiam
- Molecular formula
- C18H23N9O4S3
- Molecular weight
- 525.63
Names & synonyms
cefotiam61622-34-2CefotiamumAspilJ01DC07CHEBI:355510(6R,7R)-7-[2-(2-amino-1,3-thiazol-4-yl)acetamido]-3-[({1-[2-(dimethylamino)ethyl]-1H-1,2,3,4-tetrazol-5-yl}sulfanyl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid91W6Z2N718(6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)acetyl]amino]-3-[[1-[2-(dimethylamino)ethyl]tetrazol-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidDTXSID6022763Haloapor(6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)acetyl]amino]-3-[[1-(2-dimethylaminoethyl)tetrazol-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Show more names
CEFOTIAM HCLSCE 963TexodilTaketiamcgp14221ePansporin T(6r-trans)--oxoCefotiam USP/EP/BPPansporin：Pansporine
(6R,7R)-7-[2-(2-Amino-thiazol-4-yl)-acetylamino]-3-[1-(2-dimethylamino-ethyl)-1H-tetrazol-5-ylsulfanylmethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2-amino-4-thiazolyl)acetyl)amino)-3-(((1-(2-(dimethylamino)ethyl)-1H-tetrazol-5-yl)thio)methyl)-8-oxo-, (6R-trans)-(6R,7R)-7-((2-(2-amino-1,3-thiazol-4-yl)acetyl)amino)-3-((1-(2-(dimethylamino)ethyl)tetrazol-5-yl)sulfanylmethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid(6R,7R)-7-((2-(2-amino-1,3-thiazol-4-yl)acetyl)amino)-3-((1-(2-dimethylaminoethyl)tetrazol-5-yl)sulfanylmethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid(6R,7R)-7-(2-(2-amino-1,3-thiazol-4-yl)acetamido)-3-(((1-(2-(dimethylamino)ethyl)-1H-1,2,3,4-tetrazol-5-yl)sulfanyl)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid(6R,7R)-7-(2-(2-Amino-thiazol-4-yl)-acetylamino)-3-(1-(2-dimethylamino-ethyl)-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo(4.2.0)oct-2-ene-2-carboxylic acidRefChem:574975DTXCID602763
Properties
Computed structural properties
- XLogP
- -2.4
- Topological polar surface area
- 251 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 13
- Rotatable bonds
- 10
- Heavy atoms
- 34
- Formal charge
- 0
- Complexity
- 847
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
LogP-2.1
Solubility
Soluble
1.29e+00 g/L
Physical DescriptionSolid
Physicochemical properties
- Boiling point
- 843 ℃ · 843℃
- Density
- 1.8 · 1.80±0.1 g/cm3(Predicted)
- RTECS
- 366000 · XI0366000
- Flash point
- 110 ° · >110°(230°F)
- storage temp.
- 2 · 2-8°C
- pka
- 2.57 · 2.57±0.50(Predicted)
- Water Solubility
- Soluble
- CAS DataBase Reference
- 61622 · 61622-34-2(CAS DataBase Reference)
- FDA UNII
- 91 W6Z2N718 · 91W6Z2N718
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesSkin Sens. 1 (100%)
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
cefotiam
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS08
- Hazard statements
- H317-H334
- Precautionary statements
- P261-P272-P280-P302+P352-P333+P313-P321-P363-P501-P261-P285-P304+P341-P342+P311-P501
Chemistry & industry
Pharmacology
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Protein Binding40%
PharmacodynamicsCefotiam is a third generation beta-lactam cephalosporin antibiotic that works by inhibiting bacterial cell wall biosynthesis. It is a broad spectrum antibiotic that is effective against Gram positive and Gram negative bacteria.
Mechanism of ActionThe bactericidal activity of cefotiam results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).
Biological Half-LifeApproximately 1 hour.
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and ExcretionRapidly absorbed following intramuscular injection. Bioavailability is 60% following intramuscular injection.
Cellular LocationsCytoplasm
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >750
Applications
UsesAntibacterial
Upstream & downstream products
Upstream raw materials
Related reactions
1 records
Compound notes
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