Cefmetazole (CED0006139)

Record Information

Version

1.0

Creation Date

2016-05-25 18:19:25 UTC

Update Date

2026-08-19 10:38:36 UTC

Accession Number

CHEM022080

Identification

Common Name

Cefmetazole

Class

Small Molecule

Description

Cefmetazole is an organic compound with the chemical formula C15H17N7O5S3 and an average molecular weight of 471.53 g/mol. Cefmetazole belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. This substance is recorded as being found in or released from three sources: pharmaceuticals & veterinary products (Antibiotics), electrically stimulated smoking devices (Electrical & Electronic Equipment), and non electric simulated smoking devices (Household cleaning & consumer products). Recorded routes of exposure include oral and inhalation. At the molecular level, the compound interacts with six recorded protein targets. It acts as an inhibitor of Penicillin binding protein 2a (mecA), Penicillin-binding protein 1A (mrcA), Penicillin-binding protein 1B (mrcB), and Peptidoglycan D,D-transpeptidase FtsI (ftsI), in addition to two other proteins.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(6R,7S)-7-({[(cyanomethyl)sulfanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	ChEBI
Cefmetazolo	ChEBI
Cefmetazolum	ChEBI
CMZ	Kegg
(6R,7S)-7-({[(cyanomethyl)sulfanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	Generator
(6R,7S)-7-({[(cyanomethyl)sulphanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulphanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	Generator
(6R,7S)-7-({[(cyanomethyl)sulphanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulphanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	Generator
Monosodium salt, cefmetazole	HMDB
Zefazone	HMDB
Cefmetazon	HMDB
Pharmacia brand OF cefmetazole sodium	HMDB
Salt, cefmetazole monosodium	HMDB
Cefmetazole monosodium salt	HMDB
Cefmetazole sodium	HMDB
Sodium, cefmetazole	HMDB

Chemical Formula

C₁₅H₁₇N₇O₅S₃

Average Molecular Mass

471.534 g/mol

Monoisotopic Mass

471.045 g/mol

CAS Registry Number

56796-20-4

IUPAC Name

(6R,7S)-7-{2-[(cyanomethyl)sulfanyl]acetamido}-7-methoxy-3-{[(1-methyl-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

Traditional Name

cefmetazole

SMILES

[H][C@]12SCC(CSC3=NN=NN3C)=C(N1C(=O)[C@]2(NC(=O)CSCC#N)OC)C(O)=O

InChI Identifier

InChI=1S/C15H17N7O5S3/c1-21-14(18-19-20-21)30-6-8-5-29-13-15(27-2,17-9(23)7-28-4-3-16)12(26)22(13)10(8)11(24)25/h13H,4-7H2,1-2H3,(H,17,23)(H,24,25)/t13-,15+/m1/s1

InChI Key

SNBUBQHDYVFSQF-HIFRSBDPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids and derivatives

Alternative Parents

Substituents

N-acyl-alpha amino acid or derivatives
Cephem
Aryl thioether
Alkylarylthioether
Meta-thiazine
Azole
Beta-lactam
Heteroaromatic compound
Tertiary carboxylic acid amide
Tetrazole
Azetidine
Carboxamide group
Lactam
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Dialkylthioether
Carbonitrile
Nitrile
Organic 1,3-dipolar compound
Sulfenyl compound
Hemithioaminal
Thioether
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Carbonyl group
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cephalosporin (CHEBI:3489 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	2.16 g/L	ALOGPS
logP	-0.38	ALOGPS
logP	-0.65	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	3.38	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	163.33 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	124.57 m³·mol⁻¹	ChemAxon
Polarizability	44.5 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0006-9252300000-3b897b33c8f75fb7d195	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-05bf-9212320000-890b51c43c3c2ab21ca4	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-1043900000-6c51b4b1826d8fd2c6f0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01x3-7940000000-c539600c8e5309da2623	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03kl-5393000000-620b60fde9e0798480d5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00bc-2434900000-d70717dd74e62de2b0f5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-9341200000-9e56fcac14c64926ea08	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-044i-2191000000-2f3da3edb938f355e383	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0300900000-77e091905e6148c9a4f8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00xr-4850900000-81fd58ff3fbb9a095c81	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-9400000000-7442047ce9e5c1ddf3f3	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05fr-0008900000-09f33a45a1206aa0b044	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-4104900000-28beec94cf5d21f8447a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9102100000-234a13d09fa139832d83	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
3213.0	Log mg/kg	[1800:5700]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
306	Antibiotics	Healthcare, pharmaceuticals & veterinary products	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
617	Lip Care Products	Personal care & cosmetics	Not Available

Pathways

1 pathway

Cefmetazole Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Solute carrier family 22 member 6	Q4U2R8	Humans	Predicted (SEA)	4.5931
Click to view 3D structure	Organic anion transporter 3	Q8TCC7	Humans	Predicted (SEA)	3.42537
Click to view 3D structure	Solute carrier family 22 member 11	Q9NSA0	Humans	Predicted (SEA)	0.934191
Click to view 3D structure	Beta-lactamase	B2ZTR6	Acinetobacter baumannii	Predicted (SEA)	0.700643
Click to view 3D structure	ADC-11	D6NSM8	Acinetobacter baumannii	Predicted (SEA)	0.700643
Click to view 3D structure	Neutrophil elastase	P08246	Humans	Predicted (SEA)	555.065
Click to view 3D structure	Prothrombin	P00734	Humans	Predicted (SEA)	2303.25
Click to view 3D structure	Cathepsin G	P08311	Humans	Predicted (SEA)	808.308
Click to view 3D structure	PER-2 beta-lactamase	A2RP81	Citrobacter freundii	Predicted (SEA)	1.32344
Click to view 3D structure	Chymase	P23946	Humans	Predicted (SEA)	1177.78
Click to view 3D structure	Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1	Q9GZU7	Humans	Predicted (SEA)	2682.92
Click to view 3D structure	Serine protease 1	P07477	Humans	Predicted (SEA)	2896.61
Click to view 3D structure	Streptokinase A	P10520	Streptococcus pyogenes serotype M1	Predicted (SEA)	5721.22
Click to view 3D structure	Fibroblast growth factor receptor 4	Q498D6	Rattus norvegicus	Predicted (SEA)	158.812
Click to view 3D structure	Speckle-type POZ protein	O43791	Humans	Predicted (SEA)	214.942
Click to view 3D structure	Hydroxymethylglutaryl-CoA synthase, cytoplasmic	P17425	Rattus norvegicus	Predicted (SEA)	58.2312
Click to view 3D structure	Long-chain fatty acid transport protein 1	Q6PCB7	Humans	Predicted (SEA)	378.114
Click to view 3D structure	Long-chain fatty acid transport protein 1	Q60714	Mus musculus	Predicted (SEA)	432.92
Click to view 3D structure	Cathepsin B	P07858	Humans	Predicted (SEA)	5193.48
Click to view 3D structure	DNA (cytosine-5)-methyltransferase 1	P26358	Humans	Predicted (SEA)	4602.37
Click to view 3D structure	C-C chemokine receptor type 3	Q9BDS8	Macaca fascicularis	Predicted (SEA)	1196.54
Click to view 3D structure	Probable flavin-dependent thymidylate synthase	O41156	Paramecium bursaria Chlorella virus 1	Predicted (SEA)	266.789
Click to view 3D structure	Cathepsin K	P43236	Oryctolagus cuniculus	Predicted (SEA)	1595.52
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	7617.08
Click to view 3D structure	Plasminogen	Q01177	Rattus norvegicus	Predicted (SEA)	1220.05