Cefamandole (CED0005269)

Record Information

Version

1.0

Creation Date

2016-05-25 18:26:44 UTC

Update Date

2026-08-19 23:58:51 UTC

Accession Number

CHEM022282

Identification

Common Name

Cefamandole

Class

Small Molecule

Description

Cefamandole is an organic compound with the chemical formula C18H18N6O5S2 and an average molecular weight of 462.50 g/mol. Cefamandole belongs to the beta lactams, a subclass of lactams within the organic compounds. It is further classified as an organoheterocyclic compound. In terms of biological activity, cefamandole acts as an inhibitor of the protein target penicillin-binding protein 2 (pbpA). The compound is associated with six recorded sources. These include antibiotics within healthcare, pharmaceuticals, and veterinary products, as well as processing meats in food, food processing, and cookware. Additionally, it is found in television systems and video games under electrical and electronic equipment, non-electric simulated smoking devices in household cleaning and consumer products, and credit card holders among household items. Recorded routes of exposure for this substance include oral and inhalation.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(6R,7R)-7-(R)-Mandelamido-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-carboxylic acid	ChEBI
(6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-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
Cefadole	ChEBI
Cefamandol	ChEBI
Cefamandolum	ChEBI
Cephadole	ChEBI
Cephamandole	ChEBI
L-Cefamandole	ChEBI
CMD	Kegg
(6R,7R)-7-(R)-Mandelamido-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-carboxylate	Generator
(6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-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,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-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,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-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
Cefamandole nafate	HMDB
Compound 83405	HMDB

Chemical Formula

C₁₈H₁₈N₆O₅S₂

Average Molecular Mass

462.503 g/mol

Monoisotopic Mass

462.078 g/mol

CAS Registry Number

34444-01-4

IUPAC Name

(6R,7R)-7-[(2R)-2-hydroxy-2-phenylacetamido]-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

cefamandole

SMILES

[H][C@]12SCC(CSC3=NN=NN3C)=C(N1C(=O)[C@H]2NC(=O)[C@H](O)C1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C18H18N6O5S2/c1-23-18(20-21-22-23)31-8-10-7-30-16-11(15(27)24(16)12(10)17(28)29)19-14(26)13(25)9-5-3-2-4-6-9/h2-6,11,13,16,25H,7-8H2,1H3,(H,19,26)(H,28,29)/t11-,13-,16-/m1/s1

InChI Key

OLVCFLKTBJRLHI-AXAPSJFSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Peptides

Alternative Parents

Substituents

Alpha peptide
Cephalosporin
N-acyl-alpha amino acid or derivatives
N-carbamoyl-alpha-amino acid or derivatives
Alpha-amino acid amide
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Phenylacetamide
Cephem
Piperazine-1-carboxamide
Dioxopiperazine
Aryl thioether
Alkylarylthioether
1-hydroxy-2-unsubstituted benzenoid
N-acyl urea
N-alkylpiperazine
Ureide
Phenol
Benzenoid
1,4-diazinane
Piperazine
Meta-thiazine
Monocyclic benzene moiety
Dicarboximide
Azole
Tertiary carboxylic acid amide
Tetrazole
Beta-lactam
Heteroaromatic compound
Azetidine
Urea
Carboxamide group
Secondary carboxylic acid amide
Lactam
Carbonic acid derivative
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Hemithioaminal
Sulfenyl compound
Thioether
Carboxylic acid
Dialkylthioether
Organonitrogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organopnictogen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	0.58 g/L	ALOGPS
logP	-0.05	ALOGPS
logP	0.027	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	3.32	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	150.54 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	126.65 m³·mol⁻¹	ChemAxon
Polarizability	42.45 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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	splash10-0a4i-1900000000-171ae249ec803b8d5abd	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-004i-0900000000-fb3cc081c83b0d53a10c	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	splash10-05dl-4698600000-8b8ba1529bcdbe274bfa	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ab9-4956100000-2107c26a4908fb9913eb	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05fr-3390000000-2cd8861a785705076af0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014l-1910200000-8214388978bd4c2b1ca7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0aor-9710000000-6d5c2f7837d35a1fb4fe	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ar3-9530000000-32e2979223057f6e2cf1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03dj-0115900000-a9a6c926ad8c4264e63c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00dj-2985600000-bc5faa5980b8da2874ea	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0007-9671200000-347a700c832c4adbf8db	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0100900000-40b310ffa3cee38ef34c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0300-3952500000-b7a5de24cc9eeb2c9ab0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-066r-9710300000-07002f5735b982b36a8d	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹³C 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
6677.0	Log mg/kg	[3800:12000]	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
537	Television Systems	Electrical & Electronic Equipment	Not Available
539	Video Games	Electrical & Electronic Equipment	Not Available
552	Processing Meats	Food, food processing & cookware	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
572	Credit Card Holders	Household items	Not Available
643	Headwear	Textiles, leather & furnishings	Not Available
651	Purses Money Bags Wallets	Textiles, leather & furnishings	Not Available

Pathways

1 pathway

Cefamandole 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)	0.0778492
Click to view 3D structure	Organic anion transporter 3	Q8TCC7	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Solute carrier family 22 member 11	Q9NSA0	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Speckle-type POZ protein	O43791	Humans	Predicted (SEA)	0.311397
Click to view 3D structure	Streptokinase A	P10520	Streptococcus pyogenes serotype M1	Predicted (SEA)	28.2593
Click to view 3D structure	Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1	Q9GZU7	Humans	Predicted (SEA)	24.4447
Click to view 3D structure	Tyrosine-protein phosphatase non-receptor type 11	Q06124	Humans	Predicted (SEA)	146.668
Click to view 3D structure	Excitatory amino acid transporter 2	P43004	Humans	Predicted (SEA)	26.0795
Click to view 3D structure	DNA (cytosine-5)-methyltransferase 1	P26358	Humans	Predicted (SEA)	214.241
Click to view 3D structure	Beta-lactamase	B2ZTR6	Acinetobacter baumannii	Predicted (SEA)	0.856341
Click to view 3D structure	ADC-11	D6NSM8	Acinetobacter baumannii	Predicted (SEA)	0.856341
Click to view 3D structure	Neutrophil elastase	P08246	Humans	Predicted (SEA)	231.134
Click to view 3D structure	Solute carrier family 15 member 2	Q63424	Rattus norvegicus	Predicted (SEA)	16.2705
Click to view 3D structure	72 kDa type IV collagenase	P08253	Humans	Predicted (SEA)	1752.46
Click to view 3D structure	Probable flavin-dependent thymidylate synthase	O41156	Paramecium bursaria Chlorella virus 1	Predicted (SEA)	11.4438
Click to view 3D structure	Neurogenic locus notch homolog protein 2	Q04721	Humans	Predicted (SEA)	18.061
Click to view 3D structure	Neurogenic locus notch homolog protein 4	Q99466	Humans	Predicted (SEA)	18.061
Click to view 3D structure	C-C chemokine receptor type 3	Q9BDS8	Macaca fascicularis	Predicted (SEA)	93.8862
Click to view 3D structure	Apoptotic protease-activating factor 1	O14727	Humans	Predicted (SEA)	458.143
Click to view 3D structure	Procathepsin L	P07154	Rattus norvegicus	Predicted (SEA)	121.367
Click to view 3D structure	Prothrombin	P00734	Humans	Predicted (SEA)	2075.69
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	5565.36
Click to view 3D structure	Baculoviral IAP repeat-containing protein 8	Q96P09	Humans	Predicted (SEA)	57.0635
Click to view 3D structure	Dual specificity protein phosphatase 3	P51452	Humans	Predicted (SEA)	947.892
Click to view 3D structure	Neprilysin	P07861	Rattus norvegicus	Predicted (SEA)	567.988