ContaminantDB: Cefazolin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 03:38:30 UTC

Update Date

2016-11-09 01:15:26 UTC

Accession Number

CHEM016613

Identification

Common Name

Cefazolin

Class

Small Molecule

Description

A semisynthetic cephalosporin analog with broad-spectrum antibiotic action due to inhibition of bacterial cell wall synthesis. It attains high serum levels and is excreted quickly via the urine.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	ChEBI
Cefamezin	ChEBI
Cefazolina	ChEBI
Cefazoline	ChEBI
Cefazolinum	ChEBI
Cephamezine	ChEBI
Cephazolidin	ChEBI
Cephazolin	ChEBI
Cephazoline	ChEBI
CEZ	ChEBI
(6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	Generator
(6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulphanyl]methyl}-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	Generator
(6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulphanyl]methyl}-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	Generator
Cefamedin	HMDB
Cefamezine	HMDB
Sodium cephazolin	HMDB
Sodium, cefazolin	HMDB
Sodium, cephazolin	HMDB
Gramaxin	HMDB
Ancef	HMDB
Cefazolin sodium	HMDB
Cephazolin sodium	HMDB
Cephazolin, sodium	HMDB
Kefzol	HMDB
Totacef	HMDB

Chemical Formula

C₁₄H₁₄N₈O₄S₃

Average Molecular Mass

454.507 g/mol

Monoisotopic Mass

454.030 g/mol

CAS Registry Number

25953-19-9

IUPAC Name

(6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[2-(1H-1,2,3,4-tetrazol-1-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Traditional Name

cefazolin

SMILES

[H][C@]12SCC(CSC3=NN=C(C)S3)=C(N1C(=O)[C@H]2NC(=O)CN1C=NN=N1)C(O)=O

InChI Identifier

InChI=1S/C14H14N8O4S3/c1-6-17-18-14(29-6)28-4-7-3-27-12-9(11(24)22(12)10(7)13(25)26)16-8(23)2-21-5-15-19-20-21/h5,9,12H,2-4H2,1H3,(H,16,23)(H,25,26)/t9-,12-/m1/s1

InChI Key

MLYYVTUWGNIJIB-BXKDBHETSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as cephalosporins. Cephalosporins are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Cephalosporins

Alternative Parents

Substituents

Cephalosporin
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Aryl thioether
Alkylarylthioether
Meta-thiazine
Azole
Heteroaromatic compound
Tertiary carboxylic acid amide
Tetrazole
Thiadiazole
Azetidine
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Azacycle
Monocarboxylic acid or derivatives
Dialkylthioether
Sulfenyl compound
Hemithioaminal
Thioether
Organic oxygen compound
Organopnictogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Carbonyl group
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cephalosporin (CHEBI:474053 )
Cephems (C06880 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

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	0.49 g/L	ALOGPS
logP	-0.4	ALOGPS
logP	-1.5	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.03	ChemAxon
pKa (Strongest Basic)	0.26	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	156.09 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	119.86 m³·mol⁻¹	ChemAxon
Polarizability	41.44 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	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	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05ai-9331300000-a190d4fa6f7addfc7f8c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00e9-9310500000-949cf3462e4c45379627	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-05fr-0109500000-d35195620e6ac4356773	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0aba-0943000000-da64d40a841f7fe440fe	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0zfr-0910000000-f074c2d1d56b5f3da552	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0q2i-0900000000-bbd7d226d641cfe51521	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0l1r-0900000000-18addd569fa36108660e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0pvi-0900000000-287aa1c6700ef519dedb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0q2i-0900000000-9e7cde1888a3978aed23	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-05fr-0109500000-d35195620e6ac4356773	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0aba-0953000000-486d054de7bf3c3c59f8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0q2i-0900000000-854b2bd437ac40b2e4b9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0zfr-0910000000-c1f36584835748883d05	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-05fs-0943000000-663a761fef5117d13f02	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0zfr-0920000000-30e9df76adf5b0ab0e2e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-05fr-0109500000-a3dc371ba38a25191014	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0l1r-0900000000-ec13af7a17d51561e88a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0q39-0900000000-7fdfdaaae2066b530d9e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0pvi-0900000000-32fabc5e15ec2390ad50	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0q2i-0900000000-bbd7d226d641cfe51521	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0zfr-0910000000-f074c2d1d56b5f3da552	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ap0-2749700000-4a77f2bfb0a94e40248a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9442000000-ae982fa3122bc6aa8c09	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9328000000-5482d1c278b4443581ce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00xu-9311000000-fc7869714720e58c02c6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-4920000000-c40df0bab8447e63198d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-066r-9143000000-9ff6c941993091c7a3f9	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum