CAS 50370-12-2|CEFADROXIL|cephadroxil|p-Hydroxycephalexine|Cefamox|(6R,7R)-7-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid|(6R,7R)-...

General Information

Structure

Molecular Formula

C₁₆H₁₇N₃O₅S

Molecular Mass

363.38828

Exact Mass

363.08889166

Charge

InChI

InChI=1S/C16H17N3O5S/c1-7-6-25-15-11(14(22)19(15)12(7)16(23)24)18-13(21)10(17)8-2-4-9(20)5-3-8/h2-5,10-11,15,20H,6,17H2,1H3,(H,18,21)(H,23,24)/t10-,11-,15-/m1/s1

InChIKey

BOEGTKLJZSQCCD-UEKVPHQBSA-N

Canonic Smiles

O=C([C@@H](c1ccc(cc1)O)N)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)C

Isomeric Smiles

O=C1N2C(=C(CS[C@@H]2[C@@H]1NC(=O)[C@@H](c1ccc(O)cc1)N)C)C(=O)O

Calculated Properties

JChem

LogD (pH = 7.4)

-2.81

LogD (pH = 5.5)

-2.45

Log P

-2.45

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

3.25

Polar Surface Area

132.96

Polarizability

35.90

Molar Refractivity

90.95

LOG S

-3.52

Data Source

Names and Identifiers

Synonyms

CEFADROXILp-HydroxycephalexineCefamox(6R,7R)-7-((R)-2-amino-2-(4-hydroxyphenyl)acetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid头孢羟氨苄CefadroxilCefadroxBaxanCefadrilCephadroxilBidocefDuricefCefroxil(6R,7R)-7-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidCDXCephadroxilcefadroxilCefadroxilCefadroxil anhydrousD-Cefadroxil

IUPAC Traditional name

cephadroxil (6R,7R)-7-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

IUPAC name

(6R,7R)-7-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

API Name

Cefadroxil

International Nonproprietary Name (INN)

cefadroxilumcefadroxilo

Names and Identifiers

Registration numbers

EC Number

CAS Number

MDL Number

PubChem CID

PubChem SID

1620912172489292187322627

DrugBank ID

DB01140

UniProt Database

Q04649Q90X89P18111O14627Q05095P81193Q9DEB6P43241Q99626Q07424Q8VQF4A2T7H5P47902Q91622

BKMS React Database

2076556128207654

MetaboLights Database

MTBLS2406MTBLS2825MTBLS379MTBLS1918MTBLS3725

Patent number

DE2216113US3816253NL6812382US3489752

BRENDA Database

3.5.2.67.4.2.53.4.16.43.1.1.433.5.1.11

PubMed Citation Links

24080658246677412322497829017833913147021425867128335702441269223959853

SureChEMBL Database

SCHEMBL151320

BRENDA Ligand Database

CHEMBL

KEGG ID

KEGG DRUG Database

SABIO-RK Database

CHEBI ID

CompTox Database

Drug Central Database

Reaxys Registry

ACToR Database

LINCS Database

Beilstein Number

Wikipedia Title

IEDB Database

Registration numbers

Properties

Product Information

Download link

Broad-spectrum antibiotic effective in Gram-positive and Gram-negative bacterial infections.

It is a bactericidal antibiotic

Physical Property

197°C

Pharmacology Properties

Mucopeptide-synthesis inhibitor;

Cell wall synthesis inhibitor

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

MP Biomedicals

02150581

White crystalline powder
m.p. 197°C

Sigma Aldrich

C7020

Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C7020.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

ChEBI

CHEBI:3479

A cephalosporin bearing methyl and (2R)-2-amino-2-(4-hydroxyphenyl)acetamido groups at positions 3 and 7, respectively, of the cephem skeleton.

Molecule Details

References

PubChem Literature

From Data Sources

• Leitner, F. et al., J. Antimicrob. Chemother., Suppl. B, 1982, 10, 1, (numerous papers)

• Kemperman, G.J. et al., Eur. J. Org. Chem., 2001, 1817-1820, (synth)

• Dunn, G. et al., J. Antibiot., 1976, 29, 65, (synth)

• U.S. Pat., 1979, 4 160 863; CA, 91, 175376, (synth, cryst struct)

• Tanrisever, B. et al., Drugs, 1986, 32, 1, (rev)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 5179, (synonyms)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DYF700

• Ger. Pat., 1973, 2 263 861; CA, 79, 78822, (synth)

• Shin, W. et al., Acta Cryst. C, 1992, 48, 1454, (cryst struct)

• Ger. Pat., 1975, 2 460 607; CA, 83, 145764, (synth)

• Neuman, M., Drugs of Today (Barcelona), 1977, 13, 471, (rev)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 163

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC Traditional name

cephadroxil (6R,7R)-7-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

IUPAC name

(6R,7R)-7-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

API Name

Cefadroxil

International Nonproprietary Name (INN)

cefadroxilumcefadroxilo

Registration numbers

EC Number

CAS Number

MDL Number

PubChem CID

PubChem SID

1620912172489292187322627

DrugBank ID

DB01140

UniProt Database

Q04649Q90X89P18111O14627Q05095P81193Q9DEB6P43241Q99626Q07424Q8VQF4A2T7H5P47902Q91622

BKMS React Database

2076556128207654

MetaboLights Database

MTBLS2406MTBLS2825MTBLS379MTBLS1918MTBLS3725

Patent number

DE2216113US3816253NL6812382US3489752

BRENDA Database

3.5.2.67.4.2.53.4.16.43.1.1.433.5.1.11

PubMed Citation Links

24080658246677412322497829017833913147021425867128335702441269223959853

SureChEMBL Database

SCHEMBL151320

BRENDA Ligand Database

CHEMBL

KEGG ID

KEGG DRUG Database

SABIO-RK Database

CHEBI ID

CompTox Database

Drug Central Database

Reaxys Registry

ACToR Database

LINCS Database

Beilstein Number

Wikipedia Title

IEDB Database

Molecule Details

White crystalline powder
m.p. 197°C

Sigma Aldrich

C7020

ChEBI

CHEBI:3479

A cephalosporin bearing methyl and (2R)-2-amino-2-(4-hydroxyphenyl)acetamido groups at positions 3 and 7, respectively, of the cephem skeleton.

References

PubChem Literature

From Data Sources

• Leitner, F. et al., J. Antimicrob. Chemother., Suppl. B, 1982, 10, 1, (numerous papers)

• Kemperman, G.J. et al., Eur. J. Org. Chem., 2001, 1817-1820, (synth)

• Dunn, G. et al., J. Antibiot., 1976, 29, 65, (synth)

• U.S. Pat., 1979, 4 160 863; CA, 91, 175376, (synth, cryst struct)

• Tanrisever, B. et al., Drugs, 1986, 32, 1, (rev)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 5179, (synonyms)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DYF700

• Ger. Pat., 1973, 2 263 861; CA, 79, 78822, (synth)

• Shin, W. et al., Acta Cryst. C, 1992, 48, 1454, (cryst struct)

• Ger. Pat., 1975, 2 460 607; CA, 83, 145764, (synth)

• Neuman, M., Drugs of Today (Barcelona), 1977, 13, 471, (rev)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 163

Bioactivity

PubChem BioAssay

Properties

Product Information

Download link

Broad-spectrum antibiotic effective in Gram-positive and Gram-negative bacterial infections.

It is a bactericidal antibiotic

Physical Property

197°C

Pharmacology Properties

Mucopeptide-synthesis inhibitor;

Cell wall synthesis inhibitor

Molecule

ID:103102