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Substance Name: Cefamandole sodium [USP:JAN]
RN: 30034-03-8
UNII: IY6234ODVR
InChIKey: OJMNTWPPFNMOCJ-CFOLLTDRSA-M

Note

  • Semisynthetic wide-spectrum cephalosporin with prolonged action, probably due to beta-lactamase resistance. It is used also as the nafate.

Molecular Formulas

  • C18-H17-N6-Na-O5-S2
  • C18-H17-N6-O5-S2.Na
  • C18-H18-N6-O5-S2.Na

Molecular Weight

  • 484.4913
 

Classification Codes

  • Antibacterial
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Cefamandole sodium [USP:JAN]

Synonyms

  • 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((hydroxyphenylacetyl)amino)-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-, (6R-(6alpha,7beta(R*)))-, monosodium salt
  • Cefamandole sodium
  • EINECS 250-009-0
  • Monosodium (6R,7R)-7-(R)-mandelamido-3-(((1-methyl-1-H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate
  • NSC 758169
  • Sodium cefamandole
  • UNII-IY6234ODVR

Systematic Names

  • 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((hydroxyphenylacetyl)amino)-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-, (6R-(6alpha,7beta(R*)))-, monosodium salt
  • 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-mandelamido-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-, monosodium salt, D-
  • Sodium (6R-(6alpha,7beta(R*)))-7-((hydroxyphenylacetyl)amino)-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

Registry Numbers

CAS Registry Number

  • 30034-03-8

FDA UNII

  • IY6234ODVR

System Generated Number

  • 0030034038

Molecular Formulas

Molecular Formulas

  • C18-H17-N6-Na-O5-S2
  • C18-H17-N6-O5-S2.Na
  • C18-H18-N6-O5-S2.Na

Molecular Formula Fragments

  • C18-H17-N6-O5-S2
  • C18-H18-N6-O5-S2
  • COMPONENT
  • Na

Structure Descriptors

InChI

InChI=1S/C18H18N6O5S2.Na/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);/q;+1/p-1/t11-,13-,16-;/m1./s1

InChIKey

OJMNTWPPFNMOCJ-CFOLLTDRSA-M

Smiles

[Na+].Cn1nnnc1SCC2=C(N3[C@H](SC2)[C@H](NC(=O)[C@H](O)c4ccccc4)C3=O)C(=O)[O-]

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 4460mg/kg (4460mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 26, Pg. 115, 1984.
mouse LD50 oral > 19900mg/kg (19900mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 26, Pg. 115, 1984.
mouse LD50 subcutaneous 10300mg/kg (10300mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 26, Pg. 115, 1984.
rabbit LD intravenous > 2gm/kg (2000mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION

BEHAVIORAL: FOOD INTAKE (ANIMAL)

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
Chemotherapy Vol. 27(Suppl,
rat LD50 intravenous 4410mg/kg (4410mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 26, Pg. 115, 1984.
rat LD50 oral > 16600mg/kg (16600mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 26, Pg. 115, 1984.
rat LD50 subcutaneous 12100mg/kg (12100mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 26, Pg. 115, 1984.