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Substance Name: Moxalactam disodium [USAN:USP]
RN: 64953-12-4
UNII: 5APW73W3QZ
InChIKey: GRIXGZQULWMCLU-HUTAOCTPSA-L

Note

  • Broad- spectrum beta-lactam antibiotic similar in structure to the CEPHALOSPORINS except for the substitution of an oxaazabicyclo moiety for the thiaazabicyclo moiety of certain CEPHALOSPORINS. It has been proposed especially for the meningitides because it passes the blood-brain barrier and for anaerobic infections.

Molecular Formulas

  • C20-H18-N6-Na2-O9-S
  • C20-H18-N6-O9-S.2Na
  • C20-H20-N6-O9-S.2Na

Molecular Weight

  • 564.4412
 

Classification Codes

  • Anti-Infective
  • Drug / Therapeutic Agent
  • Human Data
  • Natural Product
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Moxalactam disodium
  • Moxalactam disodium [USAN:USP]

Synonyms

  • 5-Oxa-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((carboxy(4-hydroxyphenyl)acetyl)amino)-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-, disodium salt
  • 6059-S
  • 6059S
  • Antibiotic 6059-S
  • Disodium latamoxef
  • EINECS 265-288-4
  • Latamoxef sodium
  • LY 127935
  • Moxalactam disodium
  • Moxam
  • N-((6R,7R)-2-Carboxy-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-oxa-1-azabicyclo(4.2.0)oct-2-en-7-yl)-2-(p-hydroxyphenyl)malonamic acid disodium salt
  • Shionogi 6059S
  • UNII-5APW73W3QZ

Systematic Names

  • 5-Oxa-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((carboxy(4-hydroxyphenyl)acetyl)amino)-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-, disodium salt
  • Disodium 7-((carboxylato(4-hydroxyphenyl)acetyl)amino)-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-oxa-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

Registry Numbers

CAS Registry Number

  • 64953-12-4

FDA UNII

  • 5APW73W3QZ

System Generated Number

  • 0064953124

Molecular Formulas

Molecular Formulas

  • C20-H18-N6-Na2-O9-S
  • C20-H18-N6-O9-S.2Na
  • C20-H20-N6-O9-S.2Na

Molecular Formula Fragments

  • C20-H18-N6-O9-S
  • C20-H20-N6-O9-S
  • COMPONENT
  • Na

Structure Descriptors

InChI

1S/C20H20N6O9S.2Na/c1-25-19(22-23-24-25)36-8-10-7-35-18-20(34-2,17(33)26(18)13(10)16(31)32)21-14(28)12(15(29)30)9-3-5-11(27)6-4-9;;/h3-6,12,18,27H,7-8H2,1-2H3,(H,21,28)(H,29,30)(H,31,32);;/q;2*+1/p-2/t12?,18-,20+;;/m1../s1

InChIKey

GRIXGZQULWMCLU-HUTAOCTPSA-L

Smiles

[Na+].[Na+].CO[C@]1(NC(=O)C(C(=O)[O-])c2ccc(O)cc2)[C@H]3OCC(=C(N3C1=O)C(=O)[O-])CSc4nnnn4C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man LDLo intravenous 371mg/kg/17D- (371mg/kg) BLOOD: THROMBOCYTOPENIA Drug Intelligence and Clinical Pharmacy. Vol. 18, Pg. 140, 1984.
man TDLo intravenous 1143mg/kg/10D (1143mg/kg) BLOOD: HEMORRHAGE Drug Intelligence and Clinical Pharmacy. Vol. 18, Pg. 721, 1984.
man TDLo oral 571mg/kg/20D- (571mg/kg) GASTROINTESTINAL: ULCERATION OR BLEEDING FROM SMALL INTESTINE

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM LARGE INTESTINE

BLOOD: HEMORRHAGE
JAMA, Journal of the American Medical Association. Vol. 250, Pg. 730, 1983.
monkey LD intravenous > 5gm/kg (5000mg/kg)   Chemotherapy Vol. 28(Suppl,
mouse LD50 intraperitoneal 8100mg/kg (8100mg/kg)   Drugs in Japan Vol. 6, Pg. APP-21, 1982.
mouse LD50 intravenous 5300mg/kg (5300mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Chemotherapy Vol. 28(Suppl,
mouse LD50 oral > 10gm/kg (10000mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Chemotherapy Vol. 28(Suppl,
mouse LD50 subcutaneous 9gm/kg (9000mg/kg)   Drugs in Japan Vol. 6, Pg. APP-21, 1982.
rat LD50 intraperitoneal 8100mg/kg (8100mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Chemotherapy Vol. 28(Suppl,
rat LD50 intravenous 5500mg/kg (5500mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Chemotherapy Vol. 28(Suppl,
rat LD50 oral > 10gm/kg (10000mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Chemotherapy Vol. 28(Suppl,
rat LD50 subcutaneous 9gm/kg (9000mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Chemotherapy Vol. 28(Suppl,