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Substance Name: Cefotetan disodium [USAN:USP]
RN: 74356-00-6
UNII: 0GXP746VXB
InChIKey: ZQQALMSFFARWPK-GLHLDKNHSA-L

Note

  • A semisynthetic cephamycin antibiotic that is administered intravenously or intramuscularly. The drug is highly resistant to a broad spectrum of beta-lactamases and is active against a wide range of both aerobic and anaerobic gram-positive and gram-negative microorganisms.

Molecular Formulas

  • C17-H15-N7-Na2-O8-S4
  • C17-H17-N7-O8-S4.2Na

Molecular Weight

  • 619.5905
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial
  • Drug / Therapeutic Agent
  • Human Data
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Cefotetan disodium [USAN:USP]

Synonyms

  • (6R,7S)-4-((2-Carboxy-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-7-yl)carbamoyl)-1,3-dithietane-delta(sup 2,alpha)-malonamic acid, disodium salt
  • (6R,7S)-7-(4-(Carbamoylcarboxymethylene)-1,3-dithietane-2-carboxamido)-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, disodium salt
  • 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietan-2-yl)carbonyl)amino)-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-, disodium salt, (6R-(6alpha,7alpha))-
  • Apatef
  • Cefotan
  • Cefotan in plastic container
  • Cefotetan
  • Cefotetan and dextrose in duplex container
  • Cefotetan disodium
  • Cefotetan disodium salt
  • Cefotetan sodium
  • Ceftenon
  • Cepan
  • Darvilen
  • EINECS 277-834-9
  • ICI 156834 disodium
  • UNII-0GXP746VXB
  • Yamatetan
  • YM 09330
  • YM-09330

Systematic Name

  • 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietan-2-yl)carbonyl)amino)-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-, disodium salt, (6R-(6alpha,7alpha))-

Registry Numbers

CAS Registry Number

  • 74356-00-6

FDA UNII

  • 0GXP746VXB

Related Registry Number

  • 69712-56-7 (Parent)

System Generated Number

  • 0074356006

Molecular Formulas

Molecular Formulas

  • C17-H15-N7-Na2-O8-S4
  • C17-H17-N7-O8-S4.2Na

Molecular Formula Fragments

  • C17-H17-N7-O8-S4
  • COMPONENT
  • Na

Structure Descriptors

InChI

1S/C17H17N7O8S4.2Na/c1-23-16(20-21-22-23)34-4-5-3-33-15-17(32-2,14(31)24(15)7(5)11(29)30)19-9(26)13-35-12(36-13)6(8(18)25)10(27)28;;/h13,15H,3-4H2,1-2H3,(H2,18,25)(H,19,26)(H,27,28)(H,29,30);;/q;2*+1/p-2/b12-6-;;/t13?,15-,17+;;/m1../s1

InChIKey

ZQQALMSFFARWPK-GLHLDKNHSA-L

Smiles

Cn1c(nnn1)SCC2=C(N3[C@@H]([C@@](C3=O)(NC(=O)C4SC(=C(C(=O)N)C(=O)[O-])S4)OC)SC2)C(=O)[O-].[Na+].[Na+]

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous > 6gm/kg (6000mg/kg)   Drugs in Japan Vol. -, Pg. 565, 1990.
dog LD50 oral > 6gm/kg (6000mg/kg)   Drugs in Japan Vol. -, Pg. 661, 1995.
man TDLo intravenous 800mg/kg/4W-I (800mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Annals of Internal Medicine. Vol. 116, Pg. 522, 1992.
man TDLo intravenous 814mg/kg/18D- (814mg/kg) KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS

SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE"
American Journal of Kidney Diseases. Vol. 16, Pg. 259, 1990.
monkey LD50 oral > 6gm/kg (6000mg/kg)   Drugs in Japan Vol. -, Pg. 661, 1995.
mouse LD50 intraperitoneal 8120mg/kg (8120mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Chemotherapy Vol. 30(Suppl,
mouse LD50 intravenous 4990mg/kg (4990mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: TREMOR
Chemotherapy Vol. 30(Suppl,
mouse LD50 oral > 10gm/kg (10000mg/kg)   Drugs in Japan Vol. -, Pg. 565, 1990.
mouse LD50 subcutaneous > 10gm/kg (10000mg/kg)   Drugs in Japan Vol. -, Pg. 565, 1990.
rabbit LD50 intravenous > 6gm/kg (6000mg/kg)   Drugs in Japan Vol. -, Pg. 565, 1990.
rat LD50 intraperitoneal 8250mg/kg (8250mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Chemotherapy Vol. 30(Suppl,
rat LD50 intravenous 6790mg/kg (6790mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: TREMOR

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA
Chemotherapy Vol. 30(Suppl,
rat LD50 oral > 10gm/kg (10000mg/kg)   Drugs in Japan Vol. -, Pg. 565, 1990.
rat LD50 subcutaneous > 10gm/kg (10000mg/kg)   Drugs in Japan Vol. -, Pg. 565, 1990.