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Substance Name: Piperacillin sodium [USAN:USP:JAN]
RN: 59703-84-3
UNII: M98T69Q7HP
InChIKey: WCMIIGXFCMNQDS-IDYPWDAWSA-M

Note

  • Semisynthetic, broad-spectrum, AMPICILLIN derived ureidopenicillin antibiotic proposed for PSEUDOMONAS infections. It is also used in combination with other antibiotics.

Molecular Formulas

  • C23-H26-N5-Na-O7-S
  • C23-H26-N5-O7-S.Na
  • C23-H27-N5-O7-S.Na

Molecular Weight

  • 539.5424
 

Classification Codes

  • Antibacterial
  • Drug / Therapeutic Agent
  • Human Data
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Piperacillin sodium [USAN:USP:JAN]

Synonyms

  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((((4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl)amino)phenylacetyl)amino)-3,3-dimethyl-7-oxo-, monosodium salt, (2S-(2alpha,5alpha,6beta(S*)))
  • CCRIS 2591
  • CL 227,193
  • CL 227193
  • EINECS 261-868-6
  • Pentcillin
  • Piperacillin
  • Piperacillin sodium
  • Pipracil
  • Pipracil Sterile
  • Sodium (2S,5R,6R)-6-((R)-2-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate
  • Sodium piperacillin
  • T 1220
  • T-1220
  • UNII-M98T69Q7HP

Systematic Names

  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((((4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl)amino)phenylacetyl)amino)-3,3-dimethyl-7-oxo-, monosodium salt, (2S-(2alpha,5alpha,6beta(S*)))-
  • Piperacillin sodium

Mixture Names

  • Zosyn
  • Zosyn Sterile

Registry Numbers

CAS Registry Number

  • 59703-84-3

FDA UNII

  • M98T69Q7HP

Related Registry Number

  • 61477-96-1 (Parent)

System Generated Number

  • 0059703843

Molecular Formulas

Molecular Formulas

  • C23-H26-N5-Na-O7-S
  • C23-H26-N5-O7-S.Na
  • C23-H27-N5-O7-S.Na

Molecular Formula Fragments

  • C23-H26-N5-O7-S
  • C23-H27-N5-O7-S
  • COMPONENT
  • Na

Structure Descriptors

InChI

1S/C23H27N5O7S.Na/c1-4-26-10-11-27(19(32)18(26)31)22(35)25-13(12-8-6-5-7-9-12)16(29)24-14-17(30)28-15(21(33)34)23(2,3)36-20(14)28;/h5-9,13-15,20H,4,10-11H2,1-3H3,(H,24,29)(H,25,35)(H,33,34);/q;+1/p-1/t13-,14-,15+,20-;/m1./s1

InChIKey

WCMIIGXFCMNQDS-IDYPWDAWSA-M

Smiles

N12[C@H]([C@H](NC([C@@H](c3ccccc3)NC(N3C(C(N(CC)CC3)=O)=O)=O)=O)C2=O)SC(C)(C)[C@H]1C(=O)[O-].[Na+]

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous > 6gm/kg (6000mg/kg)   Japanese Journal of Antibiotics. Vol. 36, Pg. 653, 1983.
monkey LD50 intravenous > 4gm/kg (4000mg/kg)   Drugs in Japan Vol. 6, Pg. 634, 1982.
mouse LD50 intraperitoneal 9770mg/kg (9770mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Chemotherapy Vol. 25, Pg. 816, 1977.
mouse LD50 intravenous 4900mg/kg (4900mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Chemotherapy Vol. 25, Pg. 816, 1977.
mouse LD50 oral > 10gm/kg (10000mg/kg)   Drugs in Japan Vol. 6, Pg. 634, 1982.
mouse LD50 subcutaneous > 10gm/kg (10000mg/kg)   Drugs in Japan Vol. 6, Pg. 634, 1982.
rat LD50 intraperitoneal 7600mg/kg (7600mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Chemotherapy Vol. 25, Pg. 816, 1977.
rat LD50 intravenous 2260mg/kg (2260mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 10, Pg. 884, 1979.
rat LD50 oral > 10gm/kg (10000mg/kg)   Drugs in Japan Vol. 6, Pg. 634, 1982.
rat LD50 subcutaneous 8800mg/kg (8800mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 10, Pg. 884, 1979.
rat LD50 unreported 2gm/kg (2000mg/kg)   United States Patent Document. Vol. #4535078,
women TDLo intramuscular 960mg/kg/3D-I (960mg/kg) BLOOD: HEMORRHAGE Southern Medical Journal. Vol. 78, Pg. 363, 1985.
women TDLo intravenous 2180mg/kg/6D- (2180mg/kg) BLOOD: LEUKOPENIA

BLOOD: NORMOCYTIC ANEMIA
Southern Medical Journal. Vol. 79, Pg. 255, 1986.