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Substance Name: Pivampicillin hydrochloride [USAN]
RN: 26309-95-5
UNII: V9HOC53L7L
InChIKey: DQECFVGMGBQCPA-GLCLSGQWSA-N

Note

  • Pivalate ester analog of AMPICILLIN.

Classification Codes

  • Antibacterial
  • Reproductive Effect

Molecular Formula

  • C22-H29-N3-O6-S.Cl-H

Molecular Weight

  • 500.013
 
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Names and Synonyms

Name of Substance

  • Pivampicillin hydrochloride [USAN]

Synonyms

  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, monohydrochloride, (2S-(2alpha,5alpha,6beta(S*)))-
  • 6-(D-alpha-Aminophenylacetamido)penicillanic acid pivaloyloxymethyl ester hydrochloride
  • Alphacilina
  • Alphacillin
  • Ampicillin pivaloyloxymethyl ester hydrochloride
  • Berocillin
  • Centurina
  • Devonium
  • Diancina
  • EINECS 247-604-2
  • Hydroxymethyl D-(-)-6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate pivalate (ester) monohydrochloride
  • Inacilin
  • Maxifen
  • Pivaloyloxymethyl D-alpha-aminobenzylpenicillinate hydrochloride
  • Pivampicillin HCl
  • Pivampicillin hydrochloride
  • Pivatil
  • Pondocillin
  • Sanguicillin
  • UNII-V9HOC53L7L

Systematic Names

  • (Pivaloyloxy)methyl (2S-(2alpha,5alpha,6beta(S*)))-6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate monohydrochloride
  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, hydrochloride
  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, monohydrochloride, (2S-(2alpha,5alpha,6beta(S*)))-

Registry Numbers

CAS Registry Number

  • 26309-95-5

FDA UNII

  • V9HOC53L7L

Related Registry Number

  • 33817-20-8 (Parent)

System Generated Number

  • 0026309955

Molecular Formulas

Molecular Formula

  • C22-H29-N3-O6-S.Cl-H

Molecular Formula Fragments

  • C22-H29-N3-O6-S
  • Cl-H
  • COMPONENT

Structure Descriptors

InChI

1S/C22H29N3O6S.ClH/c1-21(2,3)20(29)31-11-30-19(28)15-22(4,5)32-18-14(17(27)25(15)18)24-16(26)13(23)12-9-7-6-8-10-12;/h6-10,13-15,18H,11,23H2,1-5H3,(H,24,26);1H/t13-,14-,15+,18-;/m1./s1

InChIKey

DQECFVGMGBQCPA-GLCLSGQWSA-N

Smiles

CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](c3ccccc3)N)C(=O)OCOC(=O)C(C)(C)C)C.Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 245mg/kg (245mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Chemotherapy Vol. 22, Pg. 357, 1974.
mouse LD50 intravenous 150mg/kg (150mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Chemotherapy Vol. 22, Pg. 357, 1974.
mouse LD50 oral 2819mg/kg (2819mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Chemotherapy Vol. 22, Pg. 357, 1974.
mouse LD50 subcutaneous 3312mg/kg (3312mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Chemotherapy Vol. 22, Pg. 357, 1974.
rat LD50 intraperitoneal 632mg/kg (632mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Chemotherapy Vol. 22, Pg. 357, 1974.
rat LD50 intravenous 145mg/kg (145mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Chemotherapy Vol. 22, Pg. 357, 1974.
rat LD50 oral > 6gm/kg (6000mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Chemotherapy Vol. 22, Pg. 357, 1974.
rat LD50 subcutaneous 6459mg/kg (6459mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Chemotherapy Vol. 22, Pg. 357, 1974.