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Substance Name: Benzylpenicillin [INN:BAN]
RN: 61-33-6
UNII: Q42T66VG0C
InChIKey: JGSARLDLIJGVTE-MBNYWOFBSA-N

Note

  • A penicillin derivative commonly used in the form of its sodium or potassium salts in the treatment of a variety of infections. It is effective against most gram-positive bacteria and against gram-negative cocci. It has also been used as an experimental convulsant because of its actions on GAMMA-AMINOBUTYRIC ACID mediated synaptic transmission.

Molecular Formula

  • C16-H18-N2-O4-S

Molecular Weight

  • 334.3942
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Natural Product
  • Tumor Data

Names and Synonyms

Name of Substance

  • Benzylpenicillin [INN:BAN]
  • Penicillin G

MeSH Heading

  • Penicillin G

Synonyms

  • (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
  • (5R,6R)-Benzylpenicillin
  • (Phenylmethyl)penicillin
  • (Phenylmethyl)penicillinic acid
  • 4-27-00-05861 (Beilstein Handbook Reference)
  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-((phenylacetyl)amino)-, (2S-(2alpha,5alpha,6beta))-
  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-
  • Abbocillin
  • Bencilpenicilina
  • Bencilpenicilina [Spanish]
  • Benzopenicillin
  • Benzyl penicillin
  • Benzyl-6-aminopenicillinic acid
  • Benzylpenicillin
  • Benzylpenicillin G
  • Benzylpenicilline
  • Benzylpenicilline [French]
  • Benzylpenicillinic acid
  • Benzylpenicillinum
  • Benzylpenicillinum [Latin]
  • BRN 0044740
  • Cilloral
  • Cilopen
  • Compocillin G
  • Cosmopen
  • Dropcillin
  • EINECS 200-506-3
  • Free benzylpenicillin
  • Free penicillin G
  • Free penicillin II
  • Galofak
  • Gelacillin
  • HSDB 3166
  • Liquacillin
  • NSC 193396
  • Pencillin G
  • Penicillin G
  • Penicillin, (phenylmethyl)-
  • Penicillinic acid, (phenylmethyl)-
  • Penicillinic acid, benzyl-
  • Pharmacillin
  • Phenylacetamidopenicillanic acid
  • Pradupen
  • Specilline G
  • UNII-Q42T66VG0C

Systematic Names

  • (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6- (2-phenylacetamido)-
  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-((phenylacetyl)amino)- (2S-(2alpha,5alpha,6beta))-
  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-(2-phenylacetamido)- (8CI)
  • 6-(2-Phenylacetamido)penicillanic acid

Registry Numbers

CAS Registry Number

  • 61-33-6

FDA UNII

  • Q42T66VG0C

Related Registry Numbers

  • 113-98-4 (mono-potassium salt)
  • 69-57-8 (mono-hydrochloride salt)

System Generated Number

  • 0000061336

Structure Descriptors

InChI

1S/C16H18N2O4S/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1

InChIKey

JGSARLDLIJGVTE-MBNYWOFBSA-N

Smiles

CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)Cc3ccccc3)C(=O)O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo parenteral 15000units/kg (15000units/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

SENSE ORGANS AND SPECIAL SENSES: CHANGES IN COCHLEAR STRUCTURE OR FUNCTION: EAR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Lancet. Vol. 1, Pg. 394, 1986.
dog LD50 intracrebral 1118ug/kg (1.118mg/kg) BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES Journal of Laboratory and Clinical Medicine. Vol. 34, Pg. 126, 1949.
dog LD50 unreported 4940ug/kg (4.94mg/kg) BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES Journal of Laboratory and Clinical Medicine. Vol. 34, Pg. 126, 1949.
guinea pig LD50 unreported 38mg/kg (38mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 42(9), Pg. 10, 1977.
hamster LD50 oral 24mg/kg (24mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: FOOD INTAKE (ANIMAL)
Toxicology and Applied Pharmacology. Vol. 14, Pg. 510, 1969.
hamster LD50 subcutaneous 96mg/kg (96mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Toxicology and Applied Pharmacology. Vol. 14, Pg. 510, 1969.
mouse LD50 intracrebral 5700ug/kg (5.7mg/kg) BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES Journal of Laboratory and Clinical Medicine. Vol. 34, Pg. 126, 1949.
mouse LD50 intraperitoneal 3500mg/kg (3500mg/kg)   Antimicrobial Agents and Chemotherapy Vol. -, Pg. 619, 1967.
mouse LD50 intravenous 329mg/kg (329mg/kg)   Biochemical Pharmacology. Vol. 16, Pg. 1365, 1967.
mouse LD50 oral > 5gm/kg (5000mg/kg)   Antimicrobial Agents and Chemotherapy Vol. -, Pg. 619, 1967.
mouse LD50 unreported 7800mg/kg (7800mg/kg)   Antibiotiki. Vol. 23, Pg. 317, 1978.
rabbit LD50 intracrebral 653ug/kg (0.653mg/kg) BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES Journal of Laboratory and Clinical Medicine. Vol. 34, Pg. 126, 1949.
rat LD50 oral 8gm/kg (8000mg/kg)   Antibiotics and Chemotherapy Vol. 12, Pg. 249, 1962.
rat LD50 unreported 9gm/kg (9000mg/kg)   Antibiotiki. Vol. 23, Pg. 317, 1978.

Physical Properties

Physical Property Value Units Temp (deg C) Source
pKa Dissociation Constant 2.74 (none) 25 EXP
log P (octanol-water) 1.83 (none)   EXP
Water Solubility 210 mg/L 25 EST
Vapor Pressure 2.55E-12 mm Hg 25 EST
Henry's Law Constant 1.16E-14 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 6.97E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.