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Substance Name: Penicillin V [USAN:USP]
RN: 87-08-1
UNII: Z61I075U2W
InChIKey: BPLBGHOLXOTWMN-MBNYWOFBSA-N

Note

  • A broad-spectrum penicillin antibiotic used orally in the treatment of mild to moderate infections by susceptible gram-positive organisms.

Molecular Formula

  • C16-H18-N2-O5-S

Molecular Weight

  • 350.3932
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data

Names and Synonyms

Name of Substance

  • Penicillin V
  • Penicillin V [USAN:USP]
  • Phenoxymethylpenicillin [INN]

MeSH Heading

  • Penicillin V

Synonyms

  • (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
  • 3,3-Dimethyl-7-oxo-6-((phenyloxyacetyl)amino)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
  • 4-27-00-05884 (Beilstein Handbook Reference)
  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-((phenoxyacetyl)amino)-, (2S-(2alpha,5alpha,6beta))-
  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-
  • 6-Phenoxyacetamidopenicillanic acid
  • Acipen V
  • Apopen
  • Beromycin
  • BRN 0096259
  • Calcipen
  • CCRIS 752
  • Compocillin V
  • Crystapen V
  • Distaquaine V
  • EINECS 201-722-0
  • Eskacillian V
  • Eskacillin V
  • Fenacilin
  • Fenospen
  • Fenossimetilpenicillina
  • Fenossimetilpenicillina [DCIT]
  • Fenoximetilpenicilina
  • Fenoximetilpenicilina [INN-Spanish]
  • Fenoxypen
  • HSDB 6314
  • Meropenin
  • Oracillin
  • Oratren
  • Ospen
  • P-Mega-Tablinen
  • Pen-Oral
  • Pen-V
  • Pen-Vee
  • Penicillin phenoxymethyl
  • Penicillin V
  • Phenocillin
  • Phenomycilline
  • Phenopenicillin
  • Phenoximethylpenicillinum
  • Phenoxymethyl penicillin
  • Phenoxymethylenepenicillinic acid
  • Phenoxymethylpenicillin
  • Phenoxymethylpenicilline
  • Phenoxymethylpenicilline [INN-French]
  • Phenoxymethylpenicillinic acid
  • Phenoxymethylpenicillinum
  • Phenoxymethylpenicillinum [INN-Latin]
  • Rocilin
  • Stabicillin
  • UNII-Z61I075U2W
  • V-Cil
  • V-Cillin
  • V-Cylina
  • V-Cyline
  • V-Tablopen
  • Vebecillin

Systematic Names

  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-((phenoxyacetyl)amino)-, (2S,5R,6R)-
  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-((phenoxyacetyl)amino)-, (2S-(2alpha,5alpha,6beta))-
  • Penicillanic acid, 6-phenoxyacetamido-
  • Penicillin V
  • Phenoxymethylpenicillin

Registry Numbers

CAS Registry Number

  • 87-08-1

FDA UNII

  • Z61I075U2W

Related Registry Numbers

  • 1098-87-9 (mono-hydrochloride salt)
  • 132-98-9 (mono-potassium salt)
  • 147-48-8 (mono-hydrochloride salt)

System Generated Number

  • 0000087081

Structure Descriptors

InChI

1S/C16H18N2O5S/c1-16(2)12(15(21)22)18-13(20)11(14(18)24-16)17-10(19)8-23-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1

InChIKey

BPLBGHOLXOTWMN-MBNYWOFBSA-N

Smiles

CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)COc3ccccc3)C(=O)O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 intramuscular 1096mg/kg (1096mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Antibiotics Annual. Vol. 3, Pg. 534, 1955/1956.
guinea pig LD50 intraperitoneal 822mg/kg (822mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Antibiotics Annual. Vol. 3, Pg. 534, 1955/1956.
mouse LD50 intramuscular > 1775mg/kg (1775mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Antibiotics Annual. Vol. 3, Pg. 534, 1955/1956.
mouse LD50 intraperitoneal 1351mg/kg (1351mg/kg)   Antibiotics Annual. Vol. 3, Pg. 540, 1955/1956.
mouse LD50 oral 6578mg/kg (6578mg/kg)   Antibiotiki. Vol. 3(4), Pg. 37, 1958.
mouse LD50 subcutaneous > 4gm/kg (4000mg/kg)   Antibiotics Annual. Vol. 3, Pg. 540, 1955/1956.
rat LD50 intramuscular > 1600mg/kg (1600mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Antibiotics Annual. Vol. 3, Pg. 534, 1955/1956.
rat LD50 intraperitoneal > 2gm/kg (2000mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Antibiotics Annual. Vol. 3, Pg. 534, 1955/1956.
rat LD50 intravenous > 1775mg/kg (1775mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Antibiotics Annual. Vol. 3, Pg. 534, 1955/1956.
rat LD50 oral > 2220mg/kg (2220mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Antibiotics Annual. Vol. 3, Pg. 534, 1955/1956.
women TDLo oral 10mg/kg/2D (10mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

LIVER: LIVER FUNCTION TESTS IMPAIRED
Lancet. Vol. 2, Pg. 1297, 1976.

Physical Properties

Physical Property Value Units Temp (deg C) Source
pKa Dissociation Constant 2.79 (none)   EXP
log P (octanol-water) 2.09 (none)   EXP
Water Solubility 101 mg/L 25 EST
Vapor Pressure 1.06E-12 mm Hg 25 EST
Henry's Law Constant 4.42E-15 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 8.99E-11 cm3/molecule-sec 25 EST

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