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Substance Name: Bupivacaine [USAN:INN:BAN]
RN: 38396-39-3
UNII: Y8335394RO
InChIKey: LEBVLXFERQHONN-UHFFFAOYSA-N

Note

  • A widely used local anesthetic agent.

Molecular Formula

  • C18-H28-N2-O

Molecular Weight

  • 288.4322
 

Classification Codes

  • Anesthetic (Local)
  • Anesthetics
  • Anesthetics, Local
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Drug / Therapeutic Agent
  • Human Data
  • Peripheral Nervous System Agents
  • Reproductive Effect
  • Sensory System Agents
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Names and Synonyms

Name of Substance

  • Bupivacaine
  • Bupivacaine [USAN:INN:BAN]

MeSH Heading

  • Bupivacaine

Synonyms

  • (+-)-Bupivacaine
  • 1-Butyl-2',6'-pipecoloxylidide
  • AH 250
  • Anekain
  • Bupivacaina
  • Bupivacaina [INN-Spanish]
  • Bupivacaine
  • Bupivacaine liposome injectable suspension
  • Bupivacainum
  • Bupivacainum [INN-Latin]
  • dl-1-Butyl-2',6'-pipecoloxylidide
  • DL-Bupivacaine
  • EINECS 218-553-3
  • EINECS 253-911-2
  • Exparel
  • HSDB 7790
  • SKY 0402
  • SKY0402
  • UNII-Y8335394RO
  • Win 11318

Systematic Names

  • (1)-1-Butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
  • 2',6'-Pipecoloxylidide, 1-butyl-
  • 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-
  • 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, (+-)-
  • Bupivacaine

Registry Numbers

CAS Registry Number

  • 38396-39-3

FDA UNII

  • Y8335394RO

Other Registry Number

  • 2180-92-9

System Generated Number

  • 0038396393

Structure Descriptors

InChI

1S/C18H28N2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21)

InChIKey

LEBVLXFERQHONN-UHFFFAOYSA-N

Smiles

CCCCN1CCCCC1C(=O)Nc2c(cccc2C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 intraperitoneal 36600ug/kg (36.6mg/kg)   United States Patent Document. Vol. #3632766,
human TDLo intravenous 4300ug/kg (4.3mg/kg) VASCULAR: MEASUREMENT OF REGIONAL BLOOD FLOW

BEHAVIORAL: EUPHORIA
Acta Anaesthesiologica Scandinavica. Vol. 21, Pg. 521, 1977.
mouse LD50 intravenous 7100ug/kg (7.1mg/kg)   United States Patent Document. Vol. #3632766,
mouse LD50 subcutaneous 35mg/kg (35mg/kg)   United States Patent Document. Vol. #3632766,
rabbit LD50 intratracheal 12500ug/kg (12.5mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 78, 1976.
rabbit LD50 intravenous 1620ug/kg (1.62mg/kg)   Anesthesia and Analgesia Vol. 64, Pg. 209, 1985.
rabbit LD50 parenteral 64mg/kg (64mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 78, 1976.
rat LD50 intravenous 5600ug/kg (5.6mg/kg)   Acta Pharmacologica et Toxicologica. Vol. 31, Pg. 273, 1972.
rat LD50 subcutaneous 47mg/kg (47mg/kg)   United States Patent Document. Vol. #3632766,

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 107-108 deg C   EXP
log P (octanol-water) 3.41 (none)   EXP
Water Solubility 2400 mg/L 25 EXP
Vapor Pressure 1.79E-08 mm Hg 25 EST
Henry's Law Constant 1.79E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.33E-10 cm3/molecule-sec 25 EST

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