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Substance Name: Bupivacaine hydrochloride [JAN]
RN: 18010-40-7
UNII: AKA908P8J1
InChIKey: SIEYLFHKZGLBNX-UHFFFAOYSA-N

Note

  • A widely used local anesthetic agent.

Classification Codes

  • Anesthetic (Local)
  • Drug / Therapeutic Agent

Molecular Formula

  • C18-H28-N2-O.Cl-H

Molecular Weight

  • 324.8931
 
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Names and Synonyms

Name of Substance

  • Bupivacaine hydrochloride [JAN]

Synonyms

  • (+-)-Bupivacaine hydrochloride
  • 1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide monohydrochloride
  • 2',6'-Pipecoloxylidide, 1-butyl-, hydrochloride
  • 2',6'-Pipecoloxylidide, 1-butyl-, monohydrochloride
  • AH 2250
  • Bicain
  • Bupivacaine HCl
  • Bupivacaine hydrochloride
  • Bupivacaine hydrochloride anhydrous
  • Bupivacaine hydrochloride kit
  • Bupivacaine hydrochloride preservation free
  • Carbostesin
  • EINECS 241-917-8
  • LAC 43
  • Marcaine
  • Marcaine hydrochloride preservation free
  • Marcaine spinal
  • MNarcaine hydrochloride
  • Sensorcaine
  • SKY 0302
  • UNII-AKA908P8J1
  • Win 11,318

Systematic Names

  • 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, monohydrochloride
  • Bupivacaine hydrochloride

Mixture Name

  • Vivacaine

Registry Numbers

CAS Registry Number

  • 18010-40-7

FDA UNII

  • AKA908P8J1

Other Registry Number

  • 14252-80-3

System Generated Number

  • 0018010407

Molecular Formulas

Molecular Formula

  • C18-H28-N2-O.Cl-H

Molecular Formula Fragments

  • C18-H28-N2-O
  • Cl-H
  • COMPONENT

Structure Descriptors

InChI

InChI=1S/C18H28N2O.ClH/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);1H

InChIKey

SIEYLFHKZGLBNX-UHFFFAOYSA-N

Smiles

Cl.CCCCN1CCCCC1C(=O)Nc2c(C)cccc2C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
domestic animals - goat/sheep LDLo intravenous 150mg/kg (150mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE
Anesthesia and Analgesia Vol. 86, Pg. 797, 1998.
guinea pig LD50 intraperitoneal 50mg/kg (50mg/kg)   Drugs in Japan Vol. 6, Pg. 680, 1982.
mouse LD50 intramuscular 22753ug/kg (22.753mg/kg)   Drug Development Research. Vol. 21, Pg. 277, 1990.
mouse LD50 intraperitoneal 58700ug/kg (58.7mg/kg) BEHAVIORAL: ANTICONVULSANT

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Anesthesia and Analgesia Vol. 60, Pg. 385, 1981.
mouse LD50 intravenous 6100ug/kg (6.1mg/kg)   Anesthesia Progress. Vol. 36, Pg. 79, 1989.
mouse LD50 subcutaneous 59mg/kg (59mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 200, Pg. 359, 1972.
rabbit LD50 intratracheal 11mg/kg (11mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 200, Pg. 359, 1972.
rabbit LD50 intravenous 3400ug/kg (3.4mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 200, Pg. 359, 1972.
rabbit LD50 oral 18mg/kg (18mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 200, Pg. 359, 1972.
rabbit LD50 parenteral 48mg/kg (48mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 200, Pg. 359, 1972.
rat LD50 intravenous 6mg/kg (6mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 200, Pg. 359, 1972.
rat LD50 parenteral 30mg/kg (30mg/kg)   Anesthesiology. Vol. 89, Pg. 1199, 1998.
rat LD50 subcutaneous 43mg/kg (43mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 200, Pg. 359, 1972.