levobupivacaine indications/contra

Stem definitionDrug idCAS RN
local anaesthetics 4 27262-47-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • levobupivacaine
  • chirocain
  • levobupivacaine hydrochloride
  • levobupivacaine HCl
S-enantiomer of bupivacaine, local anaesthetic
  • Molecular weight: 288.44
  • Formula: C18H28N2O
  • CLOGP: 3.69
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 1
  • TPSA: 32.34
  • ALOGS: -3.47
  • ROTB: 5

Drug dosage:

None

Approvals:

DateAgencyCompanyOrphan
Aug. 5, 1999 FDA PURDUE PHARMA LP

FDA Adverse Event Reporting System

None

Pharmacologic Action:

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SourceCodeDescription
ATC N01BB10 NERVOUS SYSTEM
ANESTHETICS
ANESTHETICS, LOCAL
Amides
MeSH PA D000777 Anesthetics
MeSH PA D000779 Anesthetics, Local
CHEBI has role CHEBI:36333 local anaesthetic
CHEBI has role CHEBI:37887 adrenergic antagonist
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018689 Sensory System Agents

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Anesthesia for cesarean section indication 4847005
Local anesthesia indication 386761002
Regional Anesthesia for Surgery indication
Regional Anesthesia for Labor Pain indication
Major Nerve Block for Surgery indication
Regional Anesthesia for Postoperative Pain indication
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Kidney disease contraindication 90708001 DOID:2527
Myasthenia gravis contraindication 91637004 DOID:437
Disease of liver contraindication 235856003 DOID:409
Deficiency of cholinesterase contraindication 360607009

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.24 acidic
pKa2 7.92 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Sodium channel protein type 4 subunit alpha Ion channel BLOCKER WOMBAT-PK CHEMBL
Cytochrome P450 2D6 Enzyme IC50 6.71 DRUG MATRIX
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 4.89 CHEMBL
Potassium voltage-gated channel subfamily D member 3 Ion channel IC50 4.50 WOMBAT-PK
Prostaglandin E2 receptor EP1 subtype GPCR WOMBAT-PK
Sodium channel protein type 1 subunit alpha Ion channel IC50 5.79 WOMBAT-PK
Potassium voltage-gated channel subfamily A member 5 Ion channel WOMBAT-PK
5-hydroxytryptamine receptor 3A Ion channel WOMBAT-PK

External reference:

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IDSource
4021287 VUID
N0000148724 NUI
C0873118 UMLSCUI
7211 IUPHAR_LIGAND_ID
D01287 KEGG_DRUG
DB01002 DRUGBANK_ID
92253 PUBCHEM_CID
116103003 SNOMEDCT_US
387011006 SNOMEDCT_US
259453 RXNORM
4021287 VANDF
d04449 MMSL
8289 MMSL
N0000148724 NDFRT
N0000010142 NDFRT
008081 NDDF
A5H73K9U3W UNII
7465 INN_ID
CHEBI:6149 CHEBI
CHEMBL1200749 ChEMBL_ID
CHEMBL1201193 ChEMBL_ID
27262-48-2 SECONDARY_CAS_RN
C476513 MESH_SUPPLEMENTAL_RECORD_UI

Pharmaceutical products:

None