butorphanol Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
opioid receptor antagonists/agonists, morphinan derivates 454 42408-82-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • butorphanol
  • (-)-Butorphanol
  • butorphanol tartrate
  • BC 2627
  • BC-2627
Butorphanol is a mixed agonist-antagonist with low intrinsic activity at receptors of the mu-opioid type (morphine-like). It is also an agonist at k-opioid receptors. Its interactions with these receptors in the central nervous system apparently mediate most of its pharmacologic effects, including analgesia.
  • Molecular weight: 327.47
  • Formula: C21H29NO2
  • CLOGP: 3.73
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 2
  • TPSA: 43.70
  • ALOGS: -3.31
  • ROTB: 2

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
12 mg P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 2 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 2 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.82 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 17 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 12 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 41 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.17 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 4.80 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Aug. 22, 1978 FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug hypersensitivity 122.14 62.96 28 35 46615 2311407

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug hypersensitivity 17.13 0 4 12 15131 1731634

Pharmacologic Action:

SourceCodeDescription
ATC N02AF01 NERVOUS SYSTEM
ANALGESICS
OPIOIDS
Morphinan derivatives
FDA MoA N0000175686 Competitive Opioid Antagonists
FDA EPC N0000175692 Opioid Agonist/Antagonist
FDA MoA N0000175685 Partial Opioid Agonists
MeSH PA D000700 Analgesics
MeSH PA D000701 Analgesics, Opioid
CHEBI has role CHEBI:51177 antitussive
CHEBI has role CHEBI:35482 opioid analgesic
CHEBI has role CHEBI:55322 mu-opioid receptor agonist
CHEBI has role CHEBI:59282 kappa-opioid receptor agonist
MeSH PA D000996 Antitussive Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D009292 Narcotic Antagonists
MeSH PA D009294 Narcotics
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D019141 Respiratory System Agents
MeSH PA D018689 Sensory System Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Pain indication 22253000
General anesthesia indication 50697003
Labor pain indication 247412007
Sedation as Adjunct to Anesthesia indication
Migraine off-label use 37796009 DOID:6364
Chronic disease of respiratory system contraindication 17097001
Myocardial infarction contraindication 22298006 DOID:5844
Chronic heart failure contraindication 48447003
Substance abuse contraindication 66214007
Benign intracranial hypertension contraindication 68267002 DOID:11459
Opioid dependence contraindication 75544000 DOID:2559
Decreased respiratory function contraindication 80954004
Injury of head contraindication 82271004
Impaired renal function disorder contraindication 197663003
Disease of liver contraindication 235856003 DOID:409
Disorder of coronary artery contraindication 414024009

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.7 acidic
pKa2 8.56 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Kappa-type opioid receptor GPCR PARTIAL AGONIST Ki 9.92 CHEMBL CHEMBL
Mu-type opioid receptor GPCR PARTIAL AGONIST Ki 9.92 CHEMBL CHEMBL
Delta-type opioid receptor GPCR Ki 7.92 CHEMBL

External reference:

IDSource
D002077 MESH_DESCRIPTOR_UI
4019650 VUID
N0000147743 NUI
C0006491 UMLSCUI
D00837 KEGG_DRUG
2L7I72RUHN UNII
58786-99-5 SECONDARY_CAS_RN
13936006 SNOMEDCT_US
4019650 VANDF
004635 NDDF
1841 RXNORM
373467000 SNOMEDCT_US
d00838 MMSL
CHEMBL33986 ChEMBL_ID
CHEMBL299400 ChEMBL_ID
DB00611 DRUGBANK_ID
3620 INN_ID
CHEBI:3242 CHEBI
7591 IUPHAR_LIGAND_ID
5361092 PUBCHEM_CID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Butorphanol Tartrate HUMAN PRESCRIPTION DRUG LABEL 1 0054-3090 SPRAY, METERED 10 mg NASAL ANDA 15 sections
Butorphanol Tartrate HUMAN PRESCRIPTION DRUG LABEL 1 0143-9864 INJECTION, SOLUTION 1 mg INTRAMUSCULAR ANDA 14 sections
Butorphanol Tartrate HUMAN PRESCRIPTION DRUG LABEL 1 0143-9867 INJECTION, SOLUTION 2 mg INTRAMUSCULAR ANDA 14 sections
Butorphanol Tartrate HUMAN PRESCRIPTION DRUG LABEL 1 0378-9639 SPRAY 10 mg NASAL ANDA 15 sections
Butorphanol Tartrate HUMAN PRESCRIPTION DRUG LABEL 1 0409-1623 INJECTION, SOLUTION 1 mg INTRAMUSCULAR ANDA 14 sections
BUTORPHANOL TARTRATE HUMAN PRESCRIPTION DRUG LABEL 1 0409-1626 INJECTION, SOLUTION 2 mg INTRAMUSCULAR ANDA 14 sections
Butorphanol Tartrate HUMAN PRESCRIPTION DRUG LABEL 1 60505-0813 SPRAY 10 mg NASAL ANDA 15 sections