U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H29NO2
Molecular Weight 327.4605
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUTORPHANOL

SMILES

OC1=CC=C2C[C@H]3N(CC4CCC4)CC[C@@]5(CCCC[C@@]35O)C2=C1

InChI

InChIKey=IFKLAQQSCNILHL-QHAWAJNXSA-N
InChI=1S/C21H29NO2/c23-17-7-6-16-12-19-21(24)9-2-1-8-20(21,18(16)13-17)10-11-22(19)14-15-4-3-5-15/h6-7,13,15,19,23-24H,1-5,8-12,14H2/t19-,20+,21-/m1/s1

HIDE SMILES / InChI

Description

Butorphanol is a synthetic opioid agonist-antagonist analgesic with a pharmacological and therapeutic profile that has been well established since its launch as a parenteral formulation in 1978. The introduction of a transnasal formulation of butorphanol represents a new and noninvasive presentation of an analgesic for moderate to severe pain. This route of administration bypasses the gastrointestinal tract, and this is an advantage for a drug such as butorphanol that undergoes significant first-pass metabolism after oral administration. The onset of action and systemic bioavailability of butorphanol following transnasal delivery are similar to those after parenteral administration. Butorphanol blocks pain impulses at specific sites in the brain and spinal cord. Butorphanol has agonistic activity at the κ-receptor and antagonistic activity at the μ-receptor. It also exhibits partial agonistic activity at the σ-receptor.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
12.0 nM [Ki]
0.12 nM [Ki]
0.22 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Butorphanol tartrate
PubMed

PubMed

TitleDatePubMed
Tolerance to the analgesic effect of buprenorphine, butorphanol, nalbuphine, and cyclorphan, and cross-tolerance to morphine.
2001
Cardiopulmonary assessment of medetomidine, ketamine, and butorphanol anesthesia in captive Thomson's gazelles (Gazella thomsoni).
2001 Jun
Diagnosis and management of a patent urachus in a white rhinoceros calf (Ceratotherium simum simum).
2001 Mar
Comparison of transdermal administration of fentanyl versus intramuscular administration of butorphanol for analgesia after onychectomy in cats.
2002 Apr 1
Effect of medetomidine-butorphanol-ketamine anaesthesia and atipamezole on heart and respiratory rate and cloacal temperature of domestic pigeons.
2002 Aug
Do butalbital-containing products have a role in the management of migraine?
2002 Aug
Nasal administration of opioids for pain management in adults.
2002 Aug
Evaluation of sedative and cardiorespiratory effects of romifidine and romifidine-butorphanol in cats.
2002 Aug 15
Effects of treatment with oxytocin, xylazine butorphanol, guaifenesin, acepromazine, and detomidine on esophageal manometric pressure in conscious horses.
2002 Dec
In vitro effects of oxytocin, acepromazine, detomidine, xylazine, butorphanol, terbutaline, isoproterenol, and dantrolene on smooth and skeletal muscles of the equine esophagus.
2002 Dec
Effects of medetomidine-midazolam, acepromazine-butorphanol, and midazolam-butorphanol on induction dose of thiopental and propofol and on cardiopulmonary changes in dogs.
2002 Dec
Butorphanol dependence and withdrawal decrease hippocampal kappa 2-opioid receptor binding.
2002 Dec 27
The effects of xylazine, detomidine, acepromazine and butorphanol on equine solid phase gastric emptying rate.
2002 Jul
Age-related differences in sensitivity to the antinociceptive effects of kappa opioids in adult male rats.
2002 Jul
Cardiorespiratory effects of medetomidine-butorphanol, medetomidine-butorphanol-diazepam, and medetomidine-butorphanol-ketamine in captive red wolves (Canis rufus).
2002 Jun
Withdrawal from dependence upon butorphanol uniquely increases kappa(1)-opioid receptor binding in the rat brain.
2002 Jun
Animal behavior case of the month. Attention-getting behavior.
2002 Mar 1
Butorphanol decreases edema following carrageenan-induced paw inflammation in rats.
2002 Nov
Evaluation of intravenous administration of meloxicam for perioperative pain management following stifle joint surgery in dogs.
2002 Nov
Effects of preoperative administration of ketoprofen on anesthetic requirements and signs of postoperative pain in dogs undergoing elective ovariohysterectomy.
2002 Nov 1
Activation profiles of opioid ligands in HEK cells expressing delta opioid receptors.
2002 Nov 18
A comparison of thiopental, propofol, and diazepam-ketamine anesthesia for evaluation of laryngeal function in dogs premedicated with butorphanol-glycopyrrolate.
2002 Nov-Dec
Antinociceptive effects of the selective delta opioid agonist SNC80 alone and in combination with mu opioids in the squirrel monkey titration procedure.
2002 Oct
Sex-related differences in mechanical nociception and antinociception produced by mu- and kappa-opioid receptor agonists in rats.
2002 Oct 4
Influence of gonadectomy on the antinociceptive effects of opioids in male and female rats.
2002 Sep
[Comparative effect of partial opiate agonists buprenorphine and butorphanol on the phospholipid composition of hepatocytes plasma membranes during hemorrhagic shock in cats].
2002 Sep-Oct
WHO Expert Committee on Drug Dependence.
2003
Sensitivity to the effects of opioids in rats with free access to exercise wheels: mu-opioid tolerance and physical dependence.
2003 Aug
Comparison of electroacupuncture and butorphanol on respiratory and cardiovascular effects and rectal pain threshold after controlled rectal distention in mares.
2003 Feb
Postoperative hypoxemia and hypercarbia in healthy dogs undergoing routine ovariohysterectomy or castration and receiving butorphanol or hydromorphone for analgesia.
2003 Feb 1
Chemical restraint of peccaries with tiletamine/zolazepam and xylazine or tiletamine/zolazepam and butorphanol.
2003 Jan
Possible mechanism involved in the anticonvulsant action of butorphanol in mice.
2003 Jan
Evaluation of the sedative and cardiorespiratory effects of dexmedetomidine, dexmedetomidine-butorphanol, and dexmedetomidine-ketamine in cats.
2003 Jan 1
Activity of opioid ligands in cells expressing cloned mu opioid receptors.
2003 Jan 4
Reduction and stabilization of hip luxation by the transposition of the ligamentum sacrotuberale in dogs: an in vivo study.
2003 Jan-Feb
A comparison of the analgesic effects of butorphanol with those of meloxicam after elective ovariohysterectomy in dogs.
2003 Jul
Comparison of the efficacy and cardiorespiratory effects of medetomidine-based anesthetic protocols in ring-tailed lemurs (Lemur catta).
2003 Jun
Effect of drugs on cholesterol crystallization in an artificial bile model and relation of this effect to drug binding to albumin.
2003 Jun
Postoperative analgesia in children undergoing myringotomy and placement equalization tubes in ambulatory surgery.
2003 Jun
The cardiac anesthetic index of isoflurane in green iguanas.
2003 Jun 1
Minimum alveolar concentration of isoflurane in green iguanas and the effect of butorphanol on minimum alveolar concentration.
2003 Jun 1
Enhanced binding of nor-binaltorphimine to kappa-opioid receptors in rats dependent on butorphanol.
2003 Jun 15
Comparison of the cardiorespiratory effects of medetomidine-butorphanol-ketamine and medetomidine-butorphanol-midazolam in patas monkeys (Erythrocebus patas).
2003 Mar
Progressive changes in ophthalmic blood velocities in Beagles with primary open angle glaucoma.
2003 Mar
Effects of alpha-2 adrenoceptor agonists during recovery from isoflurane anaesthesia in horses.
2003 Mar
Interactions between opioids and cocaine on locomotor activity in rats: influence of an opioid's relative efficacy at the mu receptor.
2003 May
The competitive N-methyl-D-aspartate receptor antagonist (-)-6-phosphonomethyl-deca-hydroisoquinoline-3-carboxylic acid (LY235959) potentiates the antinociceptive effects of opioids that vary in efficacy at the mu-opioid receptor.
2003 Nov
Dose ratio is important in maximizing naloxone enhancement of nalbuphine analgesia in humans.
2003 Nov 6
Cisplatin and doxorubicin toxicosis in dogs with osteosarcoma.
2003 Sep-Oct
Physicians and the pharmaceutical industry: a dysfunctional relationship.
2003 Spring
Patents

Sample Use Guides

In Vivo Use Guide
Preoperative Medication: Initial dose: 2 mg intramuscularly 60 to 90 minutes before surgery Balanced Anesthesia: Initial dose: 2 mg intravenously shortly before induction and/or 0.5 mg to 1 mg in increments during anesthesia. The increments may be higher, up to 0.06 mg/kg (4 mg/70 kg) depending on the previous sedative, analgesic, and hypnotic drugs administered. The total dose needed will vary. However, patients have generally been reported to have needed between a total dosage of 4 mg to 12.5 mg (approximately 0.06 to 0.18 mg/kg). Usual Adult Dose for Labor Pain For use In the treatment of patients at full term early in labor: Initial dose: 1 or 2 mg intravenously or intramuscularly once. This dose may be repeated in 4 hours if necessary. Usual Adult Dose for Pain Initial dose: 1 mg intravenously once. Depending on the severity of the pain, effective intravenous doses range from 0.5 to 2 mg.
Route of Administration: intravenously or intramuscularly
In Vitro Use Guide
At high concentration (100 uM) butorphanol greatly inhibited the depolarization of the rat cerebrocortical brain slices by veratrine as determined by the reduced release of K+.
Name Type Language
BUTORPHANOL
INN   MI   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
(-)-17-(CYCLOBUTYLMETHYL)MORPHINAN-3,14-DIOL
Systematic Name English
MORPHINAN-3,14-DIOL, 17-(CYCLOBUTYLMETHYL)-
Systematic Name English
BUTORPHANOL [USAN]
Common Name English
BUTORPHANOL [WHO-DD]
Common Name English
LEVO-BC-2627
Code English
BUTORPHANOL [INN]
Common Name English
BUTORPHANOL [MI]
Common Name English
BUTORPHANOL [VANDF]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175692
Created by admin on Tue Oct 22 00:29:12 UTC 2019 , Edited by admin on Tue Oct 22 00:29:12 UTC 2019
NDF-RT N0000175686
Created by admin on Tue Oct 22 00:29:12 UTC 2019 , Edited by admin on Tue Oct 22 00:29:12 UTC 2019
NCI_THESAURUS C241
Created by admin on Tue Oct 22 00:29:12 UTC 2019 , Edited by admin on Tue Oct 22 00:29:12 UTC 2019
NCI_THESAURUS C1506
Created by admin on Tue Oct 22 00:29:12 UTC 2019 , Edited by admin on Tue Oct 22 00:29:12 UTC 2019
CFR 21 CFR 520.246
Created by admin on Tue Oct 22 00:29:12 UTC 2019 , Edited by admin on Tue Oct 22 00:29:12 UTC 2019
WHO-VATC QN02AF01
Created by admin on Tue Oct 22 00:29:12 UTC 2019 , Edited by admin on Tue Oct 22 00:29:12 UTC 2019
DEA NO. 9720
Created by admin on Tue Oct 22 00:29:12 UTC 2019 , Edited by admin on Tue Oct 22 00:29:12 UTC 2019
CFR 21 CFR 522.246
Created by admin on Tue Oct 22 00:29:12 UTC 2019 , Edited by admin on Tue Oct 22 00:29:12 UTC 2019
NDF-RT N0000175685
Created by admin on Tue Oct 22 00:29:12 UTC 2019 , Edited by admin on Tue Oct 22 00:29:12 UTC 2019
WHO-VATC QR05DA90
Created by admin on Tue Oct 22 00:29:12 UTC 2019 , Edited by admin on Tue Oct 22 00:29:12 UTC 2019
WHO-ATC N02AF01
Created by admin on Tue Oct 22 00:29:12 UTC 2019 , Edited by admin on Tue Oct 22 00:29:12 UTC 2019
LIVERTOX 133
Created by admin on Tue Oct 22 00:29:12 UTC 2019 , Edited by admin on Tue Oct 22 00:29:12 UTC 2019
Code System Code Type Description
MESH
D002077
Created by admin on Tue Oct 22 00:29:12 UTC 2019 , Edited by admin on Tue Oct 22 00:29:12 UTC 2019
PRIMARY
EVMPD
SUB06035MIG
Created by admin on Tue Oct 22 00:29:12 UTC 2019 , Edited by admin on Tue Oct 22 00:29:12 UTC 2019
PRIMARY
DRUG BANK
DB00611
Created by admin on Tue Oct 22 00:29:12 UTC 2019 , Edited by admin on Tue Oct 22 00:29:12 UTC 2019
PRIMARY
IUPHAR
7591
Created by admin on Tue Oct 22 00:29:12 UTC 2019 , Edited by admin on Tue Oct 22 00:29:12 UTC 2019
PRIMARY
LactMed
42408-82-2
Created by admin on Tue Oct 22 00:29:12 UTC 2019 , Edited by admin on Tue Oct 22 00:29:12 UTC 2019
PRIMARY
MERCK INDEX
M2802
Created by admin on Tue Oct 22 00:29:12 UTC 2019 , Edited by admin on Tue Oct 22 00:29:12 UTC 2019
PRIMARY Merck Index
ChEMBL
CHEMBL33986
Created by admin on Tue Oct 22 00:29:12 UTC 2019 , Edited by admin on Tue Oct 22 00:29:12 UTC 2019
PRIMARY
ECHA (EC/EINECS)
255-808-8
Created by admin on Tue Oct 22 00:29:12 UTC 2019 , Edited by admin on Tue Oct 22 00:29:12 UTC 2019
PRIMARY
EPA CompTox
42408-82-2
Created by admin on Tue Oct 22 00:29:12 UTC 2019 , Edited by admin on Tue Oct 22 00:29:12 UTC 2019
PRIMARY
RXCUI
1841
Created by admin on Tue Oct 22 00:29:12 UTC 2019 , Edited by admin on Tue Oct 22 00:29:12 UTC 2019
PRIMARY RxNorm
NCI_THESAURUS
C61659
Created by admin on Tue Oct 22 00:29:12 UTC 2019 , Edited by admin on Tue Oct 22 00:29:12 UTC 2019
PRIMARY
INN
3620
Created by admin on Tue Oct 22 00:29:12 UTC 2019 , Edited by admin on Tue Oct 22 00:29:12 UTC 2019
PRIMARY
WIKIPEDIA
BUTORPHANOL
Created by admin on Tue Oct 22 00:29:12 UTC 2019 , Edited by admin on Tue Oct 22 00:29:12 UTC 2019
PRIMARY
PUBCHEM
5361092
Created by admin on Tue Oct 22 00:29:12 UTC 2019 , Edited by admin on Tue Oct 22 00:29:12 UTC 2019
PRIMARY
CAS
42408-82-2
Created by admin on Tue Oct 22 00:29:12 UTC 2019 , Edited by admin on Tue Oct 22 00:29:12 UTC 2019
PRIMARY