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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H29NO2.C4H6O6
Molecular Weight 477.5483
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUTORPHANOL TARTRATE

SMILES

C1CC[C@]2([C@@]3([H])Cc4ccc(cc4[C@]2(C1)CCN3CC5CCC5)O)O.[C@]([H])([C@@]([H])(C(=O)O)O)(C(=O)O)O

InChI

InChIKey=GMTYREVWZXJPLF-AFHUBHILSA-N
InChI=1S/C21H29NO2.C4H6O6/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;5-1(3(7)8)2(6)4(9)10/h6-7,13,15,19,23-24H,1-5,8-12,14H2;1-2,5-6H,(H,7,8)(H,9,10)/t19-,20+,21-;1-,2-/m10/s1

HIDE SMILES / InChI

Molecular Formula C21H29NO2
Molecular Weight 327.4612
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C4H6O6
Molecular Weight 150.087
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Curator's Comment:: Butorphanol crosses the blood-brain barrier and placenta

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Butorphanol tartrate

Approved Use

Butorphanol tartrate injection is indicated as a preoperative or preanesthetic medication, as a supplement to balanced anesthesia, for the relief of pain during labor, and for the management of pain severe enough to require an opioid analgesic and for which alternative treatments are inadequate.

Launch Date

2.72591995E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1376 pg/mL
1 mg 4 times / day steady-state, nasal
dose: 1 mg
route of administration: Nasal
experiment type: STEADY-STATE
co-administered:
BUTORPHANOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1542 pg/mL
1 mg single, nasal
dose: 1 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
BUTORPHANOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
4130 pg × h/mL
1 mg 4 times / day steady-state, nasal
dose: 1 mg
route of administration: Nasal
experiment type: STEADY-STATE
co-administered:
BUTORPHANOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
4612 pg × h/mL
1 mg single, nasal
dose: 1 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
BUTORPHANOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7.6 h
1 mg 4 times / day steady-state, nasal
dose: 1 mg
route of administration: Nasal
experiment type: STEADY-STATE
co-administered:
BUTORPHANOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
4.23 h
1 mg single, nasal
dose: 1 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
BUTORPHANOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
2.7 h
4 mg 1 times / day multiple, intramuscular
dose: 4 mg
route of administration: Intramuscular
experiment type: MULTIPLE
co-administered:
BUTORPHANOL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
4 mg 1 times / day single, intramuscular
Dose: 4 mg, 1 times / day
Route: intramuscular
Route: single
Dose: 4 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
likely
PubMed

PubMed

TitleDatePubMed
Butorphanol agonist effects and acute physical dependence in opioid abusers: comparison with morphine.
1998 Dec 1
Tolerance to the analgesic effect of buprenorphine, butorphanol, nalbuphine, and cyclorphan, and cross-tolerance to morphine.
2001
Calcification of the intervertebral discs and curvature of the radius and ulna: a radiographic survey of Finnish miniature dachshunds.
2001
Analgesic effect of butorphanol and levomethadone in detomidine sedated horses.
2001 Aug
Age-related differences in sensitivity to the antinociceptive effects of opioids in male rats. Influence of nociceptive intensity and intrinsic efficacy at the mu receptor.
2001 Aug
Sex differences in opioid antinociception: kappa and 'mixed action' agonists.
2001 Aug 1
[Medetomidine-butorphanol combination anesthesia in the dog].
2001 Dec
Cardiopulmonary assessment of medetomidine, ketamine, and butorphanol anesthesia in captive Thomson's gazelles (Gazella thomsoni).
2001 Jun
Three-choice discrimination in pigeons is based on relative efficacy differences among opioids.
2001 Jun
The influence of divalent cations on the analgesic effect of opioid and non-opioid drugs.
2001 Jun
Diagnosis and management of a patent urachus in a white rhinoceros calf (Ceratotherium simum simum).
2001 Mar
Comparison of sevoflurane with isoflurane for rapid mask induction in midazolam and butorphanol-sedated dogs.
2001 May
Enadoline and butorphanol: evaluation of kappa-agonists on cocaine pharmacodynamics and cocaine self-administration in humans.
2001 Oct
The effect of a combination of medetomidine-butorphanol and medetomidine, butorphanol, atropine on glomerular filtration rate in dogs.
2001 Sep-Oct
Analysis of synovial fluid from clinically normal alpacas and llamas.
2002 Apr
Comparison of transdermal administration of fentanyl versus intramuscular administration of butorphanol for analgesia after onychectomy in cats.
2002 Apr 1
Focal kappa-opioid receptor-mediated dependence and withdrawal in the nucleus paragigantocellularis.
2002 Dec
Butorphanol dependence and withdrawal decrease hippocampal kappa 2-opioid receptor binding.
2002 Dec 27
Effect of acepromazine and butorphanol on isoflurane minimum alveolar concentration in goats.
2002 Feb
Age-related differences in sensitivity to the antinociceptive effects of kappa opioids in adult male rats.
2002 Jul
Evaluation of the perioperative stress response in dogs administered medetomidine or acepromazine as part of the preanesthetic medication.
2002 Jul
Effects of medetomidine-midazolam, midazolambutorphanol, or acepromazine-butorphanol as premedicants for mask induction of anesthesia with sevoflurane in dogs.
2002 Jul
Validation and application of a sensitive assay for butorphanol in human plasma by high-performance liquid chromatography with tandem mass spectrometry detection.
2002 Jul 25
Effects of preoperative administration of ketoprofen on whole blood platelet aggregation, buccal mucosal bleeding time, and hematologic indices in dogs undergoing elective ovariohysterectomy.
2002 Jun 15
Animal behavior case of the month. Attention-getting behavior.
2002 Mar 1
A pharmacokinetic interaction study between butorphanol and sumatriptan nasal sprays in healthy subjects: importance of the timing of butorphanol administration.
2002 May
Evaluation of intravenous administration of meloxicam for perioperative pain management following stifle joint surgery in dogs.
2002 Nov
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
Investigation on the influx transport mechanism of pentazocine at the blood-brain barrier in rats using the carotid injection technique.
2002 Oct
[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
Sensitivity to the effects of opioids in rats with free access to exercise wheels: mu-opioid tolerance and physical dependence.
2003 Aug
Chemical restraint of peccaries with tiletamine/zolazepam and xylazine or tiletamine/zolazepam and butorphanol.
2003 Jan
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
The cardiac anesthetic index of isoflurane in green iguanas.
2003 Jun 1
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
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: Can be used as nasal spray: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=b8e48063-0b40-ee43-85c1-4ef2de80c404#nlm34090-1
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: Other
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+.
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:54:10 UTC 2021
Edited
by admin
on Fri Jun 25 20:54:10 UTC 2021
Record UNII
2L7I72RUHN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BUTORPHANOL TARTRATE
GREEN BOOK   JAN   MART.   MI   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
USAN  
Official Name English
BUTORPHANOL TARTRATE [USAN]
Common Name English
(-)-17-(CYCLOBUTYLMETHYL)MORPHINAN-3,14-DIOL D-(-)-TARTRATE (1:1) (SALT)
Common Name English
LEVO-BC-2627 TARTRATE
Code English
BUTORPHANOL TARTRATE [USP MONOGRAPH]
Common Name English
BUTORPHANOL TARTRATE [MI]
Common Name English
TORBUGESIC
Brand Name English
BUTORPHANOL TARTRATE [JAN]
Common Name English
BUTORPHANOL TARTRATE [ORANGE BOOK]
Common Name English
BUTORPHANOL TARTRATE CIV [USP-RS]
Common Name English
TORBUTROL
Brand Name English
MORPHINAN-3,14-DIOL, 17-(CYCLOBUTYLMETHYL)-, (-)-, (S-(R*,R*))-2,3-DIHYDROXYBUTANEDIOATE (1:1) (SALT)
Common Name English
BUTORPHANOL TARTRATE [WHO-DD]
Common Name English
BUTORPHANOL TARTRATE [GREEN BOOK]
Common Name English
STADOL
Brand Name English
BUTORPHANOL TARTRATE CIV
USP-RS  
Common Name English
BUTORPHANOL TARTRATE [MART.]
Common Name English
BUTORPHANOL TARTRATE [VANDF]
Common Name English
DOLOREX
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C1506
Created by admin on Fri Jun 25 20:54:10 UTC 2021 , Edited by admin on Fri Jun 25 20:54:10 UTC 2021
DEA NO. 9720
Created by admin on Fri Jun 25 20:54:10 UTC 2021 , Edited by admin on Fri Jun 25 20:54:10 UTC 2021
NCI_THESAURUS C241
Created by admin on Fri Jun 25 20:54:10 UTC 2021 , Edited by admin on Fri Jun 25 20:54:10 UTC 2021
Code System Code Type Description
EVMPD
SUB00920MIG
Created by admin on Fri Jun 25 20:54:10 UTC 2021 , Edited by admin on Fri Jun 25 20:54:10 UTC 2021
PRIMARY
FDA UNII
2L7I72RUHN
Created by admin on Fri Jun 25 20:54:10 UTC 2021 , Edited by admin on Fri Jun 25 20:54:10 UTC 2021
PRIMARY
ChEMBL
CHEMBL33986
Created by admin on Fri Jun 25 20:54:10 UTC 2021 , Edited by admin on Fri Jun 25 20:54:10 UTC 2021
PRIMARY
NCI_THESAURUS
C61658
Created by admin on Fri Jun 25 20:54:10 UTC 2021 , Edited by admin on Fri Jun 25 20:54:10 UTC 2021
PRIMARY
RXCUI
203170
Created by admin on Fri Jun 25 20:54:10 UTC 2021 , Edited by admin on Fri Jun 25 20:54:10 UTC 2021
PRIMARY RxNorm
ECHA (EC/EINECS)
261-443-5
Created by admin on Fri Jun 25 20:54:10 UTC 2021 , Edited by admin on Fri Jun 25 20:54:10 UTC 2021
PRIMARY
CAS
58786-99-5
Created by admin on Fri Jun 25 20:54:10 UTC 2021 , Edited by admin on Fri Jun 25 20:54:10 UTC 2021
PRIMARY
MERCK INDEX
M2802
Created by admin on Fri Jun 25 20:54:10 UTC 2021 , Edited by admin on Fri Jun 25 20:54:10 UTC 2021
PRIMARY Merck Index
DRUG BANK
DBSALT000276
Created by admin on Fri Jun 25 20:54:10 UTC 2021 , Edited by admin on Fri Jun 25 20:54:10 UTC 2021
PRIMARY
PUBCHEM
5464090
Created by admin on Fri Jun 25 20:54:10 UTC 2021 , Edited by admin on Fri Jun 25 20:54:10 UTC 2021
PRIMARY
USP_CATALOG
1082504
Created by admin on Fri Jun 25 20:54:10 UTC 2021 , Edited by admin on Fri Jun 25 20:54:10 UTC 2021
PRIMARY USP-RS
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY