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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H29NO2.C4H6O6
Molecular Weight 477.5473
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUTORPHANOL TARTRATE

SMILES

O[C@@H]([C@H](O)C(O)=O)C(O)=O.OC1=CC2=C(C[C@H]3N(CC4CCC4)CC[C@@]25CCCC[C@@]35O)C=C1

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 327.4605
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C4H6O6
Molecular Weight 150.0868
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
Tolerance to the analgesic effect of buprenorphine, butorphanol, nalbuphine, and cyclorphan, and cross-tolerance to morphine.
2001
[Medetomidine-butorphanol combination anesthesia in the dog].
2001 Dec
Pharmacokinetics and pharmacodynamics of butorphanol in llamas after intravenous and intramuscular administration.
2001 Nov 1
Enadoline and butorphanol: evaluation of kappa-agonists on cocaine pharmacodynamics and cocaine self-administration in humans.
2001 Oct
Enadoline, a selective kappa opioid agonist: comparison with butorphanol and hydromorphone in humans.
2001 Sep
The effect of a combination of medetomidine-butorphanol and medetomidine, butorphanol, atropine on glomerular filtration rate in dogs.
2001 Sep-Oct
Noninvasive drug delivery.
2001 Winter
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
Effects of morphine, butorphanol, buprenorphine, and U50488H on the minimum alveolar concentration of isoflurane in cats.
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
Effects of gonadal steroid hormone treatments on opioid antinociception in ovariectomized rhesus monkeys.
2002 Jan
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
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
Withdrawal from dependence upon butorphanol uniquely increases kappa(1)-opioid receptor binding in the rat brain.
2002 Jun
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
Simultaneous determination of in total 17 opium alkaloids and opioids in blood and urine by fast liquid chromatography-diode-array detection-fluorescence detection, after solid-phase extraction.
2002 Jun 15
Evaluation of the bispectral index as an indicator of degree of central nervous system depression in isoflurane-anesthetized horses.
2002 Mar
A pharmacokinetic interaction study between butorphanol and sumatriptan nasal sprays in healthy subjects: importance of the timing of butorphanol administration.
2002 May
Quantitative electroencephalography of medetomidine, medetomidine-midazolam and medetomidine-midazolam-butorphanol in dogs.
2002 May
Stadol nasal spray for headache.
2002 May
Effects of preoperative administration of ketoprofen on anesthetic requirements and signs of postoperative pain in dogs undergoing elective ovariohysterectomy.
2002 Nov 1
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
Effects of two preanesthetic regimens for ophthalmic surgery on intraocular pressure and cardiovascular measurements in dogs.
2002 Spring
Agonist/antagonist properties of nalbuphine, butorphanol and (-)-pentazocine in male vs. female rats.
2003 Apr
Sensitivity to the effects of opioids in rats with free access to exercise wheels: mu-opioid tolerance and physical dependence.
2003 Aug
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
Activity of opioid ligands in cells expressing cloned mu opioid receptors.
2003 Jan 4
Minimum alveolar concentration of isoflurane in green iguanas and the effect of butorphanol on minimum alveolar concentration.
2003 Jun 1
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
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
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 Dec 15 15:23:31 UTC 2023
Edited
by admin
on Fri Dec 15 15:23:31 UTC 2023
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
Morphinan-3,14-diol, 17-(cyclobutylmethyl)-, (2S,3S)-2,3-dihydroxybutanedioate (1:1) (salt)
Systematic 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 [USP-RS]
Common Name English
Morphinan-3,14-diol, 17-(cyclobutylmethyl)-, (2S,3S)-2,3-dihydroxybutanedioate (1:1)
Systematic Name English
TORBUTROL
Brand Name English
Butorphanol tartrate [WHO-DD]
Common Name English
MORPHINAN-3,14-DIOL, 17-(CYCLOBUTYLMETHYL)-, (-)-, (S-(R*,R*))-2,3-DIHYDROXYBUTANEDIOATE (1:1) (SALT)
Common Name English
Morphinan-3,14-diol, 17-(cyclobutylmethyl)-, [S-(R*,R*)]-2,3-dihydroxybutanedioate (1:1) (salt)
Systematic Name English
BUTORPHANOL TARTRATE [GREEN BOOK]
Common Name English
STADOL
Brand 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 Dec 15 15:23:31 UTC 2023 , Edited by admin on Fri Dec 15 15:23:31 UTC 2023
DEA NO. 9720
Created by admin on Fri Dec 15 15:23:31 UTC 2023 , Edited by admin on Fri Dec 15 15:23:31 UTC 2023
NCI_THESAURUS C241
Created by admin on Fri Dec 15 15:23:31 UTC 2023 , Edited by admin on Fri Dec 15 15:23:31 UTC 2023
Code System Code Type Description
EVMPD
SUB00920MIG
Created by admin on Fri Dec 15 15:23:31 UTC 2023 , Edited by admin on Fri Dec 15 15:23:31 UTC 2023
PRIMARY
FDA UNII
2L7I72RUHN
Created by admin on Fri Dec 15 15:23:31 UTC 2023 , Edited by admin on Fri Dec 15 15:23:31 UTC 2023
PRIMARY
ChEMBL
CHEMBL33986
Created by admin on Fri Dec 15 15:23:31 UTC 2023 , Edited by admin on Fri Dec 15 15:23:31 UTC 2023
PRIMARY
NCI_THESAURUS
C61658
Created by admin on Fri Dec 15 15:23:31 UTC 2023 , Edited by admin on Fri Dec 15 15:23:31 UTC 2023
PRIMARY
RXCUI
203170
Created by admin on Fri Dec 15 15:23:31 UTC 2023 , Edited by admin on Fri Dec 15 15:23:31 UTC 2023
PRIMARY RxNorm
DAILYMED
2L7I72RUHN
Created by admin on Fri Dec 15 15:23:31 UTC 2023 , Edited by admin on Fri Dec 15 15:23:31 UTC 2023
PRIMARY
EPA CompTox
DTXSID50904569
Created by admin on Fri Dec 15 15:23:31 UTC 2023 , Edited by admin on Fri Dec 15 15:23:31 UTC 2023
PRIMARY
ECHA (EC/EINECS)
261-443-5
Created by admin on Fri Dec 15 15:23:31 UTC 2023 , Edited by admin on Fri Dec 15 15:23:31 UTC 2023
PRIMARY
CAS
58786-99-5
Created by admin on Fri Dec 15 15:23:31 UTC 2023 , Edited by admin on Fri Dec 15 15:23:31 UTC 2023
PRIMARY
SMS_ID
100000084861
Created by admin on Fri Dec 15 15:23:31 UTC 2023 , Edited by admin on Fri Dec 15 15:23:31 UTC 2023
PRIMARY
RS_ITEM_NUM
1082504
Created by admin on Fri Dec 15 15:23:31 UTC 2023 , Edited by admin on Fri Dec 15 15:23:31 UTC 2023
PRIMARY
MERCK INDEX
m2802
Created by admin on Fri Dec 15 15:23:31 UTC 2023 , Edited by admin on Fri Dec 15 15:23:31 UTC 2023
PRIMARY Merck Index
DRUG BANK
DBSALT000276
Created by admin on Fri Dec 15 15:23:31 UTC 2023 , Edited by admin on Fri Dec 15 15:23:31 UTC 2023
PRIMARY
PUBCHEM
5464090
Created by admin on Fri Dec 15 15:23:31 UTC 2023 , Edited by admin on Fri Dec 15 15:23:31 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY