Butorphanol Systematic (IUPAC) name 17-cyclobutylmethyl-morphinan-3,14-diol Clinical data Trade names Stadol AHFS/Drugs.com MedlinePlus Pregnancy cat. C/D (United States) Legal status Schedule IV (US) Routes IV, intranasal Pharmacokinetic data Bioavailability Nasal: 60-70% Metabolism Hepatic hydroxylated & glucuronidated Half-life 4-7 hours Excretion Renal, 75%
Identifiers CAS number ATC code N02 QR05 PubChem DrugBank ChemSpider UNII KEGG ChEBI ChEMBL Chemical data Formula C21H29NO2 Mol. mass 327.473 g/mol SMILES & (what is this?)
Butorphanol (Stadol) (INN) is a morphinan-type synthetic opioid analgesic developed by Bristol-Myers. Brand name Stadol was recently discontinued by the manufacturer. It is now only available in its generic formulations, manufactured by Novex, Mylan, Apotex and Ben Venue Laboratories. Butorphanol is most closely structurally related to levorphanol. Butorphanol is available only as butorphanol tartrate in injectable,tablet, and intranasal spray formulations.
Mechanism of action
Butorphanol exhibits partial agonist and antagonist activity at the μ opioid receptor and agonist activity at the κ opioid receptor. Stimulation of these receptors on central nervous system neurons causes an intracellular inhibition of adenylate cyclase, closing of influx membrane calcium channels, and opening of membrane potassium channels. This leads to hyperpolarization of the cell membrane potential and suppression of action potential transmission of ascending pain pathways. Because of its κ-agonist activity, at analgesic doses butorphanol increases pulmonary arterial pressure and cardiac work. Additionally, κ-agonism can cause dysphoria at therapeutic or supertherapeutic doses; this gives butorphanol a lower potential for abuse than other opioid drugs.
Place in therapy
The most common indication for butorphanol is management of migraine using the intranasal spray formulation. It may also be used parenterally for management of moderate-to-severe pain, as a supplement for balanced general anesthesia, and management of pain during labor. Butorphanol is more effective in reducing pain in women than in men.
In veterinary use, butorphanol ("Torbugesic") is widely used as a sedative and analgesic in dogs, cats and horses. For sedation, it may be combined with tranquilizers such as alpha-2 agonists (medetomidine (Domitor)), benzodiazepines, or phenothiazines (acepromazine) in dogs, cats and exotic animals. It is frequently combined with xylazine or detomidine (Domosedan etc.) in horses.
As with other opioid analgesics, central nervous system effects (such as sedation, confusion, and dizziness) are considerations with butorphanol. Nausea and vomiting are common. Less common are the gastrointestinal effects of other opioids (mostly constipation).
Butorphanol is available in the U.S. as a generic drug; it is available in various nations under one of any number of trade names, including Moradol and Beforal (Brand name Stadol no longer available in the US); veterinary trade names include Butorphic, Dolorex, Morphasol, Torbugesic, and Torbutrol.
Use in horses
Butorphanol is a commonly used narcotic for pain relief in horses. It is administered either IM or IV, with its analgestic properties beginning to take effect about 15 minutes after injection and lasting 4 hours. It is also commonly paired with sedatives, such as xylazine and detomidine, to make the horse easier to handle during veterinary procedures.
Side effects, overdose, and precautions
Side effects specific to horses include sedation, CNS excitement (displayed by head pressing or tossing). Overdosing may result in seizures, falling, salivation, constipation, and muscle twitching. If an overdose occurs, a narcotic antagonist, such as naloxone, may be given. Caution should be used if Butorphanol is administered in addition to other narcotics, sedatives, depressants, or antihistamines as it will cause an additive effect.
Butorphanol can cross the placenta, and it will be present in the milk of lactating mares who are given the drug.
The drug is also prohibited for use in competition by most equestrian organizations, including the FEI, which considers it a class A drug.
In addition to horses, butorphanol with or without acepromazine is frequently used in veterinary settings for post-operative and accident-related pain in small mammals such as dogs, cats, ferrets, coatis, raccoons, mongooses, various marsupials, some rodents and perhaps some larger birds both in the operating suite and as a regular prescription medication for home use for management of moderate to severe pain. The efficacy of opioids (as well as other drugs that slow down the system like anaesthetics) in treating reptiles is a question about which there is currently not a lot of data.
- ^ US Patent 3775414 - Process for the Preparation of 14-hydroxymorphinan Derivatives
- ^ a b Gear, RW; Miaskowski C, Gordon NC, Paul SM, Heller PH, Levine JD (November 1999). "The kappa opioid nalbuphine produces gender- and dose-dependent analgesia and antianalgesia in patients with postoperative pain". Pain 83 (2): 339–45. doi:10.1016/S0304-3959(99)00119-0. PMID 10534607.
- ^ NOAH Compendium of Data Sheets for Animal Medicines 2005
- Katzung, Bertam G. (Ed.) (2001) Basic & Clinical Pharmacology (8th ed.). New York: McGraw-Hill. ISBN 0-8385-0598-8.
- DiPiro, Joseph T. et al. (2005) Pharmacotherapy: A Pathophysiologic Approach (6th ed.). New York: McGraw-Hill. ISBN 0-07-141613-7.
- Stadol NS - monograph
- Forney, Barbara C, MS, VMD. Equine Medications, Revised Edition.' Blood Horse Publications. Lexington. Kentucky. Copyright 2007.
- The Merck Manual of Veterinary Medicine, 2004 edition (English)
- The Merck Manual, 2004 Edition (German)
- Mosby's Drug Guide 2004
Analgesics (N02A, N02B) Opioids
See also: Opioids templateOpium & alkaloids thereofSemi-synthetic opium
Pyrazolones Cannabinoids Anilides Non-steroidal
See also: NSAIDs templatePropionic acid classOxicam classAcetic acid classAnthranilic acid
Meclofenamate • Mefenamic acidSalicylates
Atypical, adjuvant and potentiators,
Metabolic agents and miscellaneousAmitryptiline • Befiradol • Bicifadine • Carisoprodol • Camphor • Cimetidine • Clonidine • Chlorzoxazone • Cyclobenzaprine • Duloxetine • Esreboxetine • Flupirtine • Gabapentin • Glafenine • Hydroxyzine • Ketamine • Menthol • Mephenoxalone • Methocarbamol • Nefopam • Orphenadrine • Pregabalin • Proglumide • Scopolamine • Tebanicline • Trazodone • Gabapentin enacarbil • Ziconotide
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Butorphanol — Général Nom IUPAC 17 (cyclobutylméthyl) morphinane 3,14 diol No CAS … Wikipédia en Français
butorphanol — /byooh tawr feuh nawl , nol /, n. Pharm. a narcotic analgesic, C21H29NO2, administered by injection to treat moderate to severe pain. [as contr. of the chemical name 17 (cyclobutylmethyl)morphinan 3,14 diol] * * * … Universalium
butorphanol — noun A particular narcotic painkiller … Wiktionary
butorphanol — bu·tor·pha·nol .byüt ȯr fə .nȯl n a synthetic analgesic and antitussive opioid drug administered in the form of its tartrate C21H29NO2·C4H6O6 as a nasal spray or by injection esp. for the relief of pain see STADOL * * * bu·tor·pha·nol (bu… … Medical dictionary
butorphanol — /byooh tawr feuh nawl , nol /, n. Pharm. a narcotic analgesic, C21H29NO2, administered by injection to treat moderate to severe pain. [as contr. of the chemical name 17 (cyclobutylmethyl)morphinan 3,14 diol] … Useful english dictionary
butorphanol tartrate — A potent mixed agonist/antagonist narcotic analgesic agent, used by injection and in the form of a nasal spray. * * * [USP] the tartrate salt of butorphanol, administered intramuscularly, intravenously, or intranasally as an analgesic and… … Medical dictionary
42408-82-2 — Butorphanol Butorphanol Général Nom IUPAC 17 (cyclobutylméthyl) morphinane 3,14 diol No CAS … Wikipédia en Français
C21H29NO2 — Butorphanol Butorphanol Général Nom IUPAC 17 (cyclobutylméthyl) morphinane 3,14 diol No CAS … Wikipédia en Français
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