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a salt or ester of tartaric acid

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/06/18 13:23:14」(JST)

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Butorphanol (INN) is a morphinan-type synthetic opioid analgesic developed by Bristol-Myers.^[1] 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[edit]

Butorphanol exhibits partial agonist and antagonist activity at the μ opioid receptor there is competitive antagonist activity and partial agonist activity at the κ opioid receptor.^[2] 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[edit]

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.^[2]

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.^[3]

Adverse effects[edit]

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).

Proprietary preparations[edit]

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[edit]

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[edit]

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.

Notes[edit]

^ 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

References[edit]

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

UpToDate Contents

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1. 妊娠時のブプレノルフィン補充療法 buprenorphine substitution therapy in pregnancy
2. オピオイド中毒治療中の医師監督下の離脱 medically supervised opioid withdrawal during treatment for addiction
3. 思春期におけるオピオイド離脱 opioid withdrawal in adolescents
4. 陣痛および分娩時の疼痛の薬理学的マネージメント pharmacologic management of pain during labor and delivery
5. 最後の数週間における疼痛の評価およびマネージメント pain assessment and management in the last weeks of life

English Journal

Sedative and mechanical hypoalgesic effects of butorphanol in xylazine-premedicated donkeys.

Lizarraga I1, Castillo-Alcala F.
Equine veterinary journal.Equine Vet J.2015 May;47(3):308-12. doi: 10.1111/evj.12274. Epub 2014 May 28.
REASONS FOR PERFORMING STUDY: Combinations of α2 -adrenoceptor and opioid agonists are commonly used in equids, but little scientific information is available on donkeys.OBJECTIVES: To compare the sedative and hypoalgesic effects of xylazine alone or in combination with different dosages of butorph
PMID 24735190

Cardiopulmonary and anesthetic effects of the combination of butorphanol, midazolam and alfaxalone in Beagle dogs.

Seo JI1, Han SH, Choi R, Han J, Lee L, Hyun C.
Veterinary anaesthesia and analgesia.Vet Anaesth Analg.2015 May;42(3):304-8. doi: 10.1111/vaa.12223. Epub 2014 Aug 12.
OBJECTIVE: To evaluate the physiological variables, arterial blood gas values, induction of anesthesia quality, and recovery quality using the combination of butorphanol, midazolam and alfaxalone in dogs.ANIMALS: Ten healthy adult Beagle dogs weighing 8.3 ± 3.1 kg.METHODS: Rectal temperature (T)
PMID 25112420

Postoperative analgesic effects of either a constant rate infusion of fentanyl, lidocaine, ketamine, dexmedetomidine, or the combination lidocaine-ketamine-dexmedetomidine after ovariohysterectomy in dogs.

Gutierrez-Blanco E1, Victoria-Mora JM, Ibancovichi-Camarillo JA, Sauri-Arceo CH, Bolio-González ME, Acevedo-Arcique CM, Marin-Cano G, Steagall PV.
Veterinary anaesthesia and analgesia.Vet Anaesth Analg.2015 May;42(3):309-18. doi: 10.1111/vaa.12215. Epub 2014 Jul 14.
OBJECTIVE: To evaluate the postoperative analgesic effects of a constant rate infusion (CRI) of either fentanyl (FENT), lidocaine (LIDO), ketamine (KET), dexmedetomidine (DEX), or the combination lidocaine-ketamine-dexmedetomidine (LKD) in dogs.STUDY DESIGN: Randomized, prospective, blinded, clinica
PMID 25039918

Japanese Journal

犬の術後鎮痛における酒石酸ブトルファノールの有効性に関する研究

URANO Kimiyo
日本獣医生命科学大学研究報告 (60), 186-188, 2011-12
NAID 40019203404

Laboratory animal science: Usage of analgesic in a murine model infected latently with pseudorabies virus

Tanaka Seiichi,Mannen Kazuaki
日本獣醫學会会誌 73(3), 351-354, 2011-03
NAID 40018785958

Usage of Analgesic in a Murine Model Infected Latently with Pseudorabies Virus

TANAKA Seiichi,MANNEN Kazuaki
Journal of Veterinary Medical Science 73(3), 351-354, 2011
… Butorphanol tartrate (BT) was injected into mice before injection with acetylcholine in a murine model infected latently with pseudorabies virus. …
NAID 130000444202

「ブトルファノール」

Butorphanol
Systematic (IUPAC) name
	17-cyclobutylmethyl-morphinan-3,14-diol
Clinical data
Trade names	Stadol
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a682667
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%; Biliary, 11-14%; Fecal, 15%
Identifiers
CAS number	42408-82-2
ATC code	N02AX02 QR05DA90
PubChem	CID 5361092
DrugBank	DB00611
ChemSpider	16735714
UNII	QV897JC36D
KEGG	D00837
ChEBI	CHEBI:3242
ChEMBL	CHEMBL33986
Chemical data
Formula	C21H29NO2
Mol. mass	327.473 g/mol
	SMILES OC1=CC2=C(C=C1)C[C@H]3N(CC[C@@]24CCCC[C@@]34O)CC5CCC5;
	InChI 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 ; Key:IFKLAQQSCNILHL-QHAWAJNXSA-N ;
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