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QuickView for butorphanol (compound)

Summary
General Info

PubChem

PubChem Compound 2487

Name:	Butorphanol
PubChem Compound ID:	2487
Description:	A synthetic morphinan analgesic with narcotic antagonist action. It is used in the management of severe pain.
Molecular formula:	C₂₁H₂₉NO₂
Molecular weight:	327.461 g/mol
Synonyms:	Morphinan-3,14-diol, 17-(cyclobutylmethyl)-; Butorphanol

DrugBank

Identification

Name:	Butorphanol
Name (isomeric):	DB00611
Drug Type:	small molecule
Description:	A synthetic morphinan analgesic with narcotic antagonist action. It is used in the management of severe pain.
Synonyms:	Butorfanol [INN-Spanish]; Butorfanol; Butorphanolum [INN-Latin]; Butorphanol Tartrate
Brand:	Moradol, Beforal, Stadol NS, Stadol
Category:	Narcotic Antagonists, Narcotics, Antitussive Agents, Analgesics, Opioid
CAS number:	58786-99-5

Pharmacology

Indication:	For the relief of moderate to severe pain.
Pharmacology:	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... show more » 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. show less «
Mechanism of Action:	The exact mechanism of action is unknown, but is believed to interact with an opiate receptor site in the CNS (probably in or associated with the limbic system). The opiate antagonistic effect may result from competitive inhibition at the opiate receptor, but may also be a result of other mechanisms. Butorphanol is a mixed agonist-antagonist that e... show more » The exact mechanism of action is unknown, but is believed to interact with an opiate receptor site in the CNS (probably in or associated with the limbic system). The opiate antagonistic effect may result from competitive inhibition at the opiate receptor, but may also be a result of other mechanisms. Butorphanol is a mixed agonist-antagonist that exerts antagonistic or partially antagonistic effects at mu opiate receptor sites, but is thought to exert its agonistic effects principally at the kappa and sigma opiate receptors. show less «
Absorption:	Rapidly absorbed after intramuscular injection and peak plasma levels are reached in 20-40 minutes. The absolute bioavailability is 60-70% and is unchanged in patients with allergic rhinitis. In patients using a nasal vasoconstrictor (oxymetazoline) the fraction of the dose absorbed was unchanged, but the rate of absorption was slowed. Oral bioavailability is only 5-17% because of extensive first-pass metabolism.
Protein binding:	Serum protein binding is approximately 80%.
Biotransformation:	Extensively metabolized in the liver. The pharmacological activity of butorphanol metabolites has not been studied in humans; in animal studies, butorphanol metabolites have demonstrated some analgesic activity.
Route of elimination:	Butorphanol is extensively metabolized in the liver. Elimination occurs by urine and fecal excretion.
Half Life:	The elimination half-life of butorphanol is about 18 hours. In renally impaired patients with creatinine clearances <30 mL/min the elimination half-life is approximately doubled. After intravenous administration to patients with hepatic impairment, the elimination half-life of butorphanol was approximately tripled.
Clearance:	99 +/- 23 L/h [Young with IV 2 mg] 82 +/- 21 [Eldery with IV 2 mg]
Toxicity:	The clinical manifestations of butorphanol overdose are those of opioid drugs in general. The most serious symptoms are hypoventilation, cardiovascular insufficiency, coma, and death.
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Avoid alcohol.

Drug interaction:

Droperidol	Droperidol may enhance the CNS depressant effect of butorphanol. Consider dose reductions of droperidol or of other CNS agents (e.g., opioids, barbiturates) with concomitant use.
Alvimopan	Opioid analgesics such as butorphanol may enhance the adverse/toxic effect of alvimopan. This is most notable for patients receiving long-term (i.e., more than 7 days) opiates prior to alvimopan initiation. According to alvimopan prescribing information, alvimopan is contraindicated in patients receiving therapeutic doses of opioids for more than 7 consecutive days immediately prior to alvimopan initiation. Monitor for increased alvimopan adverse effects in patients using opioids prior to alvimopan.
Triprolidine	The CNS depressants, Triprolidine and Butorphanol, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.

Targets

Kappa-type opioid receptor

Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for dynorphins. May play a role in arousal and regulation of autonomic and neuroendocrine functions

UniProt ID:

P41145

Gene:

OPRK1

Actions:

agonist

References:

Vivian JA, DeYoung MB, Sumpter TL, Traynor JR, Lewis JW, Woods JH: kappa-Opioid receptor effects of butorphanol in rhesus monkeys. J Pharmacol Exp Ther. 1999 Jul;290(1):259-65.
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Park Y, Jang CG, Ho IK, Ko KH: kappa-opioid agonist stimulated regional distribution of [(35)S]GTPgammas binding in butorphanol continuously infused rat. Brain Res Bull. 2000 May 1;52(1):17-20.
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Fan LW, Tanaka S, Tien LT, Ma T, Rockhold RW, Ho IK: Withdrawal from dependence upon butorphanol uniquely increases kappa(1)-opioid receptor binding in the rat brain. Brain Res Bull. 2002 Jun;58(2):149-60.
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Fan LW, Tanaka S, Park Y, Sasaki K, Ma T, Tien LT, Rockhold RW, Ho IK: Butorphanol dependence and withdrawal decrease hippocampal kappa 2-opioid receptor binding. Brain Res. 2002 Dec 27;958(2):277-90.
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Commiskey S, Fan LW, Ho IK, Rockhold RW: Butorphanol: effects of a prototypical agonist-antagonist analgesic on kappa-opioid receptors. J Pharmacol Sci. 2005 Jun;98(2):109-16. Epub 2005 Jun 8.
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Picker MJ, Benyas S, Horwitz JA, Thompson K, Mathewson C, Smith MA: Discriminative stimulus effects of butorphanol: influence of training dose on the substitution patterns produced by Mu, Kappa and Delta opioid agonists. J Pharmacol Exp Ther. 1996 Dec;279(3):1130-41.
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Wakabayashi H, Tokuyama S, Ho IK: Simultaneous measurement of biogenic amines and their metabolites in rat brain regions after acute administration of and abrupt withdrawal from butorphanol or morphine. Neurochem Res. 1995 Oct;20(10):1179-85.
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Narita M, Feng Y, Makimura M, Hoskins B, Ho IK: Repeated administration of opioids alters characteristics of membrane-bound phorbol ester binding in rat brain. Eur J Pharmacol. 1994 Dec 27;271(2-3):547-50.
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Ohta S, Niwa M, Nozaki M, Tsurumi K, Shimonaka H, Tanahashi T, Uematsu H, Yamamoto M, Fujimura H: [Kappa-type opioid receptor in human placental membrane] Masui. 1989 Oct;38(10):1293-300.
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Walsh SL, Chausmer AE, Strain EC, Bigelow GE: Evaluation of the mu and kappa opioid actions of butorphanol in humans through differential naltrexone blockade. Psychopharmacology (Berl). 2008 Jan;196(1):143-55. Epub 2007 Oct 2.
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Delta-type opioid receptor

Mu-type opioid receptor

Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for beta-endorphin

UniProt ID:

P35372

Gene:

OPRM1

Actions:

partial antagonist

References:

Vivian JA, DeYoung MB, Sumpter TL, Traynor JR, Lewis JW, Woods JH: kappa-Opioid receptor effects of butorphanol in rhesus monkeys. J Pharmacol Exp Ther. 1999 Jul;290(1):259-65.
View Article

Picker MJ: Discriminative stimulus effects of the mixed-opioid agonist/antagonist dezocine: cross-substitution by mu and delta opioid agonists. J Pharmacol Exp Ther. 1997 Dec;283(3):1009-17.
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