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Butorphanol

Catalog No. DB00611 Name DrugBank
CAS Number 58786-99-5 Website http://www.ualberta.ca/
M. F. C21H29NO2 Telephone (780) 492-3111
M. W. 327.46046 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 493

SYNONYMS

IUPAC name
(1S,9R,10S)-17-(cyclobutylmethyl)-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-triene-4,10-diol
IUPAC Traditional name
butorphanol
Brand Name
Stadol
Stadol NS
Moradol
Beforal
Synonyms
Butorfanol [INN-Spanish]
Butorfanol
Butorphanolum [INN-Latin]
Butorphanol Tartrate

DATABASE IDS

PubChem SID 46507553
PubChem CID 6916249
CAS Number 58786-99-5

PROPERTIES

Hydrophobicity(logP) 3.3
Solubility Moderate

DETAILS

Description (English)
Item Information
Drug Groups illicit; approved
Description A synthetic morphinan analgesic with narcotic antagonist action. It is used in the management of severe pain. [PubChem]
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 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.
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
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.
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.
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.
Protein Binding Serum protein binding is approximately 80%.
Elimination Butorphanol is extensively metabolized in the liver. Elimination occurs by urine and fecal excretion.
Distribution * 305 to 901 L
Clearance * 99 +/- 23 L/h [Young with IV 2 mg]
* 82 +/- 21 [Eldery with IV 2 mg]
References
Gear RW, Miaskowski C, Gordon NC, Paul SM, Heller PH, Levine JD: The kappa opioid nalbuphine produces gender- and dose-dependent analgesia and antianalgesia in patients with postoperative pain. Pain. 1999 Nov;83(2):339-45. [Pubmed]
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. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

  • Gear RW, Miaskowski C, Gordon NC, Paul SM, Heller PH, Levine JD: The kappa opioid nalbuphine produces gender- and dose-dependent analgesia and antianalgesia in patients with postoperative pain. Pain. 1999 Nov;83(2):339-45. Pubmed
  • 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. Pubmed