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药品详细

Butorphanol(布托啡诺)

化学结构式图
中文名
布托啡诺
英文名
Butorphanol
分子式
C21H29NO2
化学名
(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
分子量
Average: 327.4605
Monoisotopic: 327.219829177
CAS号
58786-99-5
ATC分类
N02A 未知
药物类型
small molecule
阶段
illicit, approved
商品名
同义名
基本介绍

A synthetic morphinan analgesic with narcotic antagonist action. It is used in the management of severe pain. [PubChem]

生产厂家
  • Apothecon inc div bristol myers squibb
  • Bedford laboratories div ben venue laboratories inc
  • Bristol myers squibb co pharmaceutical research institute
  • Claris lifesciences ltd
  • Hikma farmaceutica (portugal) sa
  • Hikma farmaceutica sa
  • Hospira inc
  • Mylan pharmaceuticals inc
  • Novex pharma
  • Roxane laboratories inc
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. 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
  2. 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
剂型
规格
化合物类型
Type small molecule
Classes
  • Morphinans
  • Benzylisoquinolines
Substructures
  • Morphinans
  • Hydroxy Compounds
  • Naphthalenes
  • Phenols and Derivatives
  • Benzylisoquinolines
  • Benzene and Derivatives
  • Phenylpiperidines
  • Aliphatic and Aryl Amines
  • Alcohols and Polyols
  • Cyclobutane and Derivatives
  • Phenanthrenes
  • Phenethylamines
  • Heterocyclic compounds
  • Aromatic compounds
  • Phenylpropylamines
  • (Iso)quinolines and Derivatives
  • Cyclohexenes and Derivatives
  • Phenyl Esters
  • Amphetamines
  • Piperidines
适应症
药理
Indication For the relief of moderate to severe pain.
Pharmacodynamics 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.
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 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.
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.
Volume of distribution
  • 305 to 901 L
Protein binding Serum protein binding is approximately 80%.
Metabolism
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
Pathways Not Available
理化性质
Properties
State solid
Experimental Properties
Property Value Source
water solubility Moderate Not Available
logP 3.3 Not Available
Predicted Properties
Property Value Source
water solubility 1.60e-01 g/l ALOGPS
logP 3.65 ALOGPS
logP 2.89 ChemAxon
logS -3.3 ALOGPS
pKa (strongest acidic) 9.86 ChemAxon
pKa (strongest basic) 10.7 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 3 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 43.7 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 95.92 ChemAxon
polarizability 37.94 ChemAxon
药物相互作用
Drug Interaction
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.
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.
Triprolidine The CNS depressants, Triprolidine and Butorphanol, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
食物相互作用
  • Avoid alcohol.

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