Butorphanol
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Butorphanol
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| Systematic (IUPAC) name | |
| 17-cyclobutylmethyl- morphinan-3,14-diol |
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| Identifiers | |
| CAS number | |
| ATC code | N02 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C21H29NO2 |
| Mol. mass | 327.473 |
| Pharmacokinetic data | |
| Bioavailability | Nasal: 60-70% |
| Metabolism | Hepatic hydroxylated & glucuronidated |
| Half life | 4-7 hours |
| Excretion | Renal, 75% Biliary, 11-14% Fecal, 15% |
| Therapeutic considerations | |
| Pregnancy cat. |
C/D (U.S.) |
| Legal status | |
| Routes | IV, intranasal |
Butorphanol (INN) is a morphinan-type synthetic opioid analgesic marketed in the U.S. under the trade name Stadol. It is most closely structurally related to dextromethorphan. Butorphanol is available only as butorphanol tartrate in injectable and intranasal spray formulations.
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[edit] Mechanism of action
Butorphanol exhibits partial agonist and antagonist activity at the μ opioid receptor and agonist activity at the κ opioid receptor.[1] 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, and narcotic addicts do not like it.
[edit] 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.[1]
[edit] Adverse effects
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).
[edit] Proprietary preparations
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, Beforal, Stadol, and Stadol NS; veterinary trade names include Butorphic, Dolorex, Morphasol, Torbugesic, and Torbutrol.
[edit] References
- 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
- ^ 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. PMID 10534607. Retrieved on 2007-02-12.
[edit] External links
| Analgesics (N02A, N02B) | |
|---|---|
| Opioids | Bezitramide, Buprenorphine, Butorphanol, Dextromoramide, Dextropropoxyphene, Diamorphine, Dihydrocodeine, Fentanyl, Hydromorphone, Ketobemidone, Methadone, Morphine, Nalbufine, Nicomorphine, Opium, Oxycodone, Papaveretum, Pethidine, Piritramide, Tramadol (see also longer list) |
| Salicylic acid and derivatives | Aspirin (Acetylsalicylic Acid), Diflunisal, Ethenzamide -- See also: NSAIDs |
| Pyrazolones | Aminophenazone, Metamizole, Phenazone |
| Anilides | Paracetamol (acetaminophen), Phenacetin |
| Others | Ziconotide, Tetrahydrocannabinol, Ibuprofen, Ketoprofen, Mefenamic Acid, Naproxen, Diclofenac, Flurbiprofen, Diflunisal, Fenoprofen, Indomethacin, Ketorolac, Meclofenamate, Meloxicam, Piroxicam, Tolmetin |
