Butorphanol

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Butorphanol chemical structure
Butorphanol
Systematic (IUPAC) name
17-cyclobutylmethyl-
morphinan-3,14-diol
Identifiers
CAS number 42408-82-2
ATC code N02AX02
PubChem 5361092
DrugBank APRD00835
Chemical data
Formula C21H29NO2 
Mol. weight 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

Schedule IV(US)
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.

Contents

[edit] Mechanism of action

Butorphanol exhibits partial agonist and antagonist activity at the μ opioid receptor and agonist activity at the κ opioid receptor. 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.

[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 vaious 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


[edit] External links


Analgesics (N02A, N02B) edit
Opioids:

6-methylene-dihydromorphine, Acedicon, Acetorphine, Acetyldihydrocodeine, Acetyldihydrocodeinone, Acetylmorphone, Alfentanil, Allylprodine, Alphaprodine, Anileridine, Bemidone, Benzylmorphine, Betmeprodine, Betaprodine, Bezitramide, Buprenorphine, Butorphanol, Carfentanil, Clonitazene, Codeine-N-Oxide, Codeine, Codeineone, Cyclazocine, Cyclorphan, Desomorphine, Dextromethorphan, Dextropropoxyphene, Dextromoramide, Dezocine, Diacetyldihydromorphine, Diethylthiambutene, Difenoxin, Dihydromorphine, Dihydrocodeine, Dihydrocodeine enol acetate, Dihydroetorphine, Dihydroisocodeine, Dimethylthiambutene, Diphenoxylate, Dipipanone, Ethylketocyclazocine, Ethylmorphine, Etonitazene, Etorphine, Fentanyl, Diamorphine (Heroin), Hydromorphone, Hydrocodone, Isomethadone, Ketobemidone, Laudanum, Lefetamine, Levallorphan, Levo-alphacetylmethadol, Levomethadone, Levomethorphan, Levorphanol, Loperamide, Meptazinol, Metazocine, MPPP, Methadone, Methyldihydromorphine, Metopon, Morphine, Morphineone, Morphine-N-Oxide, Myorphine, Nalbuphine, Nicocodeine, Nicodicodeine, Nicomorphine, Norcodeine, Ohmefentanyl, Omnopon, Opium, Oxycodone, Oxymorphone, PEPAP, Pantopon, Papaveretum, Paregoric, Pentazocine, Pethidine(Meperidine), Phenadoxone, Phenazocine, Phenoperidine, Pholcodeine, Piminodine, Piritramide, Prodine, Proheptazine, Propiram, Propoxyphene, Racemethorphan, Racemorphan, Remifentanil, Sufentanil, Tetrapon, Thebacon, Tilidine, Tramadol, Trimeperidine
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,
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