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14-September-2008 18:02:37 - Naloxone Naloxone Systematic IUPAC name 17-allyl-4,5α-epoxy-3,14-dihydroxymorphinan-6-one Identifiers CAS number 465-65-6 ATC code V03AB15 PubChem 4425 DrugBank APRD00025 Chemical data Formula C19H21NO4 Mol. mass 327.27 g/mol Pharmacokinetic data Bioavailability 2% 90% absorption but high first-pass metabolism Metabolism Liver Half life 1-1.5 hours Excretion Urine, Biliary Therapeutic considerations Pregnancy cat. B USA B1 Aus Legal status Prescription Only S4AU Schedule ICA Routes IV, IM Naloxone is a drug used to counter the effects of opioid overdose, for example heroin or morphine overdose. Naloxone is specifically used to counteract life-threatening depression of the central nervous system and respiratory system. It is marketed under various trademarks including Narcan, Nalone, and Narcanti, and has sometimes been mistakenly called naltrexate. It is not to be confused with Naltrexone, another opioid receptor antagonist with qualitatively different effects, used for dependence treatment rather than emergency overdose treatment. Contents 1 Pharmacodynamics 2 Chemistry 3 Administration 4 Uses 5 Legal status 6 Identification 7 References 8 External links Pharmacodynamics Naloxone has an extremely high affinity for μ-opioid receptors in the central nervous system. Naloxone is a μ-opioid receptor competitive antagonist, and its rapid blockade of those receptors often produces rapid onset of withdrawal symptoms. Naloxone also has an antagonist action, though with a lower affinity, at κ- and δ-opioid receptors. Chemistry Naloxone is synthesized from thebaine. The chemical structure of naloxone resembles that of oxymorphone, the only difference being the substitution of the N-methyl group with an allyl prop-2-enyl group. The name naloxone has been derived from N-allyl and oxymorphone. Administration Naloxone is most commonly injected intravenously for fastest action. The drug acts after about two minutes, and its effects may last about 45 minutes. It can also be administered via intramuscular or subcutaneous injection. Use of a wedge device nasal Atomizerattached to a syringe to create a mist delivering the drug to the nasal mucosa1 may also be utilized, although this solution is more likely utilized outside of a clinical facility. Uses This section needs additional citations for verification. July 2008 Naloxone has been distributed as part of emergency kits to heroin users, and this has been shown to reduce rates of fatal overdose. Projects of this type are under way in San Francisco, New Mexico, Philadelphia, New York State, Baltimore, Boston, Los Angeles and Chicago, with pilot projects started in Scotland in 2006. The drug also blocks the action of pain-lowering endorphins which the body produces naturally. The likely reason for this is that these endorphins operate on the same opioid receptors. Naloxone is capable of blocking a placebo pain-lowering response, both in clinical and experimental pain, if the placebo is administered together with a hidden or blind injection of naloxone.2 While naloxone is still often used in emergency treatments for opioid overdose, its clinical use in the long-term treatment of opioid addiction is being increasingly superseded by naltrexone. Naltrexone is structurally similar but has a slightly increased affinity for κ-opioid receptors over naloxone, can be administered orally and has a longer duration of action. Enteral naloxone has been successfully used in the reduction of gastritis and oesophagitis associated with opioid therapy in mechanically-ventilated acute care patients. Naloxone is also being used as a secondary chemical in the FDA approved medicine Suboxone. Suboxone and Subutex were created as part of a detox program to help opiate addicted patients stop using opiates. Suboxone contains 4 parts buprenorphine and 1 part naloxone, while Subutex contains only buprenorphrine. Naloxone was added to Suboxone in an effort to dissuade patients from grinding up the Suboxone tablet and using it as part of a combination of opiates that the user would inject into their body. Intravenously administered naloxone is supposed to block the effects of any opiates and cause the user to go into immediate withdrawal. However, buprenorphine has a higher affinity for the opiate receptors, and many users have reported that Suboxone is injectable without inducing withdrawal effects.citation needed Oral or sublingual administration affects only the gastronintestinal tract, and has the added benefit of helping to reverse constipation and lowered bowel motility caused by chronic medical use or abuse of a variety of opioids. Buprenorphine itself has less of an effect on the central nervous system and produces far less euphoria than other opioid drugs, while still being effective in the treatment of pain. For this reason, buprenorphine is gaining acceptance in the treatment of chronic pain, as well as opioid addiction withdrawal, since it produces fewer side effects and less sedation. On the whole, it is a drug moderately useful in pain management that is further attractive due to its relative lack of desirability to opioid abusers. Currently, only certified addictionologists physicians specializing in the treatment of drug addiction and dependence are legally permitted to prescribe Suboxone or other drugs containing buprenorphine. Like methadone, buprenorphine has only recently been approved for use in the management of pain, and likely restrictions on prescribing authority will be eased over time as buprenorphine sees wider use and acceptance by the medical profession, and concerns over diversion and abuse lessen. The addition of naloxone to buprenorphine in Suboxone tablets is intended to prevent misuse and abuse by injection. However, the Naloxone in Suboxone does cause side effects in some people. These side effects include, but are not limited to, asthenia, chills, headache, infection, pain, abdominal pain, back pain, withdrawal syndrome, vasodilation, constipation, diarrhea, nausea, vomiting, insomnia, and sweating. Because of these side effects, the FDA recommends that doctors begin any chemical detox using Subutex, which does not contain any Naloxone. In this way, if for some reason the doctor moves the patient to Suboxone and the patient begins having side effects related to naloxone, the doctor can easily move the patient back to Subutex. For these reasons and others, it has been reported that Subutex is easier to withdraw from than is Suboxone. Legal status The patent for Naloxone has expired and the drug is currently available in various generic forms. Identification The CAS number of naloxone is 465-65-6; the anhydrous hydrochloride salt has CAS 357-08-4 and the hydrochloride salt with 2 molecules of water has CAS 51481-60-8. References British National Formulary 55, March 2008; ISBN 9780853697763 ^ Journal of Emergency Nursing. ^ Sauro, Marie D; Greenberg, Roger P. Endogenous opiates and the placebo effect: A meta-analytic review. Journal of Psychosomatic Research. Vol 582 Feb 2005, 115-120. External links Chicago Recovery Alliance's naloxone distribution project Report on Naloxone and other opiate antidotes, by the International Programme on Chemical Safety v d e Opioids N02A Opium derivatives Whole Opium Preparations Diascordium Dover's powder Granulated Opium Laudanum Mithridate Opium Paregoric Poppy Straw Concentrate Poppy tea Powdered Opium Raw Opium Smoking Opium Theriac Natural Opiates Opium Alkaloids see also: Components of Opium 16-Hydroxythebaine Allocryptopine Berberine Bulbocapnine Canadine Codamine Codeine Coptisine Coreximine Corytuberine Cotarnine Cryptopine Cycloartenol Cycloartenone Cyclolaudenol Dehydroreticuline Dihydrosanguinarine Eupaverine Glaucine Hydrocotarnine Isoboldine Isocorypalmine Laudanidine Laudanine Laudanosine Magnoflorine Morphine Narceine Narceinone Narcotoline Neopine Norlaudanosoline Norsanguinarine Noscapine Oripavine Oxysanguinarine Palaudine Papaverine Papaveraldine Papaverrubine B O-Methyl-Porphyroxine Papaverrubine C Epiporphyroxine Papaverrubine D Porphyroxine Perparin Pseudomorphine Reticuline Salutaridine Sinoacutine Sanguinarine Scoulerine Somniferine Stepholidine Thebaine Alkaloid Salts Mixtures Omnopon Pantopon Papaveretum Tetrapon Semisynthetics Morphine Family 14-hydroxydihydromorphine Hydromorphinol 2,4-Dinitrophenylmorphine 6-Methyldihydromorphine 6-Methylenedihydrodesoxymorphine Apomorphine Desomorphine Diacetyldihydromorphine Dihydrodesoxymorphine Dihydroheroin Dihydromorphine Dipropanoylmorphine Ethyldihydromorphine Heroin Diamorphine Heroin-7,8-Oxide Methyldesorphine Methyldihydromorphine Nicomorphine N-Phenethylnormorphine Codeine-Dionine Family Acetylcodeine Benzylmorphine Codeine Desocodeine Dihydroheterocodeine Ethylmorphine Dionine Heterocodeine Isocodeine Morpholinylethylmorphine Pholcodine Myrophine Nalodeine Transisocodeine Morphinones 14-Ethoxymetopon 14-Methoxymetopon 14-O-Methyloxymorphone 14-Phenylpropoxymetopon 14-Hydroxydihydromorphinone Oxymorphone 7-Spiroindanyloxymorphone 8,14-Dihydroxydihydromorphinone Acetylmorphone Ethyldihydromorphinone Hydromorphinol Hydromorphinone Hydromorphone Hydroxycodeine Methyldihydromorphinone Metopon Morphinol Morphinone N-Phenethyl-14-ethoxymetopon Oxymorphone Pentamorphone Semorphone Codeinones 1-carboxy-14-hydroxydihydrocodeinone 1-carbethoxy-14-hydroxydihydrocodeinone 14-Hydroxydihydrocodeinone Oxycodone Acetyldihydrocodeinone Codeinone Codorphone Codoxime Dihydrocodeinone enol acetate Dihydrohydroxycodeinone Hydrocodone Oxycodone Thebacon Dihydrocodeine Series 14-hydroxydihydrocodeine Acetyldihydrocodeine Dihydrocodeine Dihydrodesoxycodeine/Desocodeine Dihydroisocodeine Nicocodeine Nicodicodeine Nitrogen Morphine Derivatives Codeine-N-Oxide Heroin-N-Oxide Hydromorphone-N-Oxide Morphine-N-Oxide Others α-chlorocodide Azidomorphine Chloromorphide Hydromorphazone Morphazone Oxymorphazone Pholcodine Active Opiate Metabolites Codeine-N-Oxide Genocodeine Hydromorphone-N-Oxide Heroin-7,8-Oxide Morphine-3-glucuronide Morphine-6-glucuronide Monoacetylmorphine Morphine-N-Oxide Genomorphine Naltrexol Norcodeine Normorphine Morphinans Morphinan Series 4-chlorophenylpyridomorphinan Cyclorphan Dextro-3-hydroxy-N-allylmorphinan Dextromethorphan Dextrorphan Dimemorfan Levargorphan Levallorphan Levorphanol Levorphan Levophenacylmorphan Levomethorphan Norlevorphanol N-Methylmorphinan Oxilorphan Phenomorphan Racemethorphan Racemorphan Stephodeline Xorphanol Others 1-Nitroaknadinine 14-episinomenine 5,6-Dihydronorsalutaridine 6-Ketonalbuphine Aknadinine Butorphanol Cephakicine Cephasamine Cyprodime Drotebanol Fenfangjine G Nalbuphine Sinococuline Sinomenine Cocculine Tannagine Benzomorphans 5,9-DEHB Allylnormetazocine Anazocine Bremazocine Cogazocine Cyclazocine Dezocine Eptazocine Etazocine Ethylketocyclazocine Fluorophen Ketazocine Metazocine Pentazocine Phenazocine Quadazocine Thiazocine 4-Phenylpiperidines Pethidines Meperidines Allylnorpethidine Anileridine Benzethidine Carperidine Difenoxin Diphenoxylate Etoxeridine Carbetidine Furethidine Hydroxypethidine Bemidone Hydroxymethoxypethidine Morpheridine Oxpheneridine Carbamethidine Meperidine-N-Oxide Pethidine Meperidine Pethidine Intermediate A Pethidine Intermediate B Norpethidine Pethidine Intermediate C Pethidinic Acid Pheneridine Phenoperidine Piminodine Properidine Ipropethidine Sameridine Prodines Allylprodine α-meprodine α-prodine β-meprodine β-prodine Isopromedol Meprodine MPPP PEPAP Prodine Prosidol Trimeperidine Promedol Ketobemidones Acetoxyketobemidone Droxypropine Ketobemidone Methylketobemidone Propylketobemidone Others Alvimopan Loperamide Picenadol Open Chain Opioids Amidones Dextromethadone Dextroisomethadone Dipipanone Hexalgon Norpipanone Isomethadone Levoisomethadone Levomethadone Methadone Methadone intermediate Normethadone Norpipanone Phenadoxone Heptazone Pipidone Methadols Acetylmethadol α-methadol α-acetylmethadol β-methadol β-acetylmethadol Dimepheptanol Racemethadol Levo-α-acetylmethadol Noracymethadol Moramides Dextromoramide Levomoramide Moramide intermediate Racemoramide Thiambutenes Diethylthiambutene Dimethylthiambutene Ethylmethylthiambutene Piperidylthiambutene Pyrrolidinylthiambutene Thiambutene Tipepidine Phenalkoxams Dextropropoxyphene Dimenoxadol Dioxaphetyl Butyrate Levopropoxyphene Propoxyphene Ampromides Diampromide Phenampromide Propiram Others IC-26 Isoaminile Lefetamine R-4066 Anilidopiperidines 3-Allylfentanyl 3-Methylfentanyl 3-Methylthiofentanyl Alfentanil α-methylacetylfentanyl α-methylfentanyl α-methylthiofentanyl Benzylfentanyl β-hydroxyfentanyl β-hydroxythiofentanyl β-methylfentanyl Brifentanil Carfentanil Fentanyl Lofentanil Mirfentanil Ohmefentanyl Parafluorofentanyl Phenaridine Remifentanil Sufentanil Thenylfentanyl Thiofentanyl Trefentanil Oripavine derivatives 7-PET Acetorphine Alletorphine BU-48 Buprenorphine Butorphine Cyprenorphine Dihydroetorphine Diprenorphine M5050 Etorphine N-cyclopropylmethyl-noretorphine Nepenthone Norbuprenorphine Thevinone Thienorphine Phenazepines Ethoheptazine Meptazinol Metheptazine Metethoheptazine Proheptazine Pirinitramides Bezitramide Piritramide Benzimidazoles Clonitazene Etonitazene Nitazine Indoles 7-Acetoxymitragynine 7-Hydroxymitragynine Akuammidine Akuammine Eseroline Hodgkinsine Ibogaine Mitragynine Pericine ψ-Akuammigine Diphenylmethylpiperazines BW373U86 DPI-221 DPI-287 DPI-3290 SNC-80 Opioid Peptides Casomorphin DADLE DALDA DAMGO Dermenkephalin Dermorphin Deltorphin DPDPE Dynorphin Endomorphin Endorphin Enkephalin Gliadorphin Morphiceptin Nociceptin Octreotide Opiorphin Rubiscolin TRIMU 5 Others 4-p-Bromophenyl-4-dimethylamino-1-phenethylcyclohexanol Azaprocin Bisnortilidine C-8813 Ciramadol Cyclohexyloxy-α-phenethylamine Enadoline Faxeladol Herkinorin JTC-801 Methopholine NNC 63-0532 Nortilidine O-Desmethyltramadol Prodilidine Salvinorin A SC-17599 RWJ-394,674 Tapentadol Tifluadom Tilidine Tramadol Viminol W-18 Zipeprol Opioid Antagonists 5'-Guanidinonaltrindole β-Funaltrexamine 6β-Naltrexol Alvimopan Amiphenazole Binaltorphimine Clocinnamox Cyclazocine Cyprodime Diprenorphine M5050 Fedotozine Levallorphan Methocinnamox Methylnaltrexone Nalfurafine Nalmefene Nalmexone Naloxazone Naloxonazine Naloxone Naloxone benzoylhydrazone Nalorphine Naltrexone Naltrindole Norbinaltorphimine Oxilorphan S-allyl-3-hydroxy-17-thioniamorphinan SAHTM v d e Antidotes V03AB Methanol / Ethylene glycol Ethanol - Fomepizole Paracetamol Acetaminophen Acetylcysteine - Glutathione - Methionine Arsenic Dimercaprol - Succimer Cyanide 4-Dimethylaminophenol - Amyl nitrite - Hydroxocobalamin - Methylene blue - Sodium nitrite - Sodium thiosulfate Heparin Protamine Nerve agent / Organophosphate pesticide Atropine - Biperiden - Diazepam - Oximes Pralidoxime, Obidoxime - see also Cholinesterase Opioid Diprenorphine - Doxapram - Nalorphine - Naloxone - Naltrexone - Nalmefene Barbiturate Bemegride - Ethamivan Benzodiazepine Cyprodenate - Flumazenil GHB Lorazepam - Physostigmine - SCH-50911 Toxic metals Cadmium, Mercury, Lead, Thallium Edetates - Dimercaprol - Prussian blue Other Ipecacuanha - Prednisolone/promethazine - Methylthioninium chloride - Potassium permanganate - Copper sulfate - Potassium iodide - Digoxin Immune Fab Retrieved from http://en..org/wiki/Naloxone Categories: Opioids | Analgesics | Antidotes | Opioid antagonistsHidden categories: Articles needing additional references from July 2008 | All articles with statements | Articles with statements since June 2008 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages БългарÑ?ки Dansk Deutsch Español Français Italiano עברית 日本語 ‪Norsk bokmÃ¥l‬ Polski Português Română РуÑ?Ñ?кий Svenska This page was last modified on 6 September 2008, at 23:3
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