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20-September-2008 09:55:50 - Apomorphine Apomorphine Systematic IUPAC name 5,6,6a,7-Tetrahydro-6-methyl-4H- dibenzode,gquinolin-10,11-diol ? Identifiers CAS number 41372-20-7 ATC code G04BE07 N04BC07 PubChem 6005 DrugBank APRD00531 Chemical data Formula C17H17NO2 Mol. mass 267.322 g/mol SMILES eMolecules PubChem Pharmacokinetic data Bioavailability 100% following sc injection Protein binding ~50% Metabolism hepatic Half life 40 minutes range 30-60 minutes Excretion ? Therapeutic considerations Pregnancy cat. ? Legal status II California, non-scheduled Rest of USA Routes sc Apomorphine is a type of dopaminergic agonist, a morphine derivative but does not actually contain morphine, or bind to opioid receptors. Apomorphine is a relatively non-selective dopamine receptor agonist, having possible slightly higher affinity for D2-like dopamine receptors. Historically, apomorphine has been tried for a variety of uses including psychiatric treatment of homosexuality in the early 20th century. Currently, apomorphine is used in the treatment of Parkinson's disease and under the name Uprima of erectile dysfunction. It was also successfully used in the treatment of heroin addiction, a purpose for which it was championed by the author William S. Burroughs. It is a potent emetic i.e. it induces vomiting and should not be administered without an antiemetic such as domperidone. The emetic properties of apomorphine are exploited in veterinary medicine to induce therapeutic emesis in canines that have recently ingested toxic or foreign substances. For treatment of erectile dysfunction, it is believed that dopamine receptors in the hypothalamic region of the brain are the main target, as although dopamine receptors in the penis do facilitate erection, they do so far more weakly than those in the brain.1 Apomorphine is clear as a liquid but stains green. Therefore care must be taken to avoid splashes. Apormophine does not remain stable for more than 24 hours in a plastic container, so syringes are discarded if not used within 24 hours. Contents 1 Use in Parkinson's disease 2 Erectile dysfunction 3 References 4 External links Use in Parkinson's disease First mooted as a treatment for Parkinson's disease as early as 1951,2 its clinical use was first reported in 1970 by Cotzias et al,3 although its emetic properties and short half-life made oral use impractical. A later study found that combining the drug with the antiemetic domperidone improved results significantly.4 Therapeutic use in Parkinson's disease is effective because of the drug's strong dopaminergic action, with a rapid effect within 3-20 minutes of injection but a brief duration.5 While apomorphine can be used in combination with l-dopa, the intention is usually to wean patients off of this, as by this stage they will probably be experiencing a great deal of dopa-induced dyskinesias and off periods.5 Following a successful apomorphine challenge, training of patient and caregiver, and careful dose titration, there is no reason why an apomorphine pump can not be an effective monotherapy.5 Erectile dysfunction Apomorphine hydrochloride trade name Uprima is used in the treatment of erectile dysfunction male impotence. It is its mode of stimulating dopamine in the brain which is believed to enhance the sexual response. It was found to be of poor efficacy6 in a large-scale study by Researchers at the UK's Drug Safety Research Unit and University of Portsmouth and discontinued in the UK in January 2006.6 Around 65-70% of doctors felt it was ineffective, with 60% of over 11,000 patients avg age 61 discontinuing in month 1 and a further 23% in month 2.6 7 References ^ Matsumoto K, Yoshida M, Andersson K, Hedlund P 2005. Effects in vitro and in vivo by apomorphine in the rat corpus cavernosum.. Br J Pharmacol 146 2: 259-67. doi:10.1038/sj.bjp.0706317. PMID 16025145. ^ Schwab R, Amador L, Lettvin J. Apomorphine in Parkinson's disease.. Trans Am Neurol Assoc 56: 251-3. PMID 14913646. ^ Cotzias G, Papavasiliou P, Fehling C, Kaufman B, Mena I 1970. Similarities between neurologic effects of L-dopa and of apomorphine.. N Engl J Med 282 1: 31-3. PMID 4901383. ^ Corsini G, Del Zompo M, Gessa G, Mangoni A 1979. Therapeutic efficacy of apomorphine combined with an extracerebral inhibitor of dopamine receptors in Parkinson's disease.. Lancet 1 8123: 954-6. doi:10.1016/S0140-67367991725-2. PMID 87620. ^ a b c Chaudhuri K, Clough C 1998. Subcutaneous apomorphine in Parkinson's disease.. BMJ 316 7132: 641. PMID 9522772. ^ a b c Pharmaceutical Business Review, Study shows Abbott's Uprima ineffective for most UK patients ^ MedicineNet study review External links PDSP Ki database Apomorphine - Frequently Asked Questions. Britannia Pharmaceuticals. Andrew Lees and Kirsten Turner 2002. Apomorphine for Parkinson's Disease PDF. Practical Neurology 2: 280-287. doi:10.1046/j.1474-7766.2002.00086.x. - Detailed usage guide for Apomorphine pumps for Parkinson's 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 Narcotine 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 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 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 5,6-Dihydronorsalutaridine 6-Ketonalbuphine Aknadinine Butorphanol Cyprodime Drotebanol Fenfangjine G Nalbuphine Sinococuline Sinomenine Cocculine 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 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 Amiphenazole Binaltorphimine Clocinnamox Cyclazocine Cyprodime Diprenorphine Fedotozine M5050 Levallorphan Methocinnamox Methylnaltrexone Nalfurafine Nalmefene Nalmexone Naloxazone Naloxonazine Naloxone Naloxone benzoylhydrazone Nalorphine Naltrexone Naltrindole Norbinaltorphimine Oxilorphan v d e Anti-parkinson drugs: dopaminergic agents N04B Dopa and derivatives Droxidopa Levodopa Melevodopa Etilevodopa Adamantane derivatives Amantadine Dopamine agonists A-412,997 Apomorphine Bromocriptine Cabergoline Dihydrexidine Dihydroergocryptine mesylate Fenoldopam Lisuride Pergolide Piribedil Pramipexole Propylnorapomorphine Quinpirole Ropinirole Rotigotine SKF 38393 SKF 82958 MAOIs B Selegiline Rasagiline COMT inhibitors Entacapone Tolcapone Other Budipine dopa decarboxylase inhibitor Carbidopa v d e Urologicals G04 Acidifiers Ammonium chloride, Calcium chloride Urinary antispasmodics primarily antimuscarinics Darifenacin, Emepronium, Fesoterodine, Flavoxate, Imidafenacin, Meladrazine, Oxybutynin, Propiverine, Solifenacin, Terodiline, Tolterodine, Trospium For erectile dysfunction Prostaglandins E Alprostadil PDE5 inhibitors Avanafil - Sildenafil - Tadalafil - Udenafil - Vardenafil Alpha blockers Moxisylyte - Phentolamine - Yohimbine Others Apomorphine - Papaverine Other urologicals Acetohydroxamic acid, Collagen, Dimethyl sulfoxide, Magnesium hydroxide, Pentosan polysulfate, Phenazopyridine, Phenyl salicylate, Succinimide For BPH 5α-reductase inhibitors Dutasteride, Finasteride Alpha blockers α1 Alfuzosin, Doxazosin, Silodosin, Tamsulosin, Terazosin Herbals Pygeum africanum, Serenoa repens Retrieved from http://en..org/wiki/Apomorphine Categories: Opioids | Analgesics | Alkaloids | Dopamine agonists | Erectile dysfunction drugs | Heterocyclic compounds 4 or more rings | Sexual orientation and medicine | Morphinans 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 Deutsch Français Magyar 日本語 Polski Português РуÑ?Ñ?кий УкраїнÑ?ька This page was last modified on 7 August 2008, at 04:04
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