オキシメテバノール
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2013/07/22 11:49:49」(JST)
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Drotebanol
|
Systematic (IUPAC) name |
3,4-Dimethoxy-9a-methylmorphinan-6β,14-diol |
Clinical data |
AHFS/Drugs.com |
International Drug Names |
Pregnancy cat. |
? |
Legal status |
Controlled (S8) (AU) Schedule I (US) |
Identifiers |
CAS number |
3176-03-2 N |
ATC code |
None |
PubChem |
CID 5463863 |
ChemSpider |
16736125 Y |
UNII |
7RS2Q8MCK8 Y |
KEGG |
D01496 Y |
Synonyms |
Drotebanol, Oxymethebanol |
Chemical data |
Formula |
C19H27NO4 |
Mol. mass |
333.42 g/mol |
SMILES
- CN1CC[C@]23C[C@@H](CC[C@]2([C@H]1CC4=C3C(=C(C=C4)OC)OC)O)O
|
InChI
-
InChI=1S/C19H27NO4/c1-20-9-8-18-11-13(21)6-7-19(18,22)15(20)10-12-4-5-14(23-2)17(24-3)16(12)18/h4-5,13,15,21-22H,6-11H2,1-3H3/t13-,15-,18-,19-/m1/s1 Y
Key:LCAHPIFLPICNRW-SVYNMNNPSA-N Y
|
Physical data |
Melt. point |
165–167 °C (329–333 °F) |
N (what is this?) (verify)
|
Drotebanol (Oxymethebanol) is a morphinan derivative that acts as an opioid agonist. It was invented by Sankyo Company in Japan during the 1970s. It is synthesised from thebaine.
Drotebanol has powerful antitussive (cough suppressant) effects, and is around 10x more potent than codeine in producing this effect. It also has analgesic effects several times stronger than codeine, but weaker than morphine.[1] In animal studies it was found to be moderately addictive and produced limited physical dependence, but not as severe as that seen with morphine or pethidine.[2] It was previously marketed for human use under the brand name Metebanyl, although it is now no longer used in medicine.
References[edit]
- ^ Kobayashi, S; Hasegawa, K; Mori, M; Takagi, H (1970). "Pharmacological studies on a new specifically potent antitussive agent, 14-hydroxydihydro-6 beta-thebainol-4-methylether (oxymethebanol)". Arzneimittel-Forschung 20 (1): 43–6. PMID 5467447.
- ^ Yanagita T, Miyasato K, Oinuma N, Kiyohara H. Dependence potential of drotebanol, codeine and thebaine tested in rhesus monkeys. UNODC Bulletin on Narcotics. 1977 Issue 1.
Opioids
|
|
Opium and
poppy straw
derivatives |
Crude opiate
extracts /
whole opium
products |
- B&O Supprettes
- Diascordium
- Dover's powder
- Kendal Black Drop
- Laudanum
- Mithridate
- Opium
- Paregoric
- Polish heroin (compote/kompot)
- Poppy straw
- Poppy tea
- Smoking opium
- Theriac
|
|
Natural opiates |
Opium
alkaloids |
- Codeine
- Morphine
- Oripavine
- Pseudomorphine
- Thebaine
|
|
Alkaloid
salts mixtures |
- Pantopon
- Papaveretum (Omnopon)
|
|
|
Semisynthetics
including
Bentley
compounds |
Morphine
family |
- 2,4-Dinitrophenylmorphine
- 6-MDDM
- Azidomorphine
- Chlornaltrexamine
- Desocodeine
- Desomorphine
- Dihydromorphine
- Hydromorphinol
- Methyldesorphine
- N-Phenethylnormorphine
- RAM-378
|
|
3,6-diesters
of morphine |
- Acetylpropionylmorphine
- Diacetyldihydromorphine
- Dibenzoylmorphine
- Dipropanoylmorphine
- Heroin
- Nicomorphine
|
|
Codeine-dionine
family |
- 6-Monoacetylcodeine
- Benzylmorphine
- Codeine methylbromide
- Ethylmorphine
- Heterocodeine
- Isocodeine
- Myrophine
- Pholcodine
|
|
Morphinones
and morphols |
- 14-Cinnamoyloxycodeinone
- 14-Ethoxymetopon
- 14-Methoxymetopon
- 14-Phenylpropoxymetopon
- 3-Acetyloxymorphone
- 3,14-Diacetyloxymorphone
- 6-MDDM
- 7-Spiroindanyloxymorphone
- Acetylmorphone
- Codeinone
- Codoxime
- Conorfone
- Hydrocodone
- Hydromorphone
- IBNtxA
- Methyldihydromorphine
- Metopon
- Morphinone
- N-Phenethyl-14-ethoxymetopon
- Nalmexone
- Oxycodone
- Oxymorphol
- Oxymorphone
- Pentamorphone
- Semorphone
- Thebacon
|
|
Morphides |
- α-Chlorocodide
- Chloromorphide
|
|
Dihydrocodeine
series |
- 14-Hydroxydihydrocodeine
- Acetyldihydrocodeine
- Dihydrocodeine
- Nicocodeine
- Nicodicodeine
|
|
Nitrogen
morphine
derivatives |
- Codeine-N-oxide
- Morphine-N-oxide
|
|
Hydrazones |
|
|
Halogenated
morphine
derivatives |
|
|
|
Active opiate
metabolites |
- 6-Monoacetylmorphine
- Morphine-6-glucuronide
- Norcodeine
- Normorphine
|
|
|
Morphinans |
- 3-Hydroxymorphinan
- Butorphanol
- Cyclorphan
- Cyprodime
- Dextrallorphan
- Drotebanol
- Ketorfanol
- Levallorphan
- Levomethorphan
- Levophenacylmorphan
- Levorphanol
- Nalbuphine
- Norlevorphanol
- Oxilorphan
- Phenomorphan
- Proxorphan
- Racemethorphan/Methorphan
- Racemorphanol/Morphanol
- Ro4-1539
- Sinomenine/Cocculine
- Xorphanol
|
|
Benzomorphans |
- 8-CAC
- Alazocine
- Anazocine
- Bremazocine
- Butinazocine
- Carbazocine
- Cogazocine
- Dezocine
- Eptazocine
- Etazocine
- Ethylketazocine
- Fluorophen
- Ibazocine
- Ketazocine
- Metazocine
- Moxazocine
- Pentazocine
- Phenazocine
- Tonazocine
- Volazocine
- Zenazocine
|
|
4-Phenylpiperidines |
Pethidines
(Meperidines) |
- 4-Fluoropethidine
- Allylnorpethidine
- Anileridine
- Benzethidine
- Carperidine
- Difenoxin
- Diphenoxylate
- Etoxeridine (Carbetidine)
- Furethidine
- Hydroxypethidine (Bemidone)
- Morpheridine
- Oxpheneridine (Carbamethidine)
- Pethidine (Meperidine)
- Pethidine intermediate A
- Pethidine intermediate B (Norpethidine)
- Pethidine intermediate C (Pethidinic Acid)
- Pheneridine
- Phenoperidine
- Piminodine
- Properidine (Ipropethidine)
- Sameridine
|
|
Prodines |
- Allylprodine
- Meprodine (α-meprodine / β-meprodine)
- MPPP (Desmethylprodine)
- PEPAP
- Prodine (α-prodine / β-prodine)
- Prosidol
- Trimeperidine (Promedol)
|
|
Ketobemidones |
- Acetoxyketobemidone
- Droxypropine
- Ketobemidone
- Methylketobemidone
- Propylketobemidone
|
|
Others |
- Alvimopan
- Loperamide
- Picenadol
|
|
|
Open chain
opioids |
Amidones |
- Dipipanone
- Isomethadone
- Levomethadone
- Methadone
- Normethadone
- Norpipanone
- Phenadoxone (Heptazone)
|
|
Methadols |
- Acetylmethadol
- Alphacetylmethadol
- Alphamethadol
- Betacetylmethadol
- Betamethadol
- Dimepheptanol (methadol)
- Isomethadol
- Levacetylmethadol
- Noracymethadol
|
|
Moramides |
- Desmethylmoramide
- Dextromoramide
- Levomoramide
- Moramide/Racemoramide
|
|
Thiambutenes |
- Diethylthiambutene
- Dimethylthiambutene
- Ethylmethylthiambutene
- Piperidylthiambutene
- Pyrrolidinylthiambutene
- Tipepidine
|
|
Phenalkoxams |
- Dextropropoxyphene
- Dimenoxadol
- Dioxaphetyl butyrate
- Levopropoxyphene
- Norpropoxyphene
|
|
Ampromides |
- Diampromide
- Phenampromide
- Propiram
|
|
Others |
- Alimadol
- IC-26
- Isoaminile
- Lefetamine
- R-4066
|
|
|
Anilidopiperidines |
- 3-Allylfentanyl
- 3-Methylfentanyl
- 3-Methylthiofentanyl
- 4-Phenylfentanyl
- α-methylacetylfentanyl
- α-Methylfentanyl
- α-methylthiofentanyl
- β-hydroxyfentanyl
- β-hydroxythiofentanyl
- β-methylfentanyl
- Alfentanil
- Brifentanil
- Carfentanil
- Fentanyl
- Lofentanil
- Mirfentanil
- Ocfentanil
- Ohmefentanyl
- Parafluorofentanyl
- Phenaridine
- Remifentanil
- Sufentanil
- Thiofentanyl
- Trefentanil
|
|
Oripavine
derivatives |
- 7-PET
- Acetorphine
- Alletorphine
- BU-48
- Buprenorphine
- Cyprenorphine
- Dihydroetorphine
- Etorphine
- Homprenorphine
- Norbuprenorphine
|
|
Phenazepanes |
- Ethoheptazine
- Meptazinol
- Metethoheptazine
- Metheptazine
- Proheptazine
|
|
Pirinitramides |
|
|
Benzimidazoles |
|
|
Indoles |
- 18-MC
- 7-Hydroxymitragynine
- Akuammine
- Eseroline
- Hodgkinsine
- Ibogaine
- Mitragynine
- Noribogaine
- Pericine
|
|
Diphenylmethyl-
piperazines |
- BW373U86
- DPI-221
- DPI-287
- DPI-3290
- SNC-80
|
|
Opioid peptides |
- Adrenorphin
- Amidorphin
- Biphalin
- Casokefamide
- Casomorphin
- Cytochrophin
- DADLE
- DAMGO
- Deltorphin
- Dermorphin
- Dynorphin
- Endomorphin
- Endorphins
- Enkephalin
- Frakefamide
- Gliadorphin
- Hemorphin
- Leumorphin
- Metkefamide
- Morphiceptin
- Neoendorphin
- Nociceptin
- Octreotide
- Opiorphin
- Rubiscolin
- Spinorphin
- TRIMU 5
- Tynorphin
- Valorphin
|
|
Others |
- AD-1211
- AH-7921
- Azaprocin
- BRL-52537
- Bromadol
- Bromadoline
- C-8813
- Ciprefadol
- Ciramadol
- Doxpicomine
- Enadoline
- Ethanol
- Faxeladol
- GR-89696
- Herkinorin
- ICI-199,441
- ICI-204,448
- J-113,397
- JTC-801
- LPK-26
- MCOPPB
- Metofoline
- MT-45
- N-Desmethylclozapine
- NNC 63-0532
- Nortilidine
- O-Desmethyltramadol
- Phenadone
- Phencyclidine
- Prodilidine
- Profadol
- Ro64-6198
- Salvinorin A
- SB-612,111
- SC-17599
- RWJ-394,674
- TAN-67
- Tapentadol
- Tifluadom
- Tilidine
- Tramadol
- Trimebutine
- U-50,488
- U-69,593
- Viminol
- W-18
|
|
Opioid
antagonists &
inverse agonists |
- 5'-Guanidinonaltrindole
- Alvimopan
- Chlornaltrexamine
- Chloroxymorphamine
- Conorfone
- Cyclazocine
- Cyprodime
- Diacetylnalorphine
- Difenamizole
- Diprenorphine (M5050)
- Gemazocine
- JDTic
- Levallorphan
- LY-255,582
- Methylnaltrexone
- Nalbuphine
- Naldemedine
- Nalmefene
- Nalmexone
- Nalorphine
- Nalorphine dinicotinate
- Naloxazone
- Naloxegol
- Naloxonazine
- Naloxone
- Naltrexol-d4
- Naltrexone
- Naltriben
- Naltrindole
- Norbinaltorphimine
- Oxilorphan
- Quadazocine
- Samidorphan
- Tonazocine
- Zenazocine
|
|
Uncategorized
opioids |
- Anilopam
- Asimadoline
- Axomadol
- FE 200665
- Fedotozine
- Nalfurafine
- Nalorphine
- Nalorphine dinicotinate
- SoRI-9409
|
|
|
|
English Journal
- Effects of antitussive drugs on the activity of the recurrent laryngeal nerve in cats.
- Mori M, Sakai Y.
- Japanese journal of pharmacology.Jpn J Pharmacol.1975 Dec;25(6):671-80.
- Reflex responses in the recurrent laryngeal (RL) nerve to stimulation of superior laryngeal (SL) nerve and the effects of antitussive drugs on these reflex responses were studied in order to elucidate the site of action of these drugs in encéphale isolé cats. The RL nerve fibers were classified in
- PMID 1228252
- [Electrophysiological study on the site of action of antitussives, with particular reference to oxymetebanol, a new antitussive].
- Mori M, Sakai Y, Hara T.
- Nihon yakurigaku zasshi. Folia pharmacologica Japonica.Nihon Yakurigaku Zasshi.1973 Jan;69(1):163-75.
- PMID 4737517
Japanese Journal
- EFFECTS OF ANTITUSSIVE DRUGS ON THE ACTIVITY OF THE RECURRENT LARYNGEAL NERVE IN CATS
- 鎮咳薬の作用点に関する電気生理学的研究:新鎮咳薬Oxymetebanolを中心として
- 慢性非特異性肺疾患に対するOxymetebanolの使用経験
Related Links
- 英語化学名: Drotebanol. 英語别名: Metebanyl;Drotebanol;oxymetebanol; Oxymethebanol;Dihydro-14-hydroxy-4-O-methyl-6b-thebainol;Dihydro-14- hydroxy-4-O-Methyl-6β-thebainol;3,4-Dimethoxy-17-methylmorphinan-6β,14-diol ;3 ...
- KEGG, DRUG: D01496, Help. エントリ. D01496 Drug.
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