| Revision as of 11:39, 17 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 456596741 of page Ethoheptazine for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Latest revision as of 13:47, 9 December 2024 edit Marbletan (talk | contribs)Extended confirmed users5,418 editsNo edit summary |
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{{Short description|Opioid analgesic drug}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| Verifiedfields = changed |
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| verifiedrevid = 399922197 |
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| verifiedrevid = 461096586 |
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| IUPAC_name = Ethyl 1-methyl-4-phenylazepane-4-carboxylate |
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| IUPAC_name = Ethyl 1-methyl-4-phenylazepane-4-carboxylate |
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| image = Ethoheptazine.png |
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| image = Ethoheptazine2DACS.svg |
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| image2 = Ethoheptazine-3D-balls.png |
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| width = 200 |
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| width = 200 |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = Zactane, Equagesic |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| legal_CA = |
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| legal_CA = |
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| legal_UK = |
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| legal_UK = |
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| legal_US = Schedule V |
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| legal_US = Schedule IV |
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| legal_US_comment = (Some preparations) |
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| legal_status = |
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| legal_status = |
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| routes_of_administration = Oral |
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| routes_of_administration = Oral |
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| protein_bound = |
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| protein_bound = |
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| elimination_half-life = |
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| elimination_half-life = |
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| excretion = |
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| excretion = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = <!-- blanked - oldvalue: 77-15-6 --> |
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| CAS_number = 77-15-6 |
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| ATC_prefix = none |
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| ATC_prefix = none |
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| ATC_suffix = |
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| ATC_suffix = |
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| PubChem = 6469 |
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| PubChem = 6469 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| DrugBank = |
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| ChEMBL = 170797 |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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| DrugBank = DB08988 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 6225 |
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| ChemSpiderID = 6225 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 3A4G3A848U |
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| UNII = 3A4G3A848U |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=16 | H=23 | N=1 | O=2 |
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| C=16 | H=23 | N=1 | O=2 |
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| molecular_weight = 261.36 g/mol |
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| smiles = O=C(OCC)C2(c1ccccc1)CCN(C)CCC2 |
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| smiles = O=C(OCC)C2(c1ccccc1)CCN(C)CCC2 |
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| InChI = 1/C16H23NO2/c1-3-19-15(18)16(14-8-5-4-6-9-14)10-7-12-17(2)13-11-16/h4-6,8-9H,3,7,10-13H2,1-2H3 |
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| InChIKey = WGJHHMKQBWSQIY-UHFFFAOYAJ |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C16H23NO2/c1-3-19-15(18)16(14-8-5-4-6-9-14)10-7-12-17(2)13-11-16/h4-6,8-9H,3,7,10-13H2,1-2H3 |
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| StdInChI = 1S/C16H23NO2/c1-3-19-15(18)16(14-8-5-4-6-9-14)10-7-12-17(2)13-11-16/h4-6,8-9H,3,7,10-13H2,1-2H3 |
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| synonyms = Zactane |
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| synonyms = Zactane |
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}} |
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}} |
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'''Ethoheptazine'''<ref>{{cite patent | country = ES | number = 310184 | title = Procedure for the preparation of a new derivative of pirazolidine-hexametilenimina with therapeutic properties. }}</ref> (trade name '''Zactane''') is an ] ] from the phenazepane family. It was invented in the 1950s<ref name="pmid13469802">{{cite journal | vauthors = Batterman RC, Golbey M, Grossman AJ, Leifer P | title = Analgesic effectiveness of orally administered ethoheptazine in man | journal = The American Journal of the Medical Sciences | volume = 234 | issue = 4 | pages = 413–9 | date = October 1957 | pmid = 13469802 | doi = 10.1097/00000441-195710000-00004 | s2cid = 32299049 }}</ref> and is a ring expanded analogue of ].<ref name="pmid14186026">{{cite journal | vauthors = Diamond J, Bruce WF, Tyson FT | title = Synthesis and Properties of the Analgesic DL-α-1,3-dimethyl-4-phenyl-4-propionoxyazacycloheptane (Proheptazine). | journal = Journal of Medicinal Chemistry | volume = 7 | pages = 57–60 | date = January 1964 | pmid = 14186026 | doi = 10.1021/jm00331a013 }}</ref> |
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Ethoheptazine produces similar effects to other opioids, including ], ], ], and ].<ref name="pmid13879557">{{cite journal | vauthors = Cinelli P, Zucchini M | title = | language = it | journal = Minerva Medica | volume = 53 | pages = 637–42 | date = March 1962 | pmid = 13879557 }}</ref> It was sold by itself as Zactane, and is still available as a combination product with ] and ] as ], which is used for the treatment of conditions where both pain and anxiety are present.<ref name="pmid4214668">{{cite journal | vauthors = Scheiner JJ, Richards DJ | title = Treatment of musculoskeletal pain and associated anxiety with an ethoheptazine-aspirin-meprobamate combination (equagesic): a controlled study | journal = Current Therapeutic Research, Clinical and Experimental | volume = 16 | issue = 9 | pages = 928–36 | date = September 1974 | pmid = 4214668 }}</ref> It was also investigated for use as an antitussive.<ref name="pmid41087">{{cite journal | vauthors = Overton DA, Batta SK | title = Investigation of narcotics and antitussives using drug discrimination techniques | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 211 | issue = 2 | pages = 401–8 | date = November 1979 | pmid = 41087 | pmc = 8331839 }}</ref> |
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It is no longer prescribed, as it is no longer FDA approved, and not available for United States' Pharmacy Processing. Revocation of FDA Approved Medications Status stems from a combination of efficacy vs. toxicity, and the more-varied and historically safer benzodiazepines class. Only reversal of the FDA's decision, allows removing the drug from the CSD. Ethoheptazine is not listed as a controlled substance under the Controlled Substances Act, 1970 in the United States.<ref name = "CFCS_DEA" /> The controlled status (Schedule IV) of Equagesic was due to the ] content.<ref>PDR 1978, pp 1618</ref><ref name = "CFCS_DEA">{{cite web | title = Conversion Factors for Controlled Substances | url = http://www.deadiversion.usdoj.gov/quotas/conv_factor/index.html | work = Diversion Control Division | publisher = Drug Enforcement Agency, U.S. Department of Justice | access-date = 2016-02-27 | archive-date = 2016-03-02 | archive-url = https://web.archive.org/web/20160302162948/http://deadiversion.usdoj.gov/quotas/conv_factor/index.html | url-status = dead }}</ref> Regulation elsewhere varies. |
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== References == |
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{{Reflist|30em}} |
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{{Analgesics}} |
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{{Opioidergics}} |
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] |
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] |
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] |
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] |