| Revision as of 19:41, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 469586434 of page Abecarnil for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Latest revision as of 19:20, 6 November 2024 edit OAbot (talk | contribs)Bots441,761 editsm Open access bot: pmc updated in citation with #oabot. |
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{{short description|Chemical compound}} |
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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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{{cs1 config|name-list-style=vanc|display-authors=6}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changes |
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| verifiedrevid = 438081138 |
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| verifiedrevid = 477237117 |
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| IUPAC_name = propan-2-yl 4-(methoxymethyl)-6-(phenylmethoxy) -9''H''-pyridoindole-3-carboxylate |
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| IUPAC_name = propan-2-yl 4-(methoxymethyl)-6-(phenylmethoxy) -9''H''-pyridoindole-3-carboxylate |
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| image = Abecarnil.svg |
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| image = Abecarnil-2D-by-AHRLS-2012.png |
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<!--Clinical data--> |
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<!--Clinical data--> |
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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: 111841-85-1 --> |
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| CAS_number = 111841-85-1 |
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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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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=24 | H=24 | N=2 | O=4 |
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| C=24 | H=24 | N=2 | O=4 |
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| smiles = COCc3c(C(=O)OC(C)C)ncc4c2ccc(OCc1ccccc1)cc2c34 |
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| molecular_weight = 404.458 g/mol |
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| smiles = O=C(OC(C)C)c4ncc3c(c2c(ccc(OCc1ccccc1)c2)n3)c4COC |
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| InChI = 1/C24H24N2O4/c1-15(2)30-24(27)23-19(14-28-3)22-18-11-17(29-13-16-7-5-4-6-8-16)9-10-20(18)26-21(22)12-25-23/h4-12,15,26H,13-14H2,1-3H3 |
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| InChIKey = RLFKILXOLJVUNF-UHFFFAOYAF |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C24H24N2O4/c1-15(2)30-24(27)23-19(14-28-3)22-18-11-17(29-13-16-7-5-4-6-8-16)9-10-20(18)26-21(22)12-25-23/h4-12,15,26H,13-14H2,1-3H3 |
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| StdInChI = 1S/C24H24N2O4/c1-15(2)30-24(27)23-19(14-28-3)22-18-11-17(29-13-16-7-5-4-6-8-16)9-10-20(18)26-21(22)12-25-23/h4-12,15,26H,13-14H2,1-3H3 |
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| StdInChIKey = RLFKILXOLJVUNF-UHFFFAOYSA-N |
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| StdInChIKey = RLFKILXOLJVUNF-UHFFFAOYSA-N |
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}} |
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}} |
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'''Abecarnil''' ('''ZK-112,119''') is an ] ] from the ] family. It is one of a relatively recently developed class of medicines known as the ]s, which have similar effects to the older ] group, but with quite different ]s. It is a ] acting ] at the ] of the ].<ref>{{cite journal | vauthors = Ozawa M, Nakada Y, Sugimachi K, Yabuuchi F, Akai T, Mizuta E, Kuno S, Yamaguchi M | title = Pharmacological characterization of the novel anxiolytic beta-carboline abecarnil in rodents and primates | journal = Japanese Journal of Pharmacology | volume = 64 | issue = 3 | pages = 179–187 | date = March 1994 | pmid = 7912751 | doi = 10.1254/jjp.64.179 | doi-access = free }}</ref> |
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== Development == |
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Abecarnil was originally developed as an anti-anxiety drug, but has not as yet been commercially developed for use in humans. It has mainly been used for research into the development of other new ] and ] drugs. Investigations are continuing into its actions, and it is likely to be developed for use in the treatment of anxiety<ref>{{cite journal | vauthors = Aufdembrinke B | title = Abecarnil, a new beta-carboline, in the treatment of anxiety disorders | journal = The British Journal of Psychiatry. Supplement | volume = 34 | issue = 34 | pages = 55–63 | year = 1998 | pmid = 9829018 | doi = 10.1192/S0007125000293537 | s2cid = 24311570 }}</ref> and as a less addictive substitute drug for the treatment of benzodiazepine<ref>{{cite journal | vauthors = Pinna G, Galici R, Schneider HH, Stephens DN, Turski L | title = Alprazolam dependence prevented by substituting with the beta-carboline abecarnil | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 94 | issue = 6 | pages = 2719–2723 | date = March 1997 | pmid = 9122263 | pmc = 20156 | doi = 10.1073/pnas.94.6.2719 | doi-access = free | bibcode = 1997PNAS...94.2719P }}</ref> and ]<ref>{{cite journal | vauthors = Jung ME, Wallis CJ, Gatch MB, Lal H | title = Abecarnil and alprazolam reverse anxiety-like behaviors induced by ethanol withdrawal | journal = Alcohol | volume = 21 | issue = 2 | pages = 161–168 | date = June 2000 | pmid = 10963939 | doi = 10.1016/S0741-8329(00)00079-3 }}</ref> ]. |
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== Pharmacology == |
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Abecarnil is a relatively subtype-selective drug that produces primarily anxiolytic effects, with comparatively fewer sedative or ] properties.<ref>{{cite journal | vauthors = Krause W, Schütt B, Duka T | title = Pharmacokinetics and acute toleration of the beta-carboline derivative abecarnil in man | journal = Arzneimittel-Forschung | volume = 40 | issue = 5 | pages = 529–532 | date = May 1990 | pmid = 1974428 }}</ref><ref>{{cite journal | vauthors = Duka T, Schütt B, Krause W, Dorow R, McDonald S, Fichte K | title = Human studies on abecarnil a new beta-carboline anxiolytic: safety, tolerability and preliminary pharmacological profile | journal = British Journal of Clinical Pharmacology | volume = 35 | issue = 4 | pages = 386–394 | date = April 1993 | pmid = 8097921 | pmc = 1381549 | doi = 10.1111/j.1365-2125.1993.tb04155.x }}</ref> Additionally, it does not significantly potentiate the effects of alcohol.<ref>{{cite journal | vauthors = Stephens DN, Schneider HH, Kehr W, Andrews JS, Rettig KJ, Turski L, Schmiechen R, Turner JD, Jensen LH, Petersen EN | title = Abecarnil, a metabolically stable, anxioselective beta-carboline acting at benzodiazepine receptors | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 253 | issue = 1 | pages = 334–343 | date = April 1990 | pmid = 1970361 }}</ref> |
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== Potential advantages == |
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Abecarnil may have fewer problems with ] and withdrawal compared to nonselective ] benzodiazepine acting drugs.<ref>{{cite journal | vauthors = Löscher W, Hönack D | title = Withdrawal precipitation by benzodiazepine receptor antagonists in dogs chronically treated with diazepam or the novel anxiolytic and anticonvulsant beta-carboline abecarnil | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 345 | issue = 4 | pages = 452–460 | date = April 1992 | pmid = 1352384 | doi = 10.1007/BF00176624 | s2cid = 20486955 }}</ref> |
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The abuse potential of abecarnil is thought to be less than that of benzodiazepines,<ref>{{cite journal | vauthors = Sannerud CA, Ator NA, Griffiths RR | title = Behavioral pharmacology of abecarnil in baboons: self-injection, drug discrimination and physical dependence | journal = Behavioural Pharmacology | volume = 3 | issue = 5 | pages = 507–516 | date = October 1992 | pmid = 11224153 | doi = 10.1097/00008877-199210000-00009 | s2cid = 32081258 }}</ref> with only mild withdrawal symptoms noted after abrupt discontinuation of treatment.<ref>{{cite journal | vauthors = Ballenger JC, McDonald S, Noyes R, Rickels K, Sussman N, Woods S, Patin J, Singer J | title = The first double-blind, placebo-controlled trial of a partial benzodiazepine agonist abecarnil (ZK 112-119) in generalized anxiety disorder | journal = Psychopharmacology Bulletin | volume = 27 | issue = 2 | pages = 171–179 | year = 1991 | pmid = 1681563 }}</ref> |
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== Photoswitchable analog == |
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A ] analog of abecarnil (azocarnil) has been developed to locally and reversibly control ] with light in wildtype animals.<ref>{{cite journal | vauthors = Maleeva G, Nin-Hill A, Wirth U, Rustler K, Ranucci M, Opar E, Rovira C, Bregestovski P, Zeilhofer HU, König B, Alfonso-Prieto M, Gorostiza P | title = Light-Activated Agonist-Potentiator of GABA<sub>A</sub> Receptors for Reversible Neuroinhibition in Wildtype Mice | journal = Journal of the American Chemical Society | date = October 2024 | pmid = 39383450 | doi = 10.1021/jacs.4c08446 | pmc = 11503767 }}</ref> |
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== See also == |
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*] |
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*] |
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== References == |
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{{reflist}} |
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{{Anxiolytics}} |
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{{GABAAR PAMs}} |
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] |
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] |
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] |
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] |
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] |
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] |