Enadolin

Enadolin
(IUPAC) ime
	2-(benzofuran-4-yl)-N-methyl-N-((5R,7S,8S)-7- (pyrrolidin-1-yl)-1-oxaspiro[4.5] decan-8-yl)ethanamide
Klinički podaci
Identifikatori
CAS broj	124378-77-4
ATC kod	nije dodeljen
PubChem	60768
ChemSpider	54765
ChEMBL	CHEMBL318859
Hemijski podaci
Formula	C24H32N2O3
Mol. masa	396.52 g/mol
SMILES	eMolekuli & PubHem
InChI
	InChI=1S/C24H32N2O3/c1-25(23(27)16-18-6-4-7-22-19(18)9-15-28-22)20-8-11-24(10-5-14-29-24)17-21(20)26-12-2-3-13-26/h4,6-7,9,15,20-21H,2-3,5,8,10-14,16-17H2,1H3/t20-,21-,24-/m0/s1 ; Key: JMBYBVLCYODBJQ-HFMPRLQTSA-N
Farmakoinformacioni podaci
Trudnoća	?
Pravni status

Enadolin je lek koji deluje kao visoko selektivni agonist κ-opioidnog receptora.

U ispitivanjima na ljudima je pokazano da proizvodi vizuelne distorzije i osećaje disocijacije, slično efektima salvinorina A.^[5] Ispitivan je kao potencijalni analgetik, ali je to obustavljeno zbog pojave disforije na većim dozama, što se može očekivati od κ-opioidnog agonista. Razmatrana je mogućnost njegove primene u lečenju komatoznih povreda glave ili žrtava moždanog udara, gde bi taj tip nuspojave bio nevažan.^[6]

Sinteza

Hemijska sinteza enadolina je slična sintezi spiradolina, pošto oba jedinjenja imaju isti intermedijar i samo se međusobno razlikuju u pogledu finalnog koraka.^[7]

Povezano

Salvinorin A

Literatura

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit
↑ Walsh SL, Strain EC, Abreu ME, Bigelow GE (2001). „Enadoline, a selective kappa opioid agonist: comparison with butorphanol and hydromorphone in humans”. Psychopharmacology (Berl.) 157 (2): 151–62. DOI:10.1007/s002130100788. PMID 11594439.
↑ Barber A, Gottschlich R (1997). „Novel developments with selective, non-peptidic kappa-opioid receptor agonists”. Expert Opin Investig Drugs 6 (10): 1351–68. DOI:10.1517/13543784.6.10.1351. PMID 15989506.
↑ Halfpenny, Paul R.; Horwell, David C.; Hughes, John; Hunter, John C.; Rees, David C. (1990). „Highly selective .kappa.-opioid analgesics. 3. Synthesis and structure-activity relationships of novel N-[2-(1-pyrrolidinyl)-4- or -5-substituted cyclohexyl]arylacetamide derivatives”. Journal of Medicinal Chemistry 33 (1): 286. DOI:10.1021/jm00163a047. PMID 2153208.

Spoljašnje veze

	Portal Medicina
	Portal Hemija

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[2] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[3] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[4] Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit

[pmid11594439-5] Walsh SL, Strain EC, Abreu ME, Bigelow GE (2001). „Enadoline, a selective kappa opioid agonist: comparison with butorphanol and hydromorphone in humans”. Psychopharmacology (Berl.) 157 (2): 151–62. DOI:10.1007/s002130100788. PMID 11594439.

[pmid15989506-6] Barber A, Gottschlich R (1997). „Novel developments with selective, non-peptidic kappa-opioid receptor agonists”. Expert Opin Investig Drugs 6 (10): 1351–68. DOI:10.1517/13543784.6.10.1351. PMID 15989506.

[7] Halfpenny, Paul R.; Horwell, David C.; Hughes, John; Hunter, John C.; Rees, David C. (1990). „Highly selective .kappa.-opioid analgesics. 3. Synthesis and structure-activity relationships of novel N-[2-(1-pyrrolidinyl)-4- or -5-substituted cyclohexyl]arylacetamide derivatives”. Journal of Medicinal Chemistry 33 (1): 286. DOI:10.1021/jm00163a047. PMID 2153208.

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