A-86929

A-86929
	9,10-Dihidroksi-2-propil-4,5,5a(R),6,7,11b(S)-heksahidrobenzo[f]tieno[2,3-c]hinolin
Identifikacija
CAS registarski broj	166591-11-3
PubChem	9841398
ChemSpider	8017113
ChEMBL	CHEMBL28338
Jmol-3D slike	Slika 1
SMILES
	Oc1cc3c(cc1O)CCC4C3c2cc(CCC)sc2CN4
InChI
	InChI=1S/C18H21NO2S/c1-2-3-11-7-13-17(22-11)9-19-14-5-4-10-6-15(20)16(21)8-12(10)18(13)14/h6-8,14,18-21H,2-5,9H2,1H3/t14-,18+/m1/s1 ; Kod: REHAKLRYABHSQJ-KDOFPFPSSA-N InChI=1/C18H21NO2S/c1-2-3-11-7-13-17(22-11)9-19-14-5-4-10-6-15(20)16(21)8-12(10)18(13)14/h6-8,14,18-21H,2-5,9H2,1H3/t14-,18+/m1/s1; Kod: REHAKLRYABHSQJ-KDOFPFPSBO
Svojstva
Molekulska formula	C18H21NO2S
Molarna masa	315,429 g/mol
	(šta je ovo?) (verifikuj) ; Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
	Infobox references

A-86929 je sintetičko jedinjenje koje deluje kao selektivni agonist dopaminskog receptora D₁.^[5]^[6] On je razvijen kao mogući treatment za Parkinsonovu bolest,^[7] kao i za druge primene, poput kokainske adikcije.^[8]^[9] On ima relativno dobru efikasnost na ljudima, međutim uzrokuje diskinezije, te je njegov razvoj prekinut.^[10]^[11] On je uglavnom korišten u obliku diacetatnog estra, proleka adrogolid (ABT-431), koji ima bolju biodostupnost.^[12]^[13]

Reference[uredi | uredi kod]

↑ 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
↑ Michaelides MR, Hong Y, DiDomenico S, Asin KE, Britton DR, Lin CW, Williams M, Shiosaki K (September 1995). „(5aR,11bS)-4,5,5a,6,7,11b-hexahydro-2-propyl-3-thia-5-azacyclopent-1- ena[c]-phenanthrene-9,10-diol (A-86929): a potent and selective dopamine D1 agonist that maintains behavioral efficacy following repeated administration and characterization of its diacetyl prodrug (ABT-431)”. Journal of Medicinal Chemistry 38 (18): 3445–7. DOI:10.1021/jm00018a002. PMID 7658429.
↑ Ehrlich PP, Ralston JW, Michaelides MR (May 1997). „An Efficient Enantioselective Synthesis of the D1 Agonist (5aR,11bS)-4,5,5a,6,7,11b-Hexahydro-2-propyl-3-thia- 5-azacyclopenta[c]phenanthrene-9,10-diol (A-86929)”. The Journal of Organic Chemistry 62 (9): 2782–2785. DOI:10.1021/jo970066l. PMID 11671640.
↑ Rascol O, Blin O, Thalamas C, Descombes S, Soubrouillard C, Azulay P, Fabre N, Viallet F, Lafnitzegger K, Wright S, Carter JH, Nutt JG (June 1999). „ABT-431, a D1 receptor agonist prodrug, has efficacy in Parkinson's disease”. Annals of Neurology 45 (6): 736–41. DOI:10.1002/1531-8249(199906)45:6<736::AID-ANA7>3.0.CO;2-F. PMID 10360765.
↑ Haney M, Collins ED, Ward AS, Foltin RW, Fischman MW (March 1999). „Effect of a selective dopamine D1 agonist (ABT-431) on smoked cocaine self-administration in humans”. Psychopharmacology 143 (1): 102–10. DOI:10.1007/s002130050925. PMID 10227086.
↑ Gorelick DA, Gardner EL, Xi ZX (2004). „Agents in development for the management of cocaine abuse”. Drugs 64 (14): 1547–73. DOI:10.2165/00003495-200464140-00004. PMID 15233592.
↑ Rascol O, Nutt JG, Blin O, Goetz CG, Trugman JM, Soubrouillard C, Carter JH, Currie LJ, Fabre N, Thalamas C, Giardina WW, Wright S (February 2001). „Induction by dopamine D1 receptor agonist ABT-431 of dyskinesia similar to levodopa in patients with Parkinson disease”. Archives of Neurology 58 (2): 249–54. DOI:10.1001/archneur.58.2.249. PMID 11176963.
↑ Zhang J, Xiong B, Zhen X, Zhang A (March 2009). „Dopamine D1 receptor ligands: where are we now and where are we going”. Medicinal Research Reviews 29 (2): 272–94. DOI:10.1002/med.20130. PMID 18642350.
↑ Shiosaki K, Jenner P, Asin KE, Britton DR, Lin CW, Michaelides M, Smith L, Bianchi B, Didomenico S, Hodges L, Hong Y, Mahan L, Mikusa J, Miller T, Nikkel A, Stashko M, Witte D, Williams M (January 1996). „ABT-431: the diacetyl prodrug of A-86929, a potent and selective dopamine D1 receptor agonist: in vitro characterization and effects in animal models of Parkinson's disease”. The Journal of Pharmacology and Experimental Therapeutics 276 (1): 150–60. PMID 8558425.
↑ Giardina WJ, Williams M (2001). „Adrogolide HCl (ABT-431; DAS-431), a prodrug of the dopamine D1 receptor agonist, A-86929: preclinical pharmacology and clinical data”. CNS Drug Reviews 7 (3): 305–16. DOI:10.1111/j.1527-3458.2001.tb00201.x. PMID 11607045.

[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

[pmid7658429-5] Michaelides MR, Hong Y, DiDomenico S, Asin KE, Britton DR, Lin CW, Williams M, Shiosaki K (September 1995). „(5aR,11bS)-4,5,5a,6,7,11b-hexahydro-2-propyl-3-thia-5-azacyclopent-1- ena[c]-phenanthrene-9,10-diol (A-86929): a potent and selective dopamine D1 agonist that maintains behavioral efficacy following repeated administration and characterization of its diacetyl prodrug (ABT-431)”. Journal of Medicinal Chemistry 38 (18): 3445–7. DOI:10.1021/jm00018a002. PMID 7658429.

[pmid11671640-6] Ehrlich PP, Ralston JW, Michaelides MR (May 1997). „An Efficient Enantioselective Synthesis of the D1 Agonist (5aR,11bS)-4,5,5a,6,7,11b-Hexahydro-2-propyl-3-thia- 5-azacyclopenta[c]phenanthrene-9,10-diol (A-86929)”. The Journal of Organic Chemistry 62 (9): 2782–2785. DOI:10.1021/jo970066l. PMID 11671640.

[pmid10360765-7] Rascol O, Blin O, Thalamas C, Descombes S, Soubrouillard C, Azulay P, Fabre N, Viallet F, Lafnitzegger K, Wright S, Carter JH, Nutt JG (June 1999). „ABT-431, a D1 receptor agonist prodrug, has efficacy in Parkinson's disease”. Annals of Neurology 45 (6): 736–41. DOI:10.1002/1531-8249(199906)45:6<736::AID-ANA7>3.0.CO;2-F. PMID 10360765.

[pmid10227086-8] Haney M, Collins ED, Ward AS, Foltin RW, Fischman MW (March 1999). „Effect of a selective dopamine D1 agonist (ABT-431) on smoked cocaine self-administration in humans”. Psychopharmacology 143 (1): 102–10. DOI:10.1007/s002130050925. PMID 10227086.

[pmid15233592-9] Gorelick DA, Gardner EL, Xi ZX (2004). „Agents in development for the management of cocaine abuse”. Drugs 64 (14): 1547–73. DOI:10.2165/00003495-200464140-00004. PMID 15233592.

[pmid11176963-10] Rascol O, Nutt JG, Blin O, Goetz CG, Trugman JM, Soubrouillard C, Carter JH, Currie LJ, Fabre N, Thalamas C, Giardina WW, Wright S (February 2001). „Induction by dopamine D1 receptor agonist ABT-431 of dyskinesia similar to levodopa in patients with Parkinson disease”. Archives of Neurology 58 (2): 249–54. DOI:10.1001/archneur.58.2.249. PMID 11176963.

[pmid18642350-11] Zhang J, Xiong B, Zhen X, Zhang A (March 2009). „Dopamine D1 receptor ligands: where are we now and where are we going”. Medicinal Research Reviews 29 (2): 272–94. DOI:10.1002/med.20130. PMID 18642350.

[pmid8558425-12] Shiosaki K, Jenner P, Asin KE, Britton DR, Lin CW, Michaelides M, Smith L, Bianchi B, Didomenico S, Hodges L, Hong Y, Mahan L, Mikusa J, Miller T, Nikkel A, Stashko M, Witte D, Williams M (January 1996). „ABT-431: the diacetyl prodrug of A-86929, a potent and selective dopamine D1 receptor agonist: in vitro characterization and effects in animal models of Parkinson's disease”. The Journal of Pharmacology and Experimental Therapeutics 276 (1): 150–60. PMID 8558425.

[pmid11607045-13] Giardina WJ, Williams M (2001). „Adrogolide HCl (ABT-431; DAS-431), a prodrug of the dopamine D1 receptor agonist, A-86929: preclinical pharmacology and clinical data”. CNS Drug Reviews 7 (3): 305–16. DOI:10.1111/j.1527-3458.2001.tb00201.x. PMID 11607045.

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A-86929

Reference[uredi | uredi kod]

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