A-86929

Last updated

A-86929
A-86929.svg
Names
Preferred IUPAC name
(5aR,11bS)-2-Propyl-4,5,5a,6,7,11b-hexahydrobenzo[f]thieno[2,3-c]quinoline-9,10-diol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • 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 Yes check.svgY
    Key: REHAKLRYABHSQJ-KDOFPFPSSA-N Yes check.svgY
  • 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
    Key: REHAKLRYABHSQJ-KDOFPFPSBO
  • Oc1cc3c(cc1O)CCC4C3c2cc(CCC)sc2CN4
Properties
C18H21NO2S
Molar mass 315.429 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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A-86929 is a synthetic compound that acts as a selective dopamine receptor D1 agonist. [1] [2] It was developed as a possible treatment for Parkinson's disease, [3] as well as for other applications such as treatment of cocaine addiction, [4] [5] but while it had reasonable efficacy in humans it also caused dyskinesias and has not been continued. [6] [7] It has mainly been used as its diacetate ester prodrug adrogolide (ABT-431), which has better bioavailability. [8] [9]

Adrogolide Adrogolide.svg
Adrogolide

References

  1. ↑ 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.
  2. ↑ 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.
  3. ↑ 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. S2CID   26090362.
  4. ↑ 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. S2CID   24283309.
  5. ↑ 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. S2CID   5421657.
  6. ↑ 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.
  7. ↑ 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. S2CID   25334596.
  8. ↑ 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.
  9. ↑ 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. PMC   6741696 . PMID   11607045.


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