(-)-GSK598809 free base | CAS#863680-45-9 | D3R Antagonist

MedKoo Cat#: 525229 | Name: (-)-GSK598809 free base

Description:

WARNING: This product is for research use only, not for human or veterinary use.

(-)-GSK598809, also known as (1S,5R)-GSK598809, is a selective D(3)R antagonist recently progressed in Phase I trials. GSK-598809 may decrease the rewarding effects of contextual cues associated with drug intake preclinically, which may reduce drug craving in humans.

Chemical Structure

(-)-GSK598809 free base

CAS#863680-46-0 (free base)

Theoretical Analysis

MedKoo Cat#: 525229

Name: (-)-GSK598809 free base

CAS#: 863680-46-0 (free base)

Chemical Formula: C23H25F4N5OS

Exact Mass: 495.1716

Molecular Weight: 495.54

Elemental Analysis: C, 55.75; H, 5.09; F, 15.34; N, 14.13; O, 3.23; S, 6.47

Price and Availability

Size	Price	Availability
5mg	USD 1,650.00	2 Weeks
10mg	USD 2,950.00	2 Weeks
100mg	USD 4,950.00	2 Weeks

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Related CAS #

863680-46-0 (free base) 863680-45-9 (free base) 863766-31-8 (HCl) 1310803-30-5 (free base) 1008521-08-1 (tartrate) 1008521-09-2 (tartrate hydrate)

Synonym

(1S,5R)-GSK598809; (-)-GSK-598809; GSK598809; GSK 598809; GSK-598809;

IUPAC/Chemical Name

5-(5-((3-((1S,5R)-1-(2-fluoro-4-(trifluoromethyl)phenyl)-3-azabicyclo[3.1.0]hexan-3-yl)propyl)thio)-4-methyl-4H-1,2,4-triazol-3-yl)-4-methyloxazole

InChi Key

ZKRWPAYTJMRKLJ-BTYIYWSLSA-N

InChi Code

InChI=1S/C22H23F4N5OS/c1-13-18(32-12-27-13)19-28-29-20(30(19)2)33-7-3-6-31-10-15-9-21(15,11-31)16-5-4-14(8-17(16)23)22(24,25)26/h4-5,8,12,15H,3,6-7,9-11H2,1-2H3/t15-,21-/m0/s1

SMILES Code

CC1=C(C2=NN=C(SCCCN3C[C@@]4(C5=CC=C(C(F)(F)F)C=C5F)C[C@@]4([H])C3)N2C)OC=N1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 495.54 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

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PMID: 28701746; PMCID: PMC5520792. 3: Murphy A, Nestor LJ, McGonigle J, Paterson L, Boyapati V, Ersche KD, Flechais R, Kuchibatla S, Metastasio A, Orban C, Passetti F, Reed L, Smith D, Suckling J, Taylor E, Robbins TW, Lingford-Hughes A, Nutt DJ, Deakin JF, Elliott R; ICCAM Platform. Acute D3 Antagonist GSK598809 Selectively Enhances Neural Response During Monetary Reward Anticipation in Drug and Alcohol Dependence. Neuropsychopharmacology. 2017 Jun;42(7):1559. doi: 10.1038/npp.2017.47. Erratum for: Neuropsychopharmacology. 2017 Apr;42(5):1049-1057. PMID: 28496172; PMCID: PMC5436126. 4: Murphy A, Nestor LJ, McGonigle J, Paterson L, Boyapati V, Ersche KD, Flechais R, Kuchibatla S, Metastasio A, Orban C, Passetti F, Reed L, Smith D, Suckling J, Taylor E, Robbins TW, Lingford-Hughes A, Nutt DJ, Deakin JF, Elliott R. Acute D3 Antagonist GSK598809 Selectively Enhances Neural Response During Monetary Reward Anticipation in Drug and Alcohol Dependence. Neuropsychopharmacology. 2017 Apr;42(5):1049-1057. doi: 10.1038/npp.2016.289. Epub 2017 Jan 2. Erratum in: Neuropsychopharmacology. 2017 Jun;42(7):1559. Erratum in: Neuropsychopharmacology. 2017 Aug;42(9):1925-1926. PMID: 28042871; PMCID: PMC5423526. 5: Sokoloff P, Le Foll B. The dopamine D3 receptor, a quarter century later. Eur J Neurosci. 2017 Jan;45(1):2-19. doi: 10.1111/ejn.13390. Epub 2016 Oct 3. PMID: 27600596. 6: Paterson LM, Flechais RS, Murphy A, Reed LJ, Abbott S, Boyapati V, Elliott R, Erritzoe D, Ersche KD, Faluyi Y, Faravelli L, Fernandez-Egea E, Kalk NJ, Kuchibatla SS, McGonigle J, Metastasio A, Mick I, Nestor L, Orban C, Passetti F, Rabiner EA, Smith DG, Suckling J, Tait R, Taylor EM, Waldman AD, Robbins TW, Deakin JF, Nutt DJ, Lingford-Hughes AR; ICCAM Platform. The Imperial College Cambridge Manchester (ICCAM) platform study: An experimental medicine platform for evaluating new drugs for relapse prevention in addiction. Part A: Study description. J Psychopharmacol. 2015 Sep;29(9):943-60. doi: 10.1177/0269881115596155. Epub 2015 Aug 5. PMID: 26246443. 7: Appel NM, Li SH, Holmes TH, Acri JB. Dopamine D3 Receptor Antagonist (GSK598809) Potentiates the Hypertensive Effects of Cocaine in Conscious, Freely-Moving Dogs. J Pharmacol Exp Ther. 2015 Sep;354(3):484-92. doi: 10.1124/jpet.115.224121. Epub 2015 Jul 15. PMID: 26177654; PMCID: PMC4538869. 8: Elrashidi MY, Ebbert JO. Emerging drugs for the treatment of tobacco dependence: 2014 update. Expert Opin Emerg Drugs. 2014 Jun;19(2):243-60. doi: 10.1517/14728214.2014.899580. Epub 2014 Mar 22. PMID: 24654737. 9: Erritzoe D, Tziortzi A, Bargiela D, Colasanti A, Searle GE, Gunn RN, Beaver JD, Waldman A, Nutt DJ, Bani M, Merlo-Pich E, Rabiner EA, Lingford-Hughes A. In vivo imaging of cerebral dopamine D3 receptors in alcoholism. Neuropsychopharmacology. 2014 Jun;39(7):1703-12. doi: 10.1038/npp.2014.18. Epub 2014 Jan 28. PMID: 24469594; PMCID: PMC4023144. 10: Searle GE, Beaver JD, Tziortzi A, Comley RA, Bani M, Ghibellini G, Merlo- Pich E, Rabiner EA, Laruelle M, Gunn RN. Mathematical modelling of [¹¹C]-(+)-PHNO human competition studies. Neuroimage. 2013 Mar;68:119-32. doi: 10.1016/j.neuroimage.2012.11.033. Epub 2012 Nov 30. PMID: 23207573. 11: Mugnaini M, Iavarone L, Cavallini P, Griffante C, Oliosi B, Savoia C, Beaver J, Rabiner EA, Micheli F, Heidbreder C, Andorn A, Merlo Pich E, Bani M. Occupancy of brain dopamine D3 receptors and drug craving: a translational approach. Neuropsychopharmacology. 2013 Jan;38(2):302-12. doi: 10.1038/npp.2012.171. Epub 2012 Sep 12. PMID: 22968817; PMCID: PMC3527111. 12: Newman AH, Blaylock BL, Nader MA, Bergman J, Sibley DR, Skolnick P. Medication discovery for addiction: translating the dopamine D3 receptor hypothesis. Biochem Pharmacol. 2012 Oct 1;84(7):882-90. doi: 10.1016/j.bcp.2012.06.023. Epub 2012 Jul 3. PMID: 22781742; PMCID: PMC3836213. 13: Mogg K, Bradley BP, O'Neill B, Bani M, Merlo-Pich E, Koch A, Bullmore ET, Nathan PJ. Effect of dopamine D₃ receptor antagonism on approach responses to food cues in overweight and obese individuals. Behav Pharmacol. 2012 Sep;23(5-6):603-8. doi: 10.1097/FBP.0b013e3283566a4a. PMID: 22772335. 14: Dodds CM, O'Neill B, Beaver J, Makwana A, Bani M, Merlo-Pich E, Fletcher PC, Koch A, Bullmore ET, Nathan PJ. Effect of the dopamine D3 receptor antagonist GSK598809 on brain responses to rewarding food images in overweight and obese binge eaters. Appetite. 2012 Aug;59(1):27-33. doi: 10.1016/j.appet.2012.03.007. Epub 2012 Mar 21. PMID: 22445776. 15: te Beek ET, Zoethout RW, Bani MS, Andorn A, Iavarone L, Klaassen ES, Fina P, van Gerven JM. Pharmacokinetics and central nervous system effects of the novel dopamine D3 receptor antagonist GSK598809 and intravenous alcohol infusion at pseudo-steady state. J Psychopharmacol. 2012 Feb;26(2):303-14. doi: 10.1177/0269881111431750. Epub 2012 Jan 4. PMID: 22219221. 16: Nathan PJ, O'Neill BV, Mogg K, Bradley BP, Beaver J, Bani M, Merlo-Pich E, Fletcher PC, Swirski B, Koch A, Dodds CM, Bullmore ET. The effects of the dopamine D₃ receptor antagonist GSK598809 on attentional bias to palatable food cues in overweight and obese subjects. Int J Neuropsychopharmacol. 2012 Mar;15(2):149-61. doi: 10.1017/S1461145711001052. Epub 2011 Jul 12. PMID: 21745436. 17: Searle G, Beaver JD, Comley RA, Bani M, Tziortzi A, Slifstein M, Mugnaini M, Griffante C, Wilson AA, Merlo-Pich E, Houle S, Gunn R, Rabiner EA, Laruelle M. Imaging dopamine D3 receptors in the human brain with positron emission tomography, [11C]PHNO, and a selective D3 receptor antagonist. Biol Psychiatry. 2010 Aug 15;68(4):392-9. doi: 10.1016/j.biopsych.2010.04.038. PMID: 20599188.