SB-277011 HCl | CAS#1226917-67-4 | D3 receptor antagonist

MedKoo Cat#: 526764 | Name: SB-277011 HCl

Description:

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

SB-277011, also known as SB-277011-A, is an orally active, potent and selective dopamine D(3) receptor antagonist with high oral bioavailability and CNS penetration in the rat. SB-277011 potentiated phMRI response to acute amphetamine challenge in the rat brain. SB-277011 attenuated ethanol consumption in ethanol preferring (P) and non-preferring (NP) rats.

Chemical Structure

SB-277011 HCl

CAS#1226917-67-4 (HCl)

Theoretical Analysis

MedKoo Cat#: 526764

Name: SB-277011 HCl

CAS#: 1226917-67-4 (HCl)

Chemical Formula: C28H32Cl2N4O

Exact Mass: 0.0000

Molecular Weight: 511.49

Elemental Analysis: C, 65.75; H, 6.31; Cl, 13.86; N, 10.95; O, 3.13

Price and Availability

Size	Price	Availability
25mg	USD 450.00	2 Weeks
50mg	USD 750.00	2 Weeks
100mg	USD 1,350.00	2 Weeks
200mg	USD 2,350.00	2 Weeks

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Related CAS #

215803-78-4 (free base) 1226917-67-4 (HCl)

Synonym

SB-277011; SB 277011; SB277011; SB-277011A; SB277011A; SB 277011A; SB-277011A HCl; SB-277011A dihydrochloride

IUPAC/Chemical Name

N-((1r,4r)-4-(2-(6-cyano-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)cyclohexyl)quinoline-4-carboxamide dihydrochloride

InChi Key

HEZIOTGUXSPDAK-ONAIBGCWSA-N

InChi Code

InChI=1S/C28H30N4O.2ClH/c29-18-21-5-8-23-19-32(16-13-22(23)17-21)15-12-20-6-9-24(10-7-20)31-28(33)26-11-14-30-27-4-2-1-3-25(26)27;;/h1-5,8,11,14,17,20,24H,6-7,9-10,12-13,15-16,19H2,(H,31,33);2*1H/t20-,24-;;

SMILES Code

O=C(C1=CC=NC2=CC=CC=C12)N[C@H]3CC[C@H](CCN4CC5=C(C=C(C#N)C=C5)CC4)CC3.[H]Cl.[H]Cl

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

Related CAS# 215803-78-4 ( SB-277011 free base) 1226917-67-4 (SB-277011A hydrochlordie)

Product Data

Product Data

Instruction

View handling instruction

Biological target:

SB-277011 HCl is a selective dopamine D3 receptor antagonist (pKi values = 8.0, 6.0, 5.0 and <5.2 for D3, D2, 5-HT1D and 5-HT1B, respectively).

In vitro activity:

In this study, the D3 receptor antagonists tested, one of which being SB-277011, at concentrations >100 μM, did not significantly affect the viability of H460-MX20, S1M1-80, A549-MX10 or wild type ABCG2 overexpressing HEK293-R2 cells. However, at concentrations ranging from 0.01 to 10 μM, the D3 receptor antagonists, including SB-277011, significantly increased the efficacy of the anticancer drugs mitoxantrone and doxorubicin in ABCG2-overexpressing MDR cells. Reference: Cancer Lett. 2017 Jun 28;396:167-180. https://pubmed.ncbi.nlm.nih.gov/28323029/

In vivo activity:

This study found that SB-277011 consistently and persistently decreased binge-like alcohol consumption at 30 mg/kg. SB-277011 decreased binge-like consumption on days 3, 7, 9, and 11-13 at 15 mg/kg. Reference: Synapse. 2015 Jun;69(6):295-8. https://pubmed.ncbi.nlm.nih.gov/25764479/

	Solvent	mg/mL	mM
Solubility
	DMSO	25.6	50.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 511.49 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

Formulation protocol:

1. Hussein N, Amawi H, Karthikeyan C, Hall FS, Mittal R, Trivedi P, Ashby CR Jr, Tiwari AK. The dopamine D3 receptor antagonists PG01037, NGB2904, SB277011A, and U99194 reverse ABCG2 transporter-mediated drug resistance in cancer cell lines. Cancer Lett. 2017 Jun 28;396:167-180. doi: 10.1016/j.canlet.2017.03.015. Epub 2017 Mar 18. PMID: 28323029. 2. Ashby CR Jr, Rice OV, Heidbreder CA, Gardner EL. The selective dopamine D₃ receptor antagonist SB-277011A attenuates drug- or food-deprivation reactivation of expression of conditioned place preference for cocaine in male Sprague-Dawley rats. Synapse. 2015 Jun;69(6):336-44. doi: 10.1002/syn.21820. PMID: 25851636. 3. Rice OV, Schonhar CA, Gaál J, Gardner EL, Ashby CR Jr. The selective dopamine D₃ receptor antagonist SB-277011-A significantly decreases binge-like consumption of ethanol in C57BL/J6 mice. Synapse. 2015 Jun;69(6):295-8. doi: 10.1002/syn.21816. PMID: 25764479.

In vitro protocol:

In vivo protocol:

1. Ashby CR Jr, Rice OV, Heidbreder CA, Gardner EL. The selective dopamine D₃ receptor antagonist SB-277011A attenuates drug- or food-deprivation reactivation of expression of conditioned place preference for cocaine in male Sprague-Dawley rats. Synapse. 2015 Jun;69(6):336-44. doi: 10.1002/syn.21820. PMID: 25851636. 2. Rice OV, Schonhar CA, Gaál J, Gardner EL, Ashby CR Jr. The selective dopamine D₃ receptor antagonist SB-277011-A significantly decreases binge-like consumption of ethanol in C57BL/J6 mice. Synapse. 2015 Jun;69(6):295-8. doi: 10.1002/syn.21816. PMID: 25764479.

1: Franco-García A, Guerrero-Bautista R, Hidalgo JM, Gómez-Murcia V, Milanés MV, Núñez C. Dopamine D3 Receptor Modulates Akt/mTOR and ERK1/2 Pathways Differently during the Reinstatement of Cocaine-Seeking Behavior Induced by Psychological versus Physiological Stress. Int J Mol Sci. 2023 Jul 7;24(13):11214. doi: 10.3390/ijms241311214. PMID: 37446391; PMCID: PMC10342329. 2: Rodd ZA, Swartzwelder HS, Waeiss RA, Soloviov SO, Lahiri DK, Engleman EA, Truitt WA, Bell RL, Hauser SR. Negative and positive allosteric modulators of the α7 nicotinic acetylcholine receptor regulates the ability of adolescent binge alcohol exposure to enhance adult alcohol consumption. Front Behav Neurosci. 2023 Apr 4;16:954319. doi: 10.3389/fnbeh.2022.954319. PMID: 37082421; PMCID: PMC10113115. 3: Rivera-Mancilla E, Altamirano-Espinoza AH, Manrique-Maldonado G, Villanueva- Castillo B, Villalón CM. Streptozotocin-induced diabetes in rats modifies the role D2 , D3 and D4 dopamine receptors play in cardiac sympathetic inhibition. Basic Clin Pharmacol Toxicol. 2022 Oct;131(4):262-269. doi: 10.1111/bcpt.13774. Epub 2022 Jul 22. PMID: 35834260. 4: Guerrero-Bautista R, Franco-García A, Hidalgo JM, Fernández-Gómez FJ, Ribeiro Do Couto B, Milanés MV, Núñez C. Distinct Regulation of Dopamine D3 Receptor in the Basolateral Amygdala and Dentate Gyrus during the Reinstatement of Cocaine CPP Induced by Drug Priming and Social Stress. Int J Mol Sci. 2021 Mar 18;22(6):3100. doi: 10.3390/ijms22063100. PMID: 33803578; PMCID: PMC8002864. 5: Zingales V, Torrisi SA, Leggio GM, Bucolo C, Drago F, Salomone S. Pharmacological and Genetic Evidence of Dopamine Receptor 3-Mediated Vasoconstriction in Isolated Mouse Aorta. Biomolecules. 2021 Mar 11;11(3):418. doi: 10.3390/biom11030418. PMID: 33799860; PMCID: PMC8001456. 6: García-Pedraza JÁ, Morán A, Martín ML, Ollauri-Ibáñez C, Rodríguez-Barbero A, Villalón CM, García-Domingo M. Dopamine D4 receptor subtype activation reduces the rat cardiac parasympathetic discharge. Pflugers Arch. 2020 Dec;472(12):1693-1703. doi: 10.1007/s00424-020-02452-8. Epub 2020 Aug 21. PMID: 32820344. 7: Guerrero-Bautista R, Franco-García A, Hidalgo JM, Fernández-Gómez F, Milanés MV, Núñez C. Blockade of D3 receptor prevents changes in DAT and D3R expression in the mesolimbic dopaminergic circuit produced by social stress- and cocaine prime-induced reinstatement of cocaine-CPP. J Psychopharmacol. 2020 Nov;34(11):1300-1315. doi: 10.1177/0269881120936468. Epub 2020 Jul 10. PMID: 32648812. 8: Meier MA, Lemercier CE, Kulisch C, Kiss B, Lendvai B, Adham N, Gerevich Z. The novel antipsychotic cariprazine stabilizes gamma oscillations in rat hippocampal slices. Br J Pharmacol. 2020 Apr;177(7):1622-1634. doi: 10.1111/bph.14923. Epub 2020 Feb 19. PMID: 31722437; PMCID: PMC7060372. 9: Jordan CJ, Humburg BA, Thorndike EB, Shaik AB, Xi ZX, Baumann MH, Newman AH, Schindler CW. Newly Developed Dopamine D3 Receptor Antagonists, R-VK4-40 and R-VK4-116, Do Not Potentiate Cardiovascular Effects of Cocaine or Oxycodone in Rats. J Pharmacol Exp Ther. 2019 Dec;371(3):602-614. doi: 10.1124/jpet.119.259390. Epub 2019 Sep 27. PMID: 31562201; PMCID: PMC6863462. 10: Manrique-Maldonado G, Altamirano-Espinoza AH, Rivera-Mancilla E, Hernández- Abreu O, Villalón CM. Activation of Dopamine D3 Receptor Subtypes Inhibits the Neurogenic Systemic Vasodilation Induced by Stimulation of the Perivascular CGRPergic Discharge. ACS Chem Neurosci. 2019 Aug 21;10(8):3751-3757. doi: 10.1021/acschemneuro.9b00277. Epub 2019 Aug 5. PMID: 31343160. 11: Scuppa G, Tambalo S, Pfarr S, Sommer WH, Bifone A. Aberrant insular cortex connectivity in abstinent alcohol-dependent rats is reversed by dopamine D3 receptor blockade. Addict Biol. 2020 May;25(3):e12744. doi: 10.1111/adb.12744. Epub 2019 Mar 24. PMID: 30907042; PMCID: PMC7187338. 12: Guerrero-Bautista R, Do Couto BR, Hidalgo JM, Cárceles-Moreno FJ, Molina G, Laorden ML, Núñez C, Milanés MV. Modulation of stress- and cocaine prime-induced reinstatement of conditioned place preference after memory extinction through dopamine D3 receptor. Prog Neuropsychopharmacol Biol Psychiatry. 2019 Jun 8;92:308-320. doi: 10.1016/j.pnpbp.2019.01.017. Epub 2019 Jan 29. PMID: 30707990. 13: Delcourte S, Ashby CR Jr, Rovera R, Kiss B, Adham N, Farkas B, Haddjeri N. The novel atypical antipsychotic cariprazine demonstrates dopamine D2 receptor-dependent partial agonist actions on rat mesencephalic dopamine neuronal activity. CNS Neurosci Ther. 2018 Dec;24(12):1129-1139. doi: 10.1111/cns.12867. Epub 2018 May 4. PMID: 29729086; PMCID: PMC6282959. 14: Rice OV, Ashby CR Jr, Dixon C, Laurenzo W, Hayden J, Song R, Li J, Tiwari AK, Gardner EL. Selective dopamine D3 receptor antagonism significantly attenuates stress-induced immobility in a rat model of post- traumatic stress disorder. Synapse. 2018 Aug;72(8):e22035. doi: 10.1002/syn.22035. Epub 2018 Jun 7. PMID: 29704283; PMCID: PMC6574226. 15: Fukushima A, Fukui A, Takemura Y, Maeda Y, Ono H. The anti-influenza drug oseltamivir evokes hypothermia in mice through dopamine D2 receptor activation via central actions. J Pharmacol Sci. 2018 Jan;136(1):39-41. doi: 10.1016/j.jphs.2017.12.005. Epub 2017 Dec 15. PMID: 29292053. 16: Hussein N, Amawi H, Karthikeyan C, Hall FS, Mittal R, Trivedi P, Ashby CR Jr, Tiwari AK. The dopamine D3 receptor antagonists PG01037, NGB2904, SB277011A, and U99194 reverse ABCG2 transporter-mediated drug resistance in cancer cell lines. Cancer Lett. 2017 Jun 28;396:167-180. doi: 10.1016/j.canlet.2017.03.015. Epub 2017 Mar 18. PMID: 28323029. 17: McGinnis MM, Siciliano CA, Jones SR. Dopamine D3 autoreceptor inhibition enhances cocaine potency at the dopamine transporter. J Neurochem. 2016 Sep;138(6):821-9. doi: 10.1111/jnc.13732. Epub 2016 Aug 15. PMID: 27393374; PMCID: PMC5017912. 18: Newton CL, Wood MD, Strange PG. Examining the Effects of Sodium Ions on the Binding of Antagonists to Dopamine D2 and D3 Receptors. PLoS One. 2016 Jul 5;11(7):e0158808. doi: 10.1371/journal.pone.0158808. PMID: 27379794; PMCID: PMC4933336. 19: Zheng F, Robertson AP, Abongwa M, Yu EW, Martin RJ. The Ascaris suum nicotinic receptor, ACR-16, as a drug target: Four novel negative allosteric modulators from virtual screening. Int J Parasitol Drugs Drug Resist. 2016 Feb 10;6(1):60-73. doi: 10.1016/j.ijpddr.2016.02.001. PMID: 27054065; PMCID: PMC4805779. 20: Seo JH, Kuzhikandathil EV. Dopamine D3 Receptor Mediates Preadolescent Stress-Induced Adult Psychiatric Disorders. PLoS One. 2015 Nov 30;10(11):e0143908. doi: 10.1371/journal.pone.0143908. PMID: 26619275; PMCID: PMC4664486.