Sonepiprazole | CAS#170858-33-0 | D4 antagonist

MedKoo Cat#: 585322 | Name: Sonepiprazole

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Description:

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

Sonepiprazole is a a selective dopamine D4 antagonist with tested applications in schizophrenia treatment and symptom alleviation.

Chemical Structure

Sonepiprazole

CAS#170858-33-0

Theoretical Analysis

MedKoo Cat#: 585322

Name: Sonepiprazole

CAS#: 170858-33-0

Chemical Formula: C21H27N3O3S

Exact Mass: 401.1773

Molecular Weight: 401.53

Elemental Analysis: C, 62.82; H, 6.78; N, 10.47; O, 11.95; S, 7.98

Price and Availability

Size	Price	Availability
5mg	USD 400.00	2 Weeks
10mg	USD 650.00	2 Weeks
25mg	USD 950.00	2 Weeks

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Related CAS #

170857-36-0 (HCl) 170858-33-0 170858-34-1 (mesylate)

Synonym

Sonepiprazole; U-101387; U101387; U 101387

IUPAC/Chemical Name

4-[4-[2-[(1S)-3,4-dihydro-1H-isochromen-1-yl]ethyl]piperazin-1-yl]benzenesulfonamide

InChi Key

WNUQCGWXPNGORO-NRFANRHFSA-N

InChi Code

InChI=1S/C21H27N3O3S/c22-28(25,26)19-7-5-18(6-8-19)24-14-12-23(13-15-24)11-9-21-20-4-2-1-3-17(20)10-16-27-21/h1-8,21H,9-16H2,(H2,22,25,26)/t21-/m0/s1

SMILES Code

O=S(C1=CC=C(N2CCN(CC[C@H]3C4=C(C=CC=C4)CCO3)CC2)C=C1)(N)=O

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

>3 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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Sonepiprazole is a selective D4 dopamine antagonist with Kis of 3.6, 10.1, 5147, and 7430 nM for rD4-Dopamine, hD4.2-Dopamine, rD2-Dopamine, and Histamine-H1 receptors, respectively.

In vitro activity:

This study found that sonepiprazole was ineffective for the treatment of patients with schizophrenia. 467 hospitalized schizophrenia patients with scores of > or = 60 on the Positive and Negative Syndrome Scale (PANSS) were treated with sonepiprazole, olanzapine, or placebo once daily for 6 weeks. However, there were no statistically significant differences observed between placebo and any sonepiprazole dose. Reference: Biol Psychiatry. 2004 Mar 1;55(5):445-51. https://pubmed.ncbi.nlm.nih.gov/15023570/

In vivo activity:

To be determined

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	125.0	311.32

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 401.53 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. Corrigan MH, Gallen CC, Bonura ML, Merchant KM; Sonepiprazole Study Group. Effectiveness of the selective D4 antagonist sonepiprazole in schizophrenia: a placebo-controlled trial. Biol Psychiatry. 2004 Mar 1;55(5):445-51. doi: 10.1016/j.biopsych.2003.10.004. PMID: 15023570. 2. Arnsten AF, Murphy B, Merchant K. The selective dopamine D4 receptor antagonist, PNU-101387G, prevents stress-induced cognitive deficits in monkeys. Neuropsychopharmacology. 2000 Oct;23(4):405-10. doi: 10.1016/S0893-133X(00)00133-0. PMID: 10989267.

In vitro protocol:

In vivo protocol:

To be determined

1: TenBrink RE, Bergh CL, Duncan JN, Harris DW, Huff RM, Lahti RA, Lawson CF, Lutzke BS, Martin IJ, Rees SA, Schlachter SK, Sih JC, Smith MW. (S)-(-)-4-[4-[2-(isochroman-1-yl)ethyl]-piperazin-1-yl] benzenesulfonamide, a selective dopamine D4 antagonist. J Med Chem. 1996 Jun 21;39(13):2435-7. doi: 10.1021/jm960084f. PMID: 8691438. 2: Merchant KM, Gill GS, Harris DW, Huff RM, Eaton MJ, Lookingland K, Lutzke BS, Mccall RB, Piercey MF, Schreur PJ, Sethy VH, Smith MW, Svensson KA, Tang AH, Vonvoigtlander PF, Tenbrink RE. Pharmacological characterization of U-101387, a dopamine D4 receptor selective antagonist. J Pharmacol Exp Ther. 1996 Dec;279(3):1392-403. PMID: 8968364. 3: Unangst PC, Capiris T, Connor DT, Heffner TG, MacKenzie RG, Miller SR, Pugsley TA, Wise LD. Chromeno[3,4-c]pyridin-5-ones: selective human dopamine D4 receptor antagonists as potential antipsychotic agents. J Med Chem. 1997 Aug 15;40(17):2688-93. doi: 10.1021/jm970170v. PMID: 9276014. 4: Mansbach RS, Brooks EW, Sanner MA, Zorn SH. Selective dopamine D4 receptor antagonists reverse apomorphine-induced blockade of prepulse inhibition. Psychopharmacology (Berl). 1998 Jan;135(2):194-200. doi: 10.1007/s002130050501. PMID: 9497025. 5: Noda-Saita K, Matsumoto M, Hidaka K, Hatanaka K, Ohmori J, Okada M, Yamaguchi T. Dopamine D4-like binding sites labeled by [3H]nemonapride include substantial serotonin 5-HT2A receptors in primate cerebral cortex. Biochem Biophys Res Commun. 1999 Feb 16;255(2):367-70. doi: 10.1006/bbrc.1999.0220. PMID: 10049714. 6: Arnsten AF, Murphy B, Merchant K. The selective dopamine D4 receptor antagonist, PNU-101387G, prevents stress-induced cognitive deficits in monkeys. Neuropsychopharmacology. 2000 Oct;23(4):405-10. doi: 10.1016/S0893-133X(00)00133-0. PMID: 10989267. 7: Rubinstein M, Cepeda C, Hurst RS, Flores-Hernandez J, Ariano MA, Falzone TL, Kozell LB, Meshul CK, Bunzow JR, Low MJ, Levine MS, Grandy DK. Dopamine D4 receptor-deficient mice display cortical hyperexcitability. J Neurosci. 2001 Jun 1;21(11):3756-63. doi: 10.1523/JNEUROSCI.21-11-03756.2001. PMID: 11356863; PMCID: PMC6762699. 8: Corrigan MH, Gallen CC, Bonura ML, Merchant KM; Sonepiprazole Study Group. Effectiveness of the selective D4 antagonist sonepiprazole in schizophrenia: a placebo-controlled trial. Biol Psychiatry. 2004 Mar 1;55(5):445-51. doi: 10.1016/j.biopsych.2003.10.004. PMID: 15023570. 9: Hertel P, Didriksen M, Pouzet B, Brennum LT, Søby KK, Larsen AK, Christoffersen CT, Ramirez T, Marcus MM, Svensson TH, Di Matteo V, Esposito E, Bang-Andersen B, Arnt J. Lu 35-138 ((+)-(S)-3-{1-[2-(1-acetyl-2,3-dihydro-1H-ind ol-3-yl)ethyl]-3,6-dihydro-2H-pyridin-4-yl}-6-chloro-1H-indole), a dopamine D4 receptor antagonist and serotonin reuptake inhibitor: characterisation of its in vitro profile and pre-clinical antipsychotic potential. Eur J Pharmacol. 2007 Nov 14;573(1-3):148-60. doi: 10.1016/j.ejphar.2007.06.052. Epub 2007 Jul 4. PMID: 17689529. 10: Marona-Lewicka D, Nichols DE. WAY 100635 produces discriminative stimulus effects in rats mediated by dopamine D(4) receptor activation. Behav Pharmacol. 2009 Feb;20(1):114-8. doi: 10.1097/FBP.0b013e3283242f1a. PMID: 19179855. 11: Hawley M, Morozowich W. Modifying the diffusion layer of soluble salts of poorly soluble basic drugs to improve dissolution performance. Mol Pharm. 2010 Oct 4;7(5):1441-9. doi: 10.1021/mp100117k. Epub 2010 Jul 27. PMID: 20731341. 12: Richter H, Rohlmann R, García Mancheño O. Catalyzed selective direct α- and γ-alkylation of aldehydes with cyclic benzyl ethers by using T(+)BF4- in the presence of an inexpensive organic acid or anhydride. Chemistry. 2011 Oct 4;17(41):11622-7. doi: 10.1002/chem.201101786. Epub 2011 Aug 31. PMID: 21953932. 13: Raveendra B, Maity S, Das BG, Ghorai P. Organocatalytic, Enantioselective Synthesis of 1- and 3-Substituted Isochromans via Intramolecular Oxa-Michael Reaction of Alkoxyboronate: Synthesis of (+)-Sonepiprazole. J Org Chem. 2015 Jul 17;80(14):7008-18. doi: 10.1021/acs.joc.5b00719. Epub 2015 Jul 7. PMID: 26102523. 14: Britto-Júnior J, Ximenes L, Ribeiro A, Fregonesi A, Campos R, Ricardo de Almeida Kiguti L, Mónica FZ, Antunes E, De Nucci G. 6-Nitrodopamine is an endogenous mediator of rat isolated epididymal vas deferens contractions induced by electric-field stimulation. Eur J Pharmacol. 2021 Nov 15;911:174544. doi: 10.1016/j.ejphar.2021.174544. Epub 2021 Oct 1. PMID: 34606837.