Sonepiprazole information

Sonepiprazole
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	In general: uncontrolled;
Identifiers
	IUPAC name 4-(4-{2-[(1S)-3,4-dihydro-1H-isochromen-1-yl]ethyl}piperazin-1-yl)benzenesulfonamide;
CAS Number	170858-33-0 ; as salt: 170858-34-1 ;
PubChem CID	133079;
IUPHAR/BPS	980;
ChemSpider	117441;
UNII	O609V24217; as salt: 980MD32QLW ;
CompTox Dashboard (EPA)	DTXSID801317650 ;
Chemical and physical data
Formula	C21H27N3O3S
Molar mass	401.53 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=S(=O)(N)c1ccc(cc1)N2CCN(CC2)CC[C@@H]4OCCc3ccccc34;

Sonepiprazole (U-101,387, PNU-101,387-G) is a drug of the phenylpiperazine class which acts as a highly selective D₄ receptor antagonist.^[1] In animals, unlike D₂ receptor antagonists like haloperidol, sonepiprazole does not block the behavioral effects of amphetamine or apomorphine, does not alter spontaneous locomotor activity on its own, and lacks extrapyramidal and neuroendocrine effects.^[2] However, it does reverse the prepulse inhibition deficits induced by apomorphine,^[3] and has also been shown to enhance cortical activity and inhibit stress-induced cognitive impairment.^[4]^[5] As a result, it was investigated as an antipsychotic for the treatment of schizophrenia in a placebo-controlled clinical trial, but in contrast to its comparator olanzapine no benefits were found and it was not researched further for this indication.^[6]^[7]

^ TenBrink RE, Bergh CL, Duncan JN, et al. (June 1996). "(S)-(−)-4-[4-[2-(isochroman-1-yl)ethyl]-piperazin-1-yl] benzenesulfonamide, a selective dopamine D4 antagonist". Journal of Medicinal Chemistry. 39 (13): 2435–7. doi:10.1021/jm960084f. PMID 8691438.
^ Merchant KM, Gill GS, Harris DW, et al. (December 1996). "Pharmacological characterization of U-101387, a dopamine D4 receptor selective antagonist". The Journal of Pharmacology and Experimental Therapeutics. 279 (3): 1392–403. PMID 8968364.
^ Mansbach RS, Brooks EW, Sanner MA, Zorn SH (January 1998). "Selective dopamine D4 receptor antagonists reverse apomorphine-induced blockade of prepulse inhibition". Psychopharmacology. 135 (2): 194–200. doi:10.1007/s002130050501. PMID 9497025. S2CID 9246828.
^ Rubinstein M, Cepeda C, Hurst RS, et al. (June 2001). "Dopamine D4 receptor-deficient mice display cortical hyperexcitability". Journal of Neuroscience. 21 (11): 3756–63. doi:10.1523/JNEUROSCI.21-11-03756.2001. hdl:11336/79333. PMC 6762699. PMID 11356863.
^ Arnsten AF, Murphy B, Merchant K (October 2000). "The selective dopamine D4 receptor antagonist, PNU-101387G, prevents stress-induced cognitive deficits in monkeys". Neuropsychopharmacology. 23 (4): 405–10. doi:10.1016/S0893-133X(00)00133-0. PMID 10989267.
^ Unangst PC, Capiris T, Connor DT, et al. (August 1997). "Chromeno[3,4-c]pyridin-5-ones: selective human dopamine D4 receptor antagonists as potential antipsychotic agents". Journal of Medicinal Chemistry. 40 (17): 2688–93. doi:10.1021/jm970170v. PMID 9276014.
^ Corrigan MH, Gallen CC, Bonura ML, Merchant KM (March 2004). "Effectiveness of the selective D4 antagonist sonepiprazole in schizophrenia: a placebo-controlled trial". Biological Psychiatry. 55 (5): 445–51. doi:10.1016/j.biopsych.2003.10.004. PMID 15023570. S2CID 108634.

[pmid8691438-1] TenBrink RE, Bergh CL, Duncan JN, et al. (June 1996). "(S)-(−)-4-[4-[2-(isochroman-1-yl)ethyl]-piperazin-1-yl] benzenesulfonamide, a selective dopamine D4 antagonist". Journal of Medicinal Chemistry. 39 (13): 2435–7. doi:10.1021/jm960084f. PMID 8691438.

[pmid8968364-2] Merchant KM, Gill GS, Harris DW, et al. (December 1996). "Pharmacological characterization of U-101387, a dopamine D4 receptor selective antagonist". The Journal of Pharmacology and Experimental Therapeutics. 279 (3): 1392–403. PMID 8968364.

[pmid9497025-3] Mansbach RS, Brooks EW, Sanner MA, Zorn SH (January 1998). "Selective dopamine D4 receptor antagonists reverse apomorphine-induced blockade of prepulse inhibition". Psychopharmacology. 135 (2): 194–200. doi:10.1007/s002130050501. PMID 9497025. S2CID 9246828.

[pmid11356863-4] Rubinstein M, Cepeda C, Hurst RS, et al. (June 2001). "Dopamine D4 receptor-deficient mice display cortical hyperexcitability". Journal of Neuroscience. 21 (11): 3756–63. doi:10.1523/JNEUROSCI.21-11-03756.2001. hdl:11336/79333. PMC 6762699. PMID 11356863.

[pmid10989267-5] Arnsten AF, Murphy B, Merchant K (October 2000). "The selective dopamine D4 receptor antagonist, PNU-101387G, prevents stress-induced cognitive deficits in monkeys". Neuropsychopharmacology. 23 (4): 405–10. doi:10.1016/S0893-133X(00)00133-0. PMID 10989267.

[pmid9276014-6] Unangst PC, Capiris T, Connor DT, et al. (August 1997). "Chromeno[3,4-c]pyridin-5-ones: selective human dopamine D4 receptor antagonists as potential antipsychotic agents". Journal of Medicinal Chemistry. 40 (17): 2688–93. doi:10.1021/jm970170v. PMID 9276014.

[pmid15023570-7] Corrigan MH, Gallen CC, Bonura ML, Merchant KM (March 2004). "Effectiveness of the selective D4 antagonist sonepiprazole in schizophrenia: a placebo-controlled trial". Biological Psychiatry. 55 (5): 445–51. doi:10.1016/j.biopsych.2003.10.004. PMID 15023570. S2CID 108634.

Sonepiprazole information

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Clinical data

Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name 4-(4-{2-[(1S)-3,4-dihydro-1H-isochromen-1-yl]ethyl}piperazin-1-yl)benzenesulfonamide
CAS Number	170858-33-0^Y as salt: 170858-34-1^Y
PubChem CID	133079
IUPHAR/BPS	980
ChemSpider	117441
UNII	O609V24217 as salt: 980MD32QLW^Y
CompTox Dashboard (EPA)	DTXSID801317650
Chemical and physical data
Formula	C₂₁H₂₇N₃O₃S
Molar mass	401.53 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=S(=O)(N)c1ccc(cc1)N2CCN(CC2)CC[C@@H]4OCCc3ccccc34