Nepicastat References

Nepicastat
Names
	Preferred IUPAC name 5-(Aminomethyl)-1-[(2S)-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl]-1,3-dihydro-2H-imidazole-2-thione
	Other names SYN-117
Identifiers
CAS Number	173997-05-2 ;
3D model ( JSmol)	Interactive image;
ChEBI	CHEBI:139334;
ChemSpider	7971947 ;
IUPHAR/BPS	6630;
MeSH	Nepicastat
PubChem CID	9796181;
UNII	VPG12K4540 ;
CompTox Dashboard ( EPA)	DTXSID80169740 ;
	InChI InChI=1S/C14H15F2N3S/c15-9-3-8-4-10(1-2-12(8)13(16)5-9)19-11(6-17)7-18-14(19)20/h3,5,7,10H,1-2,4,6,17H2,(H,18,20)/t10-/m0/s1 Key: YZZVIKDAOTXDEB-JTQLQIEISA-N ; InChI=1/C14H15F2N3S/c15-9-3-8-4-10(1-2-12(8)13(16)5-9)19-11(6-17)7-18-14(19)20/h3,5,7,10H,1-2,4,6,17H2,(H,18,20)/t10-/m0/s1 Key: YZZVIKDAOTXDEB-JTQLQIEIBJ;
	SMILES Fc1cc3c(c(F)c1)CC[C@H](N2/C(=C\NC2=S)CN)C3;
Properties
Chemical formula	C14H15F2N3S
Molar mass	295.35 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify ( what is ?) Infobox references

Nepicastat ( INN, codenamed SYN117, RS-25560-197) is an inhibitor of dopamine beta-hydroxylase, an enzyme that catalyzes the conversion of dopamine to norepinephrine.^[1]

It has been studied as a possible treatment for congestive heart failure, and appears to be well tolerated as such.^[2] As of 2012, clinical trials to assess nepicastat as a treatment for post-traumatic stress disorder (PTSD) and cocaine dependence have been completed.^[3]^[4] In Phase 2 study treatment with nepicastat was not effective in relieving PTSD-associated symptoms when compared to placebo. The study was funded by the U.S. Department of Defense.^[5]

References

^ Stanley WC, Li B, Bonhaus DW, et al. (August 1997). "Catecholamine modulatory effects of nepicastat (RS-25560-197), a novel, potent and selective inhibitor of dopamine-beta-hydroxylase". Br J Pharmacol. 121 (8): 1803–9. doi: 10.1038/sj.bjp.0701315. PMC 1564872. PMID 9283721.
^ Hegde SS, Friday KF (December 1998). "Dopamine-beta-hydroxylase inhibition: a novel sympatho-modulatory approach for the treatment of congestive heart failure". Current Pharmaceutical Design. 4 (6): 469–79. PMID 10197057.
^ "Pharmacogenetic Clinical Trial of Nepicastat for Post Traumatic Stress Disorder (PTSD)". ClinicalTrials.gov. U.S. National Institutes of Health. June 4, 2008. Retrieved on February 1, 2012.
^ "Study of Safety and Potential Efficacy of SYN117 in Cocaine Dependent Volunteers". ClinicalTrials.gov. U.S. National Institutes of Health. August 15, 2008. Retrieved on February 1, 2012.
^ Biotie reports top-line data from clinical study with nepicastat (SYN117) in post-traumatic stress disorder BIOTIE THERAPIES CORP. STOCK EXCHANGE RELEASE 27 December 2012.

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[1] Stanley WC, Li B, Bonhaus DW, et al. (August 1997). "Catecholamine modulatory effects of nepicastat (RS-25560-197), a novel, potent and selective inhibitor of dopamine-beta-hydroxylase". Br J Pharmacol. 121 (8): 1803–9. doi: 10.1038/sj.bjp.0701315. PMC 1564872. PMID 9283721.

[2] Hegde SS, Friday KF (December 1998). "Dopamine-beta-hydroxylase inhibition: a novel sympatho-modulatory approach for the treatment of congestive heart failure". Current Pharmaceutical Design. 4 (6): 469–79. PMID 10197057.

[3] "Pharmacogenetic Clinical Trial of Nepicastat for Post Traumatic Stress Disorder (PTSD)". ClinicalTrials.gov. U.S. National Institutes of Health. June 4, 2008. Retrieved on February 1, 2012.

[4] "Study of Safety and Potential Efficacy of SYN117 in Cocaine Dependent Volunteers". ClinicalTrials.gov. U.S. National Institutes of Health. August 15, 2008. Retrieved on February 1, 2012.

[5] Biotie reports top-line data from clinical study with nepicastat (SYN117) in post-traumatic stress disorder BIOTIE THERAPIES CORP. STOCK EXCHANGE RELEASE 27 December 2012.

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