NEPICASTAT HYDROCHLORIDE ANHYDROUS

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C14H15F2N3S.ClH
Molecular Weight	331.812
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of NEPICASTAT HYDROCHLORIDE ANHYDROUS

Structure Search

SMILES

Cl.NCC1=CNC(=S)N1[C@H]2CCC3=C(F)C=C(F)C=C3C2

InChI

InChIKey=DIPDUAJWNBEVOY-PPHPATTJSA-N

InChI=1S/C14H15F2N3S.ClH/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);1H/t10-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C14H15F2N3S
Molecular Weight	295.351
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9283721
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25602710 https://www.ncbi.nlm.nih.gov/pubmed/24983834

Nepicastat (SYN-117) is a potent and selective inhibitor of dopamine-β-hydroxylase. This compound in Phase 2 of clinical trial for the treatment cocaine addiction and posttraumatic stress disorder.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine beta-hydroxylase 17 Target ID: CHEMBL3102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9283721	Inhibitor 8504		9.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Post-traumatic stress disorder 22 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24983834	Primary		Phase II 1147	Unknown Approved Use Unknown
Cocaine use disorder 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25602710	Primary		Phase II 1147	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
160 mg 1 times / day multiple, oral Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/25602710	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/25602710	Sources: https://pubmed.ncbi.nlm.nih.gov/25602710

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY100506	https://www.001chemical.com/chem/search?q=DY100506
001 Chemical	DY100685	https://www.001chemical.com/chem/search?q=DY100685
1PlusChem LLC	1P00AC5A	https://www.1pchem.com/search?query=1P00AC5A
AK Scientific	8992AA	https://aksci.com/item_detail.php?cat=8992AA
AK Scientific	X7610	https://aksci.com/item_detail.php?cat=X7610
AKOS	AKOS026745463	http://akoscompounds.de/catalogue/AKosSamplesiSSretrieval.php?GUID=4e4caa52-3dca-4da0-b75a-caeae59e1096&IDNUMBERS=AKOS026745463
Ambeed	A148106	http://www.ambeed.com/search/Search.html?keyword=A148106
Angene	AGN-PC-0WH8K0	http://www.angenechemical.com/productshow/AGN-PC-0WH8K0.html
ApexBio Technology	A4332	https://www.apexbt.com/catalogsearch/result/?q=A4332
AstaTech	C10002	http://astatechinc.com/CPSResult.php?CRNO=C10002
BOC Sciences	170151-24-3	http://www.bocsci.com/description.asp?cas=170151-24-3
Chem Scene	CS-3559	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-3559
ChemShuttle	135198	https://www.chemshuttle.com/catalogsearch/result/?q=135198
ChemShuttle	151761	https://www.chemshuttle.com/catalogsearch/result/?q=151761
Combi-Blocks	QM-3878	http://www.combi-blocks.com/cgi-bin/find.cgi?QM-3878
eMolecules	260986634	https://orderbb.emolecules.com/search/#?query=260986634
eMolecules	300526107	https://orderbb.emolecules.com/search/#?query=300526107
eMolecules	32278096	https://orderbb.emolecules.com/search/#?query=32278096
eMolecules	37153247	https://orderbb.emolecules.com/search/#?query=37153247
eMolecules	49572907	https://orderbb.emolecules.com/search/#?query=49572907
eNovation Chemicals	D320190	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D320190&searchbtn.x=0&searchbtn.y=0
eNovation Chemicals	D491513	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D491513&searchbtn.x=0&searchbtn.y=0
Excenen	EX-A2109	http://www.excenen.com/searchresultlist.php?id=EX-A2109
KeyOrganics	AS-58425	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-58425
Lab Network	LN00192664	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00192664
Lab Network	LN00198830	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00198830
Lab Seeker	SC-94536	http://www.labseeker.com/search.php?keywords=SC-94536&category=0
LabSeeker	SC-94536	http://www.labseeker.com/search.php?keywords=SC-94536&category=0
Matrix Scientific	93133	http://www.matrixscientific.com/093133.html
Matrix Scientific	97227	http://www.matrixscientific.com/097227.html
mcule	MCULE-2654373969	https://mcule.com/MCULE-2654373969/
mcule	MCULE-5863304023	https://mcule.com/MCULE-5863304023/
mcule	MCULE-7244408726	https://mcule.com/MCULE-7244408726/
mcule	MCULE-8955151413	https://mcule.com/MCULE-8955151413/
mcule	MCULE-9453034993	https://mcule.com/MCULE-9453034993/
MedChem Express	HY-13289A	https://www.medchemexpress.com/search.html?q=HY-13289A&ft=&fa=&fp=
Molcore	MC100506	http://www.molcore.com/CatMC100506.html
Molcore	MC100685	http://www.molcore.com/CatMC100685.html
Molnova	M12599	https://www.molnova.com/en/serch-list.html?keywords=M12599
Molnova	M12642	https://www.molnova.com/en/serch-list.html?keywords=M12642
MuseChem	I008277	https://www.musechem.com/product/I008277.html
MuseChem	R061136	https://www.musechem.com/product/R061136.html
Nanjing Raymon Biotech Co Ltd	R0013U	http://www.raymonbio.com/en/search.html?key=R0013U&type=code
Selleck Chemicals	S2695	http://www.selleckchem.com/search.html?searchDTO.searchParam=S2695
Selleck Chemicals	S4926	http://www.selleckchem.com/search.html?searchDTO.searchParam=S4926
ShangHai Biochempartner	BCP000705	http://www.biochempartner.com/search_BCP000705
ShangHai Biochempartner	BCP05303	http://www.biochempartner.com/search_BCP05303
ShangHai Biochempartner	BCP06517	http://www.biochempartner.com/search_BCP06517
TargetMol	T6356	https://www.targetmol.com/search?keyword=T6356
Tocris	5037	https://www.tocris.com/search.php?Type=QuickSearch&Value=5037
Toronto Research Chemicals	B682553	https://www.trc-canada.com/product-detail/?CatNum=B682553
Toronto Research Chemicals	N389855	https://www.trc-canada.com/product-detail/?CatNum=N389855
Wonderchem	WD05DDS	http://www.wonder-chem.com/search.html?text=WD05DDS

PubMed

Title	Date	PubMed
Disulfiram attenuates drug-primed reinstatement of cocaine seeking via inhibition of dopamine β-hydroxylase.	2010-11	20736996
Effects of disulfiram and dopamine beta-hydroxylase knockout on cocaine-induced seizures.	2008-06	18329701
Synthesis and biological evaluation of novel, peripherally selective chromanyl imidazolethione-based inhibitors of dopamine beta-hydroxylase.	2006-02-09	16451083
Catecholamine modulatory effects of nepicastat (RS-25560-197), a novel, potent and selective inhibitor of dopamine-beta-hydroxylase.	1997-08	9283721

Sample Use Guides

In Vivo Use Guide

Post Traumatic Stress Disorder: 120 mg/day Cocaine Dependence: Nepicastat 120 mg and 100 mg riboflavin (once per day) for 11 weeks

Route of Administration: Oral

In Vitro Use Guide

Nepicastat produced concentration-dependent inhibition of bovine and human dopamine-beta-hydroxylase activity. The calculated IC50s for nepicastat were 8.5+0.8 nM and 9.0+0.8 nM for the bovine and human enzyme, respectively.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:25:51 GMT 2025` Edited by `admin` on `Mon Mar 31 21:25:51 GMT 2025`
Record UNII	3WK068D17I
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

(S)-5-(AMINOMETHYL)-1-(5,7-DIFLUORO-1,2,3,4-TETRAHYDRO-2-NAPHTHALENYL)-1,3-DIHYDRO-2H-IMIDAZOLE-2-THIONE MONOHYDROCHLORIDE

Preferred Name

English

NEPICASTAT HYDROCHLORIDE ANHYDROUS

Common Name

English

2H-IMIDAZOLE-2-THIONE, 5-(AMINOMETHYL)-1-((2S)-5,7-DIFLUORO-1,2,3,4-TETRAHYDRO-2-NAPHTHALENYL)-1,3-DIHYDRO-, HYDROCHLORIDE (1:1)

Systematic Name

English

Code System Code Type Description

SMS_ID

300000055542