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Details

Stereochemistry ABSOLUTE
Molecular Formula C14H15F2N3S.ClH.H2O
Molecular Weight 349.827
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NEPICASTAT HYDROCHLORIDE

SMILES

O.Cl.NCC1=CNC(=S)N1[C@H]2CCC3=C(C2)C=C(F)C=C3F

InChI

InChIKey=AILBEJJAAWNNIR-XRIOVQLTSA-N
InChI=1S/C14H15F2N3S.ClH.H2O/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;1H2/t10-;;/m0../s1

HIDE SMILES / InChI
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
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 H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

CNS Penetrant
2554
Curator's Comment: Nepicastat is direct, competitive inhibitor of DBH that does not chelate copper, can cross the blood–brain barrier

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 9.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
160 mg 1 times / day multiple, oral
Dose: 160 mg, 1 times / day
Route: oral
Route: multiple
Dose: 160 mg, 1 times / day
Co-administed with::
сocaine
Sources:
https://pubmed.ncbi.nlm.nih.gov/25602710
Page: p.8
unhealthy, ADULT
n = 13
Health Status: unhealthy
Condition: cocaine abuse
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 13
Sources:
https://pubmed.ncbi.nlm.nih.gov/25602710
Page: p.8
Sources:
https://pubmed.ncbi.nlm.nih.gov/25602710
Page: p.8
Sourcing

Sourcing

Vendor/AggregatorIDURL
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
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
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
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
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/
PubMed

PubMed

TitleDatePubMed
Disulfiram attenuates drug-primed reinstatement of cocaine seeking via inhibition of dopamine β-hydroxylase.
2010 Nov

Sample Use Guides

In Vivo Use Guide
Curator's Comment: https://clinicaltrials.gov/ct2/show/NCT01704196?term=NEPICASTAT&rank=3
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 Fri Dec 15 16:28:03 GMT 2023
Edited
by admin
on Fri Dec 15 16:28:03 GMT 2023
Record UNII
VJ9868NW5X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NEPICASTAT HYDROCHLORIDE
USAN  
USAN  
Official Name English
NEPICASTAT HYDROCHLORIDE MONOHYDRATE
Common Name English
2H-IMIDAZOLE-2-THIONE, 5-(AMINOMETHYL)-1-(5,7-DIFLUORO-1,2,3,4-TETRAHYDRO-2-NAPHTHALENYL)-1,3-DIHYDRO-, MONOHYDROCHLORIDE, MONOHYDRATE, (S)-
Common Name English
NEPICASTAT HYDROCHLORIDE [USAN]
Common Name English
(S)-5-(AMINOMETHYL)-1-(5,7-DIFLUORO-1,2,3,4-TETRAHYDRO-2-NAPHTHALENYL)-1,3-DIHYDRO-2H-IMIDAZOLE-2-THIONE MONOHYDROCHLORIDE, MONOHYDRATE
Systematic Name English
5-(Aminomethyl)-1-[(S)-5,7-difluoro-1,2,3,4-tetrahydro-2-naphthyl]-4-imidazoline-2-thione monohydrochloride, monohydrate
Systematic Name English
RS-25560-197
Code English
Classification Tree Code System Code
NCI_THESAURUS C471
Created by admin on Fri Dec 15 16:28:03 GMT 2023 , Edited by admin on Fri Dec 15 16:28:03 GMT 2023
Code System Code Type Description
MESH
C109487
Created by admin on Fri Dec 15 16:28:03 GMT 2023 , Edited by admin on Fri Dec 15 16:28:03 GMT 2023
PRIMARY
PUBCHEM
11954368
Created by admin on Fri Dec 15 16:28:03 GMT 2023 , Edited by admin on Fri Dec 15 16:28:03 GMT 2023
PRIMARY
ChEMBL
CHEMBL1188395
Created by admin on Fri Dec 15 16:28:03 GMT 2023 , Edited by admin on Fri Dec 15 16:28:03 GMT 2023
PRIMARY
EPA CompTox
DTXSID30938968
Created by admin on Fri Dec 15 16:28:03 GMT 2023 , Edited by admin on Fri Dec 15 16:28:03 GMT 2023
PRIMARY
CAS
177645-08-8
Created by admin on Fri Dec 15 16:28:03 GMT 2023 , Edited by admin on Fri Dec 15 16:28:03 GMT 2023
PRIMARY
FDA UNII
VJ9868NW5X
Created by admin on Fri Dec 15 16:28:03 GMT 2023 , Edited by admin on Fri Dec 15 16:28:03 GMT 2023
PRIMARY
NCI_THESAURUS
C84004
Created by admin on Fri Dec 15 16:28:03 GMT 2023 , Edited by admin on Fri Dec 15 16:28:03 GMT 2023
PRIMARY
CHEBI
139334
Created by admin on Fri Dec 15 16:28:03 GMT 2023 , Edited by admin on Fri Dec 15 16:28:03 GMT 2023
PRIMARY
USAN
II-85
Created by admin on Fri Dec 15 16:28:03 GMT 2023 , Edited by admin on Fri Dec 15 16:28:03 GMT 2023
PRIMARY
Related Record Type Details
Structure of NEPICASTAT HYDROCHLORIDE ANHYDROUS
ANHYDROUS->SOLVATE
Structure of NEPICASTAT HYDROCHLORIDE ANHYDROUS
ANHYDROUS->SOLVATE
Structure of NEPICASTAT
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of NEPICASTAT
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