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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(F)C=C(F)C=C3C2

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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
2,588

Originator

Roche
93

Approval Year

Unknown
149,124

Targets

Primary TargetPharmacologyConditionPotency
Dopamine beta-hydroxylase
17
Inhibitor
8,504
 9.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Post-traumatic stress disorder
22
 Primary
Phase II
1,147
Unknown
Cocaine use disorder
5
 Primary
Phase II
1,147
Unknown

Doses

PubMed

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
Record UNII
VJ9868NW5X
Record Status Validated (UNII)
Record Version
NIH
NCATS
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