Structure via PubChem · Public domain (PubChem)
nepicastat
Sign in to saveAlso known as RS-25560-197, SYN117
Nepicastat (; developmental code names SYN117, RS-25560-197) is an inhibitor of dopamine β-hydroxylase (DBH), an enzyme that catalyzes the conversion of dopamine to norepinephrine.
Chemical data
- Formula
- C14H15F2N3S
- Molecular weight
- 295.35 g/mol
- IUPAC name
- 4-(aminomethyl)-3-[(2S)-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl]-1H-imidazole-2-thione
- SMILES
- C1CC2=C(C[C@H]1N3C(=CNC3=S)CN)C=C(C=C2F)F
- InChIKey
- YZZVIKDAOTXDEB-JTQLQIEISA-N
- XLogP
- 1.4
- Polar surface area
- 73.4 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- post-traumatic stress disorder, cocaine dependence
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 295.095475
Show 5 more facts
- chemical formula
- C₁₄H₁₅F₂N₃S
- isomeric SMILES
- C1CC2=C(C=C(C=C2C[C@H]1N3C(=CNC3=S)CN)F)F
- canonical SMILES
- C1CC2=C(C=C(C=C2CC1N3C(=CNC3=S)CN)F)F
- physically interacts with
- dopamine beta-hydroxylase
- Commons category
- Nepicastat
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
Nepicastat (; developmental code names SYN117, RS-25560-197) is an inhibitor of dopamine β-hydroxylase (DBH), an enzyme that catalyzes the conversion of dopamine to norepinephrine.
It has been studied as a possible treatment for congestive heart failure, and appears to be well tolerated as such. As of 2012, clinical trials to assess nepicastat as a treatment for post-traumatic stress disorder (PTSD) and cocaine dependence have been completed. 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. As of October 2024, development has been discontinued for most indications.
Excerpted from Wikipedia’s “nepicastat” article, available under the CC BY-SA 4.0 licence.