CHEBI:139334 - nepicastat

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ChEBI Name nepicastat
ChEBI ID CHEBI:139334
Definition A member of the class of 1,3-dihydroimidazole-2-thiones that is 1,3-dihydro-2H-imidazole-2-thione in which one of the nitrogens is substituted by a 5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl group while the carbon adjacent to it is substituted by an aminomethyl group (the S enantiomer). It is a potent and selective inhibitor of both bovine and human dopamine β-hydroxylase, an enzyme that catalyzes the conversion of dopamine to norepinephrine.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Sabrina Toro
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Formula C14H15F2N3S
Net Charge 0
Average Mass 295.352
Monoisotopic Mass 295.095
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
InChIKey YZZVIKDAOTXDEB-JTQLQIEISA-N
SMILES N1C(N(C(=C1)CN)[C@@H]2CC3=C(C(=CC(=C3)F)F)CC2)=S
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): EC 1.14.17.1 (dopamine beta-monooxygenase) inhibitor
An EC 1.14.17.* (oxidoreductase acting on paired donors, with incorporation or reduction of molecular oxygen and with reduced ascorbate as one donor, and incorporation of one atom of oxygen) inhibitor that interferes with the action of dopamine monooxygenase (EC 1.14.17.1).
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ChEBI Ontology
Outgoing nepicastat (CHEBI:139334) has role EC 1.14.17.1 (dopamine β-monooxygenase) inhibitor (CHEBI:139339)
nepicastat (CHEBI:139334) is a 1,3-dihydroimidazole-2-thiones (CHEBI:139340)
nepicastat (CHEBI:139334) is a organofluorine compound (CHEBI:37143)
nepicastat (CHEBI:139334) is a primary amino compound (CHEBI:50994)
nepicastat (CHEBI:139334) is a tetralins (CHEBI:36786)
IUPAC Name
5-(aminomethyl)-1-[(2S)-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl]-1,3-dihydro-2H-imidazole-2-thione
INNs Sources
nepicastat WHO MedNet
nepicastat WHO MedNet
népicastat WHO MedNet
nepicastatum WHO MedNet
Synonyms Sources
(S)-5-aminomethyl-1-(5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl)-1,3-dihydroimidazole-2-thione ChEBI
RS-25560-197 ChEBI
SYN117 ChEBI
Manual Xrefs Databases
9796181 PubChem
DB12979 DrugBank
Nepicastat Wikipedia
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Registry Numbers Types Sources
173997-05-2 CAS Registry Number ChemIDplus
9425404 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11034950 PubMed citation Europe PMC
23289939 PubMed citation Europe PMC
23303068 PubMed citation Europe PMC
23561307 PubMed citation Europe PMC
25257286 PubMed citation Europe PMC
25602710 PubMed citation Europe PMC
9283721 PubMed citation Europe PMC
9641484 PubMed citation Europe PMC
Last Modified
20 December 2017