NCS-382

NCS-382
Names
IUPAC name
(2E)-(5-hydroxy-5,7,8,9-tetrahydro-6H-benzo[a][7]annulen-6-ylidene ethanoic acid
Identifiers
CAS Number
  • 131733-92-1 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 4730868 ☒N
MeSH NCS-382
PubChem CID
  • 5875451
UNII
  • 6QI4I5N23X checkY
InChI
  • InChI=1S/C13H14O3/c14-12(15)8-10-6-3-5-9-4-1-2-7-11(9)13(10)16/h1-2,4,7-8,13,16H,3,5-6H2,(H,14,15)/b10-8+ ☒N
    Key: UADPGHINQMWEAG-CSKARUKUSA-N ☒N
  • InChI=1/C13H14O3/c14-12(15)8-10-6-3-5-9-4-1-2-7-11(9)13(10)16/h1-2,4,7-8,13,16H,3,5-6H2,(H,14,15)/b10-8+
    Key: UADPGHINQMWEAG-CSKARUKUBJ
  • c1ccc2c(c1)CCC/C(=C\C(=O)O)/C2O
Properties
Chemical formula
 C13H14O3
Molar mass 218.248
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references
Chemical compound

NCS-382 is a moderately selective antagonist for the GHB receptor.[1][2] It blocks the effects of GHB in animals and has both anti-sedative and anticonvulsant effects.[3][4][5] It has been proposed as a treatment for GHB overdose in humans as well as the genetic metabolic disorder succinic semialdehyde dehydrogenase deficiency (SSADHD), but has never been developed for clinical use.[6]

References

  1. ^ Castelli MP, Pibiri F, Carboni G, Piras AP (2004). "A review of pharmacology of NCS-382, a putative antagonist of gamma-hydroxybutyric acid (GHB) receptor". CNS Drug Reviews. 10 (3): 243–260. doi:10.1111/j.1527-3458.2004.tb00025.x. PMC 6741708. PMID 15492774.
  2. ^ Ticku MK, Mehta AK (October 2008). "Characterization and pharmacology of the GHB receptor". Annals of the New York Academy of Sciences. 1139 (1): 374–385. Bibcode:2008NYASA1139..374T. doi:10.1196/annals.1432.048. PMID 18991884. S2CID 37091049.
  3. ^ Maitre M, Hechler V, Vayer P, Gobaille S, Cash CD, Schmitt M, Bourguignon JJ (Nov 1990). "A specific gamma-hydroxybutyrate receptor ligand possesses both antagonistic and anticonvulsant properties". Journal of Pharmacology and Experimental Therapeutics. 255 (2): 657–63. PMID 2173754.
  4. ^ Schmidt C, Gobaille S, Hechler V, Schmitt M, Bourguignon JJ, Maitre M (Oct 1991). "Anti-sedative and anti-cataleptic properties of NCS-382, a gamma-hydroxybutyrate receptor antagonist". European Journal of Pharmacology. 203 (3): 393–7. doi:10.1016/0014-2999(91)90896-X. PMID 1773824.
  5. ^ Colombo G, Agabio R, Bourguignon J, Fadda F, Lobina C, Maitre M, Reali R, Schmitt M, Gessa GL (Sep 1995). "Blockade of the discriminative stimulus effects of gamma-hydroxybutyric acid (GHB) by the GHB receptor antagonist NCS-382". Physiology & Behavior. 58 (3): 587–590. doi:10.1016/0031-9384(95)00086-X. PMID 8587968. S2CID 45842160.
  6. ^ Gupta M, Greven R, Jansen EE, Jakobs C, Hogema BM, Froestl W, Snead OC, Bartels H, Grompe M, Gibson KM (Jul 2002). "Therapeutic intervention in mice deficient for succinate semialdehyde dehydrogenase (gamma-hydroxybutyric aciduria)". Journal of Pharmacology and Experimental Therapeutics. 302 (1): 180–187. doi:10.1124/jpet.302.1.180. PMID 12065715. S2CID 24503217.
  • v
  • t
  • e
GHB receptor modulators
Receptor
(ligands)
GHBRTooltip GHB receptor
GABABTooltip γ-Aminobutyric acid B receptor
  • See here instead.
Transporter
(blockers)
MCTsTooltip Monocarboxylate transporters
SMCTsTooltip Sodium-coupled monocarboxylate transporters
VIATTTooltip Vesicular inhibitory amino acid transporter
Enzyme
(inhibitors)
SSRTooltip Succinic semialdehyde reductase
GHBDHTooltip 4-Hydroxybutyrate dehydrogenase
HOTTooltip Hydroxyacid-oxoacid transhydrogenase
ADHTooltip Alcohol dehydrogenase
ALDHTooltip Aldehyde dehydrogenase
See also
Receptor/signaling modulators
GABA receptor modulators
Glutamate receptor modulators
Glycine receptor modulators