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Golexanolone

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Chemical compound Pharmaceutical compound

Golexanolone
Clinical data

Other names	GR-3027; 3α-Ethynyl-3β-hydroxyandrostan-17E-one oxime
Identifiers
IUPAC name (3S,5S,8R,9S,10S,13S,14S,17E)-3-Ethynyl-17-hydroxyimino-10,13-dimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopentaphenanthren-3-ol
CAS Number	2089238-18-4
PubChem CID	132190533
ChemSpider	76826990
UNII	9C48F08TP2
Chemical and physical data
Formula	C₂₁H₃₁NO₂
Molar mass	329.484 g·mol
3D model (JSmol)	Interactive image
SMILES C12CC(C1CC32CC\4(3CC/C4=N\O)C)(C#C)O
InChI InChI=1S/C21H31NO2/c1-4-21(23)12-11-19(2)14(13-21)5-6-15-16-7-8-18(22-24)20(16,3)10-9-17(15)19/h1,14-17,23-24H,5-13H2,2-3H3/b22-18+/t14-,15-,16-,17-,19-,20-,21-/m0/s1 Key:FFIBGVYTWNPLPN-BZLGYYABSA-N

Golexanolone, also known by the developmental code name GR-3027, is a neurosteroid medication which is under development for the treatment of hypersomnia and hepatic encephalopathy. It acts as a negative allosteric modulator of the GABA_A receptor. The medication selectively antagonizes the stimulatory actions of inhibitory neurosteroids like allopregnanolone and tetrahydrodeoxycorticosterone (THDOC) at the GABA_A receptor, while not affecting the activation of the GABA_A receptor by γ-aminobutyric acid (GABA).

See also

List of neurosteroids § Excitatory

References

^ "Golexanolone - Umecrine Cognition". AdisInsight. Springer Nature Switzerland AG.
^ Agusti A, Llansola M, Hernández-Rabaza V, Cabrera-Pastor A, Montoliu C, Felipo V (June 2016). "Modulation of GABAA receptors by neurosteroids. A new concept to improve cognitive and motor alterations in hepatic encephalopathy". The Journal of Steroid Biochemistry and Molecular Biology. 160: 88–93. doi:10.1016/j.jsbmb.2015.08.020. PMID 26307490. S2CID 42040436.
Johansson M, Månsson M, Lins LE, Scharschmidt B, Doverskog M, Bäckström T (May 2018). "GR3027 reversal of neurosteroid-induced, GABA-A receptor-mediated inhibition of human brain function: an allopregnanolone challenge study". Psychopharmacology. 235 (5): 1533–1543. doi:10.1007/s00213-018-4864-1. PMC 5919995. PMID 29492615.
Johansson M, Agusti A, Llansola M, Montoliu C, Strömberg J, Malinina E, et al. (September 2015). "GR3027 antagonizes GABAA receptor-potentiating neurosteroids and restores spatial learning and motor coordination in rats with chronic hyperammonemia and hepatic encephalopathy". American Journal of Physiology. Gastrointestinal and Liver Physiology. 309 (5): G400-9. doi:10.1152/ajpgi.00073.2015. PMC 4556948. PMID 26138462.

External links

Golexanolone (GR-3027) - AdisInsight

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GABA receptor modulators

GABA_ATooltip γ-Aminobutyric acid A receptor

Positive modulators (abridged; see here for a full list): α-EMTBL
Alcohols (e.g., drinking alcohol, 2M2B)
Anabolic steroids
Avermectins (e.g., ivermectin)
Barbiturates (e.g., phenobarbital)
Benzodiazepines (e.g., diazepam)
Bromide compounds (e.g., potassium bromide)
Carbamates (e.g., meprobamate)
Carbamazepine
Chloralose
Chlormezanone
Clomethiazole
Dihydroergolines (e.g., ergoloid (dihydroergotoxine))
Etazepine
Etifoxine
Fenamates (e.g., mefenamic acid)
Flavonoids (e.g., apigenin, hispidulin)
Fluoxetine
Flupirtine
Imidazoles (e.g., etomidate)
Kava constituents (e.g., kavain)
Lanthanum
Loreclezole
Monastrol
Neuroactive steroids (e.g., allopregnanolone, cholesterol, THDOC)
Niacin
Niacinamide
Nonbenzodiazepines (e.g., β-carbolines (e.g., abecarnil), cyclopyrrolones (e.g., zopiclone), imidazopyridines (e.g., zolpidem), pyrazolopyrimidines (e.g., zaleplon))
Norfluoxetine
Petrichloral
Phenols (e.g., propofol)
Phenytoin
Piperidinediones (e.g., glutethimide)
Propanidid
Pyrazolopyridines (e.g., etazolate)
Quinazolinones (e.g., methaqualone)
Retigabine (ezogabine)
ROD-188
Skullcap constituents (e.g., baicalin)
Stiripentol
Sulfonylalkanes (e.g., sulfonmethane (sulfonal))
Topiramate
Valerian constituents (e.g., valerenic acid)
Volatiles/gases (e.g., chloral hydrate, chloroform, diethyl ether, paraldehyde, sevoflurane)

GABA_A-ρTooltip γ-Aminobutyric acid A-rho receptor

Negative modulators: 5α-Dihydroprogesterone
Bilobalide
Loreclezole
Picrotoxin (picrotin, picrotoxinin)
Pregnanolone
ROD-188
THDOC
Zinc

GABA_BTooltip γ-Aminobutyric acid B receptor

Negative modulators: Compound 14

See also: Receptor/signaling modulators; GABA_A receptor positive modulators; GABA metabolism/transport modulators

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