Minaxolone
Chemical compound
Minaxolone Other names 11α-(Dimethylamino)-2β-ethoxy-3α-hydroxy-5α-pregnan-20-one ATC code
1-[(1S ,2S ,4S ,5S ,7S ,10S ,11S ,14S ,15S ,17R )-17-(dimethylamino)-4-ethoxy-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7 .011,15 ]heptadecan-14-yl]ethan-1-one
CAS Number PubChem CID IUPHAR/BPS ChemSpider UNII KEGG ChEMBL CompTox Dashboard (EPA ) Formula C 25 H 43 N O 3 Molar mass −1 3D model (JSmol )
CCO[C@H]1C[C@]2([C@@H](CC[C@@H]3[C@@H]2[C@@H](C[C@]4([C@H]3CC[C@@H]4C(=O)C)C)N(C)C)C[C@@H]1O)C
InChI=1S/C25H43NO3/c1-7-29-22-14-24(3)16(12-21(22)28)8-9-17-19-11-10-18(15(2)27)25(19,4)13-20(23(17)24)26(5)6/h16-23,28H,7-14H2,1-6H3/t16-,17-,18+,19-,20+,21-,22-,23+,24-,25+/m0/s1
N Key:NCGLTZSBTFVVAW-KNXRZYMVSA-N
N N Y (what is this?) (verify)
Minaxolone (CCI-12923 ) is a neuroactive steroid which was developed as a general anesthetic but was withdrawn before registration due to toxicity seen with long-term administration in rats, and hence was never marketed.[ 1] [ 2] [ 3] positive allosteric modulator of the GABAA receptor ,[ 4] glycine receptor .[ 4] [ 5]
Chemistry
See also
References
^ Ganellin CR, Triggle DJ (21 November 1996). Dictionary of Pharmacological Agents ISBN 978-0-412-46630-4 ^ Bovill JB, Howie MC, eds. (1999). Clinical Pharmacology for Anaesthetists doi :10.1016/B978-0-323-03707-5.50031-0 . ISBN 978-0-7020-2167-1 ^ Perouansky MA, Hemmings Jr HC (2006). "Intravenous anesthetic agents" . In Hemmings HC, Hopkins PM (eds.). Foundations of Anesthesia: Basic Sciences for Clinical Practice . Elsevier Health Sciences. pp. 305–. ISBN 978-0-323-03707-5 ^ a b Lambert JJ, Harney SC, Belelli D, Peters JA (2001). "Neurosteroid modulation of recombinant and synaptic GABAA receptor" . In Biggio G, Purdy RH (eds.). Neurosteroids and Brain Function . Academic Press. pp. 196–. ISBN 978-0-12-366846-2 ^ Weir CJ, Ling AT, Belelli D, Wildsmith JA, Peters JA, Lambert JJ (May 2004). "The interaction of anaesthetic steroids with recombinant glycine and GABAA receptors". British Journal of Anaesthesia . 92 (5): 704–711. CiteSeerX 10.1.1.519.3591 doi :10.1093/bja/aeh125 . PMID 15033889 .
Alcohols Barbiturates Benzodiazepines Carbamates Flavonoids Imidazoles Kava constituentsMonoureides Neuroactive steroids Nonbenzodiazepines Phenols Piperidinediones Pyrazolopyridines Quinazolinones Volatiles /gases Others/unsorted
3-Hydroxybutanal α-EMTBL AA-29504 Alogabat Avermectins (e.g., ivermectin )Bromide compounds (e.g., lithium bromide , potassium bromide , sodium bromide )Carbamazepine Chloralose Chlormezanone Clomethiazole Darigabat DEABL Deuterated etifoxine Dihydroergolines (e.g., dihydroergocryptine , dihydroergosine , dihydroergotamine , ergoloid (dihydroergotoxine) )DS2 Efavirenz Etazepine Etifoxine Fenamates (e.g., flufenamic acid , mefenamic acid , niflumic acid , tolfenamic acid )Fluoxetine Flupirtine Hopantenic acid KRM-II-81 Lanthanum Lavender oil Lignans (e.g., 4-O-methylhonokiol , honokiol , magnolol , obovatol )Loreclezole Menthyl isovalerate (validolum) Monastrol Niacin Niacinamide Org 25,435 Phenytoin Propanidid Retigabine (ezogabine) Safranal Seproxetine Stiripentol Sulfonylalkanes (e.g., sulfonmethane (sulfonal) , tetronal , trional )Terpenoids (e.g., borneol )Topiramate Valerian constituents (e.g., isovaleric acid , isovaleramide , valerenic acid , valerenol )
Receptor (ligands )
GlyR Tooltip Glycine receptor
Positive modulators: Alcohols (e.g., brometone , chlorobutanol (chloretone) , ethanol (alcohol) , tert -butanol (2M2P)tribromoethanol , trichloroethanol , trifluoroethanol )Alkylbenzene sulfonate Anandamide Barbiturates (e.g., pentobarbital , sodium thiopental )Chlormethiazole D12-116 Dihydropyridines (e.g., nicardipine )Etomidate Ginseng constituents (e.g., ginsenosides (e.g., ginsenoside-Rf ))Glutamic acid (glutamate) Ivermectin Ketamine Neuroactive steroids (e.g., alfaxolone , pregnenolone (eltanolone) , pregnenolone acetate , minaxolone , ORG-20599 )Nitrous oxide Penicillin G Propofol Tamoxifen Tetrahydrocannabinol Triclofos Tropeines (e.g., atropine , bemesetron , cocaine , LY-278584 , tropisetron , zatosetron )Volatiles /gases (e.g., chloral hydrate , chloroform , desflurane , diethyl ether (ether) , enflurane , halothane , isoflurane , methoxyflurane , sevoflurane , toluene , trichloroethane (methyl chloroform) , trichloroethylene )Xenon Zinc Antagonists: 2-Aminostrychnine 2-Nitrostrychnine 4-Phenyl-4-formyl-N-methylpiperidine αEMBTL Bicuculline Brucine Cacotheline Caffeine Colchicine Colubrine Cyanotriphenylborate Dendrobine Diaboline Endocannabinoids (e.g., 2-AG , anandamide (AEA) )Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline N-Methylstrychnine N,N-Dimethylmuscimol Nipecotic acid Pitrazepin Pseudostrychnine Quinolines (e.g., 4-hydroxyquinoline , 4-hydroxyquinoline-3-carboxylic acid , 5,7-CIQA , 7-CIQ , 7-TFQ , 7-TFQA )RU-5135 Sinomenine Strychnine Thiocolchicoside Tutin Negative modulators: Amiloride Benzodiazepines (e.g., bromazepam , clonazepam , diazepam , flunitrazepam , flurazepam )Corymine Cyanotriphenylborate Daidzein Dihydropyridines (e.g., nicardipine , nifedipine , nitrendipine )Furosemide Genistein Ginkgo constituents (e.g., bilobalide , ginkgolides (e.g., ginkgolide A , ginkgolide B , ginkgolide C , ginkgolide J , ginkgolide M ))Imipramine NBQX Neuroactive steroids (e.g., 3α-androsterone sulfate , 3β-androsterone sulfate , deoxycorticosterone , DHEA sulfate , pregnenolone sulfate , progesterone )Opioids (e.g., codeine , dextromethorphan , dextrorphan , levomethadone , levorphanol , morphine , oripavine , pethidine , thebaine )Picrotoxin (i.e., picrotin and picrotoxinin )PMBA Riluzole Tropeines (e.g., bemesetron , LY-278584 , tropisetron , zatosetron )Verapamil Zinc NMDAR Tooltip N-Methyl-D-aspartate receptor
Transporter (blockers )
GlyT1 Tooltip Glycine transporter 1 GlyT2 Tooltip Glycine transporter 2
