エチオコラノロン
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/10/25 10:15:03」(JST)
[Wiki en表示]
Etiocholanolone
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| Clinical data |
| Synonyms |
Aetiocholanolone
5-Isoandrosterone |
| ATC code |
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| Identifiers |
IUPAC name
- (3R,5R,8R,9S,10S,13S,14S)-3-Hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
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| CAS Number |
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| PubChem CID |
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| DrugBank |
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| ChemSpider |
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| UNII |
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| ChEBI |
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| ChEMBL |
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| Chemical and physical data |
| Formula |
C19H30O2 |
| Molar mass |
290.445 g/mol |
| 3D model (JSmol) |
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SMILES
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[H][C@]12CC[C@@]3([H])[C@]4([H])CCC(=O)[C@@]4(C)CC[C@]3([H])[C@@]1(C)CC[C@@H](O)C2
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InChI
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InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,18+,19+/m1/s1 N
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Key:QGXBDMJGAMFCBF-BNSUEQOYSA-N N
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| NY (what is this?) (verify) |
Etiocholanolone, also known as 5β-androsterone, as well as 3α-hydroxy-5β-androstan-17-one or etiocholan-3α-ol-17-one, is an etiocholane (5β-androstane) steroid as well as an endogenous 17-ketosteroid that is produced from the metabolism of testosterone. It causes fever, immunostimulation, and leukocytosis, and is used to evaluate adrenal cortex function, bone marrow performance, and in neoplastic disease to stimulate the immune system. Etiocholanolone is also known to be an inhibitory androstane neurosteroid,[1] acting as a positive allosteric modulator of the GABAA receptor,[2] and possesses anticonvulsant effects.[3] The unnatural enantiomer of etiocholanolone is more potent as a positive allosteric modulator of GABAA receptors and as an anticonvulsant than the natural form.[4]
Etiocholanolone is produced from 5β-dihydrotestosterone, with 3α,5β-androstanediol as an intermediate.
Chemistry
See also: List of neurosteroids
See also
- Etiocholanolone glucuronide
- Epietiocholanolone
- Androsterone
- Epiandrosterone
References
- ^ Reddy DS (2010). "Neurosteroids: endogenous role in the human brain and therapeutic potentials". Prog. Brain Res. Progress in Brain Research. 186: 113–37. ISBN 9780444536303. PMC 3139029 . PMID 21094889. doi:10.1016/B978-0-444-53630-3.00008-7.
- ^ Li P, Bracamontes J, Katona BW, Covey DF, Steinbach JH, Akk G (June 2007). "Natural and enantiomeric etiocholanolone interact with distinct sites on the rat alpha1beta2gamma2L GABAA receptor". Mol. Pharmacol. 71 (6): 1582–90. PMID 17341652. doi:10.1124/mol.106.033407.
- ^ Kaminski RM, Marini H, Kim WJ, Rogawski MA (June 2005). "Anticonvulsant activity of androsterone and etiocholanolone". Epilepsia. 46 (6): 819–27. PMC 1181535 . PMID 15946323. doi:10.1111/j.1528-1167.2005.00705.x.
- ^ Zolkowska D, Dhir A, Krishnan K, Covey DF, Rogawski MA (September 2014). "Anticonvulsant potencies of the enantiomers of the neurosteroids androsterone and etiocholanolone exceed those of the natural forms". Psychopharmacology. 231 (17): 3325–32. PMC 4134984 . PMID 24705905. doi:10.1007/s00213-014-3546-x.
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Endogenous steroids
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| Precursors |
- Cholesterol
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- Pregnenolone
- 11β-Hydroxypregnenolone
- 17α-Hydroxypregnenolone
- 21-Hydroxypregnenolone
- 17α,21-Dihydroxypregnenolone
- 11β,17α,21-Trihydroxypregnenolone
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| Corticosteroids |
| Glucocorticoids |
- 3α,5α-Tetrahydrocorticosterone
- 5α-Dihydrocorticosterone
- 11-Deoxycorticosterone
- 11-Deoxycortisol
- 11-Ketoprogesterone
- 21-Deoxycortisol
- 21-Deoxycortisone
- Corticosterone
- Cortisol
- Cortisone
- 17α-Hydroxypregnenolone
- 17α-Hydroxyprogesterone
- Pregnenolone
- Progesterone
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| Mineralocorticoids |
- 5α-Dihydroaldosterone
- 11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)
- 11-Deoxycortisol
- 11-Deoxycorticosterone
- 11β-Hydroxyprogesterone (21-deoxycorticosterone)
- 18-Hydroxy-11-deoxycorticosterone
- 18-Hydroxycorticosterone
- 18-Hydroxyprogesterone
- Aldosterone
- Corticosterone
- Cortisol
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| Sex steroids |
| Androgens |
- 11-Ketodihydrotestosterone
- 11-Ketotestosterone
- 7β-Hydroxyepiandrosterone
- 11β-Hydroxyandrostenedione
- Adrenosterone (11-ketoandrostenedione)
- Androstenediol
- Androstenedione
- Androsterone
- Dehydroandrosterone
- DHEA
- DHEA sulfate
- Dihydrotestosterone
- Epiandrosterone
- Epitestosterone
- 16α-Hydroxyandrostenedione
- 16α-Hydroxy-DHEA
- 16α-Hydroxy-DHEA sulfate
- Testosterone
- Metabolites: 3α-Androstanediol
- 3α-Androstanediol glucuronide
- 3β-Androstanediol
- 3α,5β-Androstanediol
- 3β,5β-Androstanediol
- 5β-Androstanedione
- 5β-Dihydrotestosterone
- Androstanetriols
- Androstenediol sulfate
- Androsterone glucuronide
- Androsterone sulfate
- Dihydrotestosterone glucuronide
- Dihydrotestosterone sulfate
- Etiocholanolone
- Etiocholanolone glucuronide
- Epietiocholanolone
- Testosterone glucuronide
- Testosterone sulfate
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| Estrogens |
- Estranes: Estetrol
- Estradiol
- Estrone
- Estriol
- 16β-Epiestriol (16β-hydroxyestradiol)
- 17α-Epiestriol (16α-hydroxy-17α-estradiol)
- 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
- 2-Hydroxyestradiol
- 2-Hydroxyestriol
- 2-Hydroxyestrone
- 4-Hydroxyestradiol
- 4-Hydroxyestriol
- 4-Hydroxyestrone
- 4-Methoxyestradiol
- 16α-Hydroxyestrone
- Others: 27-Hydroxycholesterol
- 3α-Androstanediol
- 3β-Androstanediol
- 4-Androstenedione
- 5-Androstenediol
- DHEA
- DHEA sulfate
- 7-Keto-DHEA
- 7α-Hydroxy-DHEA
- 16α-Hydroxy-DHEA
- Metabolites: 2-Methoxyestradiol
- 2-Methoxyestrone
- 4-Methoxyestrone
- Estradiol glucuronide
- Estradiol sulfate
- Estrone glucuronide
- Estrone sulfate
- Estriol glucuronide
- Estriol sulfate
- Lipoidal estradiol (e.g., estradiol stearate, estradiol palmitate)
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| Progestogens |
- Progesterone
- 16α-Hydroxyprogesterone
- 17α-Hydroxyprogesterone
- 20α-Dihydroprogesterone
- 5α-Dihydroprogesterone
- 11-Deoxycorticosterone
- 5α-DHDOC
- Metabolites: Allopregnanediol
- Pregnanediol
- Pregnanediol glucuronide
- Pregnanetriol
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| Neurosteroids |
- Cholestanes: 24S-Hydroxycholesterol
- Cholesterol
- Pregnanes: 3α-Dihydroprogesterone
- 3β-Dihydroprogesterone
- 5α-Dihydrocorticosterone
- 5α-Dihydroprogesterone
- 5β-Dihydroprogesterone
- Allopregnanolone
- Corticosterone
- DHC
- DHDOC
- Deoxycorticosterone
- Epipregnanolone
- Isopregnanolone
- Pregnanolone
- Pregnenolone
- Pregnenolone sulfate
- Progesterone
- THB
- THDOC
- Androstanes: 3α-Androstanediol
- 3α-Androstenol
- 7-Keto-DHEA
- 7α-Hydroxy-DHEA
- 7β-Hydroxy-DHEA
- 7α-Hydroxyepiandrosterone
- 7β-Hydroxyepiandrosterone
- Androsterone
- DHEA
- DHEA sulfate
- Etiocholanolone
- Pheromones: 3α-Androstenol
- 3β-Androstenol
- Androstadienol
- Androstadienone
- Androstenone
- Androsterone
- Estratetraenol
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| Others |
- Vitamin D: 7-Dehydrocholesterol
- Calcidiol/Calcifediol
- Calcitriol
- Cholecalciferol
- Others: 7α-Hydroxycholesterol
- 11α-Hydroxyprogesterone
- 11β-Hydroxyprogesterone
- Cholesterol sulfate
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GABAA receptor positive modulators
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| Alcohols |
- Brometone
- Butanol
- Chloralodol
- Chlorobutanol (cloretone)
- Ethanol (alcohol) (alcoholic drink)
- Ethchlorvynol
- Isobutanol
- Isopropanol
- Menthol
- Methanol
- Methylpentynol
- Pentanol
- Petrichloral
- Propanol
- tert-Butanol (2M2P)
- tert-Pentanol (2M2B)
- Tribromoethanol
- Trichloroethanol
- Triclofos
- Trifluoroethanol
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| Barbiturates |
- (-)-DMBB
- Allobarbital
- Alphenal
- Amobarbital
- Aprobarbital
- Barbexaclone
- Barbital
- Benzobarbital
- Benzylbutylbarbiturate
- Brallobarbital
- Brophebarbital
- Butabarbital/Secbutabarbital
- Butalbital
- Buthalital
- Butobarbital
- Butallylonal
- Carbubarb
- Crotylbarbital
- Cyclobarbital
- Cyclopentobarbital
- Difebarbamate
- Enallylpropymal
- Ethallobarbital
- Eterobarb
- Febarbamate
- Heptabarb
- Heptobarbital
- Hexethal
- Hexobarbital
- Metharbital
- Methitural
- Methohexital
- Methylphenobarbital
- Narcobarbital
- Nealbarbital
- Pentobarbital
- Phenallymal
- Phenobarbital
- Phetharbital
- Primidone
- Probarbital
- Propallylonal
- Propylbarbital
- Proxibarbital
- Reposal
- Secobarbital
- Sigmodal
- Spirobarbital
- Talbutal
- Tetrabamate
- Tetrabarbital
- Thialbarbital
- Thiamylal
- Thiobarbital
- Thiobutabarbital
- Thiopental
- Thiotetrabarbital
- Valofane
- Vinbarbital
- Vinylbital
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| Benzodiazepines |
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| Carbamates |
- Carisbamate
- Carisoprodol
- Clocental
- Cyclarbamate
- Difebarbamate
- Emylcamate
- Ethinamate
- Febarbamate
- Felbamate
- Hexapropymate
- Lorbamate
- Mebutamate
- Meprobamate
- Nisobamate
- Pentabamate
- Phenprobamate
- Procymate
- Styramate
- Tetrabamate
- Tybamate
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| Flavonoids |
- 6-Methylapigenin
- Ampelopsin (dihydromyricetin)
- Apigenin
- Baicalein
- Baicalin
- Catechin
- EGC
- EGCG
- Hispidulin
- Linarin
- Luteolin
- Rc-OMe
- Skullcap constituents (e.g., baicalin)
- Wogonin
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| Imidazoles |
- Etomidate
- Metomidate
- Propoxate
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| Kava constituents |
- 10-Methoxyyangonin
- 11-Methoxyyangonin
- 11-Hydroxyyangonin
- Desmethoxyyangonin
- 11-Methoxy-12-hydroxydehydrokavain
- 7,8-Dihydroyangonin
- Kavain
- 5-Hydroxykavain
- 5,6-Dihydroyangonin
- 7,8-Dihydrokavain
- 5,6,7,8-Tetrahydroyangonin
- 5,6-Dehydromethysticin
- Methysticin
- 7,8-Dihydromethysticin
- Yangonin
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| Monoureides |
- Acecarbromal
- Apronal (apronalide)
- Bromisoval
- Carbromal
- Capuride
- Ectylurea
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| Neuroactive steroids |
- Acebrochol
- Allopregnanolone (brexanolone)
- Alfadolone
- Alfaxalone
- 3α-Androstanediol
- Androstenol
- Androsterone
- Certain anabolic-androgenic steroids
- Cholesterol
- DHDOC
- 3α-DHP
- 5α-DHP
- 5β-DHP
- DHT
- Etiocholanolone
- Ganaxolone
- Hydroxydione
- Minaxolone
- ORG-20599
- ORG-21465
- P1-185
- Pregnanolone (eltanolone)
- Progesterone
- Renanolone
- SAGE-105
- SAGE-217
- SAGE-324
- SAGE-516
- SAGE-689
- SAGE-872
- Testosterone
- THDOC
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| Nonbenzodiazepines |
- β-Carbolines: Abecarnil
- Gedocarnil
- Harmane
- SL-651,498
- ZK-93423
- Cyclopyrrolones: Eszopiclone
- Pagoclone
- Pazinaclone
- Suproclone
- Suriclone
- Zopiclone
- Imidazopyridines: Alpidem
- DS-1
- Necopidem
- Saripidem
- Zolpidem
- Pyrazolopyrimidines: Divaplon
- Fasiplon
- Indiplon
- Lorediplon
- Ocinaplon
- Panadiplon
- Taniplon
- Zaleplon
- Others: Adipiplon
- CGS-8216
- CGS-9896
- CGS-13767
- CGS-20625
- CL-218,872
- CP-615,003
- CTP-354
- ELB-139
- GBLD-345
- Imepitoin
- JM-1232
- L-838,417
- Lirequinil (Ro41-3696)
- NS-2664
- NS-2710
- NS-11394
- Pipequaline
- ROD-188
- RWJ-51204
- SB-205,384
- SX-3228
- TGSC01AA
- TP-003
- TPA-023
- TP-13
- U-89843A
- U-90042
- Viqualine
- Y-23684
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| Phenols |
- Fospropofol
- Propofol
- Thymol
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| Piperidinediones |
- Glutethimide
- Methyprylon
- Piperidione
- Pyrithyldione
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| Pyrazolopyridines |
- Cartazolate
- Etazolate
- ICI-190,622
- Tracazolate
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| Quinazolinones |
- Afloqualone
- Cloroqualone
- Diproqualone
- Etaqualone
- Mebroqualone
- Mecloqualone
- Methaqualone
- Methylmethaqualone
- Nitromethaqualone
- SL-164
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| Volatiles/gases |
- Acetone
- Acetophenone
- Acetylglycinamide chloral hydrate
- Aliflurane
- Benzene
- Butane
- Butylene
- Centalun
- Chloral
- Chloral betaine
- Chloral hydrate
- Chloroform
- Cryofluorane
- Desflurane
- Dichloralphenazone
- Dichloromethane
- Diethyl ether
- Enflurane
- Ethyl chloride
- Ethylene
- Fluroxene
- Gasoline
- Halopropane
- Halothane
- Isoflurane
- Kerosine
- Methoxyflurane
- Methoxypropane
- Nitric oxide
- Nitrogen
- Nitrous oxide
- Norflurane
- Paraldehyde
- Propane
- Propylene
- Roflurane
- Sevoflurane
- Synthane
- Teflurane
- Toluene
- Trichloroethane (methyl chloroform)
- Trichloroethylene
- Vinyl ether
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| Others/unsorted |
- 3-Hydroxybutanal
- α-EMTBL
- AA-29504
- Avermectins (e.g., ivermectin)
- Bromide compounds (e.g., lithium bromide, potassium bromide, sodium bromide)
- Carbamazepine
- Chloralose
- Chlormezanone
- Clomethiazole
- DEABL
- 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
- Lanthanum
- Lavender oil
- Lignans (e.g., 4-O-methylhonokiol, honokiol, magnolol, obovatol)
- Loreclezole
- Menthyl isovalerate (validolum)
- Monastrol
- Niacin
- Nicotinamide (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)
- Unsorted benzodiazepine site positive modulators: α-Pinene
- MRK-409 (MK-0343)
- TCS-1105
- TCS-1205
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See also: Receptor/signaling modulators • GABA receptor modulators • GABA metabolism/transport modulators
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UpToDate Contents
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English Journal
- Thermodynamic-based retention time predictions of endogenous steroids in comprehensive two-dimensional gas chromatography.
- Silva AC1, Ebrahimi-Najafadabi H, McGinitie TM, Casilli A, Pereira HM, Aquino Neto FR, Harynuk JJ.
- Analytical and bioanalytical chemistry.Anal Bioanal Chem.2015 May;407(14):4091-9. doi: 10.1007/s00216-015-8627-0. Epub 2015 Apr 7.
- This work evaluates the application of a thermodynamic model to comprehensive two-dimensional gas chromatography (GC × GC) coupled with time-of-flight mass spectrometry for anabolic agent investigation. Doping control deals with hundreds of drugs that are prohibited in sports. Drug discovery in
- PMID 25845527
- A rapid and sensitive UPLC-MS/MS method for the simultaneous quantification of serum androsterone glucuronide, etiocholanolone glucuronide, and androstan-3α, 17β diol 17-glucuronide in postmenopausal women.
- Ke Y1, Gonthier R1, Isabelle M1, Bertin J1, Simard JN1, Dury AY1, Labrie F2.
- The Journal of steroid biochemistry and molecular biology.J Steroid Biochem Mol Biol.2015 May;149:146-52. doi: 10.1016/j.jsbmb.2015.02.009. Epub 2015 Feb 18.
- Quantification of steroidal glucuronide conjugates by the indirect methods of immunoassay and GC-MS/MS may underestimate some conjugates since hydrolysis is needed in sample processing. In the present work, a sensitive and rapid liquid chromatography-tandem mass spectrometry (LC-MS/MS) method has be
- PMID 25701608
- Analytical approach for the determination of steroid profile of humans by gas chromatography isotope ratio mass spectrometry aimed at distinguishing between endogenous and exogenous steroids.
- Bulska E1, Gorczyca D2, Zalewska I3, Pokrywka A2, Kwiatkowska D2.
- Journal of pharmaceutical and biomedical analysis.J Pharm Biomed Anal.2015 Mar 15;106:159-66. doi: 10.1016/j.jpba.2014.11.017. Epub 2014 Nov 20.
- The contamination of commonly used supplements by unknown steroids as well as their metabolites (parent compounds) become a challenge for the analytical laboratories. Although the determination of steroids profile is not trivial because of the complex matrix and low concentration of single compound,
- PMID 25498150
Japanese Journal
- ガスクロマトグラフィー‐質量分析によるヒト尿中 １７－ケトステロイドの分析：抱合体の酸加水分解条件の検討と抽出‐誘導体化法の利用
- アンドロステロン,エチオコラノロン (広範囲 血液・尿化学検査 免疫学的検査(第7版・4)その数値をどう読むか) -- (内分泌学的検査 副腎皮質関係)
- Anticonvulsant Activity of Androsterone and Etiocholanolone
- Epilepsia : journal of the International League against Epilepsy 46(6), 819-827, 2005-06-01
- NAID 10017068714
Related Links
- Etiocholanolone is a 17-ketosteroid which excreted in the urine as a metabolite of steroid hormones. The most common form of etiocholanolone present in the urine is the sulfate salt. This agent, also known as 5-isoandrosterone, may ...
- Etiocholanolone is an androstenedione and testosterone metabolite that is excreted in the urine. It is produced from androstenedione and the 5-alpha and 5-beta-reductase metabolic pathways. Etiocholanolone levels help the doctor ...
- Etiocholanolone (3α-hydroxy-5β-androstan-17-one)はandrogenの代謝産物であり,大部分は肝で抱合型となり尿中に排泄され,一部は遊離型として血中に微量存在している. 1957年Kappas等がこのetiocholanoloneを筋注すると特異 ...