Dihydrodeoxycorticosterone

Dihydrodeoxycorticosterone
Names

IUPAC name (5α)-21-Hydroxypregnane-3,20-dione
Other names 5α-Dihydro-11-deoxycorticosterone
Identifiers
CAS Number	298-36-2
3D model (Jmol)	Interactive image
ChemSpider	4953958
PubChem	6451493
InChI InChI=1S/C21H32O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h13,15-18,22H,3-12H2,1-2H3/t13-,15-,16-,17-,18+,20-,21-/m0/s1 Key: USPYDUPOCUYHQL-KVHKMPIWSA-N InChI=1/C21H32O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h13,15-18,22H,3-12H2,1-2H3/t13-,15-,16-,17-,18+,20-,21-/m0/s1 Key: USPYDUPOCUYHQL-KVHKMPIWBY
SMILES C[C@]12CCC(=O)C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4C(=O)CO)C
Properties
Chemical formula	C₂₁H₃₂O₃
Molar mass	332.48 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

5α-Dihydrodeoxycorticosterone (abbreviated as DHDOC), also known as 21-hydroxy-5α-pregnan-20-one, is an endogenous progestogen and neurosteroid.^[1] It is synthesized from the adrenal hormone deoxycorticosterone (DOC) by the enzyme 5α-reductase type I.^[1] DHDOC is an agonist of the progesterone receptor, as well as a positive allosteric modulator of the GABA_A receptor, and is known to have anticonvulsant effects.^[1]^[2]

References

1 2 3 Reddy DS, Rogawski MA (May 2002). "Stress-induced deoxycorticosterone-derived neurosteroids modulate GABA(A) receptor function and seizure susceptibility". J. Neurosci. 22 (9): 3795–805. PMID 11978855.
↑ Edwards HE, Vimal S, Burnham WM (December 2005). "The acute anticonvulsant effects of deoxycorticosterone in developing rats: role of metabolites and mineralocorticoid-receptor responses". Epilepsia. 46 (12): 1888–97. doi:10.1111/j.1528-1167.2005.00295.x. PMID 16393154.

Endogenous steroids

Precursors

Corticosteroids

Glucocorticoids	Corticosterone Cortisol Cortisone DHC Deoxycortisol Deoxycorticosterone 17α-Hydroxypregnenolone 17α-Hydroxyprogesterone Pregnenolone Progesterone THB

Mineralocorticoids	Aldosterone Corticosterone Cortisol Deoxycortisol Deoxycorticosterone 5α-Dihydroaldosterone 16α,18-Dihydroxy-11-deoxycorticosterone 18-Hydroxy-11-deoxycorticosterone 18-Hydroxycorticosterone 18-Hydroxydeoxycorticosterone

Sex steroids

Androgens	11-Ketotestosterone 7β-Hydroxyepiandrosterone 11β-Hydroxyandrostenedione 4-Androstenedione 5-Androstenediol Adrenosterone (11-ketoandrostenedione) Androsterone 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 Androsterone glucuronide Dihydrotestosterone glucuronide Dihydrotestosterone sulfate Etiocholanolone Etiocholanolone glucuronide Epietiocholanolone Testosterone glucuronide Testosterone sulfate

Estrogens	27-Hydroxycholesterol 3α-Androstanediol 3β-Androstanediol 4-Androstenedione 5-Androstenediol DHEA DHEA sulfate 7-Keto-DHEA 7α-Hydroxy-DHEA 16α-Hydroxy-DHEA Estetrol Estradiol Estrone Estriol 16β-Epiestriol (16β-hydroxyestradiol) 17α-Epiestriol (16α-hydroxy-17α-estradiol) 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 2-Hydroxyestradiol 2-Hydroxyestrone 2-Methoxyestradiol 4-Hydroxyestradiol 4-Hydroxyestrone 16α-Hydroxyestrone Metabolites: Estradiol glucuronide Estradiol sulfate Estrone glucuronide Estrone sulfate Estriol glucuronide Estriol sulfate Lipoidal estradiol (e.g., estradiol stearate, estradiol palmitate)

Progestogens	Progesterone 16α-Hydroxyprogesterone 17α-Hydroxyprogesterone 20α-Dihydroprogesterone 5α-Dihydroprogesterone Deoxycorticosterone 5α-DHDOC Metabolites: Pregnanediol Pregnanediol glucuronide Pregnanetriol

Neurosteroids

Cholestane: 24S-Hydroxycholesterol
Cholesterol

Androstane: 3α-Androstanediol
3α-Androstenol
7-Keto-DHEA
7α-Hydroxy-DHEA
7β-Hydroxy-DHEA
7α-Hydroxyepiandrosterone
7β-Hydroxyepiandrosterone
Androsterone
DHEA
DHEA sulfate
Etiocholanolone

Others

Others: 11α-Hydroxyprogesterone
11β-Hydroxyprogesterone

Progesterone receptor modulators

Agonists	Progesterone derivatives: 5α-Dihydroprogesterone 9α-Bromo-11-ketoprogesterone 11-Dehydroprogesterone 11-Deoxycorticosterone 16α-Hydroxyprogesterone 20α-Dihydroprogesterone Dimepregnen Diosgenin Progesterone Quingestrone Retroprogesterone derivatives: Dydrogesterone Retroprogesterone Ro 6-3129 Trengestone 17α-Substituted progesterone derivatives: 17α-Hydroxyprogesterone (hydroxyprogesterone) 17α-Methylprogesterone Acetomepregenol (mepregenol diacetate) Algestone Algestone acetonide Algestone acetophenide Amadinone Amadinone acetate Anagestone Anagestone acetate Butagest (buterol) Chlormadinone Chlormadinone acetate Cismadinone Cismadinone acetate Clogestone Clogestone acetate Clomegestone Clomegestone acetate Cyproterone acetate Delmadinone Delmadinone acetate Edogestrone Flugestone Flugestone acetate Flumedroxone Flumedroxone acetate Gestaclone Haloprogesterone Hydromadinone (hydromadinone acetate) Hydroxyprogesterone acetate Hydroxyprogesterone caproate (hydroxyprogesterone hexanoate) Hydroxyprogesterone heptanoate (hydroxyprogesterone enanthate) Mecigestone (pentarane B) Medrogestone Medroxyprogesterone Medroxyprogesterone acetate Megestrol Megestrol acetate Melengestrol Melengestrol acetate Mometasone Mometasone furoate Osaterone Osaterone acetate Pentagestrone Pentagestrone acetate Pentarane A Proligestone 19-Norprogesterone derivatives: 19-Norprogesterone Demegestone Gestadienol Gestonorone caproate (gestronol hexanoate) Gestronol (gestonorone) Nomegestrol Nomegestrol acetate Norgestomet Org-2058 Oxogestone Oxogestone phenpropionate Promegestone Segesterone Segesterone acetate (nestorone) Trimegestone Testosterone derivatives: 6,6-Difluoronorethisterone 11β-Methyl-19-nortestosterone 11β-Methyl-19-nortestosterone dodecylcarbonate 19-Nor-5-androstenediol 19-Nor-5-androstenedione Δ^4-Tibolone Allylestrenol Altrenogest Bolandiol Bolandiol dipropionate Bolandione Chloroethynyl norgestrel Cingestol Danazol Desogestrel Dienedione Dienogest Dienolone Dimethandrolone Dimethandrolone buciclate Dimethandrolone dodecylcarbonate Dimethandrolone undecanoate Dimethisterone Dimethyltrienolone Ethisterone Ethyldienolone Ethylestrenol (ethylnandrol) Ethynerone Etonogestrel Etynodiol Etynodiol diacetate Gestodene Gestrinone Levonorgestrel Levonorgestrel butanoate Lynestrenol Methyldienolone Metribolone (R-1881) Metynodiol Metynodiol diacetate Methoxydienone (methoxygonadiene) Mibolerone Nandrolone Nandrolone esters (e.g., nandrolone decanoate, nandrolone phenylpropionate) Norelgestromin Norethisterone (norethindrone) Norethisterone acetate Norethisterone acetate oxime Norethisterone enanthate Noretynodrel Norgesterone Norgestimate Norgestrel Norgestrienone Normethandrone (methylestrenolone, normethandrolone, normethisterone) Norvinisterone Oxendolone Quingestanol Quingestanol acetate Tetrahydrogestrinone Tibolone Tigestol Tosagestin Trenbolone (trienolone) Trestolone Trestolone acetate Spirolactone derivatives: Canrenoic acid Canrenone Drospirenone Mespirenone Potassium canrenoate SC-5233 SC-8109 Spironolactone Spirorenone Non-steroidal: 3,8-Dihydrodiligustilide Riligustilide Tanaproget ZM-182345

Mixed (SPRMs)	Apigenin Asoprisnil Asoprisnil ecamate Guggulsterone Kaempferol J1042 LG-120838 Naringenin PRA-910 Syringic acid Telapristone Antagonistic: Mifepristone Org-31710 Org-33628 Ulipristal acetate ZK-137316

Antagonists	3α-Hydroxytibolone 3β-Hydroxytibolone Aglepristone Lilopristone Lonaprisan Onapristone Toripristone Valproic acid Vilaprisan Zanoterone ZM-150271 ZM-172406

mPRs
(PAQRs)

Agonists	5α-Dihydroprogesterone 5β-Dihydroprogesterone 11-Deoxycorticosterone 17α-Hydroxyprogesterone 17α,21-Dihydroxyprogesterone 21-Hydroxyprogesterone Allopregnanolone Mifepristone Pregnenolone Progesterone

Antagonists	Mifepristone

See also: Androgenics • Estrogenics • Glucocorticoidics • Mineralocorticoidics • Steroid hormone metabolism modulators

GABA_A receptor positive allosteric modulators

Alcohols	Brometone Butanol Chloralodol Chlorobutanol (cloretone) Ethanol (drinking alcohol) Ethchlorvynol Isobutanol Isopropanol Menthol Methanol Methylpentynol Pentanol Petrichloral Propanol tert-Butanol (2M2P) tert-Pentanol (2M2B) Tribromoethanol Trichloroethanol Triclofos Trifluoroethanol

Barbiturates	(-)-DMBB Allobarbital Alphenal Amobarbital Aprobarbital Barbexaclone Barbital Benzobarbital Benzylbutylbarbiturate Brallobarbital Brophebarbital Butabarbital/Secbutabarbital Butalbital Buthalital Butobarbital Butallylonal Carbubarb CP-1414S 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

Benzodiazepines	2-Oxoquazepam 3-Hydroxyphenazepam Adinazolam Alprazolam Arfendazam Avizafone Bentazepam Bretazenil Bromazepam Brotizolam Camazepam Carburazepam Chlordiazepoxide Ciclotizolam Cinazepam Cinolazepam Clazolam Climazolam Clobazam Clonazepam Clonazolam Clorazepate Clotiazepam Cloxazolam Cyprazepam Delorazepam Demoxepam Diazepam Diclazepam Doxefazepam Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam EVT-201 FG-8205 Fletazepam Flubromazepam Flubromazolam Fludiazepam Flunitrazepam Flurazepam Flutazolam Flutemazepam Flutoprazepam Fosazepam Gidazepam Halazepam Haloxazolam Iclazepam Imidazenil Irazepine Ketazolam Lofendazam Lopirazepam Loprazolam Lorazepam Lormetazepam Meclonazepam Medazepam Menitrazepam Metaclazepam Mexazolam Midazolam Motrazepam N-Desalkylflurazepam Nifoxipam Nimetazepam Nitrazepam Nitrazepate Nitrazolam Nordazepam Nortetrazepam Oxazepam Oxazolam Phenazepam Pinazepam Pivoxazepam Prazepam Premazepam Proflazepam Pyrazolam QH-II-66 Quazepam Reclazepam Remimazolam Rilmazafone Ripazepam Ro48-6791 Ro48-8684 SH-053-R-CH3-2′F Sulazepam Temazepam Tetrazepam Tolufazepam Triazolam Triflubazam Triflunordazepam (Ro5-2904) Tuclazepam Uldazepam Zapizolam Zolazepam Zomebazam

Carbamates	Carisbamate Carisoprodol Clocental Cyclarbamate Difebarbamate Emylcamate Ethinamate Febarbamate Felbamate Hexapropymate Lorbamate Mebutamate Meprobamate Nisobamate Pentabamate Phenprobamate Procymate Styramate Tetrabamate Tybamate

Flavonoids	6-Methylapigenin Ampelopsin (dihydromyricetin) Apigenin Baicalein Baicalin Catechin EGC EGCG Hispidulin Linarin Luteolin Rc-OMe Skullcap constituents (e.g., baicalin) Wogonin

Imidazoles	Etomidate Metomidate Propoxate

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

Monoureides	Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride Ectylurea

Neuroactive steroids	Acebrochol Allopregnanolone (SAGE-547) Alfadolone Alfaxalone Anabolic steroids 3α-Androstanediol Androstenol Androsterone Cholesterol DHDOC 3α-DHP 5α-DHP 5β-DHP DHT Etiocholanolone Ganaxolone Hydroxydione Minaxolone Org 20599 Org 21465 Pregnanolone (eltanolone) Progesterone Renanolone SAGE-105 SAGE-217 SAGE-324 SAGE-516 SAGE-689 SAGE-872 Testosterone THDOC

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 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

Phenols	Fospropofol Propofol Thymol

Piperidinediones	Glutethimide Methyprylon Piperidione Pyrithyldione

Pyrazolopyridines	Cartazolate Etazolate ICI-190,622 Tracazolate

Quinazolinones	Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone SL-164

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

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 PAMs: MRK-409 (MK-0343) TCS-1105 TCS-1205

See also: GABAergics

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