18-Hydroxy-11-deoxycorticosterone

Names
IUPAC name

18,21-Dihydroxypregn-4-ene-3,20-dione

Systematic IUPAC name

(1S,3aS,3bR,9aR,9bS,11aR)-1-(Hydroxyacetyl)-11a-(hydroxymethyl)-9a-methyl-1,2,3,3a,3b,4,5,8,9,9a,9b,10,11,11a-tetradecahydro-7H-cyclopenta[a]phenanthren-7-one

Other names

18,21-dihydroxy-4-pregnene-3,20-dione

Identifiers

CAS Number

* 379-68-0

3D model (JSmol)

* Interactive image

ChemSpider |

* 58495

EC Number |

* 206-834-3

MeSH | 18-hydroxydeoxycorticosterone

PubChem CID

* 64970

InChI

* InChI=1S/C21H30O4/c1-20-8-6-14(24)10-13(20)2-3-15-16(20)7-9-21(12-23)17(15)4-5-18(21)19(25)11-22/h10,15-18,22-23H,2-9,11-12H2,1H3/t15-,16+,17+,18-,20+,21-/m1/s1

Key: VPJHREHKRNIYDB-TZGXILGRSA-N

SMILES

* C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4C(=O)CO)CO

Properties

Chemical formula

| C21H30O4
Molar mass | 346.5

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

18-Hydroxy-11-deoxycorticosterone (also known as 18-OH-DOC, 18,21-dihydroxyprogesterone, and 18,21-dihydroxypregn-4-ene-3,20-dione) is an endogenous steroid and a mineralocorticoid. It is a hydroxylated metabolite of 11-deoxycorticosterone.[1]

In rats, conversion of 11-deoxycorticosterone into 18-OH-DOC is catalyzed by the CYP11B3 enzyme.[2]

In humans, 18-OH-DOC is a weak mineralocorticoid.[3] It may be increased in 17α-hydroxylase (CYP17A1) deficiency,[4] in aldosterone synthase (CYP11B2) deficiency,[5] in primary aldosteronism, and may also indicate a histologic variant of the aldosteronoma.[4] Excessive secretion of 18-OH-DOC can cause mineralocorticoid excess syndrome, although these cases are very rare.[6]

## References

1. ↑ "18,19-Dihydroxydeoxycorticosterone, a new metabolite produced from 18-hydroxydeoxycorticosterone by cytochrome P-450(11) beta. Chemical synthesis and structural analysis by 1H NMR". Biochemistry 23 (12): 2558–64. June 1984. doi:10.1021/bi00307a004. PMID 6466598.
2. ↑ "Cloning and expression of the rat adrenal cytochrome P-450 11B3 (CYP11B3) enzyme cDNA: preferential 18-hydroxylation over 11 beta-hydroxylation of DOC". Molecular and Cellular Endocrinology 114 (1–2): 137–45. October 1995. doi:10.1016/0303-7207(95)03653-o. PMID 8674838.
3. ↑ "The regulation of plasma 18-hydroxy 11-deoxycorticosterone in man". The Journal of Clinical Investigation 58 (1): 221–9. July 1976. doi:10.1172/JCI108453. PMID 180059.
4. ↑ 4.0 4.1 "Adrenocortical factors in hypertension. I. Significance of 18-hydroxy-11-deoxycorticosterone". The American Journal of Cardiology 38 (6): 814–24. November 1976. doi:10.1016/0002-9149(76)90360-x. PMID 187051.
5. ↑ "Chromatographic system for the simultaneous measurement of plasma 18-hydroxy-11-deoxycorticosterone and 18-hydroxycorticosterone by radioimmunoassay: reference data for neonates and infants and its application in aldosterone-synthase deficiency". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences 785 (2): 293–301. March 2003. doi:10.1016/s1570-0232(02)00921-2. PMID 12554142.
6. ↑ "Effect of uni-adrenalectomy on blood pressure in a patient with excessive adrenal 18-hydroxy-11-deoxycorticosterone production bilaterally". Internal Medicine (Tokyo, Japan) 42 (6): 507–12. June 2003. doi:10.2169/internalmedicine.42.507. PMID 12857050.

## External links

* 18-hydroxydeoxycorticosterone at the US National Library of Medicine Medical Subject Headings (MeSH)

* v
* t
* e

Endogenous steroids

Precursors|

* Cholesterol
* 22R-Hydroxycholesterol
* 20α,22R-Dihydroxycholesterol
* Pregnenolone
* 11β-Hydroxypregnenolone
* 17α-Hydroxypregnenolone
* 21-Hydroxypregnenolone
* 17α,21-Dihydroxypregnenolone
* 11β,17α,21-Trihydroxypregnenolone

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

* Metabolites: 5α-Dihydrocortisol
* 3α,5α-Tetrahydrocortisol

|

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

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
* 5β-Dihydrotestosterone
* 3α-Etiocholanediol
* 3β-Etiocholanediol
* Androstanetriols
* Androstenediol sulfate
* Androsterone glucuronide
* Androsterone sulfate
* Dihydrotestosterone glucuronide
* Dihydrotestosterone sulfate
* Etiocholanedione
* Etiocholanolone
* Etiocholanolone glucuronide
* Epietiocholanolone
* Testosterone glucuronide
* Testosterone sulfate

|

Estrogens|

* Estranes: Estetrol
* Estradiol
* Estrone
* Estriol
* 17α-Estradiol
* 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 3-glucuronide
* Estradiol sulfate
* Estradiol 17β-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
* 20β-Dihydroprogesterone
* 5α-Dihydroprogesterone
* 11-Deoxycorticosterone
* 5α-DHDOC

* Metabolites: Allopregnanediol
* Pregnanediol
* Pregnanediol glucuronide
* Pregnanetriol

Neurosteroids|

* Cholestanes: 24S-Hydroxycholesterol
* Cholesterol

* Pregnanes: 3α-Dihydroprogesterone
* 3β-Dihydroprogesterone
* 5α-Dihydrocorticosterone
* 5α-Dihydroprogesterone
* 5β-Dihydroprogesterone
* Allopregnanolone
* Corticosterone
* DHC
* DHDOC
* 11-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

Others|

* Vitamin D: 7-Dehydrocholesterol
* Calcidiol/Calcifediol
* Calcitriol
* Cholecalciferol

* Others: 7α-Hydroxycholesterol
* 11α-Hydroxyprogesterone
* 11β-Hydroxyprogesterone
* Cholesterol sulfate

* v
* t
* e

Mineralocorticoid receptor modulators

MR|

| Agonists|

* 11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)
* 11-Dehydrocorticosterone acetate
* 11-Deoxycorticosterone (desoxycortone, deoxycortone, desoxycorticosterone)
* Desoxycortone esters
* 11-Deoxycortisol (cortodoxone, cortexolone)
* Cortifen (cortiphen, kortifen)
* Cortodoxone acetate
* 11β-Hydroxyprogesterone
* 16α,18-Dihydroxy-11-deoxycorticosterone
* 17α-Hydroxyaldosterone
* 18-Hydroxy-11-deoxycorticosterone
* 19-Norprogesterone
* Aldosterone
* Corticosterone
* Corticosterone acetate
* Corticosterone benzoate
* Cortisol (hydrocortisone)
* Benzodrocortisone (hydrocortisone benzoate)
* Hydrocortamate (hydrocortisone diethylaminoacetate)
* Hydrocortisone esters
* Cortisone
* Cortisone acetate
* Fludrocortisone (fludrocortone)
* Fludrocortisone acetate
* Mometasone
* Mometasone furoate
* Prednisolone
* Prednazate
* Prednazoline
* Prednicarbate (prednisolone ethylcarbonate propionate)
* Prednimustine
* Prednisolamate (prednisolone diethylaminoacetate)
* Prednisolone esters
* Prednisone
* Prednisone esters

|

Antagonists|

* Steroidal: 6β-Hydroxy-7α-thiomethylspironolactone
* 7α-Acetylthio-17α-hydroxyprogesterone
* 7α-Thiomethylspironolactone (SC-26519)
* 7α-Thioprogesterone (SC-8365)
* 7α-Thiospironolactone (SC-24813)
* 16α-Hydroxyprogesterone
* 17α-Hydroxyprogesterone (hydroxyprogesterone)
* 18-Deoxyaldosterone
* 18,19-Dinorprogesterone
* Canrenoate potassium (potassium canrenoate)
* Canrenoic acid (canrenoate)
* Canrenone (canrenoate y-lactone)
* Dicirenone
* Dimethisterone
* Drospirenone
* Dydrogesterone
* Eplerenone
* Gestodene
* Guggulsterone
* Hydroxyprogesterone caproate
* Medrogestone
* Mespirenone
* Metribolone
* Mexrenoate potassium
* Mexrenoic acid (mexrenoate)
* Mexrenone
* Oxprenoic acid (oxprenoate)
* Oxprenoate potassium (RU-28318)
* Pregnenolone
* Progesterone
* Prorenoate potassium
* Prorenoic acid (prorenoate)
* Prorenone
* RO-14-9012
* RU-26752
* SC-5233 (spirolactone)
* SC-8109
* SC-11927 (CS-1)
* SC-19886
* SC-27169
* Spirorenone
* Spironolactone
* Spiroxasone
* Tibolone
* Trimegestone
* ZK-91587
* ZK-97894

* Nonsteroidal: Amlodipine
* Apararenone
* Benidipine
* BR-4628
* Esaxerenone
* Felodipine
* Finerenone
* Miricorilant (CORT-118335)
* Nifedipine
* Nimodipine
* Nitrendipine
* PF-03882845
* SM-368229

See also
Receptor/signaling modulators
Mineralocorticoids and antimineralocorticoids
Glucocorticoid receptor modulators
List of corticosteroids

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