Cortodoxone

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H30O4
Molecular Weight	346.4605
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@]34C)[C@@H]1CC[C@]2(O)C(=O)CO

InChI

InChIKey=WHBHBVVOGNECLV-OBQKJFGGSA-N

InChI=1S/C21H30O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h11,15-17,22,25H,3-10,12H2,1-2H3/t15-,16+,17+,19+,20+,21+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C21H30O4
Molecular Weight	346.4605
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28514642 | https://www.ncbi.nlm.nih.gov/pubmed/961638

11-Deoxycortisol (also known as cortodoxone) is the predominant deoxycorticosteroid and is the immediate precursor of cortisol, which is formed by the enzymatic action of 11beta-hydrozylase (P450). Deficiency of this enzyme causes congenital adrenal hyperplasia, which is characterized by hypertension. 11-deoxycortisol is measured as part of the Metyrapone Test. Metyrapone blocks the formation of cortisol, resulting in increased secretion of Adrenocorticotropic hormone (ACTH) and 11-deoxycortisol in normal individuals.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 11B1, mitochondrial 1 Target ID: P15538 Gene ID: 1584.0 Gene Symbol: CYP11B1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/28514642	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Congenital adrenal hyperplasia 62 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28514642	Diagnostic		Natural Metabolite	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Tissue culture of sockeye salmon intestine: functional response of Na+-K+-ATPase to cortisol.	2005-06	15695320
Insulin-like growth factor-I induces oocyte maturational competence but not meiotic resumption in white bass (Morone chrysops) follicles in vitro: evidence for rapid evolution of insulin-like growth factor action.	2005-05	15647455
11beta-Hydroxysteroid dehydrogenase type 2 activity is associated with left ventricular mass in essential hypertension.	2005-03	15618035
Identification of 17,20beta,21-trihydroxy-4-pregnen-3-one as an oocyte maturation-inducing steroid in black porgy, Acanthopagrus schlegeli.	2005-02	15639146
Genetic variation at the locus encompassing 11-beta hydroxylase and aldosterone synthase accounts for heritability in cortisol precursor (11-deoxycortisol) urinary metabolite excretion.	2005-02	15522937
11-deoxycorticosterone is a potent agonist of the rainbow trout (Oncorhynchus mykiss) mineralocorticoid receptor.	2005-01	15486226
Functional characterization of two novel point mutations in the CYP21 gene causing simple virilizing forms of congenital adrenal hyperplasia due to 21-hydroxylase deficiency.	2005-01	15483094
3alpha,5beta-Reduced cortisol exhibits antagonist properties on cerebral cortical GABA(A) receptors.	2004-12-15	15588732
Metyrapone tests in patients with panic disorder.	2004-12-01	15576069
Metyrapone as additive treatment in major depression: a double-blind and placebo-controlled trial.	2004-12	15583115
Congenital adrenal hyperplasia with 11 beta-hydroxylase deficiency.	2004-11	15549155
A detailed investigation of hirsutism in a Turkish population: idiopathic hyperandrogenemia as a perplexing issue.	2004-10	15505757
Evidence that 4-pregnen-17,20beta,21-triol-3-one functions as a maturation-inducing hormone and pheromonal precursor in the percid fish, Gymnocephalus cernuus.	2004-10	15474530
Periconceptional undernutrition in sheep accelerates maturation of the fetal hypothalamic-pituitary-adrenal axis in late gestation.	2004-09	15205376
Aldosterone synthase gene variation and adrenocortical response to sodium status, angiotensin II and ACTH in normal male subjects.	2004-08	15272911
Differential actions of metyrapone on the fetal pituitary-adrenal axis in the sheep fetus in late gestation.	2004-08	15265784
Overnight metyrapone and combined dexamethasone/metyrapone tests in post-traumatic stress disorder: preliminary findings.	2004-08	15163445
Congenital adrenal hyperplasia secondary to 11beta-hydroxylase deficiency in a domestic cat.	2004-07-15	15323380
Visualizing the vitreous body in the anterior chamber using 11-deoxycortisol after posterior capsule rupture in an animal model.	2004-07	15234133
Lack of defects in androgen production in children with hypospadias.	2004-06	15181062
Steroid metabolism in vitro during final oocyte maturation in white croaker Micropogonias furnieri (Pisces: Sciaenidae).	2004-05	15462293
Steroid profiles using liquid chromatography-tandem mass spectrometry with atmospheric pressure photoionization source.	2004-04	15043485
The impact of polymorphisms in the gene encoding aldosterone synthase (CYP11B2) on steroid synthesis and blood pressure regulation.	2004-03-31	15134824
Gonad development and plasma steroid profiles by HRGC/HRMS during one reproductive cycle in reference and leachate-exposed female perch (Perca fluviatilis).	2004-03-01	14998689
Investigation of the hypothalamo-pituitary-adrenal axis (HPA) by 1 microg ACTH test and metyrapone test in patients with primary fibromyalgia syndrome.	2004-01	15053242
Endogenous urinary steroids in premenopausal women with uterine leiomyomas.	2004-01	14698830
Coexistence of different phenotypes in a family with glucocorticoid-remediable aldosteronism.	2004-01	14688810
Biological profile of cortexolone 17alpha-propionate (CB-03-01), a new topical and peripherally selective androgen antagonist.	2004	15646372
Surface-activated chemical ionization ion trap mass spectrometry in the analysis of 21-deoxycortisol in blood.	2004	15174196
Analysis of 21-deoxycortisol, a marker of congenital adrenal hyperplasia, in blood by atmospheric pressure chemical ionization and electrospray ionization using multiple reaction monitoring.	2004	14689562
The prevalence of late onset congenital adrenal hyperplasia in hirsute women from Central Anatolia.	2003-12	14709856
Reference values for urinary steroids in Japanese newborn infants: gas chromatography/mass spectrometry in selected ion monitoring.	2003-12	14709852
Flexibility of the endogenous progesterone lactonisation pathway in Aspergillus tamarii KITA: transformation of a series of cortical steroid analogues.	2003-12	14698211
The effect of intrafetal infusion of metyrapone on arterial blood pressure and on the arterial blood pressure response to angiotensin II in the sheep fetus during late gestation.	2003-10-15	14561842
Dexamethasone does not exert direct intracellular feedback on steroidogenesis in human adrenal NCI-H295A cells.	2003-10	14529573
Interrenal steroid 21-hydroxylase in eels: primary structure, progesterone-specific activity and enhanced expression by ACTH.	2003-10	14519100
Delta sleep response to metyrapone in post-traumatic stress disorder.	2003-09	12799616
The mineralocorticoid receptor agonist, fludrocortisone, inhibits pituitary-adrenal activity in humans after pre-treatment with metyrapone.	2003-08-22	12888122
Molecular cloning and expression of guinea pig cytochrome P450c21 cDNA (steroid 21-hydroxylase) isolated from the adrenals.	2003-08	14568563
Association of polymorphisms in the interleukin 6 receptor complex with obesity and hyperandrogenism.	2003-08	12917504
Evidence for two distinct functional glucocorticoid receptors in teleost fish.	2003-08	12914532
Ghrelin, an endogenous ligand for the growth hormone-secretagogue receptor, is expressed in the human adrenal cortex.	2003-08	12851720
Reversed-phase high-performance liquid chromatography separation of adrenal steroids prior to radioimmunoassay: application in congenital adrenal hyperplasia.	2003-07-05	12841953
Brief undernutrition in late-gestation sheep programs the hypothalamic-pituitary-adrenal axis in adult offspring.	2003-07	12810548
Concurrent corticosteroid and phenanthrene transformation by filamentous fungus Cunninghamella elegans.	2003-05	12798358
Membrane-initiated steroid signaling (MISS): genomic steroid action starts at the plasma membrane.	2003-05	12798353
[The 1(2)-dehydrogenation of steroid substrates by Nocardioides simplex VKM Ac-2033D].	2003-04-18	12698789
Air oxidation of 17-hydroxycorticosteroids catalyzed by cupric acetate: formation of hemiacetal dimers.	2003-04	12787897
Hypothalamic-pituitary-adrenocortical axis function in patients with polymyalgia rheumatica and giant cell arteritis.	2003-02	12621591
Adrenal insufficiency and abnormal genitalia in a 46XX female with Smith-Lemli-Opitz syndrome.	2003	12714790

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:35:01 GMT 2025` Edited by `admin` on `Mon Mar 31 17:35:01 GMT 2025`
Record UNII	WDT5SLP0HQ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Cortodoxone

Official Name

English

11-DEOXYCORTISOL

Preferred Name

English

SK&F 3050

Code

English

HYDROCORTISONE IMPURITY F [EP IMPURITY]

Common Name

English

CORTIFEN

Brand Name

English

4-PREGNEN-17.ALPHA.,21-DIOL-3,20-DIONE

Common Name

English

17,21-DIHYDROXYPROGESTERONE

Common Name

English

CORTEXOLONE

Common Name

English

SKF-3050

Common Name

English

11-DEOXYCORTISONE

Common Name

English

11-DESOXY-17-HYDROXYCORTICOSTERONE [MI]

Common Name

English

11-DEOXYHYDROCORTISONE

Common Name

English

cortodoxone [INN]

Common Name

English

SUBSTANCE S

Common Name

English

SK&F-3050

Code

English

NSC-18317

Code

English

17.ALPHA.,21-DIHYDROXYPREGN-4-ENE-3,20-DIONE

Systematic Name

English

PREGN-4-ENE-3,20-DIONE, 17,21-DIHYDROXY-

Systematic Name

English

17.ALPHA.,21-DIHYDROXY-4-PREGNEN-3,20-DIONE

Systematic Name

English

17.ALPHA.,21-DIHYDROXYPROGESTERONE

Common Name

English

4-PREGNENE-17.ALPHA.,21-DIOL-3,20-DIONE

Common Name

English

CORTODOXONE [USAN]

Common Name

English

17-HYDROXY-11-DEOXYCORTICOSTERONE

Common Name

English

REICHSTEIN'S SUBSTANCE S

Common Name

English

.DELTA.4-PREGNENE-17.ALPHA.,21-DIOL-3,20-DIONE

Common Name

English

CORTISOL, 11-DEOXY-

Common Name

English

17,21-Dihydroxypregn-4-ene-3,20-dione

Systematic Name

English

17.ALPHA.-HYDROXYCORTEXONE

Common Name

English

11-DESOXY-17.ALPHA.-HYDROXYCORTICOSTERONE

Common Name

English

Classification Tree Code System Code

LOINC

55809-8