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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H30O4
Molecular Weight 346.4613
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CORTODOXONE

SMILES

C[C@@]12CCC(=O)C=C2CC[C@]3([H])[C@]1([H])CC[C@@]4(C)[C@@]3([H])CC[C@@]4(C(=O)CO)O

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 346.4613
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P15538
Gene ID: 1584
Gene Symbol: CYP11B1
Target Organism: Homo sapiens (Human)
Conditions
PubMed

PubMed

TitleDatePubMed
Effects of maturation-inducing hormone on heterologous gap junctional coupling in ovarian follicles of Atlantic croaker.
2001 Dec
Increased adrenal steroid secretion in response to CRF in women with hypothalamic amenorrhea.
2001 Sep
Coexistence of 21-hydroxylase and 11 beta-hydroxylase deficiency in adrenal incidentalomas and in subclinical Cushing's syndrome.
2002
Two-step strategy for alteration of immunoglobulin specificity by in vitro mutagenesis.
2002
Inhibitory effects of cortical steroids and adrenocorticotropic hormone on catecholamine secretion in guinea-pig perfused adrenal glands.
2002 Apr
The low-dose ACTH test does not provide a useful assessment of the hypothalamic-pituitary-adrenal axis in secondary adrenal insufficiency.
2002 Apr
Generation of a novel monoclonal antibody against cortisol-[C-4]-bovine serum albumin conjugate: application to enzyme-linked immunosorbent assay for urinary and serum cortisol.
2002 Dec
The effect of amino-acid substitutions I112P, D147E and K152N in CYP11B2 on the catalytic activities of the enzyme.
2002 Feb
Functional expression of human mitochondrial CYP11B2 in fission yeast and identification of a new internal electron transfer protein, etp1.
2002 Feb 19
11beta-hydroxysteroid dehydrogenase activity in proteinuric patients and the effect of angiotensin-II receptor blockade.
2002 Jul
Single-chain Fv fragments derived from an anti-11-deoxycortisol antibody. Affinity, specificity, and idiotype analysis.
2002 Jul
Decreased steroidogenic enzyme 17,20-lyase and increased 17-hydroxylase activities in type 2 diabetes mellitus.
2002 Mar
Common single nucleotide polymorphisms in intron 3 of the calpain-10 gene influence hirsutism.
2002 Mar
Increased 21-hydroxylase and shutdown of C(17,20) lyase activities in testicular tissues of the grouper (Epinephelus coioides) during 17alpha-methyltestosterone-induced sex inversion.
2002 May
Effects of the maturation-inducing steroid on LH secretion and the GnRH system at different stages of the gonadal cycle in Atlantic croaker.
2002 May
Clitoral cyst as a cause of ambiguous genitalia.
2002 May
A glucocorticoid-responsive mutant androgen receptor exhibits unique ligand specificity: therapeutic implications for androgen-independent prostate cancer.
2002 May
Long-term (15 years) outcome in an infant with metastatic adrenocortical carcinoma.
2002 Oct
Ovarian steroidogenesis in white sturgeon (Acipenser transmontanus) during oocyte maturation and induced ovulation.
2002 Oct 15
Endocrine control of diurnal oocyte maturation in the kyusen wrasse, Halichoeres poecilopterus.
2002 Sep
Determination of 11-deoxycortisol (Reichstein's compound S) in human plasma by clinical isotope dilution mass spectrometry using benchtop gas chromatography-mass selective detection.
2002 Sep
Air oxidation of 17-hydroxycorticosteroids catalyzed by cupric acetate: formation of hemiacetal dimers.
2003 Apr
The mineralocorticoid receptor agonist, fludrocortisone, inhibits pituitary-adrenal activity in humans after pre-treatment with metyrapone.
2003 Aug 22
Low 11-deoxycortisol to cortisol conversion reflects extra-adrenal factors in the majority of women with normo-gonadotrophic normo-estrogenic infertility.
2003 Feb
Transforming growth factor beta1 inhibits aldosterone and cortisol production in the human adrenocortical cell line NCI-H295R through inhibition of CYP11B1 and CYP11B2 expression.
2003 Jan
[The 1(2)-dehydrogenation of steroid substrates by Nocardioides simplex VKM Ac-2033D].
2003 Jan-Feb
Brief undernutrition in late-gestation sheep programs the hypothalamic-pituitary-adrenal axis in adult offspring.
2003 Jul
Monoclonal anti-idiotype antibodies recognizing the variable region of a high-affinity antibody against 11-deoxycortisol. Production, characterization and application to a sensitive noncompetitive immunoassay.
2003 Mar 1
Membrane-initiated steroid signaling (MISS): genomic steroid action starts at the plasma membrane.
2003 May
Reversed-phase high-performance liquid chromatography separation of adrenal steroids prior to radioimmunoassay: application in congenital adrenal hyperplasia.
2003 May-Jun
Dexamethasone does not exert direct intracellular feedback on steroidogenesis in human adrenal NCI-H295A cells.
2003 Oct
Delta sleep response to metyrapone in post-traumatic stress disorder.
2003 Sep
Biological profile of cortexolone 17alpha-propionate (CB-03-01), a new topical and peripherally selective androgen antagonist.
2004
Surface-activated chemical ionization ion trap mass spectrometry in the analysis of 21-deoxycortisol in blood.
2004
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
Steroid profiles using liquid chromatography-tandem mass spectrometry with atmospheric pressure photoionization source.
2004 Apr
Overnight metyrapone and combined dexamethasone/metyrapone tests in post-traumatic stress disorder: preliminary findings.
2004 Aug
Metyrapone as additive treatment in major depression: a double-blind and placebo-controlled trial.
2004 Dec
Metyrapone tests in patients with panic disorder.
2004 Dec 1
3alpha,5beta-Reduced cortisol exhibits antagonist properties on cerebral cortical GABA(A) receptors.
2004 Dec 15
Visualizing the vitreous body in the anterior chamber using 11-deoxycortisol after posterior capsule rupture in an animal model.
2004 Jul
Lack of defects in androgen production in children with hypospadias.
2004 Jun
The impact of polymorphisms in the gene encoding aldosterone synthase (CYP11B2) on steroid synthesis and blood pressure regulation.
2004 Mar 31
Congenital adrenal hyperplasia with 11 beta-hydroxylase deficiency.
2004 Nov
Periconceptional undernutrition in sheep accelerates maturation of the fetal hypothalamic-pituitary-adrenal axis in late gestation.
2004 Sep
Identification of 17,20beta,21-trihydroxy-4-pregnen-3-one as an oocyte maturation-inducing steroid in black porgy, Acanthopagrus schlegeli.
2005 Feb
Genetic variation at the locus encompassing 11-beta hydroxylase and aldosterone synthase accounts for heritability in cortisol precursor (11-deoxycortisol) urinary metabolite excretion.
2005 Feb
Tissue culture of sockeye salmon intestine: functional response of Na+-K+-ATPase to cortisol.
2005 Jun
11beta-Hydroxysteroid dehydrogenase type 2 activity is associated with left ventricular mass in essential hypertension.
2005 Mar
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 May
Patents
Substance Class Chemical
Created
by admin
on Sat Jun 26 00:56:23 UTC 2021
Edited
by admin
on Sat Jun 26 00:56:23 UTC 2021
Record UNII
WDT5SLP0HQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CORTODOXONE
INN   USAN  
INN   USAN  
Official Name English
SK&F 3050
Code English
CORTIFEN
Brand Name English
4-PREGNEN-17.ALPHA.,21-DIOL-3,20-DIONE
Common Name English
17,21-DIHYDROXYPROGESTERONE
Common Name English
HYDROCORTISONE IMPURITY F [EP]
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
11-DEOXYCORTISOL
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
Created by admin on Sat Jun 26 00:56:23 UTC 2021 , Edited by admin on Sat Jun 26 00:56:23 UTC 2021
LOINC 13872-7
Created by admin on Sat Jun 26 00:56:23 UTC 2021 , Edited by admin on Sat Jun 26 00:56:23 UTC 2021
CFR 21 CFR 862.1185
Created by admin on Sat Jun 26 00:56:23 UTC 2021 , Edited by admin on Sat Jun 26 00:56:23 UTC 2021
LOINC 34206-3
Created by admin on Sat Jun 26 00:56:23 UTC 2021 , Edited by admin on Sat Jun 26 00:56:23 UTC 2021
LOINC 1657-6
Created by admin on Sat Jun 26 00:56:23 UTC 2021 , Edited by admin on Sat Jun 26 00:56:23 UTC 2021
LOINC 53339-8
Created by admin on Sat Jun 26 00:56:23 UTC 2021 , Edited by admin on Sat Jun 26 00:56:23 UTC 2021
LOINC 53338-0
Created by admin on Sat Jun 26 00:56:23 UTC 2021 , Edited by admin on Sat Jun 26 00:56:23 UTC 2021
NCI_THESAURUS C521
Created by admin on Sat Jun 26 00:56:23 UTC 2021 , Edited by admin on Sat Jun 26 00:56:23 UTC 2021
LOINC 42572-8
Created by admin on Sat Jun 26 00:56:23 UTC 2021 , Edited by admin on Sat Jun 26 00:56:23 UTC 2021
LOINC 14567-2
Created by admin on Sat Jun 26 00:56:23 UTC 2021 , Edited by admin on Sat Jun 26 00:56:23 UTC 2021
LOINC 34205-5
Created by admin on Sat Jun 26 00:56:23 UTC 2021 , Edited by admin on Sat Jun 26 00:56:23 UTC 2021
LOINC 45184-9
Created by admin on Sat Jun 26 00:56:23 UTC 2021 , Edited by admin on Sat Jun 26 00:56:23 UTC 2021
LOINC 50071-0
Created by admin on Sat Jun 26 00:56:23 UTC 2021 , Edited by admin on Sat Jun 26 00:56:23 UTC 2021
LOINC 25315-3
Created by admin on Sat Jun 26 00:56:23 UTC 2021 , Edited by admin on Sat Jun 26 00:56:23 UTC 2021
LOINC 34204-8
Created by admin on Sat Jun 26 00:56:23 UTC 2021 , Edited by admin on Sat Jun 26 00:56:23 UTC 2021
Code System Code Type Description
CAS
152-58-9
Created by admin on Sat Jun 26 00:56:23 UTC 2021 , Edited by admin on Sat Jun 26 00:56:23 UTC 2021
PRIMARY
MERCK INDEX
M4203
Created by admin on Sat Jun 26 00:56:23 UTC 2021 , Edited by admin on Sat Jun 26 00:56:23 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
205-805-2
Created by admin on Sat Jun 26 00:56:23 UTC 2021 , Edited by admin on Sat Jun 26 00:56:23 UTC 2021
PRIMARY
PUBCHEM
440707
Created by admin on Sat Jun 26 00:56:23 UTC 2021 , Edited by admin on Sat Jun 26 00:56:23 UTC 2021
PRIMARY
FDA UNII
WDT5SLP0HQ
Created by admin on Sat Jun 26 00:56:23 UTC 2021 , Edited by admin on Sat Jun 26 00:56:23 UTC 2021
PRIMARY
EPA CompTox
152-58-9
Created by admin on Sat Jun 26 00:56:23 UTC 2021 , Edited by admin on Sat Jun 26 00:56:23 UTC 2021
PRIMARY
ChEMBL
CHEMBL253144
Created by admin on Sat Jun 26 00:56:23 UTC 2021 , Edited by admin on Sat Jun 26 00:56:23 UTC 2021
PRIMARY
WIKIPEDIA
CORTODOXONE
Created by admin on Sat Jun 26 00:56:23 UTC 2021 , Edited by admin on Sat Jun 26 00:56:23 UTC 2021
PRIMARY
INN
1830
Created by admin on Sat Jun 26 00:56:23 UTC 2021 , Edited by admin on Sat Jun 26 00:56:23 UTC 2021
PRIMARY
EVMPD
SUB06810MIG
Created by admin on Sat Jun 26 00:56:23 UTC 2021 , Edited by admin on Sat Jun 26 00:56:23 UTC 2021
PRIMARY
NCI_THESAURUS
C80813
Created by admin on Sat Jun 26 00:56:23 UTC 2021 , Edited by admin on Sat Jun 26 00:56:23 UTC 2021
PRIMARY
MESH
C058175
Created by admin on Sat Jun 26 00:56:23 UTC 2021 , Edited by admin on Sat Jun 26 00:56:23 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY