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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H30O3
Molecular Weight 330.4619
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DESOXYCORTONE

SMILES

C[C@@]12CCC(=O)C=C2CC[C@@]3([H])[C@]4([H])CC[C@]([H])(C(=O)CO)[C@@]4(C)CC[C@@]31[H]

InChI

InChIKey=ZESRJSPZRDMNHY-YFWFAHHUSA-N
InChI=1S/C21H30O3/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/h11,15-18,22H,3-10,12H2,1-2H3/t15-,16-,17-,18+,20-,21-/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including http://www.canineaddisonsinfo.com/Percorten_Florinef.html http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Summary_for_the_public/veterinary/003782/WC500196487.pdf

Desoxycorticosterone pivalate (DOCP) is a mineralocorticoid hormone and an analog of desoxycorticosterone. DOCP is a long-acting ester of desoxycorticosterone acetate (DOCA) which is recognized as having the same qualitative effects as the natural mineralocorticoid hormone aldosterone. It’s used as Percorten-V for replacement therapy for the mineralocorticoid deficit in dogs with primary adrenocortical insufficiency. Percorten-V is only available in the U.S., Canada, Australia and recently, Denmark. Percorten was originally developed for the treatment of Addison's disease in humans but the demand for it decreased significantly once Florinef was available. Unaware that their product was being prescribed “off-label” for the treatment of canine Addison’s Disease and faced with a decreased demand for Percorten, the manufacturer *almost* discontinued production until the veterinary community rose up and voiced their distress. Field trials were run and the FDA approved the use of Percorten-V (the "v" is for veterinary). DOCP like other adrenocorticoid hormones is thought to act by controlling the rate of synthesis of proteins. It reacts with receptor proteins in the cytoplasm to form a steroid-receptor complex. This complex moves into the nucleus, where it binds to chromatin that result in genetic transcription of cellular DNA to messenger RNA. The steroid hormones appear to induce transcription and synthesis of specific proteins, which produce the physiologic effects seen after administration. The most important effect of DOCP is to increase the rate of renal tubular absorption of sodium. This effect is seen most intensely in the thick portion of the ascending limb of the loop of Henle. It also increases sodium absorption in the proximal convoluted tubule but this effect is less important in sodium retention. Chloride follows the sodium out of the renal tubule. Another important effect of DOCP is enhanced renal excretion of potassium. This effect is driven by the resorption of sodium that pulls potassium from the extracellular fluid into the renal tubules, thus promoting potassium excretion.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.01 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
PERCORTEN V

Approved Use

For use as replacement therapy for the mineralocorticoid deficit in dogs with primary adrenocortical insufficiency
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Myocardial performance of STZ-diabetic DOCA-hypertensive rats.
1992 Dec
Neuronal control of the kidney: contribution to hypertension.
1992 May
Corticotropin effects on blood pressure and fluid and electrolyte homeostasis in five strains of rats.
1992 May
Baboon cytochrome P450c11 is encoded by more than one gene.
2000 Nov
Deoxycorticosterone suppresses the effects of losartan in nitric oxide-deficient hypertensive rats.
2000 Nov
Diagnosis of adrenal cortical dysfunction by liquid chromatography-tandem mass spectrometry.
2001 Apr
Primary culture system of adrenocortical cells from dogs to evaluate direct effects of chemicals on steroidogenesis.
2001 Aug 28
Gender-related plasma levels of progesterone, interleukin-8 and interleukin-10 during and after cardiopulmonary bypass in infants and children.
2001 Dec
Arterial epidermal growth factor receptor expression in deoxycorticosterone acetate-salt hypertension.
2001 Dec 1
The quantification of endogenous steroids in bovine aqueous humour and vitreous humour using isotope dilution GC-NCI-MS.
2001 Feb
Irreversible binding and adrenocorticolytic activity of the DDT metabolite 3-methylsulfonyl-DDE examined in tissue-slice culture.
2001 Feb
Selective hypoaldosteronism due to combined defects of the conversion from inactive renin to active renin and the aldosterone biosynthesis from corticosterone.
2001 Jul
An influence of variation in the aldosterone synthase gene (CYP11B2) on corticosteroid responses to ACTH in normal human subjects.
2001 Jun
Disorders of mineralocorticoid synthesis.
2001 Mar
Inhibition of aldosterone production in rat adrenal mitochondria by 18-ethynyl-11-deoxycorticosterone: a simple model for kinetic interpretation of mechanism-based inhibitors.
2001 Mar
17alpha-hydroxylase deficiency accompanied by adrenal myelolipoma.
2001 Sep
Effects of 18-hydroxylated steroids on corticosteroid production by human aldosterone synthase and 11beta-hydroxylase.
2001 Sep
Mineralocorticoids upregulate arterial contraction to epidermal growth factor.
2001 Sep
Comparative inhibitory effects of different compounds on rat oatpl (slc21a1)- and Oatp2 (Slc21a5)-mediated transport.
2002 Feb
The effect of amino-acid substitutions I112P, D147E and K152N in CYP11B2 on the catalytic activities of the enzyme.
2002 Feb
Expression of 11beta-hydroxylase in rat Leydig cells.
2002 Feb
Gene transfer of endothelial NO synthase and manganese superoxide dismutase on arterial vascular cell adhesion molecule-1 expression and superoxide production in deoxycorticosterone acetate-salt hypertension.
2002 Feb 1
Functional expression of human mitochondrial CYP11B2 in fission yeast and identification of a new internal electron transfer protein, etp1.
2002 Feb 19
A glucocorticoid-responsive mutant androgen receptor exhibits unique ligand specificity: therapeutic implications for androgen-independent prostate cancer.
2002 May
Modulation of steroid hydroxylase activity in stably transfected V79MZh11B1 and V79MZh11B2 cells by PKC and PKD inhibitors.
2002 Nov
Blood pressure effects of intravenous apomorphine in conscious deoxycorticosterone-acetate salt-hypertensive rats.
2003 Dec
Ghrelin and growth hormone secretagogue receptor are expressed in the rat adrenal cortex: Evidence that ghrelin stimulates the growth, but not the secretory activity of adrenal cells.
2003 Feb 11
Endothelin-1 increases vascular superoxide via endothelin(A)-NADPH oxidase pathway in low-renin hypertension.
2003 Feb 25
Analysis of biological samples by gas chromatography-mass spectrometry without a reference standard: measurement of urinary 18-hydroxytetrahydro-11-dehydrocorticosterone excretion rate in human subjects.
2003 Feb 5
Tert-butyl hydroperoxide-mediated vascular responses in DOCA-salt hypertensive rats.
2003 Jan
Determination of 3-keto-4-ene steroids and their hydroxylated metabolites catalyzed by recombinant human cytochrome P450 1B1 enzyme using gas chromatography-mass spectrometry with trimethylsilyl derivatization.
2003 Jul 5
Effects of chronic quercetin treatment on antioxidant defence system and oxidative status of deoxycorticosterone acetate-salt-hypertensive rats.
2004 Apr
Coexistence of different phenotypes in a family with glucocorticoid-remediable aldosteronism.
2004 Jan
Lack of defects in androgen production in children with hypospadias.
2004 Jun
The regulation of aldosterone synthase expression.
2004 Mar 31
The effect of Sutherlandia frutescens on steroidogenesis: confirming indigenous wisdom.
2004 Nov
The human mineralocorticoid receptor only partially differentiates between different ligands after expression in fission yeast.
2005 Apr
Molecular identity and gene expression of aldosterone synthase cytochrome P450.
2005 Dec 9
Mineralocorticoid receptors: distribution and activation.
2005 Jan
Adrenocortical carcinoma producing 11-deoxycorticosterone: a rare cause of mineralocorticoid hypertension.
2005 Jan
The residue E351 is essential for the activity of human 21-hydroxylase: evidence from a naturally occurring novel point mutation compared with artificial mutants generated by single amino acid substitutions.
2005 Jul
Biochemical characterization of the Arctic char (Salvelinus alpinus) ovarian progestin membrane receptor.
2005 Nov 10
Calcitonin gene-related peptide and hypertension.
2005 Sep
In vivo effects of thyroid hormone, corticosteroids and prolactin on cell proliferation and apoptosis in the anterior intestine of the euryhaline mudskipper (Periophthalmus modestus).
2006 Oct 4
Elevated cardiac tissue level of aldosterone and mineralocorticoid receptor in diastolic heart failure: Beneficial effects of mineralocorticoid receptor blocker.
2007 Feb
Salivary cortisol and DHEA levels in the Korean population: age-related differences, diurnal rhythm, and correlations with serum levels.
2007 Jun 30
Glucocorticoid receptor phosphorylation differentially affects target gene expression.
2008 Aug
Novel mutation in cytochrome P450c17 causes complete combined 17alpha-hydroxylase/17,20-lyase deficiency.
2008 Feb
Effects of ACTH, dexamethasone, and adrenalectomy on 11beta-hydroxylase (CYP11B1) and aldosterone synthase (CYP11B2) gene expression in the rat central nervous system.
2008 Feb
Real-time analysis of gene regulation by glucocorticoid hormones.
2008 May
Patents

Patents

Sample Use Guides

Unknown
Route of Administration: Intramuscular
In Vitro Use Guide
Unknown
Name Type Language
DESOXYCORTONE
INN   MART.   WHO-DD  
INN  
Official Name English
DESOXYCORTONE [MART.]
Common Name English
21-HYDROXYPROGESTERONE
Common Name English
DESOXYCORTICOSTERONE
VANDF  
Common Name English
DEOXYCORTICOSTERONE
MI  
Common Name English
11-DEOXYCORTICOSTERONE
Common Name English
DESOXYCORTONE [WHO-DD]
Common Name English
21-HYDROXY-PREGN-4-ENE-3,20-DIONE
Systematic Name English
NSC-11319
Code English
DEOXYCORTONE
Common Name English
21-HYDROXY-.DELTA.4-PREGNENE-3,20-DIONE
Systematic Name English
PREGN-4-ENE-3,20-DIONE, 21-HYDROXY-
Systematic Name English
DESOXYCORTONE [INN]
Common Name English
DEOXYCORTICOSTERONE [MI]
Common Name English
DESOXYCORTICOSTERONE [VANDF]
Common Name English
Classification Tree Code System Code
LOINC 16110-9
Created by admin on Fri Jun 25 22:55:07 UTC 2021 , Edited by admin on Fri Jun 25 22:55:07 UTC 2021
LOINC 42855-7
Created by admin on Fri Jun 25 22:55:07 UTC 2021 , Edited by admin on Fri Jun 25 22:55:07 UTC 2021
LOINC 40811-2
Created by admin on Fri Jun 25 22:55:07 UTC 2021 , Edited by admin on Fri Jun 25 22:55:07 UTC 2021
LOINC 53348-9
Created by admin on Fri Jun 25 22:55:07 UTC 2021 , Edited by admin on Fri Jun 25 22:55:07 UTC 2021
NCI_THESAURUS C521
Created by admin on Fri Jun 25 22:55:07 UTC 2021 , Edited by admin on Fri Jun 25 22:55:07 UTC 2021
LOINC 1656-8
Created by admin on Fri Jun 25 22:55:07 UTC 2021 , Edited by admin on Fri Jun 25 22:55:07 UTC 2021
LOINC 44729-2
Created by admin on Fri Jun 25 22:55:07 UTC 2021 , Edited by admin on Fri Jun 25 22:55:07 UTC 2021
CFR 21 CFR 862.1250
Created by admin on Fri Jun 25 22:55:07 UTC 2021 , Edited by admin on Fri Jun 25 22:55:07 UTC 2021
LOINC 25561-2
Created by admin on Fri Jun 25 22:55:07 UTC 2021 , Edited by admin on Fri Jun 25 22:55:07 UTC 2021
WHO-ATC H02AA03
Created by admin on Fri Jun 25 22:55:07 UTC 2021 , Edited by admin on Fri Jun 25 22:55:07 UTC 2021
LOINC 53347-1
Created by admin on Fri Jun 25 22:55:07 UTC 2021 , Edited by admin on Fri Jun 25 22:55:07 UTC 2021
WHO-VATC QH02AA03
Created by admin on Fri Jun 25 22:55:07 UTC 2021 , Edited by admin on Fri Jun 25 22:55:07 UTC 2021
LOINC 40818-7
Created by admin on Fri Jun 25 22:55:07 UTC 2021 , Edited by admin on Fri Jun 25 22:55:07 UTC 2021
LOINC 55808-0
Created by admin on Fri Jun 25 22:55:07 UTC 2021 , Edited by admin on Fri Jun 25 22:55:07 UTC 2021
Code System Code Type Description
FDA UNII
40GP35YQ49
Created by admin on Fri Jun 25 22:55:07 UTC 2021 , Edited by admin on Fri Jun 25 22:55:07 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-596-4
Created by admin on Fri Jun 25 22:55:07 UTC 2021 , Edited by admin on Fri Jun 25 22:55:07 UTC 2021
PRIMARY
DRUG CENTRAL
820
Created by admin on Fri Jun 25 22:55:07 UTC 2021 , Edited by admin on Fri Jun 25 22:55:07 UTC 2021
PRIMARY
WIKIPEDIA
11-DEOXYCORTICOSTERONE
Created by admin on Fri Jun 25 22:55:07 UTC 2021 , Edited by admin on Fri Jun 25 22:55:07 UTC 2021
PRIMARY
ChEMBL
CHEMBL1200542
Created by admin on Fri Jun 25 22:55:07 UTC 2021 , Edited by admin on Fri Jun 25 22:55:07 UTC 2021
PRIMARY
RXCUI
3256
Created by admin on Fri Jun 25 22:55:07 UTC 2021 , Edited by admin on Fri Jun 25 22:55:07 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C72737
Created by admin on Fri Jun 25 22:55:07 UTC 2021 , Edited by admin on Fri Jun 25 22:55:07 UTC 2021
PRIMARY
INN
387
Created by admin on Fri Jun 25 22:55:07 UTC 2021 , Edited by admin on Fri Jun 25 22:55:07 UTC 2021
PRIMARY
MERCK INDEX
M4172
Created by admin on Fri Jun 25 22:55:07 UTC 2021 , Edited by admin on Fri Jun 25 22:55:07 UTC 2021
PRIMARY Merck Index
PUBCHEM
6166
Created by admin on Fri Jun 25 22:55:07 UTC 2021 , Edited by admin on Fri Jun 25 22:55:07 UTC 2021
PRIMARY
EPA CompTox
64-85-7
Created by admin on Fri Jun 25 22:55:07 UTC 2021 , Edited by admin on Fri Jun 25 22:55:07 UTC 2021
PRIMARY
MESH
D003900
Created by admin on Fri Jun 25 22:55:07 UTC 2021 , Edited by admin on Fri Jun 25 22:55:07 UTC 2021
PRIMARY
CAS
64-85-7
Created by admin on Fri Jun 25 22:55:07 UTC 2021 , Edited by admin on Fri Jun 25 22:55:07 UTC 2021
PRIMARY
EVMPD
SUB07007MIG
Created by admin on Fri Jun 25 22:55:07 UTC 2021 , Edited by admin on Fri Jun 25 22:55:07 UTC 2021
PRIMARY