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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H32O4
Molecular Weight 372.4978
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DESOXYCORTICOSTERONE ACETATE

SMILES

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

InChI

InChIKey=VPGRYOFKCNULNK-ACXQXYJUSA-N
InChI=1S/C23H32O4/c1-14(24)27-13-21(26)20-7-6-18-17-5-4-15-12-16(25)8-10-22(15,2)19(17)9-11-23(18,20)3/h12,17-20H,4-11,13H2,1-3H3/t17-,18-,19-,20+,22-,23-/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
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
Pathophysiology of modulation of local glucocorticoid levels by 11beta-hydroxysteroid dehydrogenases.
2001 Dec
Arterial epidermal growth factor receptor expression in deoxycorticosterone acetate-salt hypertension.
2001 Dec 1
Irreversible binding and adrenocorticolytic activity of the DDT metabolite 3-methylsulfonyl-DDE examined in tissue-slice culture.
2001 Feb
Disorders of mineralocorticoid synthesis.
2001 Mar
Effects of 18-hydroxylated steroids on corticosteroid production by human aldosterone synthase and 11beta-hydroxylase.
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
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
A glucocorticoid-responsive mutant androgen receptor exhibits unique ligand specificity: therapeutic implications for androgen-independent prostate cancer.
2002 May
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
Tert-butyl hydroperoxide-mediated vascular responses in DOCA-salt hypertensive rats.
2003 Jan
Effects of chronic quercetin treatment on antioxidant defence system and oxidative status of deoxycorticosterone acetate-salt-hypertensive rats.
2004 Apr
Expression of cytochrome P450c17 and other steroid-converting enzymes in the rat kidney throughout the life-span.
2004 Jun
The serotonin transporter is present and functional in peripheral arterial smooth muscle.
2004 Jun
Reduced NOS3 phosphorylation mediates reduced NO/cGMP signaling in mesenteric arteries of deoxycorticosterone acetate-salt hypertensive rats.
2004 May
The effect of Sutherlandia frutescens on steroidogenesis: confirming indigenous wisdom.
2004 Nov
The adrenocortical tumor cell line NCI-H295R as an in vitro screening system for the evaluation of CYP11B2 (aldosterone synthase) and CYP11B1 (steroid-11beta-hydroxylase) inhibitors.
2005 Aug
Molecular identity and gene expression of aldosterone synthase cytochrome P450.
2005 Dec 9
Mineralocorticoid receptors: distribution and activation.
2005 Jan
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 Jan
Cyclo-oxygenase-2, endothelium and aortic reactivity during deoxycorticosterone acetate salt-induced hypertension.
2005 May
NAD(P)H oxidase/nitric oxide interactions in peroxisome proliferator activated receptor (PPAR)alpha-mediated cardiovascular effects.
2005 Nov 11
Functional effects of genetic variants in the 11beta-hydroxylase (CYP11B1) gene.
2006 Dec
Endothelin-1-induced oxidative stress in DOCA-salt hypertension involves NADPH-oxidase-independent mechanisms.
2006 Feb
Three novel point mutations of the CYP21 gene detected in classical forms of congenital adrenal hyperplasia due to 21-hydroxylase deficiency.
2006 Mar
Mineralocorticoid synthesis during the periovulatory interval in macaques.
2006 Oct
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
The glucuronidation of Delta4-3-Keto C19- and C21-hydroxysteroids by human liver microsomal and recombinant UDP-glucuronosyltransferases (UGTs): 6alpha- and 21-hydroxyprogesterone are selective substrates for UGT2B7.
2007 Mar
Synthesis and structure-activity relationships of a series of increasingly hydrophobic cationic steroid lipofection reagents.
2007 May
Quantitative determination of progesterones and corticosteroids in human urine using gas chromatography/mass spectrometry: application to pelvic organ prolapse patients.
2008 Apr
Glucocorticoid receptor phosphorylation differentially affects target gene expression.
2008 Aug
Depot-specific steroidogenic gene transcription in human adipose tissue.
2008 Dec
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
One single dose of etomidate negatively influences adrenocortical performance for at least 24h in children with meningococcal sepsis.
2008 Jan
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
DESOXYCORTICOSTERONE ACETATE
ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
DESOXYCORTONE ACETATE
EP   MART.   WHO-DD  
Common Name English
11-Deoxycorticosterone acetate
Common Name English
Desoxycortone acetate [WHO-DD]
Common Name English
NSC-9567
Code English
DESOXYCORTICOSTERONE ACETATE [VANDF]
Common Name English
DESOXYCORTICOSTERONE ACETATE [ORANGE BOOK]
Common Name English
DEOXYCORTICOSTERONE ACETATE [MI]
Common Name English
DOCA
Brand Name English
DESOXYCORTONE ACETATE [MART.]
Common Name English
DESOXYCORTICOSTERONE ACETATE [USP-RS]
Common Name English
DESOXYCORTONE ACETATE [EP IMPURITY]
Common Name English
DESOXYCORTICOSTERONE ACETATE [USP IMPURITY]
Common Name English
PREGN-4-ENE-3,20-DIONE, 21-(ACETYLOXY)-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C521
Created by admin on Fri Dec 15 15:15:54 GMT 2023 , Edited by admin on Fri Dec 15 15:15:54 GMT 2023
Code System Code Type Description
FDA UNII
6E0A168OB8
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PRIMARY
RS_ITEM_NUM
1174001
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PRIMARY
MERCK INDEX
m4172
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PRIMARY Merck Index
PUBCHEM
5952
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PRIMARY
DRUG BANK
DB06780
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PRIMARY
EPA CompTox
DTXSID6022894
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PRIMARY
CAS
56-47-3
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PRIMARY
RXCUI
258333
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PRIMARY RxNorm
ECHA (EC/EINECS)
200-275-9
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PRIMARY
NSC
9567
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PRIMARY
DRUG CENTRAL
821
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PRIMARY
WIKIPEDIA
Desoxycorticosterone acetate
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PRIMARY
SMS_ID
100000087757
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PRIMARY
ChEMBL
CHEMBL1200542
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PRIMARY
MESH
C058404
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PRIMARY
EVMPD
SUB01600MIG
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PRIMARY
NCI_THESAURUS
C65369
Created by admin on Fri Dec 15 15:15:54 GMT 2023 , Edited by admin on Fri Dec 15 15:15:54 GMT 2023
PRIMARY