Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C26H38O4 |
Molecular Weight | 414.5775 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC[C@H](C(=O)COC(=O)C(C)(C)C)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CCC4=CC(=O)CC[C@]34C
InChI
InChIKey=VVOIQBFMTVCINR-WWMZEODYSA-N
InChI=1S/C26H38O4/c1-24(2,3)23(29)30-15-22(28)21-9-8-19-18-7-6-16-14-17(27)10-12-25(16,4)20(18)11-13-26(19,21)5/h14,18-21H,6-13,15H2,1-5H3/t18-,19-,20-,21+,25-,26-/m0/s1
DescriptionCurator'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
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
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL1994 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17132855 |
0.01 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | PERCORTEN V Approved UseFor use as replacement therapy for the mineralocorticoid deficit in dogs with primary adrenocortical insufficiency |
PubMed
Title | Date | PubMed |
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Effects of desoxycorticosterone acetate (DOCA) plus saline drinking on gentamicin-mediated nephropathy in rats. | 1992 |
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Myocardial performance of STZ-diabetic DOCA-hypertensive rats. | 1992 Dec |
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Influence of enalapril on the endothelial function of DOCA-salt hypertensive rats. | 2000 Feb |
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Primary culture system of adrenocortical cells from dogs to evaluate direct effects of chemicals on steroidogenesis. | 2001 Aug 28 |
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Messenger RNA of steroid 21-hydroxylase (CYP21) is expressed in the human hippocampus. | 2001 Aug 3 |
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Arterial epidermal growth factor receptor expression in deoxycorticosterone acetate-salt hypertension. | 2001 Dec 1 |
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Effects of 18-hydroxylated steroids on corticosteroid production by human aldosterone synthase and 11beta-hydroxylase. | 2001 Sep |
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The effect of amino-acid substitutions I112P, D147E and K152N in CYP11B2 on the catalytic activities of the enzyme. | 2002 Feb |
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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 |
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Membrane-bound progesterone receptors coupled to G proteins in the fungus Rhizopus nigricans. | 2002 Jul 16 |
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Modulation of steroid hydroxylase activity in stably transfected V79MZh11B1 and V79MZh11B2 cells by PKC and PKD inhibitors. | 2002 Nov |
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Interrenal steroid 21-hydroxylase in eels: primary structure, progesterone-specific activity and enhanced expression by ACTH. | 2003 Oct |
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The serotonin transporter is present and functional in peripheral arterial smooth muscle. | 2004 Jun |
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The human mineralocorticoid receptor only partially differentiates between different ligands after expression in fission yeast. | 2005 Apr |
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The aldosterone synthase (CYP11B2) and 11beta-hydroxylase (CYP11B1) genes are not expressed in the rat heart. | 2005 Dec |
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Molecular identity and gene expression of aldosterone synthase cytochrome P450. | 2005 Dec 9 |
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Adrenocortical carcinoma producing 11-deoxycorticosterone: a rare cause of mineralocorticoid hypertension. | 2005 Jan |
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Role of activation function domain-1, DNA binding, and coactivator GRIP1 in the expression of partial agonist activity of glucocorticoid receptor-antagonist complexes. | 2005 Mar 8 |
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NAD(P)H oxidase/nitric oxide interactions in peroxisome proliferator activated receptor (PPAR)alpha-mediated cardiovascular effects. | 2005 Nov 11 |
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Bifunctional gonadotropin-releasing hormone antagonist-progesterone analogs with increased efficacy and duration of action. | 2006 Jan |
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Hydration of rainbow trout oocyte during meiotic maturation and in vitro regulation by 17,20{beta}-dihydroxy-4-pregnen-3-one and cortisol. | 2006 Mar |
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Construction of 3D models of the CYP11B family as a tool to predict ligand binding characteristics. | 2007 Aug |
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Evolution of the corticosteroid receptor signalling pathway in fish. | 2007 Aug-Sep |
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Elevated cardiac tissue level of aldosterone and mineralocorticoid receptor in diastolic heart failure: Beneficial effects of mineralocorticoid receptor blocker. | 2007 Feb |
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Salivary cortisol and DHEA levels in the Korean population: age-related differences, diurnal rhythm, and correlations with serum levels. | 2007 Jun 30 |
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Aldosterone induces epithelial-mesenchymal transition via ROS of mitochondrial origin. | 2007 Sep |
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Quantitative determination of progesterones and corticosteroids in human urine using gas chromatography/mass spectrometry: application to pelvic organ prolapse patients. | 2008 Apr |
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Glucocorticoid receptor phosphorylation differentially affects target gene expression. | 2008 Aug |
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Depot-specific steroidogenic gene transcription in human adipose tissue. | 2008 Dec |
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Classification Tree | Code System | Code | ||
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EMA VETERINARY ASSESSMENT REPORTS |
Zycortal [AUTHORISED]
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NCI_THESAURUS |
C521
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CFR |
21 CFR 522.535
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212-366-0
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DB01134
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22537
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C019323
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m11963
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808-48-0
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1175004
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50782
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Desoxycorticosterone pivalate
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100000090442
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16665T4A2X
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SUB01603MIG
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16665T4A2X
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C65370
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11876263
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CHEMBL1200592
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95278
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822
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DTXSID8046036
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CHEMBL1401691
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ACTIVE MOIETY
SUBSTANCE RECORD