Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H30O3 |
Molecular Weight | 330.4611 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@]34C)[C@@H]1CC[C@@H]2C(=O)CO
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
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 |
---|---|---|---|
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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Neuronal control of the kidney: contribution to hypertension. | 1992 May |
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Functional probing of the human glucocorticoid receptor steroid-interacting surface by site-directed mutagenesis. Gln-642 plays an important role in steroid recognition and binding. | 2000 Jun 23 |
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Baboon cytochrome P450c11 is encoded by more than one gene. | 2000 Nov |
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Deoxycorticosterone suppresses the effects of losartan in nitric oxide-deficient hypertensive rats. | 2000 Nov |
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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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The quantification of endogenous steroids in bovine aqueous humour and vitreous humour using isotope dilution GC-NCI-MS. | 2001 Feb |
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Irreversible binding and adrenocorticolytic activity of the DDT metabolite 3-methylsulfonyl-DDE examined in tissue-slice culture. | 2001 Feb |
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An influence of variation in the aldosterone synthase gene (CYP11B2) on corticosteroid responses to ACTH in normal human subjects. | 2001 Jun |
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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 |
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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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Comparative inhibitory effects of different compounds on rat oatpl (slc21a1)- and Oatp2 (Slc21a5)-mediated transport. | 2002 Feb |
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Expression of 11beta-hydroxylase in rat Leydig cells. | 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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Functional expression of human mitochondrial CYP11B2 in fission yeast and identification of a new internal electron transfer protein, etp1. | 2002 Feb 19 |
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A glucocorticoid-responsive mutant androgen receptor exhibits unique ligand specificity: therapeutic implications for androgen-independent prostate cancer. | 2002 May |
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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 |
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Endothelin-1 increases vascular superoxide via endothelin(A)-NADPH oxidase pathway in low-renin hypertension. | 2003 Feb 25 |
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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 |
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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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Do human vascular endothelial cells produce aldosterone? | 2004 Aug |
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Mineralocorticoid receptors: distribution and activation. | 2005 Jan |
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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 |
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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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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 |
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Aldosterone synthase deficiency caused by a homozygous L451F mutation in the CYP11B2 gene. | 2008 Apr |
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Glucocorticoid receptor phosphorylation differentially affects target gene expression. | 2008 Aug |
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The transcription of steroidogenic genes in the human cerebellum and hippocampus: a comparative survey of normal and Alzheimer's tissue. | 2008 Jan |
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ACTIVE MOIETY