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
Molecular Formula | C26H38O4 |
Molecular Weight | 414.5775 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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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Effects of desoxycorticosterone acetate (DOCA) plus saline drinking on gentamicin-mediated nephropathy in rats. | 1992 |
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19-Nor-deoxycorticosterone production from aldosterone-producing adenomas. | 1992 Apr |
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Influence of enalapril on the endothelial function of DOCA-salt hypertensive rats. | 2000 Feb |
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Deoxycorticosterone suppresses the effects of losartan in nitric oxide-deficient hypertensive rats. | 2000 Nov |
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Diagnosis of adrenal cortical dysfunction by liquid chromatography-tandem mass spectrometry. | 2001 Apr |
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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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Disorders of mineralocorticoid synthesis. | 2001 Mar |
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17alpha-hydroxylase deficiency accompanied by adrenal myelolipoma. | 2001 Sep |
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Mineralocorticoids upregulate arterial contraction to epidermal growth factor. | 2001 Sep |
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Reference values for urinary steroids in Japanese newborn infants: gas chromatography/mass spectrometry in selected ion monitoring. | 2003 Dec |
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Blood pressure effects of intravenous apomorphine in conscious deoxycorticosterone-acetate salt-hypertensive rats. | 2003 Dec |
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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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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 |
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Norbormide enhances late steps of steroid-hormone synthesis in rat and mouse adrenal cortex. | 2003 Mar |
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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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Steroid 21-hydroxylase expression in cultured rat astrocytes. | 2003 Oct 15 |
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Coexistence of different phenotypes in a family with glucocorticoid-remediable aldosteronism. | 2004 Jan |
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Reduced NOS3 phosphorylation mediates reduced NO/cGMP signaling in mesenteric arteries of deoxycorticosterone acetate-salt hypertensive rats. | 2004 May |
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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 |
|
Adrenocortical carcinoma producing 11-deoxycorticosterone: a rare cause of mineralocorticoid hypertension. | 2005 Jan |
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11-deoxycorticosterone is a potent agonist of the rainbow trout (Oncorhynchus mykiss) mineralocorticoid receptor. | 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 |
|
Differential expression and function of beacon in the rat adrenal cortex and medulla. | 2005 Jul |
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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 |
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Cyclo-oxygenase-2, endothelium and aortic reactivity during deoxycorticosterone acetate salt-induced hypertension. | 2005 May |
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Biochemical characterization of the Arctic char (Salvelinus alpinus) ovarian progestin membrane receptor. | 2005 Nov 10 |
|
Design of an Escherichia coli system for whole cell mediated steroid synthesis and molecular evolution of steroid hydroxylases. | 2006 Jun 25 |
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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 |
|
Mineralocorticoid synthesis during the periovulatory interval in macaques. | 2006 Oct |
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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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[11beta-hydroxylase deficiency: improvement of final height with growth hormone and gonadotropin-releasing hormone analog]. | 2007 Aug |
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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 |
|
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 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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Novel mutation in cytochrome P450c17 causes complete combined 17alpha-hydroxylase/17,20-lyase deficiency. | 2008 Feb |
|
One single dose of etomidate negatively influences adrenocortical performance for at least 24h in children with meningococcal sepsis. | 2008 Jan |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:09:27 GMT 2023
by
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on
Fri Dec 15 16:09:27 GMT 2023
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Record UNII |
16665T4A2X
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Record Status |
Validated (UNII)
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Record Version |
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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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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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DTXSID8046036
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CHEMBL1401691
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ACTIVE MOIETY |