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
[H][C@@]12CC[C@H](C(=O)CO)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CCC4=CC(=O)CC[C@]34C
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
Molecular Formula | C21H30O3 |
Molecular Weight | 330.4611 |
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 |
---|---|---|---|---|
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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Extraadrenal expression of steroid 21-hydroxylase and 11 beta-hydroxylase by a benign testicular Leydig cell tumor. | 1991 Dec |
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19-Nor-deoxycorticosterone production from aldosterone-producing adenomas. | 1992 Apr |
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Myocardial performance of STZ-diabetic DOCA-hypertensive rats. | 1992 Dec |
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Neuronal control of the kidney: contribution to hypertension. | 1992 May |
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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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A glucocorticoid-responsive mutant androgen receptor exhibits unique ligand specificity: therapeutic implications for androgen-independent prostate cancer. | 2002 May |
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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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Endothelin-1 increases vascular superoxide via endothelin(A)-NADPH oxidase pathway in low-renin hypertension. | 2003 Feb 25 |
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Tert-butyl hydroperoxide-mediated vascular responses in DOCA-salt hypertensive rats. | 2003 Jan |
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Norbormide enhances late steps of steroid-hormone synthesis in rat and mouse adrenal cortex. | 2003 Mar |
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Steroid 21-hydroxylase expression in cultured rat astrocytes. | 2003 Oct 15 |
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Effects of chronic quercetin treatment on antioxidant defence system and oxidative status of deoxycorticosterone acetate-salt-hypertensive rats. | 2004 Apr |
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Do human vascular endothelial cells produce aldosterone? | 2004 Aug |
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Expression of cytochrome P450c17 and other steroid-converting enzymes in the rat kidney throughout the life-span. | 2004 Jun |
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Lack of defects in androgen production in children with hypospadias. | 2004 Jun |
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The serotonin transporter is present and functional in peripheral arterial smooth muscle. | 2004 Jun |
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The regulation of aldosterone synthase expression. | 2004 Mar 31 |
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The effect of Sutherlandia frutescens on steroidogenesis: confirming indigenous wisdom. | 2004 Nov |
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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 |
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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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11-deoxycorticosterone is a potent agonist of the rainbow trout (Oncorhynchus mykiss) mineralocorticoid receptor. | 2005 Jan |
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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 |
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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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Cyclo-oxygenase-2, endothelium and aortic reactivity during deoxycorticosterone acetate salt-induced hypertension. | 2005 May |
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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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Functional effects of genetic variants in the 11beta-hydroxylase (CYP11B1) gene. | 2006 Dec |
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Endothelin-1-induced oxidative stress in DOCA-salt hypertension involves NADPH-oxidase-independent mechanisms. | 2006 Feb |
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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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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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Evolution of the corticosteroid receptor signalling pathway in fish. | 2007 Aug-Sep |
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Severe loss-of-function mutations in the adrenocorticotropin receptor (ACTHR, MC2R) can be found in patients diagnosed with salt-losing adrenal hypoplasia. | 2007 Feb |
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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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Concomitant secretion of glucocorticoid, androgens, and mineralocorticoid by an adrenocortical carcinoma: case report and review of literature. | 2007 Jul-Aug |
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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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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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Adrenal 20alpha-hydroxysteroid dehydrogenase in the mouse catabolizes progesterone and 11-deoxycorticosterone and is restricted to the X-zone. | 2007 Mar |
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Synthesis and structure-activity relationships of a series of increasingly hydrophobic cationic steroid lipofection reagents. | 2007 May |
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The role of polyester interstitium and aldosterone during structural development of renal tubules in serum-free medium. | 2007 Oct |
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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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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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Novel mutation in cytochrome P450c17 causes complete combined 17alpha-hydroxylase/17,20-lyase deficiency. | 2008 Feb |
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Effects of ACTH, dexamethasone, and adrenalectomy on 11beta-hydroxylase (CYP11B1) and aldosterone synthase (CYP11B2) gene expression in the rat central nervous system. | 2008 Feb |
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Purification and functional characterization of human 11beta hydroxylase expressed in Escherichia coli. | 2008 Feb |
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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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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
Substance Class |
Chemical
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on
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Fri Dec 15 16:02:37 GMT 2023
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Record UNII |
40GP35YQ49
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Validated (UNII)
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21 CFR 862.1250
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25561-2
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H02AA03
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53347-1
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QH02AA03
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40818-7
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55808-0
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11-DEOXYCORTICOSTERONE
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