U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of DESOXYCORTICOSTERONE PIVALATE

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

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
Effects of desoxycorticosterone acetate (DOCA) plus saline drinking on gentamicin-mediated nephropathy in rats.
1992
Myocardial performance of STZ-diabetic DOCA-hypertensive rats.
1992 Dec
Influence of enalapril on the endothelial function of DOCA-salt hypertensive rats.
2000 Feb
Primary culture system of adrenocortical cells from dogs to evaluate direct effects of chemicals on steroidogenesis.
2001 Aug 28
Messenger RNA of steroid 21-hydroxylase (CYP21) is expressed in the human hippocampus.
2001 Aug 3
Arterial epidermal growth factor receptor expression in deoxycorticosterone acetate-salt hypertension.
2001 Dec 1
Effects of 18-hydroxylated steroids on corticosteroid production by human aldosterone synthase and 11beta-hydroxylase.
2001 Sep
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
Membrane-bound progesterone receptors coupled to G proteins in the fungus Rhizopus nigricans.
2002 Jul 16
Modulation of steroid hydroxylase activity in stably transfected V79MZh11B1 and V79MZh11B2 cells by PKC and PKD inhibitors.
2002 Nov
Interrenal steroid 21-hydroxylase in eels: primary structure, progesterone-specific activity and enhanced expression by ACTH.
2003 Oct
The serotonin transporter is present and functional in peripheral arterial smooth muscle.
2004 Jun
The human mineralocorticoid receptor only partially differentiates between different ligands after expression in fission yeast.
2005 Apr
The aldosterone synthase (CYP11B2) and 11beta-hydroxylase (CYP11B1) genes are not expressed in the rat heart.
2005 Dec
Molecular identity and gene expression of aldosterone synthase cytochrome P450.
2005 Dec 9
Adrenocortical carcinoma producing 11-deoxycorticosterone: a rare cause of mineralocorticoid hypertension.
2005 Jan
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
NAD(P)H oxidase/nitric oxide interactions in peroxisome proliferator activated receptor (PPAR)alpha-mediated cardiovascular effects.
2005 Nov 11
Bifunctional gonadotropin-releasing hormone antagonist-progesterone analogs with increased efficacy and duration of action.
2006 Jan
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
Construction of 3D models of the CYP11B family as a tool to predict ligand binding characteristics.
2007 Aug
Evolution of the corticosteroid receptor signalling pathway in fish.
2007 Aug-Sep
Elevated cardiac tissue level of aldosterone and mineralocorticoid receptor in diastolic heart failure: Beneficial effects of mineralocorticoid receptor blocker.
2007 Feb
Salivary cortisol and DHEA levels in the Korean population: age-related differences, diurnal rhythm, and correlations with serum levels.
2007 Jun 30
Aldosterone induces epithelial-mesenchymal transition via ROS of mitochondrial origin.
2007 Sep
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
Patents

Patents

Sample Use Guides

Unknown
Route of Administration: Intramuscular
In Vitro Use Guide
Unknown
Name Type Language
DESOXYCORTICOSTERONE PIVALATE
GREEN BOOK   ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
PREGN-4-ENE-3,20-DIONE, 21-(2,2-DIMETHYL-1-OXOPROPOXY)-
Systematic Name English
11-Deoxycorticosterone pivalate
Common Name English
DESOXYCORTICOSTERONE PIVALATE [VANDF]
Common Name English
DESOXYCORTICOSTERONE PIVALATE [MI]
Common Name English
DESOXYCORTICOSTERONE PIVALATE [GREEN BOOK]
Common Name English
DESOXYCORTONE PIVALATE
MART.   WHO-DD  
Common Name English
NSC-95278
Code English
DESOXYCORTICOSTERONE TRIMETHYL ACETATE
Common Name English
Desoxycortone pivalate [WHO-DD]
Common Name English
PERCORTEN
Brand Name English
DESOXYCORTONE PIVALATE [EMA EPAR VETERINARY]
Common Name English
DESOXYCORTICOSTERONE TRIMETHYLACETATE
Common Name English
DESOXYCORTONE PIVALATE [MART.]
Common Name English
DESOXYCORTICOSTERONE PIVALATE [USP-RS]
Common Name English
DEOXYCORTONE PIVALATE
Common Name English
DESOXYCORTICOSTERONE PIVALATE [USP MONOGRAPH]
Common Name English
ZYCORTAL
Brand Name English
DESOXYCORTICOSTERONE PIVALATE [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
EMA VETERINARY ASSESSMENT REPORTS Zycortal [AUTHORISED]
Created by admin on Fri Dec 15 16:09:27 GMT 2023 , Edited by admin on Fri Dec 15 16:09:27 GMT 2023
NCI_THESAURUS C521
Created by admin on Fri Dec 15 16:09:27 GMT 2023 , Edited by admin on Fri Dec 15 16:09:27 GMT 2023
CFR 21 CFR 522.535
Created by admin on Fri Dec 15 16:09:27 GMT 2023 , Edited by admin on Fri Dec 15 16:09:27 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
212-366-0
Created by admin on Fri Dec 15 16:09:27 GMT 2023 , Edited by admin on Fri Dec 15 16:09:27 GMT 2023
PRIMARY
DRUG BANK
DB01134
Created by admin on Fri Dec 15 16:09:27 GMT 2023 , Edited by admin on Fri Dec 15 16:09:27 GMT 2023
PRIMARY
RXCUI
22537
Created by admin on Fri Dec 15 16:09:27 GMT 2023 , Edited by admin on Fri Dec 15 16:09:27 GMT 2023
PRIMARY RxNorm
MESH
C019323
Created by admin on Fri Dec 15 16:09:27 GMT 2023 , Edited by admin on Fri Dec 15 16:09:27 GMT 2023
PRIMARY
MERCK INDEX
m11963
Created by admin on Fri Dec 15 16:09:27 GMT 2023 , Edited by admin on Fri Dec 15 16:09:27 GMT 2023
PRIMARY
CAS
808-48-0
Created by admin on Fri Dec 15 16:09:27 GMT 2023 , Edited by admin on Fri Dec 15 16:09:27 GMT 2023
PRIMARY
RS_ITEM_NUM
1175004
Created by admin on Fri Dec 15 16:09:27 GMT 2023 , Edited by admin on Fri Dec 15 16:09:27 GMT 2023
PRIMARY
CHEBI
50782
Created by admin on Fri Dec 15 16:09:27 GMT 2023 , Edited by admin on Fri Dec 15 16:09:27 GMT 2023
PRIMARY
WIKIPEDIA
Desoxycorticosterone pivalate
Created by admin on Fri Dec 15 16:09:27 GMT 2023 , Edited by admin on Fri Dec 15 16:09:27 GMT 2023
PRIMARY
SMS_ID
100000090442
Created by admin on Fri Dec 15 16:09:27 GMT 2023 , Edited by admin on Fri Dec 15 16:09:27 GMT 2023
PRIMARY
DAILYMED
16665T4A2X
Created by admin on Fri Dec 15 16:09:27 GMT 2023 , Edited by admin on Fri Dec 15 16:09:27 GMT 2023
PRIMARY
EVMPD
SUB01603MIG
Created by admin on Fri Dec 15 16:09:27 GMT 2023 , Edited by admin on Fri Dec 15 16:09:27 GMT 2023
PRIMARY
FDA UNII
16665T4A2X
Created by admin on Fri Dec 15 16:09:27 GMT 2023 , Edited by admin on Fri Dec 15 16:09:27 GMT 2023
PRIMARY
NCI_THESAURUS
C65370
Created by admin on Fri Dec 15 16:09:27 GMT 2023 , Edited by admin on Fri Dec 15 16:09:27 GMT 2023
PRIMARY
PUBCHEM
11876263
Created by admin on Fri Dec 15 16:09:27 GMT 2023 , Edited by admin on Fri Dec 15 16:09:27 GMT 2023
PRIMARY
ChEMBL
CHEMBL1200592
Created by admin on Fri Dec 15 16:09:27 GMT 2023 , Edited by admin on Fri Dec 15 16:09:27 GMT 2023
PRIMARY
NSC
95278
Created by admin on Fri Dec 15 16:09:27 GMT 2023 , Edited by admin on Fri Dec 15 16:09:27 GMT 2023
PRIMARY
DRUG CENTRAL
822
Created by admin on Fri Dec 15 16:09:27 GMT 2023 , Edited by admin on Fri Dec 15 16:09:27 GMT 2023
PRIMARY
EPA CompTox
DTXSID8046036
Created by admin on Fri Dec 15 16:09:27 GMT 2023 , Edited by admin on Fri Dec 15 16:09:27 GMT 2023
PRIMARY
ChEMBL
CHEMBL1401691
Created by admin on Fri Dec 15 16:09:27 GMT 2023 , Edited by admin on Fri Dec 15 16:09:27 GMT 2023
PRIMARY