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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H32O4
Molecular Weight 372.4978
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DESOXYCORTICOSTERONE ACETATE

SMILES

[H][C@@]12CC[C@H](C(=O)COC(C)=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CCC4=CC(=O)CC[C@]34C

InChI

InChIKey=VPGRYOFKCNULNK-ACXQXYJUSA-N
InChI=1S/C23H32O4/c1-14(24)27-13-21(26)20-7-6-18-17-5-4-15-12-16(25)8-10-22(15,2)19(17)9-11-23(18,20)3/h12,17-20H,4-11,13H2,1-3H3/t17-,18-,19-,20+,22-,23-/m0/s1

HIDE SMILES / InChI

Molecular Formula C23H32O4
Molecular Weight 372.4978
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Extraadrenal expression of steroid 21-hydroxylase and 11 beta-hydroxylase by a benign testicular Leydig cell tumor.
1991 Dec
19-Nor-deoxycorticosterone production from aldosterone-producing adenomas.
1992 Apr
Myocardial performance of STZ-diabetic DOCA-hypertensive rats.
1992 Dec
Corticotropin effects on blood pressure and fluid and electrolyte homeostasis in five strains of rats.
1992 May
Reference values for urinary steroids in Japanese newborn infants: gas chromatography/mass spectrometry in selected ion monitoring.
2003 Dec
Blood pressure effects of intravenous apomorphine in conscious deoxycorticosterone-acetate salt-hypertensive rats.
2003 Dec
Endothelin-1 increases vascular superoxide via endothelin(A)-NADPH oxidase pathway in low-renin hypertension.
2003 Feb 25
Tert-butyl hydroperoxide-mediated vascular responses in DOCA-salt hypertensive rats.
2003 Jan
Norbormide enhances late steps of steroid-hormone synthesis in rat and mouse adrenal cortex.
2003 Mar
Effects of chronic quercetin treatment on antioxidant defence system and oxidative status of deoxycorticosterone acetate-salt-hypertensive rats.
2004 Apr
Do human vascular endothelial cells produce aldosterone?
2004 Aug
Coexistence of different phenotypes in a family with glucocorticoid-remediable aldosteronism.
2004 Jan
Expression of cytochrome P450c17 and other steroid-converting enzymes in the rat kidney throughout the life-span.
2004 Jun
The serotonin transporter is present and functional in peripheral arterial smooth muscle.
2004 Jun
The regulation of aldosterone synthase expression.
2004 Mar 31
The human mineralocorticoid receptor only partially differentiates between different ligands after expression in fission yeast.
2005 Apr
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
Molecular identity and gene expression of aldosterone synthase cytochrome P450.
2005 Dec 9
Mineralocorticoid receptors: distribution and activation.
2005 Jan
Adrenocortical carcinoma producing 11-deoxycorticosterone: a rare cause of mineralocorticoid hypertension.
2005 Jan
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
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
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
Cyclo-oxygenase-2, endothelium and aortic reactivity during deoxycorticosterone acetate salt-induced hypertension.
2005 May
Biochemical characterization of the Arctic char (Salvelinus alpinus) ovarian progestin membrane receptor.
2005 Nov 10
NAD(P)H oxidase/nitric oxide interactions in peroxisome proliferator activated receptor (PPAR)alpha-mediated cardiovascular effects.
2005 Nov 11
Calcitonin gene-related peptide and hypertension.
2005 Sep
Steroid signalling in the ovarian surface epithelium.
2005 Sep
Functional effects of genetic variants in the 11beta-hydroxylase (CYP11B1) gene.
2006 Dec
Endothelin-1-induced oxidative stress in DOCA-salt hypertension involves NADPH-oxidase-independent mechanisms.
2006 Feb
Design of an Escherichia coli system for whole cell mediated steroid synthesis and molecular evolution of steroid hydroxylases.
2006 Jun 25
Three novel point mutations of the CYP21 gene detected in classical forms of congenital adrenal hyperplasia due to 21-hydroxylase deficiency.
2006 Mar
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
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
[11beta-hydroxylase deficiency: improvement of final height with growth hormone and gonadotropin-releasing hormone analog].
2007 Aug
Evolution of the corticosteroid receptor signalling pathway in fish.
2007 Aug-Sep
Severe loss-of-function mutations in the adrenocorticotropin receptor (ACTHR, MC2R) can be found in patients diagnosed with salt-losing adrenal hypoplasia.
2007 Feb
Concomitant secretion of glucocorticoid, androgens, and mineralocorticoid by an adrenocortical carcinoma: case report and review of literature.
2007 Jul-Aug
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
Adrenal 20alpha-hydroxysteroid dehydrogenase in the mouse catabolizes progesterone and 11-deoxycorticosterone and is restricted to the X-zone.
2007 Mar
Synthesis and structure-activity relationships of a series of increasingly hydrophobic cationic steroid lipofection reagents.
2007 May
Aldosterone synthase deficiency caused by a homozygous L451F mutation in the CYP11B2 gene.
2008 Apr
Glucocorticoid receptor phosphorylation differentially affects target gene expression.
2008 Aug
Depot-specific steroidogenic gene transcription in human adipose tissue.
2008 Dec
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
Real-time analysis of gene regulation by glucocorticoid hormones.
2008 May
Patents

Patents

Sample Use Guides

Unknown
Route of Administration: Intramuscular
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:15:54 GMT 2023
Edited
by admin
on Fri Dec 15 15:15:54 GMT 2023
Record UNII
6E0A168OB8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DESOXYCORTICOSTERONE ACETATE
ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
DESOXYCORTONE ACETATE
EP   MART.   WHO-DD  
Common Name English
11-Deoxycorticosterone acetate
Common Name English
Desoxycortone acetate [WHO-DD]
Common Name English
NSC-9567
Code English
DESOXYCORTICOSTERONE ACETATE [VANDF]
Common Name English
DESOXYCORTICOSTERONE ACETATE [ORANGE BOOK]
Common Name English
DEOXYCORTICOSTERONE ACETATE [MI]
Common Name English
DOCA
Brand Name English
DESOXYCORTONE ACETATE [MART.]
Common Name English
DESOXYCORTICOSTERONE ACETATE [USP-RS]
Common Name English
DESOXYCORTONE ACETATE [EP IMPURITY]
Common Name English
DESOXYCORTICOSTERONE ACETATE [USP IMPURITY]
Common Name English
PREGN-4-ENE-3,20-DIONE, 21-(ACETYLOXY)-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C521
Created by admin on Fri Dec 15 15:15:54 GMT 2023 , Edited by admin on Fri Dec 15 15:15:54 GMT 2023
Code System Code Type Description
FDA UNII
6E0A168OB8
Created by admin on Fri Dec 15 15:15:54 GMT 2023 , Edited by admin on Fri Dec 15 15:15:54 GMT 2023
PRIMARY
RS_ITEM_NUM
1174001
Created by admin on Fri Dec 15 15:15:54 GMT 2023 , Edited by admin on Fri Dec 15 15:15:54 GMT 2023
PRIMARY
MERCK INDEX
m4172
Created by admin on Fri Dec 15 15:15:54 GMT 2023 , Edited by admin on Fri Dec 15 15:15:54 GMT 2023
PRIMARY Merck Index
PUBCHEM
5952
Created by admin on Fri Dec 15 15:15:54 GMT 2023 , Edited by admin on Fri Dec 15 15:15:54 GMT 2023
PRIMARY
DRUG BANK
DB06780
Created by admin on Fri Dec 15 15:15:54 GMT 2023 , Edited by admin on Fri Dec 15 15:15:54 GMT 2023
PRIMARY
EPA CompTox
DTXSID6022894
Created by admin on Fri Dec 15 15:15:54 GMT 2023 , Edited by admin on Fri Dec 15 15:15:54 GMT 2023
PRIMARY
CAS
56-47-3
Created by admin on Fri Dec 15 15:15:54 GMT 2023 , Edited by admin on Fri Dec 15 15:15:54 GMT 2023
PRIMARY
RXCUI
258333
Created by admin on Fri Dec 15 15:15:54 GMT 2023 , Edited by admin on Fri Dec 15 15:15:54 GMT 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
200-275-9
Created by admin on Fri Dec 15 15:15:54 GMT 2023 , Edited by admin on Fri Dec 15 15:15:54 GMT 2023
PRIMARY
NSC
9567
Created by admin on Fri Dec 15 15:15:54 GMT 2023 , Edited by admin on Fri Dec 15 15:15:54 GMT 2023
PRIMARY
DRUG CENTRAL
821
Created by admin on Fri Dec 15 15:15:54 GMT 2023 , Edited by admin on Fri Dec 15 15:15:54 GMT 2023
PRIMARY
WIKIPEDIA
Desoxycorticosterone acetate
Created by admin on Fri Dec 15 15:15:54 GMT 2023 , Edited by admin on Fri Dec 15 15:15:54 GMT 2023
PRIMARY
SMS_ID
100000087757
Created by admin on Fri Dec 15 15:15:54 GMT 2023 , Edited by admin on Fri Dec 15 15:15:54 GMT 2023
PRIMARY
ChEMBL
CHEMBL1200542
Created by admin on Fri Dec 15 15:15:54 GMT 2023 , Edited by admin on Fri Dec 15 15:15:54 GMT 2023
PRIMARY
MESH
C058404
Created by admin on Fri Dec 15 15:15:54 GMT 2023 , Edited by admin on Fri Dec 15 15:15:54 GMT 2023
PRIMARY
EVMPD
SUB01600MIG
Created by admin on Fri Dec 15 15:15:54 GMT 2023 , Edited by admin on Fri Dec 15 15:15:54 GMT 2023
PRIMARY
NCI_THESAURUS
C65369
Created by admin on Fri Dec 15 15:15:54 GMT 2023 , Edited by admin on Fri Dec 15 15:15:54 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY