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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
Structure of DESOXYCORTONE

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

HIDE SMILES / InChI

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

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
Depot-specific steroidogenic gene transcription in human adipose tissue.
2008-12
Glucocorticoid receptor phosphorylation differentially affects target gene expression.
2008-08
Real-time analysis of gene regulation by glucocorticoid hormones.
2008-05
Quantitative determination of progesterones and corticosteroids in human urine using gas chromatography/mass spectrometry: application to pelvic organ prolapse patients.
2008-04
Aldosterone synthase deficiency caused by a homozygous L451F mutation in the CYP11B2 gene.
2008-04
Novel mutation in cytochrome P450c17 causes complete combined 17alpha-hydroxylase/17,20-lyase deficiency.
2008-02
Effects of ACTH, dexamethasone, and adrenalectomy on 11beta-hydroxylase (CYP11B1) and aldosterone synthase (CYP11B2) gene expression in the rat central nervous system.
2008-02
Purification and functional characterization of human 11beta hydroxylase expressed in Escherichia coli.
2008-02
The transcription of steroidogenic genes in the human cerebellum and hippocampus: a comparative survey of normal and Alzheimer's tissue.
2008-01
One single dose of etomidate negatively influences adrenocortical performance for at least 24h in children with meningococcal sepsis.
2008-01
The role of polyester interstitium and aldosterone during structural development of renal tubules in serum-free medium.
2007-10
Aldosterone induces epithelial-mesenchymal transition via ROS of mitochondrial origin.
2007-09
Concomitant secretion of glucocorticoid, androgens, and mineralocorticoid by an adrenocortical carcinoma: case report and review of literature.
2007-08-03
[11beta-hydroxylase deficiency: improvement of final height with growth hormone and gonadotropin-releasing hormone analog].
2007-08
Construction of 3D models of the CYP11B family as a tool to predict ligand binding characteristics.
2007-08
Salivary cortisol and DHEA levels in the Korean population: age-related differences, diurnal rhythm, and correlations with serum levels.
2007-06-30
Synthesis and structure-activity relationships of a series of increasingly hydrophobic cationic steroid lipofection reagents.
2007-05
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.
2007-03
Adrenal 20alpha-hydroxysteroid dehydrogenase in the mouse catabolizes progesterone and 11-deoxycorticosterone and is restricted to the X-zone.
2007-03
Severe loss-of-function mutations in the adrenocorticotropin receptor (ACTHR, MC2R) can be found in patients diagnosed with salt-losing adrenal hypoplasia.
2007-02
Elevated cardiac tissue level of aldosterone and mineralocorticoid receptor in diastolic heart failure: Beneficial effects of mineralocorticoid receptor blocker.
2007-02
Functional effects of genetic variants in the 11beta-hydroxylase (CYP11B1) gene.
2006-12
In vivo effects of thyroid hormone, corticosteroids and prolactin on cell proliferation and apoptosis in the anterior intestine of the euryhaline mudskipper (Periophthalmus modestus).
2006-10-04
Mineralocorticoid synthesis during the periovulatory interval in macaques.
2006-10
Evolution of the corticosteroid receptor signalling pathway in fish.
2006-09-15
Design of an Escherichia coli system for whole cell mediated steroid synthesis and molecular evolution of steroid hydroxylases.
2006-06-25
Three novel point mutations of the CYP21 gene detected in classical forms of congenital adrenal hyperplasia due to 21-hydroxylase deficiency.
2006-03
Hydration of rainbow trout oocyte during meiotic maturation and in vitro regulation by 17,20{beta}-dihydroxy-4-pregnen-3-one and cortisol.
2006-03
Endothelin-1-induced oxidative stress in DOCA-salt hypertension involves NADPH-oxidase-independent mechanisms.
2006-02
Bifunctional gonadotropin-releasing hormone antagonist-progesterone analogs with increased efficacy and duration of action.
2006-01
Molecular identity and gene expression of aldosterone synthase cytochrome P450.
2005-12-09
The aldosterone synthase (CYP11B2) and 11beta-hydroxylase (CYP11B1) genes are not expressed in the rat heart.
2005-12
NAD(P)H oxidase/nitric oxide interactions in peroxisome proliferator activated receptor (PPAR)alpha-mediated cardiovascular effects.
2005-11-11
Biochemical characterization of the Arctic char (Salvelinus alpinus) ovarian progestin membrane receptor.
2005-11-10
Calcitonin gene-related peptide and hypertension.
2005-09
Steroid signalling in the ovarian surface epithelium.
2005-09
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.
2005-08
Differential expression and function of beacon in the rat adrenal cortex and medulla.
2005-07
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.
2005-07
Cyclo-oxygenase-2, endothelium and aortic reactivity during deoxycorticosterone acetate salt-induced hypertension.
2005-05
The human mineralocorticoid receptor only partially differentiates between different ligands after expression in fission yeast.
2005-04
Role of activation function domain-1, DNA binding, and coactivator GRIP1 in the expression of partial agonist activity of glucocorticoid receptor-antagonist complexes.
2005-03-08
Mineralocorticoid receptors: distribution and activation.
2005-01
Adrenocortical carcinoma producing 11-deoxycorticosterone: a rare cause of mineralocorticoid hypertension.
2005-01
11-deoxycorticosterone is a potent agonist of the rainbow trout (Oncorhynchus mykiss) mineralocorticoid receptor.
2005-01
Functional characterization of two novel point mutations in the CYP21 gene causing simple virilizing forms of congenital adrenal hyperplasia due to 21-hydroxylase deficiency.
2005-01
The effect of Sutherlandia frutescens on steroidogenesis: confirming indigenous wisdom.
2004-11
Expression of cytochrome P450c17 and other steroid-converting enzymes in the rat kidney throughout the life-span.
2004-06
19-Nor-deoxycorticosterone production from aldosterone-producing adenomas.
1992-04
Extraadrenal expression of steroid 21-hydroxylase and 11 beta-hydroxylase by a benign testicular Leydig cell tumor.
1991-12
Patents

Patents

Sample Use Guides

Unknown
Route of Administration: Intramuscular
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:17:14 GMT 2025
Edited
by admin
on Mon Mar 31 18:17:14 GMT 2025
Record UNII
40GP35YQ49
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DESOXYCORTONE
INN   MART.   WHO-DD  
INN  
Official Name English
DEOXYCORTICOSTERONE
MI  
Preferred Name English
DESOXYCORTONE [MART.]
Common Name English
21-HYDROXYPROGESTERONE
Common Name English
DESOXYCORTICOSTERONE
VANDF  
Common Name English
11-DEOXYCORTICOSTERONE
Common Name English
Desoxycortone [WHO-DD]
Common Name English
21-HYDROXY-PREGN-4-ENE-3,20-DIONE
Systematic Name English
NSC-11319
Code English
DEOXYCORTONE
Common Name English
21-HYDROXY-.DELTA.4-PREGNENE-3,20-DIONE
Systematic Name English
PREGN-4-ENE-3,20-DIONE, 21-HYDROXY-
Systematic Name English
desoxycortone [INN]
Common Name English
DEOXYCORTICOSTERONE [MI]
Common Name English
DESOXYCORTICOSTERONE [VANDF]
Common Name English
Classification Tree Code System Code
LOINC 16110-9
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
LOINC 42855-7
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
LOINC 40811-2
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
LOINC 53348-9
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
NCI_THESAURUS C521
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
LOINC 1656-8
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
LOINC 44729-2
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
CFR 21 CFR 862.1250
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
LOINC 25561-2
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
WHO-ATC H02AA03
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
LOINC 53347-1
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
WHO-VATC QH02AA03
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
LOINC 40818-7
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
LOINC 55808-0
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
Code System Code Type Description
FDA UNII
40GP35YQ49
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-596-4
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
PRIMARY
DRUG CENTRAL
820
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
PRIMARY
WIKIPEDIA
11-DEOXYCORTICOSTERONE
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
PRIMARY
ChEMBL
CHEMBL1200542
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
PRIMARY
RXCUI
3256
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
PRIMARY RxNorm
NCI_THESAURUS
C72737
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
PRIMARY
SMS_ID
100000083213
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
PRIMARY
INN
387
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
PRIMARY
MERCK INDEX
m4172
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
PRIMARY Merck Index
PUBCHEM
6166
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
PRIMARY
EPA CompTox
DTXSID0045254
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PRIMARY
MESH
D003900
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
PRIMARY
CAS
64-85-7
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
PRIMARY
NSC
11319
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
PRIMARY
DAILYMED
40GP35YQ49
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
PRIMARY
CHEBI
16973
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
PRIMARY
EVMPD
SUB07007MIG
Created by admin on Mon Mar 31 18:17:14 GMT 2025 , Edited by admin on Mon Mar 31 18:17:14 GMT 2025
PRIMARY
Related Record Type Details
ACTIVE MOIETY