Desoxycorticosterone Pivalate

Identification

Name
Desoxycorticosterone Pivalate
Accession Number
DB01134  (APRD00709)
Type
Small Molecule
Groups
Experimental, Vet approved
Description

Desoxycorticosterone Pivalate is a mineralocorticoid hormone and an analog of desoxycorticosterone. It is white, odorless, and stable in air. It is practically insoluble in water, sparingly soluble in acetone, slightly soluble in methanol, ether and vegetable oils. Federal (U.S.A.) law restricts this drug to use by or on the order of a licensed veterinarian.

Structure
Thumb
Synonyms
  • 11-deoxycorticosterone pivalate
  • Deoxycorticosterone Pivalate
  • Deoxycorticosterone Trimethylacetate
  • Deoxycortolone Pivalate
  • Deoxycortone Pivalate
  • Deoxycortone Trimethylacetate
  • Desoxycorticosterone Trimethylacetate
  • Desoxycortone Pivalate
  • DOCP
  • DTMA
International/Other Brands
Cortexone M / Neodin-Depositum / Percorten / Percorten M / Percorten Pivalate
Categories
UNII
16665T4A2X
CAS number
808-48-0
Weight
Average: 414.586
Monoisotopic: 414.277009704
Chemical Formula
C26H38O4
InChI Key
VVOIQBFMTVCINR-WWMZEODYSA-N
InChI
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
IUPAC Name
2-[(1S,2R,10S,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]-2-oxoethyl 2,2-dimethylpropanoate
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)C(=O)COC(=O)C(C)(C)C

Pharmacology

Indication

Examined for treatment of adrenocortical insufficiency especially in multiple sclerosis, congenital cerebral palsy, polyarteritis nodosa, and rheumatoid arthritis. Currently only approved in treating cats and dogs for the treatment of Addison's disease.

Pharmacodynamics

Used to treat adrenocortical insufficiency, desoxycorticosterone pivalate is a mineralocorticoid hormone and an analogue of desoxycorticosterone. It primarily acts on the metabolism of sodium, potassium and water. When the drug is given, there is decreased excretion of sodium accompanied by increased excretion of potassium; the concentration of sodium in the blood is thereby increased whereas that of potassium is decreased. There is a concomitant increase in the volume of blood and extracellular fluids, with a fall in hematocrit. It increases the rate of renal tubular absorption of sodium.

Mechanism of action

Desoxycorticosterone Pivalate binds to the mineralocorticoid receptor. Mineralocorticoids are a family of steroids, secreted by the adrenal cortex, necessary for the regulation of a number of metabolic processes including electrolyte regulation. Desoxycorticosterone pivalate exerts its effect through its interaction with the mineralocorticoid receptor (MR), whereby it reacts with the receptor proteins to form a steroid-receptor complex. This complex moves into the nucleus, where it binds to chromatin which results in genetic transcription of cellular DNA to messenger RNA. The steroid hormones appear to induce transcription and synthesis of specific proteins, which produce the physiological effects seen after administration.

TargetActionsOrganism
AMineralocorticoid receptor
agonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding

90%

Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Symptoms of overdose include polyuria, polydipsia, increased blood volume, edema, and cardiac enlargement.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(4R)-limoneneThe risk or severity of adverse effects can be increased when (4R)-limonene is combined with Desoxycorticosterone Pivalate.
1,10-PhenanthrolineThe risk or severity of adverse effects can be increased when Desoxycorticosterone Pivalate is combined with 1,10-Phenanthroline.
AceclofenacThe risk or severity of adverse effects can be increased when Aceclofenac is combined with Desoxycorticosterone Pivalate.
AcemetacinThe risk or severity of adverse effects can be increased when Acemetacin is combined with Desoxycorticosterone Pivalate.
AcetazolamideThe metabolism of Desoxycorticosterone Pivalate can be decreased when combined with Acetazolamide.
AlbendazoleThe metabolism of Desoxycorticosterone Pivalate can be decreased when combined with Albendazole.
AlclofenacThe risk or severity of adverse effects can be increased when Alclofenac is combined with Desoxycorticosterone Pivalate.
AlclometasoneThe metabolism of Desoxycorticosterone Pivalate can be decreased when combined with Alclometasone.
AlfentanilThe metabolism of Alfentanil can be decreased when combined with Desoxycorticosterone Pivalate.
AlfuzosinThe metabolism of Desoxycorticosterone Pivalate can be decreased when combined with Alfuzosin.
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
11876263
PubChem Substance
46506381
ChemSpider
10050591
ChEBI
50782
ChEMBL
CHEMBL1200592
Therapeutic Targets Database
DAP001106
PharmGKB
PA449245
Wikipedia
Desoxycorticosterone_Pivalate
MSDS
Download (65.5 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Baxter International Inc.
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilityInsolubleNot Available
logP4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00141 mg/mLALOGPS
logP3.9ALOGPS
logP5.57ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)17.19ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area60.44 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity117.26 m3·mol-1ChemAxon
Polarizability48.3 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9954
Blood Brain Barrier+0.9553
Caco-2 permeable+0.6211
P-glycoprotein substrateSubstrate0.6541
P-glycoprotein inhibitor IInhibitor0.9048
P-glycoprotein inhibitor IIInhibitor0.8603
Renal organic cation transporterNon-inhibitor0.6993
CYP450 2C9 substrateNon-substrate0.8702
CYP450 2D6 substrateNon-substrate0.9101
CYP450 3A4 substrateSubstrate0.8098
CYP450 1A2 substrateNon-inhibitor0.9498
CYP450 2C9 inhibitorNon-inhibitor0.8229
CYP450 2D6 inhibitorNon-inhibitor0.9356
CYP450 2C19 inhibitorNon-inhibitor0.8875
CYP450 3A4 inhibitorNon-inhibitor0.8554
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7501
Ames testNon AMES toxic0.9473
CarcinogenicityNon-carcinogens0.9159
BiodegradationNot ready biodegradable0.9231
Rat acute toxicity1.7883 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9494
hERG inhibition (predictor II)Non-inhibitor0.7297
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Pregnane steroids
Direct Parent
Gluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
20-oxosteroids / 3-oxo delta-4-steroids / Delta-4-steroids / Cyclohexenones / Alpha-acyloxy ketones / Carboxylic acid esters / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives
Substituents
Progestogin-skeleton / 20-oxosteroid / 3-oxo-delta-4-steroid / 3-oxosteroid / Oxosteroid / Delta-4-steroid / Cyclohexenone / Alpha-acyloxy ketone / Carboxylic acid ester / Cyclic ketone
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
pivalate ester, mineralocorticoid (CHEBI:50782)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Receptor for both mineralocorticoids (MC) such as aldosterone and glucocorticoids (GC) such as corticosterone or cortisol. Binds to mineralocorticoid response elements (MRE) and transactivates targ...
Gene Name
NR3C2
Uniprot ID
P08235
Uniprot Name
Mineralocorticoid receptor
Molecular Weight
107066.575 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Beaumont K, Fanestil DD: Characterization of rat brain aldosterone receptors reveals high affinity for corticosterone. Endocrinology. 1983 Dec;113(6):2043-51. [PubMed:6227474]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  5. Sekihara H, Island DP, Liddle GW: New mineralocorticoids: 5alpha-dihydroaldosterone and 5alpha-dihydro-11-deoxycorticosterone. Endocrinology. 1978 Oct;103(4):1450-2. [PubMed:744157]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Pelletier G. (2010). Progress in Brain Research. Elsevier.

Drug created on June 13, 2005 07:24 / Updated on October 11, 2018 22:27