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Identification
NameDesoxycorticosterone Pivalate
Accession NumberDB01134  (APRD00709)
TypeSmall Molecule
GroupsExperimental
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
SynonymLanguageCode
Deoxycorticosterone PivalateNot AvailableNot Available
Deoxycorticosterone TrimethylacetateNot AvailableNot Available
Deoxycortolone PivalateNot AvailableNot Available
Deoxycortone PivalateNot AvailableNot Available
Deoxycortone TrimethylacetateNot AvailableNot Available
Desoxycorticosterone TrimethylacetateNot AvailableNot Available
Desoxycortone PivalateNot AvailableNot Available
DOCPNot AvailableNot Available
DTMANot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
Cortexone MNot Available
Neodin-DepositumNot Available
PercortenNot Available
Percorten MNot Available
Percorten PivalateNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number808-48-0
WeightAverage: 414.5775
Monoisotopic: 414.277009704
Chemical FormulaC26H38O4
InChI KeyVVOIQBFMTVCINR-UHFFFAOYSA-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
IUPAC Name
2-{2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl}-2-oxoethyl 2,2-dimethylpropanoate
SMILES
CC(C)(C)C(=O)OCC(=O)C1CCC2C3CCC4=CC(=O)CCC4(C)C3CCC12C
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 20-oxosteroid
  • Oxosteroid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-4-steroid
  • Alpha-acyloxy ketone
  • Cyclic ketone
  • Ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationExamined 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.
PharmacodynamicsUsed 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 actionDesoxycorticosterone 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein binding90%
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySymptoms of overdose include polyuria, polydipsia, increased blood volume, edema, and cardiac enlargement.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.8229
CYP450 2D6 substrateNon-inhibitor0.9356
CYP450 2C19 substrateNon-inhibitor0.8875
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
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
Polarizability48.32 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (65.5 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Mineralocorticoid receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Mineralocorticoid receptor P08235 Details

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
  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
  3. Beaumont K, Fanestil DD: Characterization of rat brain aldosterone receptors reveals high affinity for corticosterone. Endocrinology. 1983 Dec;113(6):2043-51. Pubmed
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  5. Sekihara H, Island DP, Liddle GW: New mineralocorticoids: 5alpha-dihydroaldosterone and 5alpha-dihydro-11-deoxycorticosterone. Endocrinology. 1978 Oct;103(4):1450-2. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:13