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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
SaltsNot Available
Brand names
NameCompany
Cortexone MNot Available
Neodin-DepositumNot Available
PercortenNot Available
Percorten MNot Available
Percorten PivalateNot Available
Brand mixturesNot 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[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl}-2-oxoethyl 2,2-dimethylpropanoate
SMILES
CC(C)(C)C(=O)OCC(=O)C1CCC2C3CCC4=CC(=O)CCC4(C)C3CCC12C
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassGluco/mineralocorticoids, Progestogins and Derivatives
Direct parentGluco/mineralocorticoids, Progestogins and Derivatives
Alternative parentsKetosteroids; Ketones; Carboxylic Acid Esters; Polyamines; Enolates; Ethers; Aldehydes
Substituents20-keto-steroid; 3-keto-steroid; carboxylic acid ester; ketone; enolate; ether; polyamine; carboxylic acid derivative; carbonyl group; aldehyde
Classification descriptionThis compound belongs to the gluco/mineralocorticoids, progestogins and derivatives. These are steroids whose structure is based on an hydroxylated prostane moiety.
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
Property Value Probability
Human Intestinal Absorption + 0.9954
Blood Brain Barrier + 0.9553
Caco-2 permeable + 0.6211
P-glycoprotein substrate Substrate 0.6541
P-glycoprotein inhibitor I Inhibitor 0.9048
P-glycoprotein inhibitor II Inhibitor 0.8603
Renal organic cation transporter Non-inhibitor 0.6993
CYP450 2C9 substrate Non-substrate 0.8702
CYP450 2D6 substrate Non-substrate 0.9101
CYP450 3A4 substrate Substrate 0.8098
CYP450 1A2 substrate Non-inhibitor 0.9498
CYP450 2C9 substrate Non-inhibitor 0.8229
CYP450 2D6 substrate Non-inhibitor 0.9356
CYP450 2C19 substrate Non-inhibitor 0.8875
CYP450 3A4 substrate Non-inhibitor 0.8554
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7501
Ames test Non AMES toxic 0.9473
Carcinogenicity Non-carcinogens 0.9159
Biodegradation Not ready biodegradable 0.9231
Rat acute toxicity 1.7883 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9494
hERG inhibition (predictor II) Non-inhibitor 0.7297
Pharmacoeconomics
Manufacturers
  • Novartis pharmaceuticals corp
Packagers
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
water solubilityInsolubleNot Available
logP4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00141ALOGPS
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 FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
PubChem Compound13126
PubChem Substance46506381
ChemSpider12574
Therapeutic Targets DatabaseDAP001106
PharmGKBPA449245
Drug Product Database2139227
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(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