You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameDesoxycorticosterone Pivalate
Accession NumberDB01134  (APRD00709)
TypeSmall Molecule
GroupsExperimental, 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
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not 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
UNII16665T4A2X
CAS number808-48-0
WeightAverage: 414.586
Monoisotopic: 414.277009704
Chemical FormulaC26H38O4
InChI KeyVVOIQBFMTVCINR-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
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
Taxonomy
ClassificationNot classified
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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein binding90%
MetabolismNot Available
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 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 )
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
logS-5.5ALOGPS
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot 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

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 target genes. The effect of MC is to increase ion and water transport and thus raise extracellular fluid volume and blood pressure and lower potassium levels.
Gene Name:
NR3C2
Uniprot ID:
P08235
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 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on May 07, 2016 20:45