DrugBank: Desoxycorticosterone Pivalate (DB01134)

targets (1)

Identification

Name

Desoxycorticosterone Pivalate

Accession Number

DB01134 (APRD00709)

Type

small molecule

Groups

experimental

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

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Deoxycorticosterone Pivalate
Deoxycorticosterone Trimethylacetate
Deoxycortolone Pivalate
Deoxycortone Pivalate
Deoxycortone Trimethylacetate
Desoxycorticosterone Trimethylacetate
Desoxycortone Pivalate
DOCP
DTMA

Salts

Not Available

Brand names

Name	Company
Cortexone M
Neodin-Depositum
Percorten
Percorten M
Percorten Pivalate

Brand mixtures

Not Available

Categories

Diuretics
Anti-Addison Agents

CAS number

808-48-0

Weight

Average: 414.5775
Monoisotopic: 414.277009704

Chemical Formula

C₂₆H₃₈O₄

InChI Key

InChIKey=VVOIQBFMTVCINR-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

Plain Text

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

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Steroids and Steroid Derivatives

Substructures

Steroids and Steroid Derivatives
Carbonyl Compounds
Carboxylic Acids and Derivatives
Alkanes and Alkenes
Acetates
Ethers
Cyclohexenes and Derivatives
Ketones

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.

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

Pharmacoeconomics

Manufacturers

Novartis pharmaceuticals corp

Packagers

Baxter International Inc.

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

solid

Experimental Properties

Property	Value	Source
water solubility	Insoluble	Not Available
logP	4	Not Available

Predicted Properties

Property	Value	Source
water solubility	1.41e-03 g/l	ALOGPS
logP	3.9	ALOGPS
logP	5.57	ChemAxon
logS	-5.5	ALOGPS
pKa (strongest acidic)	17.19	ChemAxon
pKa (strongest basic)	-4.8	ChemAxon
physiological charge	0	ChemAxon
hydrogen acceptor count	3	ChemAxon
hydrogen donor count	0	ChemAxon
polar surface area	60.44	ChemAxon
rotatable bond count	5	ChemAxon
refractivity	117.26	ChemAxon
polarizability	48.32	ChemAxon

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
PubChem Compound	13126
PubChem Substance	46506381
ChemSpider	12574
Therapeutic Targets Database	DAP001106
PharmGKB	PA449245
Drug Product Database	2139227

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

show (65.5 KB)

Interactions

Drug Interactions

Not Available

Food Interactions

Not Available

Targets
1. Mineralocorticoid receptor Pharmacological action: yes Actions: agonist 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 Organism class: human UniProt ID: P08235 Gene: NR3C2 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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 Beaumont K, Fanestil DD: Characterization of rat brain aldosterone receptors reveals high affinity for corticosterone. Endocrinology. 1983 Dec;113(6):2043-51. Pubmed Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed Sekihara H, Island DP, Liddle GW: New mineralocorticoids: 5alpha-dihydroaldosterone and 5alpha-dihydro-11-deoxycorticosterone. Endocrinology. 1978 Oct;103(4):1450-2. Pubmed

Targets

1. Mineralocorticoid receptor

Pharmacological action: yes
Actions: agonist

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

Organism class: human
UniProt ID: P08235 Link_out

Gene: NR3C2 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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
Beaumont K, Fanestil DD: Characterization of rat brain aldosterone receptors reveals high affinity for corticosterone. Endocrinology. 1983 Dec;113(6):2043-51. Pubmed
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Sekihara H, Island DP, Liddle GW: New mineralocorticoids: 5alpha-dihydroaldosterone and 5alpha-dihydro-11-deoxycorticosterone. Endocrinology. 1978 Oct;103(4):1450-2. Pubmed

Comments

Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19