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Identification
NamePrednicarbate
Accession NumberDB01130  (APRD01197)
TypeSmall Molecule
GroupsApproved
Description

Prednicarbate is a relatively new topical corticosteroid drug. It is similar in potency to hydrocortisone. It is used in the treatment of inflammatory skin diseases, such as atopic dermatitis. It has a favorable benefit-risk ratio, with an inflammatory action similar to that of a medium potency corticosteroid, but with a low potential to cause skin atrophy. The anti-inflammation action of corticosteroids is associated with the inhibition of the interleukin 1-alpha cytokine within keratinocytes. IL-1a is also found in fibroblasts, where it is responsible for proliferation, collagenase induction and IL-6 synthesis, which are related to skin thickness.

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand names
NameCompany
DermatopNot Available
Dermatop E EmollientNot Available
Brand mixturesNot Available
Categories
CAS number73771-04-7
WeightAverage: 488.5699
Monoisotopic: 488.241018128
Chemical FormulaC27H36O8
InChI KeyFNPXMHRZILFCKX-UHFFFAOYSA-N
InChI
InChI=1S/C27H36O8/c1-5-22(31)34-15-21(30)27(35-24(32)33-6-2)12-10-19-18-8-7-16-13-17(28)9-11-25(16,3)23(18)20(29)14-26(19,27)4/h9,11,13,18-20,23,29H,5-8,10,12,14-15H2,1-4H3
IUPAC Name
2-{14-[(ethoxycarbonyl)oxy]-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl}-2-oxoethyl propanoate
SMILES
CCOC(=O)OC1(CCC2C3CCC4=CC(=O)C=CC4(C)C3C(O)CC12C)C(=O)COC(=O)CC
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassGluco/mineralocorticoids, Progestogins and Derivatives
Direct parentGluco/mineralocorticoids, Progestogins and Derivatives
Alternative parentsSteroid Esters; Ketosteroids; Hydroxysteroids; Tricarboxylic Acids and Derivatives; Cyclohexanols; Carbonic Acid Diesters; Carboxylic Acid Esters; Cyclic Alcohols and Derivatives; Ketones; Ethers; Enolates; Polyamines; Aldehydes
Substituents20-keto-steroid; 3-keto-steroid; 11-hydroxy-steroid; tricarboxylic acid derivative; cyclohexanol; carbonic acid diester; cyclic alcohol; carbonic acid derivative; secondary alcohol; carboxylic acid ester; ketone; carboxylic acid derivative; enolate; polyamine; ether; carbonyl group; alcohol; 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
IndicationFor the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.
PharmacodynamicsCorticosteroids diffuse across cell membranes and complex with specific cytoplasmic receptors. These complexes then enter the cell nucleus, bind to DNA (chromatin), and stimulate transcription of messenger RNA (mRNA) and subsequent protein synthesis of various inhibitory enzymes responsible for the anti-inflammatory effects of topical corticosteroids. These anti-inflammatory effects include inhibition of early processes such as edema, fibrin deposition, capillary dilatation, movement of phagocytes into the area, and phagocytic activities. Later processes, such as capillary production, collagen deposition, and keloid formation also are inhibited by corticosteroids.
Mechanism of actionIn common with other topical corticosteroids, prednicarbate has anti-inflammatory, antipruritic, and vasoconstrictive properties. In general, the mechanism of the anti-inflammatory activity of topical steroids is unclear. However, corticosteroids are thought to act by the induction of phospholipase A2 inhibitory proteins, collectively called lipocortins. It is postulated that these proteins control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A2.
AbsorptionAbsorbed systemically across the stratum corneum.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Primarily in skin

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
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 + 0.9958
Blood Brain Barrier + 0.984
Caco-2 permeable - 0.571
P-glycoprotein substrate Substrate 0.7928
P-glycoprotein inhibitor I Inhibitor 0.8358
P-glycoprotein inhibitor II Non-inhibitor 0.6129
Renal organic cation transporter Non-inhibitor 0.7659
CYP450 2C9 substrate Non-substrate 0.8753
CYP450 2D6 substrate Non-substrate 0.895
CYP450 3A4 substrate Substrate 0.7638
CYP450 1A2 substrate Non-inhibitor 0.9046
CYP450 2C9 substrate Non-inhibitor 0.9054
CYP450 2D6 substrate Non-inhibitor 0.9032
CYP450 2C19 substrate Non-inhibitor 0.9026
CYP450 3A4 substrate Non-inhibitor 0.8309
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.841
Ames test Non AMES toxic 0.9186
Carcinogenicity Non-carcinogens 0.9164
Biodegradation Not ready biodegradable 0.9757
Rat acute toxicity 2.4426 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8758
hERG inhibition (predictor II) Non-inhibitor 0.5989
Pharmacoeconomics
Manufacturers
  • Sanofi aventis us llc
  • Altana inc
Packagers
Dosage forms
FormRouteStrength
CreamTopical
LiquidCutaneous
LiquidIntradermal
LiquidSubcutaneous
OintmentTopical
Prices
Unit descriptionCostUnit
Prednicarbate 0.1% Ointment 60 gm Tube76.74USDtube
Dermatop 0.1% Cream 60 gm Tube75.2USDtube
Dermatop 0.1% Ointment 60 gm Tube70.06USDtube
Prednicarbate 0.1% Cream 60 gm Tube59.03USDtube
Prednicarbate 0.1% Ointment 15 gm Tube37.31USDtube
Prednicarbate 0.1% Cream 15 gm Tube24.0USDtube
Dermatop 0.1% cream1.76USDg
Prednicarbate 0.1% cream1.41USDg
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
logP2.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00562ALOGPS
logP3.08ALOGPS
logP3.83ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)14.82ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area116.2 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity127.8 m3·mol-1ChemAxon
Polarizability51.39 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. Gupta AK, Chow M: A review of prednicarbate (Dermatop). Skin Therapy Lett. 2004 Dec-2005 Jan;9(10):5-6, 9. Pubmed 15657633
External Links
ResourceLink
PubChem Compound52421
PubChem Substance46506799
ChemSpider47402
Therapeutic Targets DatabaseDAP001189
PharmGKBPA164749394
Drug Product Database2230642
RxListhttp://www.rxlist.com/cgi/generic2/prednicarbate.htm
Drugs.comhttp://www.drugs.com/cdi/prednicarbate-cream.html
WikipediaPrednicarbate
ATC CodesD07AC18V01AA07V01AA03
AHFS Codes
  • 84:06.00
  • 92:04.00*
PDB EntriesNot Available
FDA labelshow(130 KB)
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Glucocorticoid receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Glucocorticoid receptor P04150 Details

References:

  1. Boudinot FD, D’Ambrosio R, Jusko WJ: Receptor-mediated pharmacodynamics of prednisolone in the rat. J Pharmacokinet Biopharm. 1986 Oct;14(5):469-93. Pubmed
  2. Ikonomidis I, Tzortzis S, Lekakis J, Paraskevaidis I, Andreadou I, Nikolaou M, Kaplanoglou T, Katsimbri P, Skarantavos G, Soucacos P, Kremastinos DT: Lowering interleukin-1 activity with anakinra improves myocardial deformation in rheumatoid arthritis. Heart. 2009 Sep;95(18):1502-7. Epub 2009 May 28. Pubmed

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