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Identification
Name Prednicarbate
Accession Number DB01130 (APRD01197)
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Dermatop
Dermatop E Emollient
Brand mixtures Not Available
Categories
  • Anti-inflammatory Agents
  • Glucocorticoids
  • Corticosteroid
  • Anti-inflammatory
  • Steroidal
CAS number 73771-04-7
Weight Average: 488.5699
Monoisotopic: 488.241018128
Chemical Formula C27H36O8
InChI Key InChIKey=FNPXMHRZILFCKX-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
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Steroids and Steroid Derivatives
Substructures
  • Steroids and Steroid Derivatives
  • Carboxylic Acids and Derivatives
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Acetates
  • Ethers
  • Carbonic Acids and Derivatives
  • Alcohols and Polyols
  • Ketones
Pharmacology
Indication For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.
Pharmacodynamics Corticosteroids 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 action In 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.
Absorption Absorbed systemically across the stratum corneum.
Volume of distribution Not Available
Protein binding Not Available
Metabolism Primarily in skin
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Sanofi aventis us llc
  • Altana inc
Packagers
Dosage forms
Form Route Strength
Cream Topical
Liquid Cutaneous
Liquid Intradermal
Liquid Subcutaneous
Ointment Topical
Prices
Unit description Cost Unit
Prednicarbate 0.1% Ointment 60 gm Tube 76.74 USD tube
Dermatop 0.1% Cream 60 gm Tube 75.2 USD tube
Dermatop 0.1% Ointment 60 gm Tube 70.06 USD tube
Prednicarbate 0.1% Cream 60 gm Tube 59.03 USD tube
Prednicarbate 0.1% Ointment 15 gm Tube 37.31 USD tube
Prednicarbate 0.1% Cream 15 gm Tube 24.0 USD tube
Dermatop 0.1% cream 1.76 USD g
Prednicarbate 0.1% cream 1.41 USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
logP 2.9 Not Available
Predicted Properties
Property Value Source
water solubility 5.62e-03 g/l ALOGPS
logP 3.08 ALOGPS
logP 3.83 ChemAxon
logS -4.9 ALOGPS
pKa (strongest acidic) 14.82 ChemAxon
pKa (strongest basic) -2.9 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 6 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 116.2 ChemAxon
rotatable bond count 9 ChemAxon
refractivity 127.8 ChemAxon
polarizability 51.39 ChemAxon
References
Synthesis Reference Not 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
Resource Link
PubChem Compound 52421 Link_out
PubChem Substance 46506799 Link_out
ChemSpider 47402 Link_out
Therapeutic Targets Database DAP001189 Link_out
PharmGKB PA164749394 Link_out
Drug Product Database 2230642 Link_out
RxList http://www.rxlist.com/cgi/generic2/prednicarbate.htm Link_out
Drugs.com http://www.drugs.com/cdi/prednicarbate-cream.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Prednicarbate Link_out
ATC Codes
  • D07AC18
  • V01AA07
  • V01AA03
AHFS Codes
  • 84:06.00
  • 92:04.00*
PDB Entries Not Available
FDA label show (130 KB)
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Glucocorticoid receptor

Pharmacological action: yes
Actions: agonist

Receptor for glucocorticoids (GC). Has a dual mode of action:as a transcription factor that binds to glucocorticoid response elements (GRE) and as a modulator of other transcription factors. Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Could act as a coactivator for STAT5-dependent transcription upon growth hormone (GH) stimulation and could reveal an essential role of hepatic GR in the control of body growth

Organism class: human
UniProt ID: P04150 Link_out
Gene: NR3C1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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