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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
External Identifiers
  • LAS-189961
  • LAS189961
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dermatopcream1 mg/gtopicalValeant Pharmaceuticals North America LLC1993-10-29Not applicableUs
Dermatopointment1 mg/gtopicalValeant Pharmaceuticals North America LLC2014-06-23Not applicableUs
Dermatop Emollient Creamcream0.1 %topicalValeant Canada Lp Valeant Canada S.E.C.2001-03-21Not applicableCanada
Dermatop Ointmentointment0.1 %topicalValeant Canada Lp Valeant Canada S.E.C.2001-03-21Not applicableCanada
Prednicarbatecream1 mg/gtopicalOceanside Pharmaceuticals1993-10-29Not applicableUs
Prednicarbatecream1 mg/gtopicalPrasco Laboratories2007-04-30Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Prednicarbatecream1 mg/gtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2006-09-19Not applicableUs
Prednicarbateointment1 mg/gtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2007-03-09Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
Dermatop E EmollientNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIV901LV1K7D
CAS number73771-04-7
WeightAverage: 488.577
Monoisotopic: 488.241018119
Chemical FormulaC27H36O8
InChI KeyFNPXMHRZILFCKX-KAJVQRHHSA-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/t18-,19-,20-,23+,25-,26-,27-/m0/s1
IUPAC Name
SMILES
[H][C@@]12CC[C@](OC(=O)OCC)(C(=O)COC(=O)CC)[C@@]1(C)C[[email protected]](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
Taxonomy
ClassificationNot classified
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.
Related Articles
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
PropertyValueProbability
Human Intestinal Absorption+0.9958
Blood Brain Barrier+0.984
Caco-2 permeable-0.571
P-glycoprotein substrateSubstrate0.7928
P-glycoprotein inhibitor IInhibitor0.8358
P-glycoprotein inhibitor IINon-inhibitor0.6129
Renal organic cation transporterNon-inhibitor0.7659
CYP450 2C9 substrateNon-substrate0.8753
CYP450 2D6 substrateNon-substrate0.895
CYP450 3A4 substrateSubstrate0.7638
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9054
CYP450 2D6 inhibitorNon-inhibitor0.9032
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.841
Ames testNon AMES toxic0.9186
CarcinogenicityNon-carcinogens0.9164
BiodegradationNot ready biodegradable0.9757
Rat acute toxicity2.4426 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8758
hERG inhibition (predictor II)Non-inhibitor0.5989
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Creamtopical0.1 %
Ointmenttopical0.1 %
Creamtopical1 mg/g
Ointmenttopical1 mg/g
Prices
Unit descriptionCostUnit
Prednicarbate 0.1% Ointment 60 gm Tube76.74USD tube
Dermatop 0.1% Cream 60 gm Tube75.2USD tube
Dermatop 0.1% Ointment 60 gm Tube70.06USD tube
Prednicarbate 0.1% Cream 60 gm Tube59.03USD tube
Prednicarbate 0.1% Ointment 15 gm Tube37.31USD tube
Prednicarbate 0.1% Cream 15 gm Tube24.0USD tube
Dermatop 0.1% cream1.76USD g
Prednicarbate 0.1% cream1.41USD g
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 Solubility0.00562 mg/mLALOGPS
logP3.08ALOGPS
logS-4.9ALOGPS
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General References
  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
ATC CodesD07AC18
AHFS Codes
  • 84:06.00
  • 92:04.00*
PDB EntriesNot Available
FDA labelDownload (130 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AldesleukinPrednicarbate may decrease the antineoplastic activities of Aldesleukin.
CeritinibPrednicarbate may increase the hyperglycemic activities of Ceritinib.
Corticorelin ovine triflutateThe therapeutic efficacy of Corticorelin can be decreased when used in combination with Prednicarbate.
DeferasiroxThe risk or severity of adverse effects can be increased when Prednicarbate is combined with Deferasirox.
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Prednicarbate.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, 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 grow...
Gene Name:
NR3C1
Uniprot ID:
P04150
Molecular Weight:
85658.57 Da
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:2879901 ]
  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. doi: 10.1136/hrt.2009.168971. Epub 2009 May 28. [PubMed:19482847 ]
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Drug created on June 13, 2005 07:24 / Updated on May 12, 2016 15:19