Identification
- Summary
Prednicarbate is a medium potency topical corticosteroid used to manage pruritus and inflammation associated with responsive skin conditions.
- Brand Names
- Dermatop
- Generic Name
- Prednicarbate
- DrugBank Accession Number
- DB01130
- Background
Prednicarbate is a relatively new topical corticosteroid drug that displays a similar potency as 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.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Prednicarbate (DB01130)
- Weight
- Average: 488.577
Monoisotopic: 488.241018119 - Chemical Formula
- C27H36O8
- Synonyms
- Prednicarbate
- Prednicarbato
- External IDs
- LAS-189961
- LAS189961
- S 77 0777
Pharmacology
- Indication
For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Dermatoses •••••••••••• •••••••••• •• ••••••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism AGlucocorticoid receptor agonistHumans - 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Prednicarbate can be increased when it is combined with Abametapir. Acarbose The risk or severity of hyperglycemia can be increased when Prednicarbate is combined with Acarbose. Acetohexamide The risk or severity of hyperglycemia can be increased when Prednicarbate is combined with Acetohexamide. Acetyldigitoxin The risk or severity of adverse effects can be increased when Prednicarbate is combined with Acetyldigitoxin. Albiglutide The risk or severity of hyperglycemia can be increased when Prednicarbate is combined with Albiglutide. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Dermatop E Emollient
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Dermatop Cream 1 mg/1g Topical Physicians Total Care, Inc. 2003-11-21 2011-06-30 US 
Dermatop Cream 1 mg/1g Topical Valeant Pharmaceuticals North America 1993-10-29 2017-04-30 US Dermatop Cream 1 mg/1g Topical Dermik Laboratories 1993-10-29 2015-09-30 US Dermatop Ointment 1 mg/1g Topical Valeant Pharmaceuticals North America 2014-06-23 2017-04-01 US Dermatop Ointment 1 mg/1g Topical Dermik Laboratories 1991-09-23 2015-06-30 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Prednicarbate Cream 1 mg/1g Topical E. Fougera & CO., A division of Fougera Pharmaceuticals Inc. 2006-09-19 Not applicable US Prednicarbate Ointment 1.0 mg/1g Topical Fougera Pharmaceuticals Inc. 2007-03-09 Not applicable US Prednicarbate Cream 1 mg/1g Topical Oceanside Pharmaceuticals 1993-10-29 Not applicable US Prednicarbate Cream 1 mg/1g Topical Prasco, Laboratories 2007-04-30 2017-04-30 US
Categories
- ATC Codes
- D07AC18 — Prednicarbate
- Drug Categories
- Adrenal Cortex Hormones
- Anti-Inflammatory Agents
- Corticosteroid Hormone Receptor Agonists
- Corticosteroids
- Corticosteroids, Dermatological Preparations
- Corticosteroids, Potent (Group III)
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Substrates
- Dermatologicals
- Fused-Ring Compounds
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Immunosuppressive Agents
- Pregnadienes
- Pregnadienetriols
- Pregnanes
- Steroids
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Pregnane steroids
- Direct Parent
- Gluco/mineralocorticoids, progestogins and derivatives
- Alternative Parents
- Steroid esters / 20-oxosteroids / 3-oxo delta-1,4-steroids / 11-beta-hydroxysteroids / Delta-1,4-steroids / Alpha-acyloxy ketones / Carbonic acid diesters / Secondary alcohols / Cyclic ketones / Cyclic alcohols and derivatives show 4 more
- Substituents
- 11-beta-hydroxysteroid / 11-hydroxysteroid / 20-oxosteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / Alcohol / Aliphatic homopolycyclic compound / Alpha-acyloxy ketone / Carbonic acid derivative / Carbonic acid diester show 17 more
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- V901LV1K7D
- CAS number
- 73771-04-7
- InChI Key
- FNPXMHRZILFCKX-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
- 2-[(1S,2R,10S,11S,14R,15S,17S)-14-[(ethoxycarbonyl)oxy]-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-14-yl]-2-oxoethyl propanoate
- SMILES
- [H][C@@]12CC[C@](OC(=O)OCC)(C(=O)COC(=O)CC)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
References
- General References
- Gupta AK, Chow M: A review of prednicarbate (Dermatop). Skin Therapy Lett. 2004 Dec-2005 Jan;9(10):5-6, 9. [Article]
- External Links
- PubChem Compound
- 6714002
- PubChem Substance
- 46506799
- ChemSpider
- 5145991
- 34369
- ChEBI
- 135791
- ChEMBL
- CHEMBL1200386
- ZINC
- ZINC000003938652
- Therapeutic Targets Database
- DAP001189
- PharmGKB
- PA164749394
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Prednicarbate
- FDA label
- Download (130 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 2 Completed Treatment Atopic Dermatitis 1 2 Completed Treatment Candidiasis 1 2 Completed Treatment Tinea Pedis 1 1 Completed Treatment Psoriasis 1 Not Available Completed Treatment Moderate to Severe Atopic Dermatitis 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Dermik Labs
- E. Fougera and Co.
- Nycomed Inc.
- Ortho Mcneil Janssen Pharmaceutical Inc.
- Physicians Total Care Inc.
- Prasco Labs
- Sanofi-Aventis Inc.
- Dosage Forms
Form Route Strength Cream Cream Cutaneous 0.25 % Cream Topical 1 mg/1g Ointment Topical 1 mg/1g Cream 0.25 %w/w Cream 2.5 mg/g Cream Topical 0.1 % w/w Ointment Topical 0.1 % w/w Ointment Topical 0.25 g Cream Cutaneous 250.000 mg Cream 0.25 % Cream Topical 0.25 g Solution Topical 2.5 mg/g Cream Topical 2.5 MG/G Ointment Topical 1.0 mg/1g Ointment Topical 2.5 MG/G Cream Topical 0.25 % Solution Topical 0.25 % Ointment Topical 0.25 % Emulsion Topical 0.1 g Gel Topical - Prices
Unit description Cost Unit Prednicarbate 0.1% Ointment 60 gm Tube 76.74USD tube Dermatop 0.1% Cream 60 gm Tube 75.2USD tube Dermatop 0.1% Ointment 60 gm Tube 70.06USD tube Prednicarbate 0.1% Cream 60 gm Tube 59.03USD tube Prednicarbate 0.1% Ointment 15 gm Tube 37.31USD tube Prednicarbate 0.1% Cream 15 gm Tube 24.0USD tube Dermatop 0.1% cream 1.76USD g Prednicarbate 0.1% cream 1.41USD 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 0.00562 mg/mL ALOGPS logP 3.08 ALOGPS logP 3.83 Chemaxon logS -4.9 ALOGPS pKa (Strongest Acidic) 14.83 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 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 127.8 m3·mol-1 Chemaxon Polarizability 52.43 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - 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 inhibitor Non-inhibitor 0.9054 CYP450 2D6 inhibitor Non-inhibitor 0.9032 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 231.7813939 predictedDarkChem Lite v0.1.0 [M-H]- 204.97437 predictedDeepCCS 1.0 (2019) [M+H]+ 232.3868939 predictedDarkChem Lite v0.1.0 [M+H]+ 206.88559 predictedDeepCCS 1.0 (2019) [M+Na]+ 213.89552 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- 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 modula...
- Gene Name
- NR3C1
- Uniprot ID
- P04150
- Uniprot Name
- Glucocorticoid receptor
- Molecular Weight
- 85658.57 Da
References
- Boudinot FD, D'Ambrosio R, Jusko WJ: Receptor-mediated pharmacodynamics of prednisolone in the rat. J Pharmacokinet Biopharm. 1986 Oct;14(5):469-93. [Article]
- 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. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55