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Showing drug card for Prednicarbate (DB01130)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-02-19 16:04:35
Primary Accession Number DB01130
Secondary Accession Number
  • APRD01197
Name Prednicarbate
Drug Type
  • Approved
  • Small Molecule
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.
Synonyms Not Available
Brand Names
  1. Dermatop
  2. Dermatop E Emollient
Brand Mixtures Not Available
Chemical IUPAC Name [2-(17-ethoxycarbonyloxy-11-hydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl] propanoate
Chemical Formula C27H36O8
Chemical Structure Structure
CAS Registry Number 73771-04-7
InChI Identifier InChI=1/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
InChI Key FNPXMHRZILFCKX-UHFFFAOYAT
KEGG Drug Not Available
KEGG Compound Not Available
PubChem Compound 52421 Link Image
PubChem Substance 190435 Link Image
ChEBI ID Not Available
PharmGKB ID PA451095 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 02230642 Link Image
RxList Link http://www.rxlist.com/cgi/generic2/prednicarbate.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Prednicarbate Link Image
FDA Label
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Not Available
Average Molecular Weight 488.5699
Monoisotopic Molecular Weight 488.2410
State Solid
Melting Point Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 5.62e-03 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 2.9 Source: PhysProp
Predicted LogP 3.08 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -4.94 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CCOC(=O)O[C@]1(CC[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@H]3[C@H](O)C[C@]12C)C(=O)COC(=O)CC
Canonical SMILES CCOC(=O)OC1(CCC2C3CCC4=CC(=O)C=CC4(C)C3C(O)CC12C)C(=O)COC(=O)CC
Drug Category
  • Anti Inflammatory
  • Anti-inflammatory Agents
  • Corticosteroid
  • Glucocorticoids
  • Steroidal
ATC Codes
AHFS Codes
  • 84:06.00
  • 92:04.00*
Indication For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.
Pharmacology 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.
Toxicity Not Available
Protein Binding Not Available
Biotransformation Primarily in skin
Half Life Not Available
Dosage Forms
Form Route
Cream Topical
Liquid Cutaneous
Liquid Intradermal
Liquid Subcutaneous
Ointment Topical
Patient Information Not Available
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. Drugs.com Link Image
  2. Wikipedia Link Image
  3. RxList Link Image
Organisms Affected
  • Humans and other mammals
Targets
  1. Annexin A1
Drug Target 1 [top]
Target 1 ID 469
Target 1 Name Annexin A1
Target 1 Synonyms
  1. Annexin I
  2. Calpactin II
  3. Chromobindin-9
  4. Lipocortin I
  5. Phospholipase A2 inhibitory protein
  6. p35
Target 1 Gene Name ANXA1
Target 1 Protein Sequence >Annexin A1 
AMVSEFLKQAWFIENEEQEYVQTVKSSKGGPGSAVSPYPTFNPSSDVAALHKAIMVKGVD
EATIIDILTKRNNAQRQQIKAAYLQETGKPLDETLKKALTGHLEEVVLALLKTPAQFDAD
ELRAAMKGLGTDEDTLIEILASRTNKEIRDINRVYREELKRDLAKDITSDTSGDFRNALL
SLAKGDRSEDFGVNEDLADSDARALYEAGERRKGTDVNVFNTILTTRSYPQLRRVFQKYT
KYSKHDMNKVLDLELKGDIEKCLTAIVKCATSKPAFFAEKLHQAMKGVGTRHKALIRIMV
SRSEIDMNDIKAFYQKMYGISLCQAILDETKGDYEKILVALCGGN
Target 1 Number of Residues 350
Target 1 Molecular Weight 38583
Target 1 Theoretical pI 7.04
Target 1 GO Classification
Function
enzyme regulator activity
enzyme inhibitor activity
phospholipase inhibitor activity
lipid binding
phospholipid binding
calcium-dependent phospholipid binding
binding
ion binding
cation binding
calcium ion binding
Process
Not Available
Component
Not Available
Target 1 General Function Involved in calcium ion binding
Target 1 Specific Function Calcium/phospholipid-binding protein which promotes membrane fusion and is involved in exocytosis. This protein regulates phospholipase A2 activity. It seems to bind from two to four calcium ions with high affinity
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 12654863 Link Image
Target 1 UniProtKB/Swiss-Prot ID P04083 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name ANXA1_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location Not Available
Target 1 Gene Sequence >1041 bp 
ATGGCAATGGTATCAGAATTCCTCAAGCAGGCCTGGTTTATTGAAAATGAAGAGCAGGAA
TATGTTCAAACTGTGAAGTCATCCAAAGGTGGTCCCGGATCAGCGGTGAGCCCCTATCCT
ACCTTCAATCCATCCTCGGATGTCGCTGCCTTGCATAAGGCCATAATGGTTAAAGGTGTG
GATGAAGCAACCATCATTGACATTCTAACTAAGCGAAACAATGCACAGCGTCAACAGATC
AAAGCAGCATATCTCCAGGAAACAGGAAAGCCCCTGGATGAAACACTTAAGAAAGCCCTT
ACAGGTCACCTTGAGGAGGTTGTTTTAGCTCTGCTAAAAACTCCAGCGCAATTTGATGCT
GATGAACTTCGTGCTGCCATGAAGGGCCTTGGAACTGATGAAGATACTCTAATTGAGATT
TTGGCATCAAGAACTAACAAAGAAATCAGAGACATTAACAGGGTCTACAGAGAGGAACTG
AAGAGAGATCTGGCCAAAGACATAACCTCAGACACATCTGGAGATTTTCGGAACGCTTTG
CTTTCTCTTGCTAAGGGTGACCGATCTGAGGACTTTGGTGTGAATGAAGACTTGGCTGAT
TCAGATGCCAGGGCCTTGTATGAAGCAGGAGAAAGGAGAAAGGGGACAGACGTAAACGTG
TTCAATACCATCCTTACCACCAGAAGCTATCCACAACTTCGCAGAGTGTTTCAGAAATAC
ACCAAGTACAGTAAGCATGACATGAACAAAGTTCTGGACCTGGAGTTGAAAGGTGACATT
GAGAAATGCCTCACAGCTATCGTGAAGTGCGCCACAAGCAAACCAGCTTTCTTTGCAGAG
AAGCTTCATCAAGCCATGAAAGGTGTTGGAACTCGCCATAAGGCATTGATCAGGATTATG
GTTTCCCGTTCTGAAATTGACATGAATGATATCAAAGCATTCTATCAGAAGATGTATGGT
ATCTCCCTTTGCCAAGCCATCCTGGATGAAACCAAAGGAGATTATGAGAAAATCCTGGTG
GCTCTTTGTGGAGGAAACTAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID ANXA1 Link Image
Target 1 GenAtlas ID ANXA1 Link Image
Target 1 HGNC ID HGNC:533 Link Image
Target 1 Chromosome Location 9
Target 1 Locus 9q12-q21.2|9q12-q21.2
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Kovacic RT, Tizard R, Cate RL, Frey AZ, Wallner BP: Correlation of gene and protein structure of rat and human lipocortin I. Biochemistry. 1991 Sep 17;30(37):9015-21. [PubMed Link Image]
  2. Varticovski L, Chahwala SB, Whitman M, Cantley L, Schindler D, Chow EP, Sinclair LK, Pepinsky RB: Location of sites in human lipocortin I that are phosphorylated by protein tyrosine kinases and protein kinases A and C. Biochemistry. 1988 May 17;27(10):3682-90. [PubMed Link Image]
  3. Pepinsky RB, Sinclair LK, Chow EP, O'Brine-Greco B: A dimeric form of lipocortin-1 in human placenta. Biochem J. 1989 Oct 1;263(1):97-103. [PubMed Link Image]
  4. Wallner BP, Mattaliano RJ, Hession C, Cate RL, Tizard R, Sinclair LK, Foeller C, Chow EP, Browing JL, Ramachandran KL, et al.: Cloning and expression of human lipocortin, a phospholipase A2 inhibitor with potential anti-inflammatory activity. Nature. 1986 Mar 6-12;320(6057):77-81. [PubMed Link Image]
  5. Biemann K, Scoble HA: Characterization by tandem mass spectrometry of structural modifications in proteins. Science. 1987 Aug 28;237(4818):992-8. [PubMed Link Image]
  6. Arcone R, Arpaia G, Ruoppolo M, Malorni A, Pucci P, Marino G, Ialenti A, Di Rosa M, Ciliberto G: Structural characterization of a biologically active human lipocortin 1 expressed in Escherichia coli. Eur J Biochem. 1993 Jan 15;211(1-2):347-55. [PubMed Link Image]
  7. Weng X, Luecke H, Song IS, Kang DS, Kim SH, Huber R: Crystal structure of human annexin I at 2.5 A resolution. Protein Sci. 1993 Mar;2(3):448-58. [PubMed Link Image]
  8. Gao J, Li Y, Yan H: NMR solution structure of domain 1 of human annexin I shows an autonomous folding unit. J Biol Chem. 1999 Jan 29;274(5):2971-7. [PubMed Link Image]
Target 1 Drug References
  1. 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 Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.