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Showing drug card for Alclometasone (DB00240)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-02-19 16:04:25
Primary Accession Number DB00240
Secondary Accession Number
  • APRD00783
Name Alclometasone
Drug Type
  • Approved
  • Small Molecule
Description Alclometasone is synthetic glucocorticoid steroid for topical use in dermatology as anti-inflammatory, antipruritic, antiallergic, antiproliferative and vasoconstrictive agent. [Wikipedia]
Synonyms
  1. Alclometasone dipropionate
Brand Names
  1. Aclovate
Brand Mixtures Not Available
Chemical IUPAC Name [(7R,8S,9S,10R,11S,13S,14S,16R,17R)-7-chloro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-(2-propanoyloxyacetyl)-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl] propanoate
Chemical Formula C28H37ClO7
Chemical Structure Structure
CAS Registry Number 66734-13-2
InChI Identifier InChI=1/C28H37ClO7/c1-6-22(33)35-14-21(32)28(36-23(34)7-2)15(3)10-18-24-19(29)12-16-11-17(30)8-9-26(16,4)25(24)20(31)13-27(18,28)5/h8-9,11,15,18-20,24-25,31H,6-7,10,12-14H2,1-5H3/t15-,18+,19-,20+,24-,25+,26+,27+,28+/m1/s1
InChI Key DJHCCTTVDRAMEH-DUUJBDRPBB
KEGG Drug D01820 Link Image
KEGG Compound Not Available
PubChem Compound 636374 Link Image
PubChem Substance 7848882 Link Image
ChEBI ID Not Available
PharmGKB ID PA448070 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] Not Available
RxList Link http://www.rxlist.com/cgi/generic3/alclometasone.htm Link Image
PDRhealth Link http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/acl1005.shtml Link Image
Wikipedia Link http://en.wikipedia.org/wiki/Alclometasone Link Image
FDA Label
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 521.0420
Monoisotopic Molecular Weight 520.2228
State Solid
Melting Point Not Available
Experimental Water Solubility Insoluble Source: PhysProp
Predicted Water Solubility 2.81e-03 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 2.7 Source: PhysProp
Predicted LogP 3.28 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -5.27 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 CCC(=O)OCC(=O)[C@@]1(OC(=O)CC)[C@H](C)C[C@H]2[C@@H]3[C@H](Cl)CC4=CC(=O)C=C[C@]4(C)[C@H]3[C@@H](O)C[C@]12C
Canonical SMILES CCC(=O)OCC(=O)C1(OC(=O)CC)C(C)CC2C3C(Cl)CC4=CC(=O)C=CC4(C)C3C(O)CC12C
Drug Category
  • Anti-inflammatory Agents
  • Antipruritic Agents
  • Corticosteroids
  • Glucocorticoids
ATC Codes
AHFS Codes Not Available
Indication For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.
Pharmacology Alclometasone is a synthetic corticosteroid for topical dermatologic use. The corticosteroids constitute a class of primarily synthetic steroids used topically as anti-inflammatory and antipruritic agents. Alclometasone is a selective glucocorticoid receptor agonist.
Mechanism of Action The mechanism of the anti-inflammatory activity of the topical steroids, in general, 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. Alclometasone also binds the corticosteroid receptor.
Absorption Topical corticosteroids can be absorbed from normal intact skin. Studies have shown that approximately 3% of steroid is absorbed during 8 hours of contact with intact skin of normal volunteers.
Toxicity Symptoms of overdose include suppression of adrenal glands, temporary decrease in white blood cell counts, symptoms of hypersensitivity (such as skin rash, hives, itching, and difficulty breathing), and increased susceptibility to infection.
Protein Binding Not Available
Biotransformation Hepatic.
Half Life Not Available
Dosage Forms
Form Route
Cream Topical
Ointment Topical
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. Wikipedia Link Image
  2. RxList Link Image
  3. PDRhealth Link Image
Organisms Affected
  • Humans and other mammals
Phase 1 Metabolizing Enzymes
  1. Cytochrome P450 3A4 (CYP3A4)
Targets
  1. Corticosteroid-binding globulin
  2. Annexin A1
Phase 1 Metabolizing Enzyme 1 [top]
Enzyme 1 Name Cytochrome P450 3A4 (CYP3A4)
Enzyme 1 Gene Name CYP3A4
Enzyme 1 SwissProt ID P08684 Link Image
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 Protein Sequence >sp|P08684|CP3A4_HUMAN Cytochrome P450 3A4 (EC 1.14.13.67) 
ALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNILSYHKGFCMFD
MECHKKYGKVWGFYDGQQPVLAITDPDMIKTVLVKECYSVFTNRRPFGPVGFMKSAISIA
EDEEWKRLRSLLSPTFTSGKLKEMVPIIAQYGDVLVRNLRREAETGKPVTLKDVFGAYSM
DVITSTSFGVNIDSLNNPQDPFVENTKKLLRFDFLDPFFLSITVFPFLIPILEVLNICVF
PREVTNFLRKSVKRMKESRLEDTQKHRVDFLQLMIDSQNSKETESHKALSDLELVAQSII
FIFAGYETTSSVLSFIMYELATHPDVQQKLQEEIDAVLPNKAPPTYDTVLQMEYLDMVVN
ETLRLFPIAMRLERVCKKDVEINGMFIPKGWVVMIPSYALHRDPKYWTEPEKFLPERFSK
KNKDNIDPYIYTPFGSGPRNCIGMRFALMNMKLALIRVLQNFSFKPCKETQIPLKLSLGG
LLQPEKPVVLKVESRDGTVSGA
Drug Target 1 [top]
Target 1 ID 232
Target 1 Name Corticosteroid-binding globulin
Target 1 Synonyms
  1. CBG
  2. Corticosteroid-binding globulin precursor
  3. Serpin A6
  4. Transcortin
Target 1 Gene Name SERPINA6
Target 1 Protein Sequence >Corticosteroid-binding globulin precursor 
MPLLLYTCLLWLPTSGLWTVQAMDPNAAYVNMSNHHRGLASANVDFAFSLYKHLVALSPK
KNIFISPVSISMALAMLSLGTCGHTRAQLLQGLGFNLTERSETEIHQGFQHLHQLFAKSD
TSLEMTMGNALFLDGSLELLESFSADIKHYYESEVLAMNFQDWATASRQINSYVKNKTQG
KIVDLFSGLDSPAILVLVNYIFFKGTWTQPFDLASTREENFYVDETTVVKVPMMLQSSTI
SYLHDSELPCQLVQMNYVGNGTVFFILPDKGKMNTVIAALSRDTINRWSAGLTSSQVDLY
IPKVTISGVYDLGDVLEEMGIADLFTNQANFSRITQDAQLKSSKVVHKAVLQLNEEGVDT
AGSTGVTLNLTSKPIILRFNQPFIIMIFDHFTWSSLFLARVMNPV
Target 1 Number of Residues 411
Target 1 Molecular Weight 45141
Target 1 Theoretical pI 5.94
Target 1 GO Classification
Function
enzyme regulator activity
enzyme inhibitor activity
protease inhibitor activity
endopeptidase inhibitor activity
serine-type endopeptidase inhibitor activity
Process
Not Available
Component
Not Available
Target 1 General Function Involved in serine-type endopeptidase inhibitor activity
Target 1 Specific Function Major transport protein for glucocorticoids and progestins in the blood of almost all vertebrate species
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • 1-22
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 179971 Link Image
Target 1 UniProtKB/Swiss-Prot ID P08185 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name CBG_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Secreted protein
Target 1 Gene Sequence >1218 bp 
ATGCCACTCCTCCTGTACACCTGTCTTCTCTGGCTGCCCACCAGCGGCCTCTGGACCGTC
CAGGCCATGGATCCTAACGCTGCTTATGTGAACATGAGTAACCATCACCGGGGCCTGGCT
TCAGCCAACGTTGACTTTGCCTTCAGCCTGTATAAGCACCTAGTGGCCTTGAGTCCCAAA
AAGAACATTTTCATCTCCCCTGTGAGCATCTCCATGGCCTTAGCTATGCTGTCCCTGGGC
ACCTGTGGCCACACACGGGCCCAGCTTCTCCAGGGCCTGGGTTTCAACCTCACTGAGAGG
TCTGAGACTGAGATCCACCAGGGTTTCCAGCACCTGCACCAACTCTTTGCAAAGTCAGAC
ACCAGCTTAGAAATGACTATGGGCAATGCCTTGTTTCTTGATGGCAGCCTGGAGTTGCTG
GAGTCATTCTCAGCAGACATCAAGCACTACTATGAGTCAGAGGTCTTGGCTATGAATTTC
CAGGACTGGGCAACAGCCAGCAGACAGATCAACAGCTATGTCAAGAATAAGACACAGGGG
AAAATTGTCGACTTGTTTTCAGGGCTGGATAGCCCAGCCATCCTCGTCCTGGTCAACTAT
ATCTTCTTCAAAGGCACATGGACACAGCCCTTTGACCTGGCAAGCACCAGGGAGGAGAAC
TTCTATGTGGACGAGACAACTGTGGTGAAGGTGCCCATGATGTTGCAGTCGAGCACCATC
AGTTACCTTCATGACTCAGAGCTCCCCTGCCAGCTGGTGCAGATGAACTACGTGGGCAAT
GGGACTGTCTTCTTCATCCTTCCGGACAAGGGGAAGATGAACACAGTCATCGCTGCACTG
AGCCGGGACACGATTAACAGGTGGTCCGCAGGCCTGACCAGCAGCCAGGTGGACCTGTAC
ATTCCAAAGGTCACCATCTCTGGAGTCTATGACCTTGGAGATGTGCTGGAGGAAATGGGC
ATTGCAGACTTGTTCACCAACCAGGCAAATTTCTCACGCATCACCCAGGACGCCCAGCTG
AAGTCATCAAAGGTGGTCCATAAAGCTGTGCTGCAACTCAATGAGGAGGGTGTGGACACA
GCTGGCTCCACTGGGGTCACCCTAAACCTGACGTCCAAGCCTATCATCTTGCGTTTCAAC
CAGCCCTTCATCATCATGATCTTCGACCACTTCACCTGGAGCAGCCTTTTCCTGGCGAGG
GTTATGAACCCAGTGTAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID SERPINA6 Link Image
Target 1 GenAtlas ID SERPINA6 Link Image
Target 1 HGNC ID HGNC:1540 Link Image
Target 1 Chromosome Location 14
Target 1 Locus 14q32.1
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Emptoz-Bonneton A, Cousin P, Seguchi K, Avvakumov GV, Bully C, Hammond GL, Pugeat M: Novel human corticosteroid-binding globulin variant with low cortisol-binding affinity. J Clin Endocrinol Metab. 2000 Jan;85(1):361-7. [PubMed Link Image]
  2. Smith CL, Power SG, Hammond GL: A Leu----His substitution at residue 93 in human corticosteroid binding globulin results in reduced affinity for cortisol. J Steroid Biochem Mol Biol. 1992 Aug;42(7):671-6. [PubMed Link Image]
  3. Hammond GL, Smith CL, Goping IS, Underhill DA, Harley MJ, Reventos J, Musto NA, Gunsalus GL, Bardin CW: Primary structure of human corticosteroid binding globulin, deduced from hepatic and pulmonary cDNAs, exhibits homology with serine protease inhibitors. Proc Natl Acad Sci U S A. 1987 Aug;84(15):5153-7. [PubMed Link Image]
  4. Kato EA, Hsu BR, Kuhn RW: Comparative structural analyses of corticosteroid binding globulin. J Steroid Biochem. 1988 Feb;29(2):213-20. [PubMed Link Image]
  5. Bardin CW, Gunsalus GL, Musto NA, Cheng CY, Reventos J, Smith C, Underhill DA, Hammond G: Corticosteroid binding globulin, testosterone-estradiol binding globulin, and androgen binding protein belong to protein families distinct from steroid receptors. J Steroid Biochem. 1988;30(1-6):131-9. [PubMed Link Image]
  6. Van Baelen H, Power SG, Hammond GL: Decreased cortisol-binding affinity of transcortin Leuven is associated with an amino acid substitution at residue-93. Steroids. 1993 Jun;58(6):275-7. [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]
Drug Target 2 [top]
Target 2 ID 469
Target 2 Name Annexin A1
Target 2 Synonyms
  1. Annexin I
  2. Calpactin II
  3. Chromobindin-9
  4. Lipocortin I
  5. Phospholipase A2 inhibitory protein
  6. p35
Target 2 Gene Name ANXA1
Target 2 Protein Sequence >Annexin A1 
AMVSEFLKQAWFIENEEQEYVQTVKSSKGGPGSAVSPYPTFNPSSDVAALHKAIMVKGVD
EATIIDILTKRNNAQRQQIKAAYLQETGKPLDETLKKALTGHLEEVVLALLKTPAQFDAD
ELRAAMKGLGTDEDTLIEILASRTNKEIRDINRVYREELKRDLAKDITSDTSGDFRNALL
SLAKGDRSEDFGVNEDLADSDARALYEAGERRKGTDVNVFNTILTTRSYPQLRRVFQKYT
KYSKHDMNKVLDLELKGDIEKCLTAIVKCATSKPAFFAEKLHQAMKGVGTRHKALIRIMV
SRSEIDMNDIKAFYQKMYGISLCQAILDETKGDYEKILVALCGGN
Target 2 Number of Residues 350
Target 2 Molecular Weight 38583
Target 2 Theoretical pI 7.04
Target 2 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 2 General Function Involved in calcium ion binding
Target 2 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 2 Pathways Not Available
Target 2 Reactions Not Available
Target 2 Pfam Domain Function
Target 2 Signals
  • None
Target 2 Transmembrane Regions
  • None
Target 2 Essentiality Non-Essential
Target 2 GenBank ID Protein 12654863 Link Image
Target 2 UniProtKB/Swiss-Prot ID P04083 Link Image
Target 2 UniProtKB/Swiss-Prot Entry Name ANXA1_HUMAN Link Image
Target 2 PDB ID Not Available
Target 2 Cellular Location Not Available
Target 2 Gene Sequence >1041 bp 
ATGGCAATGGTATCAGAATTCCTCAAGCAGGCCTGGTTTATTGAAAATGAAGAGCAGGAA
TATGTTCAAACTGTGAAGTCATCCAAAGGTGGTCCCGGATCAGCGGTGAGCCCCTATCCT
ACCTTCAATCCATCCTCGGATGTCGCTGCCTTGCATAAGGCCATAATGGTTAAAGGTGTG
GATGAAGCAACCATCATTGACATTCTAACTAAGCGAAACAATGCACAGCGTCAACAGATC
AAAGCAGCATATCTCCAGGAAACAGGAAAGCCCCTGGATGAAACACTTAAGAAAGCCCTT
ACAGGTCACCTTGAGGAGGTTGTTTTAGCTCTGCTAAAAACTCCAGCGCAATTTGATGCT
GATGAACTTCGTGCTGCCATGAAGGGCCTTGGAACTGATGAAGATACTCTAATTGAGATT
TTGGCATCAAGAACTAACAAAGAAATCAGAGACATTAACAGGGTCTACAGAGAGGAACTG
AAGAGAGATCTGGCCAAAGACATAACCTCAGACACATCTGGAGATTTTCGGAACGCTTTG
CTTTCTCTTGCTAAGGGTGACCGATCTGAGGACTTTGGTGTGAATGAAGACTTGGCTGAT
TCAGATGCCAGGGCCTTGTATGAAGCAGGAGAAAGGAGAAAGGGGACAGACGTAAACGTG
TTCAATACCATCCTTACCACCAGAAGCTATCCACAACTTCGCAGAGTGTTTCAGAAATAC
ACCAAGTACAGTAAGCATGACATGAACAAAGTTCTGGACCTGGAGTTGAAAGGTGACATT
GAGAAATGCCTCACAGCTATCGTGAAGTGCGCCACAAGCAAACCAGCTTTCTTTGCAGAG
AAGCTTCATCAAGCCATGAAAGGTGTTGGAACTCGCCATAAGGCATTGATCAGGATTATG
GTTTCCCGTTCTGAAATTGACATGAATGATATCAAAGCATTCTATCAGAAGATGTATGGT
ATCTCCCTTTGCCAAGCCATCCTGGATGAAACCAAAGGAGATTATGAGAAAATCCTGGTG
GCTCTTTGTGGAGGAAACTAA
Target 2 GenBank Gene ID
Target 2 GeneCard ID ANXA1 Link Image
Target 2 GenAtlas ID ANXA1 Link Image
Target 2 HGNC ID HGNC:533 Link Image
Target 2 Chromosome Location 9
Target 2 Locus 9q12-q21.2|9q12-q21.2
Target 2 SNPs SNPJam Report Link Image
Target 2 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 2 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.