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Identification
Name Amcinonide
Accession Number DB00288 (APRD00788)
Type small molecule
Groups approved
Description

Amcinonide is a corticosteroid. [Wikipedia]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Cyclocort
Brand mixtures Not Available
Categories
  • Corticosteroids, topical
CAS number 51022-69-6
Weight Average: 502.5717
Monoisotopic: 502.236681679
Chemical Formula C28H35FO7
InChI Key InChIKey=ILKJAFIWWBXGDU-MOGDOJJUSA-N
InChI
InChI=1S/C28H35FO7/c1-16(30)34-15-22(33)28-23(35-26(36-28)9-4-5-10-26)13-20-19-7-6-17-12-18(31)8-11-24(17,2)27(19,29)21(32)14-25(20,28)3/h8,11-12,19-21,23,32H,4-7,9-10,13-15H2,1-3H3/t19-,20-,21-,23+,24-,25-,27-,28+/m0/s1
Plain Text
IUPAC Name
2-[(1'S,2'S,4'R,8'S,9'S,11'S,12'R,13'S)-12'-fluoro-11'-hydroxy-9',13'-dimethyl-16'-oxo-5',7'-dioxaspiro[cyclopentane-1,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane]-14',17'-dien-8'-yl]-2-oxoethyl acetate
SMILES
[H][C@@]12C[C@@]3([H])[C@]4([H])CCC5=CC(=O)C=C[C@]5(C)[C@@]4(F)[C@@H](O)C[C@]3(C)[C@@]1(OC1(CCCC1)O2)C(=O)COC(C)=O
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
  • Acetals and Derivatives
  • Alkyl Halides
  • Ethers
  • Dioxoles
  • Heterocyclic compounds
  • Alcohols and Polyols
  • Ketones
Pharmacology
Indication For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.
Pharmacodynamics Amcinonide is a topical corticosteroid. The topical corticosteroids constitute a class of primarily synthetic steroids used as anti-inflammatory and antipruritic agents. Amcinonide reduces or inhibits the actions of chemicals in the body that cause inflammation, redness, and swelling. The mechanism of anti-inflammatory activity of the topical corticosteroids is unclear. Various laboratory methods, including vasoconstrictor assays, are used to compare and predict potencies and/or clinical efficacies of the topical corticosteroids. There is some evidence to suggest that a recognizable correlation exists between vasoconstrictor potency and therapeutic efficacy in man. When in an ointment form, amcinonide also helps the skin maintain moisture.
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. Amcinonide has affinity for the glucocorticoid receptor. It has weak affinity for the progesterone receptor, and virtually no affinity for the mineralocorticoid, estrogen, or androgen receptors.
Absorption Topical corticosteroids can be absorbed from normal intact skin. Inflammation and/or other disease processes in the skin increase percutaneous absorption.
Volume of distribution Not Available
Protein binding Not Available
Metabolism Once absorbed through the skin, topical corticosteroids are handled through pharmacokinetic pathways similar to systemically administered corticosteroids. Corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys.
Route of elimination Corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys. Some of the topical corticosteroids and their metabolites are also excreted into the bile.
Half life Not Available
Clearance Not Available
Toxicity Results from acute toxicity studies do not indicate that any risk of acute intoxication is to be expected following a single dermal application of an overdose (application over a large area under conditions favorable to absorption) or inadvertent oral ingestion.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Altana inc
  • Taro pharmaceutical industries ltd
  • Astellas pharma us inc
Packagers
Dosage forms
Form Route Strength
Cream Topical
Lotion Topical
Ointment Topical
Prices
Unit description Cost Unit
Amcinonide 0.1% Cream 60 gm Tube 84.29 USD tube
Amcinonide 0.1% Ointment 60 gm Tube 84.29 USD tube
Amcinonide 0.1% Cream 30 gm Tube 28.71 USD tube
Amcinonide 0.1% Cream 15 gm Tube 20.99 USD tube
Amcinonide 0.1% cream 1.68 USD g
Cyclocort 0.1 % Cream 0.62 USD g
Cyclocort 0.1 % Ointment 0.62 USD g
Cyclocort 0.1 % Lotion 0.52 USD g
Ratio-Amcinonide 0.1 % Ointment 0.33 USD g
Ratio-Amcinonide 0.1 % Cream 0.29 USD g
Taro-Amcinonide 0.1 % Cream 0.29 USD g
Ratio-Amcinonide 0.1 % Lotion 0.27 USD g
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Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
logP 2.3 Not Available
Predicted Properties
Property Value Source
water solubility 7.74e-03 g/l ALOGPS
logP 3.16 ALOGPS
logP 3.2 ChemAxon
logS -4.8 ALOGPS
pKa (strongest acidic) 13.63 ChemAxon
pKa (strongest basic) -3.4 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 6 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 99.13 ChemAxon
rotatable bond count 4 ChemAxon
refractivity 127.88 ChemAxon
polarizability 52.23 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D01387 Link_out
PubChem Compound 443958 Link_out
PubChem Substance 46506705 Link_out
ChemSpider 392009 Link_out
ChEBI 31199 Link_out
ChEMBL 31199 Link_out
Therapeutic Targets Database DAP001044 Link_out
PharmGKB PA164746074 Link_out
Drug Product Database 2247097 Link_out
RxList http://www.rxlist.com/cgi/generic/amcinonide.htm Link_out
Drugs.com http://www.drugs.com/cdi/amcinonide-cream.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/cyc1108.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Amcinonide Link_out
ATC Codes
  • D07AC11
AHFS Codes
  • 84:06.00
PDB Entries Not Available
FDA label show (143 KB)
MSDS show (48.1 KB)
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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. 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
  3. Grossman R, Yehuda R, Golier J, McEwen B, Harvey P, Maria NS: Cognitive effects of intravenous hydrocortisone in subjects with PTSD and healthy control subjects. Ann N Y Acad Sci. 2006 Jul;1071:410-21. Pubmed
  4. Rautanen A, Eriksson JG, Kere J, Andersson S, Osmond C, Tienari P, Sairanen H, Barker DJ, Phillips DI, Forsen T, Kajantie E: Associations of body size at birth with late-life cortisol concentrations and glucose tolerance are modified by haplotypes of the glucocorticoid receptor gene. J Clin Endocrinol Metab. 2006 Nov;91(11):4544-51. Epub 2006 Aug 8. Pubmed
  5. Hammer F, Stewart PM: Cortisol metabolism in hypertension. Best Pract Res Clin Endocrinol Metab. 2006 Sep;20(3):337-53. Pubmed
  6. Shaw JR, Gabor K, Hand E, Lankowski A, Durant L, Thibodeau R, Stanton CR, Barnaby R, Coutermarsh B, Karlson KH, Sato JD, Hamilton JW, Stanton BA: Role of glucocorticoid receptor in acclimation of killifish (Fundulus heteroclitus) to seawater and effects of arsenic. Am J Physiol Regul Integr Comp Physiol. 2007 Feb;292(2):R1052-60. Epub 2006 Oct 12. Pubmed
  7. Sher L: Combined dexamethasone suppression-corticotropin-releasing hormone stimulation test in studies of depression, alcoholism, and suicidal behavior. ScientificWorldJournal. 2006 Oct 31;6:1398-404. Pubmed

2. Annexin A1

Pharmacological action: unknown
Actions: agonist

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

Organism class: human
UniProt ID: P04083 Link_out
Gene: ANXA1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. 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
  3. Serres M, Comera C, Schmitt D: Annexin 1 regulation in human epidermal cells. Cell Mol Biol (Noisy-le-grand). 1994 Jul;40(5):701-6. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19