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Identification
NameAmcinonide
Accession NumberDB00288  (APRD00788)
Typesmall molecule
Groupsapproved
Description

Amcinonide is a corticosteroid. [Wikipedia]

Structure
Thumb
Synonyms
SynonymLanguageCode
TriamcinolonacetatcyclopentanonidNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
CyclocortWyeth
MycodermNot Available
PenticortNot Available
VisdermNot Available
Brand mixturesNot Available
Categories
CAS number51022-69-6
WeightAverage: 502.5717
Monoisotopic: 502.236681679
Chemical FormulaC28H35FO7
InChI KeyInChIKey=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
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassGluco/mineralocorticoids, Progestogins and Derivatives
Direct parentGluco/mineralocorticoids, Progestogins and Derivatives
Alternative parentsHydroxysteroids; Halogenated Steroids; Ketosteroids; Cyclohexanols; 1,3-Dioxolanes; Fluorohydrins; Carboxylic Acid Esters; Cyclic Alcohols and Derivatives; Ketones; Enolates; Polyamines; Acetals; Aldehydes; Alkyl Fluorides; Organofluorides
Substituents20-keto-steroid; 3-keto-steroid; 11-hydroxy-steroid; 9-halo-steroid; cyclohexanol; meta-dioxolane; cyclic alcohol; secondary alcohol; carboxylic acid ester; ketone; halohydrin; fluorohydrin; enolate; acetal; ether; polyamine; carboxylic acid derivative; organofluoride; carbonyl group; alkyl halide; alkyl fluoride; organohalogen; alcohol; aldehyde
Classification descriptionThis compound belongs to the gluco/mineralocorticoids, progestogins and derivatives. These are steroids whose structure is based on an hydroxylated prostane moiety.
Pharmacology
IndicationFor the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.
PharmacodynamicsAmcinonide 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 actionThe 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.
AbsorptionTopical corticosteroids can be absorbed from normal intact skin. Inflammation and/or other disease processes in the skin increase percutaneous absorption.
Volume of distributionNot Available
Protein bindingNot 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 eliminationCorticosteroids 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 lifeNot Available
ClearanceNot Available
ToxicityResults 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9643
Blood Brain Barrier + 0.9897
Caco-2 permeable - 0.5844
P-glycoprotein substrate Substrate 0.7713
P-glycoprotein inhibitor I Inhibitor 0.7198
P-glycoprotein inhibitor II Inhibitor 0.5596
Renal organic cation transporter Non-inhibitor 0.7608
CYP450 2C9 substrate Non-substrate 0.8615
CYP450 2D6 substrate Non-substrate 0.9016
CYP450 3A4 substrate Substrate 0.7307
CYP450 1A2 substrate Non-inhibitor 0.8688
CYP450 2C9 substrate Non-inhibitor 0.8732
CYP450 2D6 substrate Non-inhibitor 0.8982
CYP450 2C19 substrate Non-inhibitor 0.9188
CYP450 3A4 substrate Non-inhibitor 0.8309
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8999
Ames test Non AMES toxic 0.8886
Carcinogenicity Non-carcinogens 0.941
Biodegradation Not ready biodegradable 1.0
Rat acute toxicity 2.4315 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9488
hERG inhibition (predictor II) Non-inhibitor 0.5298
Pharmacoeconomics
Manufacturers
  • Altana inc
  • Taro pharmaceutical industries ltd
  • Astellas pharma us inc
Packagers
Dosage forms
FormRouteStrength
CreamTopical
LotionTopical
OintmentTopical
Prices
Unit descriptionCostUnit
Amcinonide 0.1% Cream 60 gm Tube84.29USDtube
Amcinonide 0.1% Ointment 60 gm Tube84.29USDtube
Amcinonide 0.1% Cream 30 gm Tube28.71USDtube
Amcinonide 0.1% Cream 15 gm Tube20.99USDtube
Amcinonide 0.1% cream1.68USDg
Cyclocort 0.1 % Cream0.62USDg
Cyclocort 0.1 % Ointment0.62USDg
Cyclocort 0.1 % Lotion0.52USDg
Ratio-Amcinonide 0.1 % Ointment0.33USDg
Ratio-Amcinonide 0.1 % Cream0.29USDg
Taro-Amcinonide 0.1 % Cream0.29USDg
Ratio-Amcinonide 0.1 % Lotion0.27USDg
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
logP2.3Not Available
Predicted Properties
PropertyValueSource
water solubility7.74e-03 g/lALOGPS
logP3.16ALOGPS
logP3.2ChemAxon
logS-4.8ALOGPS
pKa (strongest acidic)13.63ChemAxon
pKa (strongest basic)-3.4ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count6ChemAxon
hydrogen donor count1ChemAxon
polar surface area99.13ChemAxon
rotatable bond count4ChemAxon
refractivity127.88ChemAxon
polarizability52.23ChemAxon
number of rings6ChemAxon
bioavailability1ChemAxon
rule of fiveNoChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Schultz, W., Sieger, G.M. and Krieger, C.: British Patent 1,442,925; July 14,1976; assigned to
American Cyanamid Company.

General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD01387
PubChem Compound443958
PubChem Substance46506705
ChemSpider392009
ChEBI31199
ChEMBLCHEMBL1200732
Therapeutic Targets DatabaseDAP001044
PharmGKBPA164746074
Drug Product Database2247097
RxListhttp://www.rxlist.com/cgi/generic/amcinonide.htm
Drugs.comhttp://www.drugs.com/cdi/amcinonide-cream.html
PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/cyc1108.shtml
WikipediaAmcinonide
ATC CodesD07AC11
AHFS Codes
  • 84:06.00
PDB EntriesNot Available
FDA labelshow(143 KB)
MSDSshow(48.1 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Glucocorticoid receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Glucocorticoid receptor P04150 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Annexin A1 P04083 Details

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 March 27, 2014 14:04