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Identification
NameAmcinonide
Accession NumberDB00288  (APRD00788)
TypeSmall Molecule
GroupsApproved
Description

Amcinonide is a corticosteroid. [Wikipedia]

Structure
Thumb
Synonyms
SynonymLanguageCode
AmcinonidaNot AvailableNot Available
AmcinonidumNot AvailableNot Available
TriamcinolonacetatcyclopentanonidNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cyclocortlotion0.1 %topicalGlaxosmithkline IncNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Cyclocortcream0.1 %topicalGlaxosmithkline IncNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Cyclocortointment0.1 %topicalGlaxosmithkline IncNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Amcinonidecream1 mg/gtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2003-05-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Amcinonideointment1 mg/gtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2014-04-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Amcinonidelotion1 mg/gtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2002-11-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Amcinonidecream1 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.2002-05-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Amcinonideointment1 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.2003-03-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
MycodermNot Available
PenticortNot Available
VisdermNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number51022-69-6
WeightAverage: 502.5717
Monoisotopic: 502.236681679
Chemical FormulaC28H35FO7
InChI KeyILKJAFIWWBXGDU-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[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 20-oxosteroid
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Halo-steroid
  • 9-halo-steroid
  • 3-oxosteroid
  • 3-oxo-delta-1,4-steroid
  • Delta-1,4-steroid
  • Alpha-acyloxy ketone
  • Acetate salt
  • Cyclic alcohol
  • Meta-dioxolane
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Halohydrin
  • Fluorohydrin
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl fluoride
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
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
PropertyValueProbability
Human Intestinal Absorption+0.9643
Blood Brain Barrier+0.9897
Caco-2 permeable-0.5844
P-glycoprotein substrateSubstrate0.7713
P-glycoprotein inhibitor IInhibitor0.7198
P-glycoprotein inhibitor IIInhibitor0.5596
Renal organic cation transporterNon-inhibitor0.7608
CYP450 2C9 substrateNon-substrate0.8615
CYP450 2D6 substrateNon-substrate0.9016
CYP450 3A4 substrateSubstrate0.7307
CYP450 1A2 substrateNon-inhibitor0.8688
CYP450 2C9 substrateNon-inhibitor0.8732
CYP450 2D6 substrateNon-inhibitor0.8982
CYP450 2C19 substrateNon-inhibitor0.9188
CYP450 3A4 substrateNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8999
Ames testNon AMES toxic0.8886
CarcinogenicityNon-carcinogens0.941
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4315 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9488
hERG inhibition (predictor II)Non-inhibitor0.5298
Pharmacoeconomics
Manufacturers
  • Altana inc
  • Taro pharmaceutical industries ltd
  • Astellas pharma us inc
Packagers
Dosage forms
FormRouteStrength
Creamtopical0.1 %
Creamtopical1 mg/g
Lotiontopical0.1 %
Lotiontopical1 mg/g
Ointmenttopical0.1 %
Ointmenttopical1 mg/g
Prices
Unit descriptionCostUnit
Amcinonide 0.1% Cream 60 gm Tube84.29USD tube
Amcinonide 0.1% Ointment 60 gm Tube84.29USD tube
Amcinonide 0.1% Cream 30 gm Tube28.71USD tube
Amcinonide 0.1% Cream 15 gm Tube20.99USD tube
Amcinonide 0.1% cream1.68USD g
Cyclocort 0.1 % Cream0.62USD g
Cyclocort 0.1 % Ointment0.62USD g
Cyclocort 0.1 % Lotion0.52USD g
Ratio-Amcinonide 0.1 % Ointment0.33USD g
Ratio-Amcinonide 0.1 % Cream0.29USD g
Taro-Amcinonide 0.1 % Cream0.29USD g
Ratio-Amcinonide 0.1 % Lotion0.27USD g
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 Solubility0.00774 mg/mLALOGPS
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 Area99.13 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity127.88 m3·mol-1ChemAxon
Polarizability52.23 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
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
ATC CodesD07AC11
AHFS Codes
  • 84:06.00
PDB EntriesNot Available
FDA labelDownload (143 KB)
MSDSDownload (48.1 KB)
Interactions
Drug Interactions
Drug
AldesleukinMay diminish the antineoplastic effect of Aldesleukin. Exceptions: Beclomethasone (Nasal); Budesonide (Nasal); Ciclesonide (Nasal); Desonide; Dexamethasone (Ophthalmic); Difluprednate; Flunisolide (Nasal); Fluocinolone (Ophthalmic); Fluticasone (Nasal); Loteprednol; Mometasone (Nasal); PrednisoLONE (Ophthalmic); Triamcinolone (Nasal); Triamcinolone (Ophthalmic).
DeferasiroxCorticosteroids may enhance the adverse/toxic effect of Deferasirox. Specifically, the risk for GI ulceration/irritation or GI bleeding may be increased.
HyaluronidaseMay diminish the therapeutic effect of Hyaluronidase.
TelaprevirCorticosteroids may decrease the serum concentration of Telaprevir. Telaprevir may increase the serum concentration of Corticosteroids.
Food InteractionsNot Available

Targets

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

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Drug created on June 13, 2005 07:24 / Updated on March 27, 2014 14:04