Identification

Name
Amcinonide
Accession Number
DB00288
Description

Amcinonide is a corticosteroid.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 502.5717
Monoisotopic: 502.236681679
Chemical Formula
C28H35FO7
Synonyms
  • Amcinónida
  • Amcinonide
  • Amcinonidum
  • Triamcinolonacetatcyclopentanonid
External IDs
  • CL 34699
  • CL-34699

Pharmacology

Indication

For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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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.

TargetActionsOrganism
AGlucocorticoid receptor
agonist
Humans
UAnnexin A1
agonist
Humans
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
Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Amcinonide can be increased when it is combined with Abametapir.
AcarboseThe risk or severity of hyperglycemia can be increased when Amcinonide is combined with Acarbose.
AcetohexamideThe risk or severity of hyperglycemia can be increased when Amcinonide is combined with Acetohexamide.
AcetyldigitoxinThe risk or severity of adverse effects can be increased when Amcinonide is combined with Acetyldigitoxin.
AlbiglutideThe risk or severity of hyperglycemia can be increased when Amcinonide is combined with Albiglutide.
AlogliptinThe risk or severity of hyperglycemia can be increased when Amcinonide is combined with Alogliptin.
AminoglutethimideThe therapeutic efficacy of Amcinonide can be decreased when used in combination with Aminoglutethimide.
BendroflumethiazideThe risk or severity of electrolyte imbalance can be increased when Amcinonide is combined with Bendroflumethiazide.
BenzthiazideThe risk or severity of electrolyte imbalance can be increased when Amcinonide is combined with Benzthiazide.
BromocriptineThe risk or severity of hyperglycemia can be increased when Amcinonide is combined with Bromocriptine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

    Learn more
  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

    Learn more
Food Interactions
No interactions found.

Products

International/Other Brands
Mycoderm / Penticort / Visderm
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CyclocortLotion0.1 %TopicalGlaxosmithkline Inc1996-09-122017-09-14Canada flag
CyclocortOintment0.1 %TopicalGlaxosmithkline Inc1997-01-202018-03-08Canada flag
CyclocortOintment1 mg/1gTopicalDPT Laboratories, Ltd.1999-02-122006-01-31US flag
CyclocortCream0.1 %TopicalGlaxosmithkline Inc1996-09-122018-01-17Canada flag
Cyclocort Crm 0.1%CreamTopicalLederle Cyanamid Canada Inc.1978-12-311997-01-29Canada flag
Cyclocort Lot 0.1%LotionTopicalLederle Cyanamid Canada Inc.1983-12-311997-01-29Canada flag
Cyclocort Ont 0.1%OintmentTopicalLederle Cyanamid Canada Inc.1983-12-311997-01-29Canada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AmcinonideOintment1 mg/1gTopicalTaro Pharmaceuticals U.S.A., Inc.2003-03-19Not applicableUS flag
AmcinonideLotion1 mg/1gTopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2002-11-06Not applicableUS flag
AmcinonideCream1 mg/1gTopicalTaro Pharmaceuticals U.S.A., Inc.2002-05-31Not applicableUS flag
AmcinonideOintment1 mg/1gTopicalE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.2014-04-03Not applicableUS flag
AmcinonideCream1 mg/1gTopicalFougera Pharmaceuticals Inc.2003-05-15Not applicableUS flag
Ratio-amcinonideOintmentTopicalTEVA Canada Limited2004-05-05Not applicableCanada flag
Ratio-amcinonideCreamTopicalTEVA Canada Limited2003-09-18Not applicableCanada flag
Ratio-amcinonideLotionTopicalTEVA Canada Limited2004-05-06Not applicableCanada flag
Taro-amcinonideOintmentTopicalTaro Pharmaceuticals, Inc.Not applicableNot applicableCanada flag
Taro-amcinonideCreamTopicalTaro Pharmaceuticals, Inc.2003-02-13Not applicableCanada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more

Categories

ATC Codes
D07AC11 — Amcinonide
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Pregnane steroids
Direct Parent
Gluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
20-oxosteroids / 11-beta-hydroxysteroids / 3-oxo delta-1,4-steroids / Halogenated steroids / Delta-1,4-steroids / Alpha-acyloxy ketones / Ketals / 1,3-dioxolanes / Fluorohydrins / Cyclic ketones
show 9 more
Substituents
11-beta-hydroxysteroid / 11-hydroxysteroid / 20-oxosteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / 9-halo-steroid / Acetal / Alcohol / Aliphatic heteropolycyclic compound / Alkyl fluoride
show 27 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
acetate ester, spiroketal, 11beta-hydroxy steroid, 20-oxo steroid, fluorinated steroid, 3-oxo-Delta(1),Delta(4)-steroid, corticosteroid (CHEBI:31199)

Chemical Identifiers

UNII
423W026MA9
CAS number
51022-69-6
InChI Key
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

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 References
Not Available
Human Metabolome Database
HMDB0014433
KEGG Drug
D01387
PubChem Compound
443958
PubChem Substance
46506705
ChemSpider
392009
RxNav
17652
ChEBI
31199
ChEMBL
CHEMBL1200732
ZINC
ZINC000003977777
Therapeutic Targets Database
DAP001044
PharmGKB
PA164746074
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Amcinonide
AHFS Codes
  • 84:06.00 — Anti-inflammatory Agents
FDA label
Download (143 KB)
MSDS
Download (48.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
  • Altana inc
  • Taro pharmaceutical industries ltd
  • Astellas pharma us inc
Packagers
  • DPT Laboratories Ltd.
  • E. Fougera and Co.
  • Nycomed Inc.
  • Physicians Total Care Inc.
  • Taro Pharmaceuticals USA
Dosage Forms
FormRouteStrength
CreamTopical0.1 %
CreamTopical1 mg/1g
LotionTopical1 mg/1g
LotionTopical0.1 %
OintmentTopical0.1 %
OintmentTopical1 mg/1g
LotionTopical
OintmentTopical
CreamTopical
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.
Patents
Not Available

Properties

State
Solid
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
Polarizability52.38 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 inhibitorNon-inhibitor0.8732
CYP450 2D6 inhibitorNon-inhibitor0.8982
CYP450 2C19 inhibitorNon-inhibitor0.9188
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-024i-3891000000-ef24dafd204a6e82ead7

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modula...
Gene Name
NR3C1
Uniprot ID
P04150
Uniprot Name
Glucocorticoid receptor
Molecular Weight
85658.57 Da
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:17139284]
  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:17016423]
  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:16891588]
  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:16895953]
  5. Hammer F, Stewart PM: Cortisol metabolism in hypertension. Best Pract Res Clin Endocrinol Metab. 2006 Sep;20(3):337-53. [PubMed:16980198]
  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:17038445]
  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:17086345]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Structural molecule activity
Specific Function
Plays important roles in the innate immune response as effector of glucocorticoid-mediated responses and regulator of the inflammatory process. Has anti-inflammatory activity (PubMed:8425544). Play...
Gene Name
ANXA1
Uniprot ID
P04083
Uniprot Name
Annexin A1
Molecular Weight
38713.855 Da
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:17139284]
  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:17016423]
  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:7981624]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Dvorak Z, Pavek P: Regulation of drug-metabolizing cytochrome P450 enzymes by glucocorticoids. Drug Metab Rev. 2010 Nov;42(4):621-35. doi: 10.3109/03602532.2010.484462. [PubMed:20482443]
  2. Monograph [Link]
  3. Cyclocort monograph [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Dvorak Z, Pavek P: Regulation of drug-metabolizing cytochrome P450 enzymes by glucocorticoids. Drug Metab Rev. 2010 Nov;42(4):621-35. doi: 10.3109/03602532.2010.484462. [PubMed:20482443]

Drug created on June 13, 2005 07:24 / Updated on October 27, 2020 11:13

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