Identification
- Summary
Amcinonide is a topical corticosteroid used in the treatment of inflammation and pruritus due to a variety of dermatoses.
- Generic Name
- Amcinonide
- DrugBank Accession Number
- DB00288
- Background
Amcinonide is a corticosteroid.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Amcinonide (DB00288)
- 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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Inflammation •••••••••••• Treatment of Pruritus •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism AGlucocorticoid receptor agonistHumans UAnnexin A1 agonistHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Amcinonide can be increased when it is combined with Abametapir. Acarbose The risk or severity of hyperglycemia can be increased when Amcinonide is combined with Acarbose. Acetohexamide The risk or severity of hyperglycemia can be increased when Amcinonide is combined with Acetohexamide. Acetyldigitoxin The risk or severity of adverse effects can be increased when Amcinonide is combined with Acetyldigitoxin. Albiglutide The risk or severity of hyperglycemia can be increased when Amcinonide is combined with Albiglutide. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Mycoderm / Penticort / Visderm
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cyclocort Lotion 0.1 % Topical Glaxosmithkline Inc 1996-09-12 2017-09-14 Canada 
Cyclocort Ointment 0.1 % Topical Glaxosmithkline Inc 1997-01-20 2018-03-08 Canada Cyclocort Ointment 1 mg/1g Topical DPT Laboratories, Ltd. 1999-02-12 2006-01-31 US 
Cyclocort Cream 0.1 % Topical Glaxosmithkline Inc 1996-09-12 2018-01-17 Canada Cyclocort Crm 0.1% Cream .1 % Topical Lederle Cyanamid Canada Inc. 1978-12-31 1997-01-29 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Amcinonide Ointment 1 mg/1g Topical Ayurax, LLC 2023-05-01 Not applicable US Amcinonide Ointment 1 mg/1g Topical Taro Pharmaceuticals U.S.A., Inc. 2003-03-19 Not applicable US Amcinonide Lotion 1 mg/1g Topical E. Fougera & Co. a division of Fougera Pharmaceuticals Inc. 2002-11-06 Not applicable US Amcinonide Cream 1 mg/1g Topical Taro Pharmaceuticals U.S.A., Inc. 2002-05-31 2024-01-03 US Amcinonide Ointment 1 mg/1g Topical E. Fougera & CO., A division of Fougera Pharmaceuticals Inc. 2014-04-03 Not applicable US
Categories
- ATC Codes
- D07AC11 — Amcinonide
- Drug Categories
- Adrenal Cortex Hormones
- Anti-Inflammatory Agents
- Corticosteroid Hormone Receptor Agonists
- Corticosteroids
- Corticosteroids, Dermatological Preparations
- Corticosteroids, Potent (Group III)
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Inducers
- Cytochrome P-450 CYP3A5 Inducers (strength unknown)
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Substrates
- Dermatologicals
- Fused-Ring Compounds
- Glucocorticoids
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Hyperglycemia-Associated Agents
- Immunosuppressive Agents
- Pregnadienes
- Pregnanes
- Steroids
- Steroids, Fluorinated
- Thyroxine-binding globulin inhibitors
- 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)
- Affected organisms
- Humans and other mammals
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
- [H][C@@]12C[C@H]3OC4(CCCC4)O[C@@]3(C(=O)COC(C)=O)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
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
- External Links
- Human Metabolome Database
- HMDB0014433
- KEGG Drug
- D01387
- PubChem Compound
- 443958
- PubChem Substance
- 46506705
- ChemSpider
- 392009
- 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
- FDA label
- Download (143 KB)
- MSDS
- Download (48.1 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
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
Form Route Strength Ointment Topical Cream Topical 1 mg/1g Lotion Topical 1 mg/1g Ointment Topical 1 mg/1g Cream Topical .1 % Lotion Topical .1 % Ointment Topical .1 % Cream Topical Lotion Topical 0.1 % Ointment Topical 0.1 % Cream Topical 0.1 % - Prices
Unit description Cost Unit Amcinonide 0.1% Cream 60 gm Tube 84.29USD tube Amcinonide 0.1% Ointment 60 gm Tube 84.29USD tube Amcinonide 0.1% Cream 30 gm Tube 28.71USD tube Amcinonide 0.1% Cream 15 gm Tube 20.99USD tube Amcinonide 0.1% cream 1.68USD g Cyclocort 0.1 % Cream 0.62USD g Cyclocort 0.1 % Ointment 0.62USD g Cyclocort 0.1 % Lotion 0.52USD g Ratio-Amcinonide 0.1 % Ointment 0.33USD g Ratio-Amcinonide 0.1 % Cream 0.29USD g Taro-Amcinonide 0.1 % Cream 0.29USD g Ratio-Amcinonide 0.1 % Lotion 0.27USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 2.3 Not Available - Predicted Properties
Property Value Source Water Solubility 0.00774 mg/mL 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 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 127.88 m3·mol-1 Chemaxon Polarizability 52.38 Å3 Chemaxon Number of Rings 6 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - 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 inhibitor Non-inhibitor 0.8732 CYP450 2D6 inhibitor Non-inhibitor 0.8982 CYP450 2C19 inhibitor Non-inhibitor 0.9188 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 224.7873468 predictedDarkChem Lite v0.1.0 [M-H]- 216.59279 predictedDeepCCS 1.0 (2019) [M+H]+ 225.1356468 predictedDarkChem Lite v0.1.0 [M+H]+ 218.4882 predictedDeepCCS 1.0 (2019) [M+Na]+ 224.3131468 predictedDarkChem Lite v0.1.0 [M+Na]+ 224.26613 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Hammer F, Stewart PM: Cortisol metabolism in hypertension. Best Pract Res Clin Endocrinol Metab. 2006 Sep;20(3):337-53. [Article]
- 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. [Article]
- 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. [Article]
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInducer
- 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
- 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
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55