Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C28H35FO7 |
Molecular Weight | 502.5717 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
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(OC6(CCCC6)O2)C(=O)COC(C)=O
InChI
InChIKey=ILKJAFIWWBXGDU-MOGDOJJUSA-N
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
Molecular Formula | C28H35FO7 |
Molecular Weight | 502.5717 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Amcinonide is a corticosteroid, which is indicated for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses. The mechanism of anti-inflammatory activity of the topical corticosteroids 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. 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. The extent of percutaneous absorption of topical corticosteroids is determined by many factors, including the vehicle, the integrity of the epidermal barrier, and the use of occlusive dressings. Topical corticosteroids can be absorbed from normal intact skin. Inflammation and/or other disease processes in the skin increase percutaneous absorption. Occlusive dressings substantially increase the percutaneous absorption of topical corticosteroids
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2034 Sources: https://www.medchemexpress.com/Amcinonide.html |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | AMCINONIDE Approved UseTopical corticosteroids are indicated for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses. Launch Date2002 |
Doses
Dose | Population | Adverse events |
---|---|---|
1 mg 3 times / day steady, topical Dose: 1 mg, 3 times / day Route: topical Route: steady Dose: 1 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Condition: corticosteroidresponsive dermatoses Sources: |
Other AEs: Itching, Irritation skin... Other AEs: Itching (4.7%) Sources: Irritation skin (4.7%) Mucosal dryness (4.7%) Folliculitis (4.7%) Hypertrichosis (4.7%) Acneiform eruption (4.7%) Skin hypopigmentation (4.7%) Perioral dermatitis (4.7%) Allergic contact dermatitis (4.7%) Skin maceration (4.7%) Secondary infection (4.7%) Skin atrophy (4.7%) Striae (4.7%) Miliaria (4.7%) |
1 mg 3 times / day steady, topical Dose: 1 mg, 3 times / day Route: topical Route: steady Dose: 1 mg, 3 times / day Sources: |
unhealthy n = 78 Health Status: unhealthy Condition: corticosteroidresponsive dermatoses Population Size: 78 Sources: |
Disc. AE: Periorbital edema... Other AEs: Hair color changes, Folliculitis... AEs leading to discontinuation/dose reduction: Periorbital edema (1 patient) Other AEs:Hair color changes (2 patients) Sources: Folliculitis (1 patient) Stinging (9 patients) Itching (17 patients) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Acneiform eruption | 4.7% | 1 mg 3 times / day steady, topical Dose: 1 mg, 3 times / day Route: topical Route: steady Dose: 1 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Condition: corticosteroidresponsive dermatoses Sources: |
Allergic contact dermatitis | 4.7% | 1 mg 3 times / day steady, topical Dose: 1 mg, 3 times / day Route: topical Route: steady Dose: 1 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Condition: corticosteroidresponsive dermatoses Sources: |
Folliculitis | 4.7% | 1 mg 3 times / day steady, topical Dose: 1 mg, 3 times / day Route: topical Route: steady Dose: 1 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Condition: corticosteroidresponsive dermatoses Sources: |
Hypertrichosis | 4.7% | 1 mg 3 times / day steady, topical Dose: 1 mg, 3 times / day Route: topical Route: steady Dose: 1 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Condition: corticosteroidresponsive dermatoses Sources: |
Irritation skin | 4.7% | 1 mg 3 times / day steady, topical Dose: 1 mg, 3 times / day Route: topical Route: steady Dose: 1 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Condition: corticosteroidresponsive dermatoses Sources: |
Itching | 4.7% | 1 mg 3 times / day steady, topical Dose: 1 mg, 3 times / day Route: topical Route: steady Dose: 1 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Condition: corticosteroidresponsive dermatoses Sources: |
Miliaria | 4.7% | 1 mg 3 times / day steady, topical Dose: 1 mg, 3 times / day Route: topical Route: steady Dose: 1 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Condition: corticosteroidresponsive dermatoses Sources: |
Mucosal dryness | 4.7% | 1 mg 3 times / day steady, topical Dose: 1 mg, 3 times / day Route: topical Route: steady Dose: 1 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Condition: corticosteroidresponsive dermatoses Sources: |
Perioral dermatitis | 4.7% | 1 mg 3 times / day steady, topical Dose: 1 mg, 3 times / day Route: topical Route: steady Dose: 1 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Condition: corticosteroidresponsive dermatoses Sources: |
Secondary infection | 4.7% | 1 mg 3 times / day steady, topical Dose: 1 mg, 3 times / day Route: topical Route: steady Dose: 1 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Condition: corticosteroidresponsive dermatoses Sources: |
Skin atrophy | 4.7% | 1 mg 3 times / day steady, topical Dose: 1 mg, 3 times / day Route: topical Route: steady Dose: 1 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Condition: corticosteroidresponsive dermatoses Sources: |
Skin hypopigmentation | 4.7% | 1 mg 3 times / day steady, topical Dose: 1 mg, 3 times / day Route: topical Route: steady Dose: 1 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Condition: corticosteroidresponsive dermatoses Sources: |
Skin maceration | 4.7% | 1 mg 3 times / day steady, topical Dose: 1 mg, 3 times / day Route: topical Route: steady Dose: 1 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Condition: corticosteroidresponsive dermatoses Sources: |
Striae | 4.7% | 1 mg 3 times / day steady, topical Dose: 1 mg, 3 times / day Route: topical Route: steady Dose: 1 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Condition: corticosteroidresponsive dermatoses Sources: |
Folliculitis | 1 patient | 1 mg 3 times / day steady, topical Dose: 1 mg, 3 times / day Route: topical Route: steady Dose: 1 mg, 3 times / day Sources: |
unhealthy n = 78 Health Status: unhealthy Condition: corticosteroidresponsive dermatoses Population Size: 78 Sources: |
Periorbital edema | 1 patient Disc. AE |
1 mg 3 times / day steady, topical Dose: 1 mg, 3 times / day Route: topical Route: steady Dose: 1 mg, 3 times / day Sources: |
unhealthy n = 78 Health Status: unhealthy Condition: corticosteroidresponsive dermatoses Population Size: 78 Sources: |
Itching | 17 patients | 1 mg 3 times / day steady, topical Dose: 1 mg, 3 times / day Route: topical Route: steady Dose: 1 mg, 3 times / day Sources: |
unhealthy n = 78 Health Status: unhealthy Condition: corticosteroidresponsive dermatoses Population Size: 78 Sources: |
Hair color changes | 2 patients | 1 mg 3 times / day steady, topical Dose: 1 mg, 3 times / day Route: topical Route: steady Dose: 1 mg, 3 times / day Sources: |
unhealthy n = 78 Health Status: unhealthy Condition: corticosteroidresponsive dermatoses Population Size: 78 Sources: |
Stinging | 9 patients | 1 mg 3 times / day steady, topical Dose: 1 mg, 3 times / day Route: topical Route: steady Dose: 1 mg, 3 times / day Sources: |
unhealthy n = 78 Health Status: unhealthy Condition: corticosteroidresponsive dermatoses Population Size: 78 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
A controlled comparison of amcinonide cream 0.1 percent and halcinonide cream 0.1 percent in the treatment of eczematous dermatitis. | 1981 Oct |
|
Treatment of psoriasis with amcinonide 0.1 percent and fluocinonide 0.05 percent ointments. A comparative double-blind study. | 1982 Jun |
|
Comparison of amcinonide ointment 0.1 percent twice daily and fluocinonide ointment 0.05 percent three times daily in the treatment of psoriasis. | 1983 May |
|
A comparative study of amcinonide and halcinonide in the treatment of eczematous dermatitis. | 1984 Aug |
|
Contact allergies to topical corticosteroids: 10 cases of contact dermatitis. | 1991 Aug |
|
Contact sensitivity and cross-reactivity of budesonide. | 1993 Apr |
|
[Contact allergy to topical glucocorticoids]. | 1993 Feb |
|
Contact allergies to topical corticosteroids. | 1993 Mar |
|
Studies in patients with corticosteroid contact allergy. Understanding cross-reactivity among different steroids. | 1995 Jan |
|
Tixocortol pivalate contact allergy in the GPMT: frequency and cross-reactivity. | 2001 Jan |
|
Exacerbation of allergic contact dermatitis from amcinonide triggered by patch testing. | 2001 Oct |
|
Patch testing with serial dilutions of budesonide, its R and S diastereomers, and potentially cross-reacting substances. | 2001 Sep |
|
Angioedema and dysphagia caused by contact allergy to inhaled budesonide. | 2003 Aug |
|
Human receptor kinetics and lung tissue retention of the enhanced-affinity glucocorticoid fluticasone furoate. | 2007 Jul 25 |
|
Allergic contact dermatitis to topical drugs--epidemiological risk assessment. | 2008 Aug |
|
Contact allergy to topical corticosteroids--results from the IVDK and epidemiological risk assessment. | 2009 Jan |
Sample Use Guides
Is generally applied to the affected area as a thin film from two to three times daily depending on the severity of the condition.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=22551518
Amcinonide inhibit NO release from activated microglia with IC50 3.38 nM. It also inhibited necrotic neuronal cells (NNC)-induced expression of the proinflammatory genes iNOS, TNF-α, and IL-1β in glial cells
Substance Class |
Chemical
Created
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admin
on
Edited
Sat Dec 16 18:04:01 GMT 2023
by
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on
Sat Dec 16 18:04:01 GMT 2023
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Record UNII |
423W026MA9
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C521
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NDF-RT |
N0000175450
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WHO-VATC |
QD07AC11
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WHO-ATC |
D07AC11
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NDF-RT |
N0000175576
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423W026MA9
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C012716
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DB00288
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C47389
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256-915-2
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AMCINONIDE
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51022-69-6
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CHEMBL1200732
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Amcinonide
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3755
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m1652
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758620
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SUB05404MIG
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DTXSID6045905
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443958
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