U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of AMCINONIDE

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

HIDE SMILES / InChI

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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
AMCINONIDE

Approved Use

Topical corticosteroids are indicated for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.

Launch Date

1.02271681E12
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2 h
1 mg/kg single, intravenous
dose: 1 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
AMCINONIDE plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse 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%)
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%)
Sources:
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)
Folliculitis (1 patient)
Stinging (9 patients)
Itching (17 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
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

PubMed

TitleDatePubMed
Management of eczematous dermatitis with amcinonide or betamethasone valerate. A double-blind comparative study.
1979 Dec
A controlled comparison of amcinonide cream 0.1 percent and halcinonide cream 0.1 percent in the treatment of eczematous dermatitis.
1981 Oct
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
Allergy to 2 new corticoid molecules.
1984 Aug
A comparative study of amcinonide and halcinonide in the treatment of eczematous dermatitis.
1984 Aug
Contact sensitivity to topical corticosteroids.
1984 May
Allergic contact dermatitis from amcinonide.
1985 Apr
Amcinonide vs. betamethasone dipropionate ointments in the treatment of psoriasis.
1985 May
Influence of depigmenting chemical agents on hair and skin color in yellow (pheomelanic) and black (eumelanic) mice.
1990 Mar-Apr
Contact allergies to topical corticosteroids: 10 cases of contact dermatitis.
1991 Aug
Contact sensitivity and cross-reactivity of budesonide.
1993 Apr
Delayed generalized allergic reactions to corticosteroids.
2000
Tixocortol pivalate contact allergy in the GPMT: frequency and cross-reactivity.
2001 Jan
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
Patents

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
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
by admin
on Thu Jul 06 23:21:58 UTC 2023
Edited
by admin
on Thu Jul 06 23:21:58 UTC 2023
Record UNII
423W026MA9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMCINONIDE
INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
AMCINONIDE [MART.]
Common Name English
NSC-758620
Code English
CL 34699
Code English
PREGNA-1,4-DIENE-3,20-DIONE, 21-(ACETYLOXY)-16,17-(CYCLOPENTYLIDENEBIS(OXY))-9-FLUORO-11-HYDROXY-, (11.BETA.,16.ALPHA.)-
Common Name English
AMCINONIDE [USP-RS]
Common Name English
9-Fluoro-11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with cyclopentanone, 21-acetate
Common Name English
CL-34699
Code English
AMCINONIDE [VANDF]
Common Name English
Amcinonide [WHO-DD]
Common Name English
AMCINONIDE [USP MONOGRAPH]
Common Name English
AMCINONIDE [JAN]
Common Name English
amcinonide [INN]
Common Name English
AMCINONIDE [MI]
Common Name English
CYCLOCORT
Brand Name English
AMCINONIDE [USAN]
Common Name English
AMCINONIDE [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C521
Created by admin on Thu Jul 06 23:21:58 UTC 2023 , Edited by admin on Thu Jul 06 23:21:58 UTC 2023
NDF-RT N0000175450
Created by admin on Thu Jul 06 23:21:58 UTC 2023 , Edited by admin on Thu Jul 06 23:21:58 UTC 2023
WHO-VATC QD07AC11
Created by admin on Thu Jul 06 23:21:58 UTC 2023 , Edited by admin on Thu Jul 06 23:21:58 UTC 2023
WHO-ATC D07AC11
Created by admin on Thu Jul 06 23:21:58 UTC 2023 , Edited by admin on Thu Jul 06 23:21:58 UTC 2023
NDF-RT N0000175576
Created by admin on Thu Jul 06 23:21:58 UTC 2023 , Edited by admin on Thu Jul 06 23:21:58 UTC 2023
Code System Code Type Description
RS_ITEM_NUM
1019202
Created by admin on Thu Jul 06 23:21:58 UTC 2023 , Edited by admin on Thu Jul 06 23:21:58 UTC 2023
PRIMARY
DAILYMED
423W026MA9
Created by admin on Thu Jul 06 23:21:58 UTC 2023 , Edited by admin on Thu Jul 06 23:21:58 UTC 2023
PRIMARY
MESH
C012716
Created by admin on Thu Jul 06 23:21:58 UTC 2023 , Edited by admin on Thu Jul 06 23:21:58 UTC 2023
PRIMARY
DRUG BANK
DB00288
Created by admin on Thu Jul 06 23:21:58 UTC 2023 , Edited by admin on Thu Jul 06 23:21:58 UTC 2023
PRIMARY
NCI_THESAURUS
C47389
Created by admin on Thu Jul 06 23:21:58 UTC 2023 , Edited by admin on Thu Jul 06 23:21:58 UTC 2023
PRIMARY
FDA UNII
423W026MA9
Created by admin on Thu Jul 06 23:21:58 UTC 2023 , Edited by admin on Thu Jul 06 23:21:58 UTC 2023
PRIMARY
CHEBI
31199
Created by admin on Thu Jul 06 23:21:58 UTC 2023 , Edited by admin on Thu Jul 06 23:21:58 UTC 2023
PRIMARY
DRUG CENTRAL
150
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PRIMARY
RXCUI
17652
Created by admin on Thu Jul 06 23:21:58 UTC 2023 , Edited by admin on Thu Jul 06 23:21:58 UTC 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
256-915-2
Created by admin on Thu Jul 06 23:21:58 UTC 2023 , Edited by admin on Thu Jul 06 23:21:58 UTC 2023
PRIMARY
WIKIPEDIA
AMCINONIDE
Created by admin on Thu Jul 06 23:21:58 UTC 2023 , Edited by admin on Thu Jul 06 23:21:58 UTC 2023
PRIMARY
IUPHAR
7060
Created by admin on Thu Jul 06 23:21:58 UTC 2023 , Edited by admin on Thu Jul 06 23:21:58 UTC 2023
PRIMARY
CAS
51022-69-6
Created by admin on Thu Jul 06 23:21:58 UTC 2023 , Edited by admin on Thu Jul 06 23:21:58 UTC 2023
PRIMARY
ChEMBL
CHEMBL1200732
Created by admin on Thu Jul 06 23:21:58 UTC 2023 , Edited by admin on Thu Jul 06 23:21:58 UTC 2023
PRIMARY
LACTMED
Amcinonide
Created by admin on Thu Jul 06 23:21:58 UTC 2023 , Edited by admin on Thu Jul 06 23:21:58 UTC 2023
PRIMARY
SMS_ID
100000087191
Created by admin on Thu Jul 06 23:21:58 UTC 2023 , Edited by admin on Thu Jul 06 23:21:58 UTC 2023
PRIMARY
INN
3755
Created by admin on Thu Jul 06 23:21:58 UTC 2023 , Edited by admin on Thu Jul 06 23:21:58 UTC 2023
PRIMARY
MERCK INDEX
M1652
Created by admin on Thu Jul 06 23:21:58 UTC 2023 , Edited by admin on Thu Jul 06 23:21:58 UTC 2023
PRIMARY Merck Index
NSC
758620
Created by admin on Thu Jul 06 23:21:58 UTC 2023 , Edited by admin on Thu Jul 06 23:21:58 UTC 2023
PRIMARY
EVMPD
SUB05404MIG
Created by admin on Thu Jul 06 23:21:58 UTC 2023 , Edited by admin on Thu Jul 06 23:21:58 UTC 2023
PRIMARY
EPA CompTox
DTXSID6045905
Created by admin on Thu Jul 06 23:21:58 UTC 2023 , Edited by admin on Thu Jul 06 23:21:58 UTC 2023
PRIMARY
PUBCHEM
443958
Created by admin on Thu Jul 06 23:21:58 UTC 2023 , Edited by admin on Thu Jul 06 23:21:58 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY