AMCINONIDE

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 Search

SMILES

CC(=O)OCC(=O)[C@@]12OC3(CCCC3)O[C@@H]1C[C@H]4[C@@H]5CCC6=CC(=O)C=C[C@]6(C)[C@@]5(F)[C@@H](O)C[C@]24C

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

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=ac5c3e79-52f7-434e-92ae-24bd32b45edc

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
Glucocorticoid receptor 173 Target ID: CHEMBL2034 Sources: https://www.medchemexpress.com/Amcinonide.html	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Corticosteroid-responsive dermatoses 17 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=ac5c3e79-52f7-434e-92ae-24bd32b45edc	Palliative		Approved 8583	AMCINONIDE Approved Use Topical corticosteroids are indicated for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses. Launch Date 2002

T_1/2

Value	Dose	Co-administered	Analyte	Population
2 h OTHER GOV http://rxproduct.taro.ca/media/oMedia/Taro-Amcinonide%20Crm_Oint.pdf	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

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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/18498s8lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/18498s8lbl.pdf	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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/18498s8lbl.pdf
1 mg 3 times / day steady, topical Dose: 1 mg, 3 times / day Route: topical Route: steady Dose: 1 mg, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/19729_Cyclocort.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/19729_Cyclocort.pdf	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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/19729_Cyclocort.pdf

AEs

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:31199	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31199
ChemicalBook	CB4419202	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4419202
eMolecules	29542661	https://www.emolecules.com/cgi-bin/more?vid=29542661
eMolecules	36552996	https://www.emolecules.com/cgi-bin/more?vid=36552996
eMolecules	533979	https://www.emolecules.com/cgi-bin/more?vid=533979
MolPort	MolPort-003-940-103	https://www.molport.com/shop/molecule-link/MolPort-003-940-103
ZINC	ZINC000003977777	http://zinc15.docking.org/substances/ZINC000003977777

PubMed

Title	Date	PubMed
Management of eczematous dermatitis with amcinonide or betamethasone valerate. A double-blind comparative study.	1979 Dec	391500
A controlled comparison of amcinonide cream 0.1 percent and halcinonide cream 0.1 percent in the treatment of eczematous dermatitis.	1981 Oct	7030645
Treatment of psoriasis with amcinonide 0.1 percent and fluocinonide 0.05 percent ointments. A comparative double-blind study.	1982 Jun	7049592
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	6851655
Allergy to 2 new corticoid molecules.	1984 Aug	6488784
A comparative study of amcinonide and halcinonide in the treatment of eczematous dermatitis.	1984 Aug	6383735
Contact sensitivity to topical corticosteroids.	1984 May	6233341
Allergic contact dermatitis from amcinonide.	1985 Apr	3160532
Amcinonide vs. betamethasone dipropionate ointments in the treatment of psoriasis.	1985 May	3891239
Investigations on the development and regression of corticosteroid-induced thinning of the skin in various parts of the human body during and after topical application of amcinonide.	1989	2924987
Allergic contact dermatitis from topical corticosteroids.	1989 Aug	2530056
Influence of depigmenting chemical agents on hair and skin color in yellow (pheomelanic) and black (eumelanic) mice.	1990 Mar-Apr	2385568
Contact allergies to topical corticosteroids: 10 cases of contact dermatitis.	1991 Aug	1834432
Contact sensitivity and cross-reactivity of budesonide.	1993 Apr	8508630
[Contact allergy to topical glucocorticoids].	1993 Feb	8449700
Contact allergies to topical corticosteroids.	1993 Mar	8462297
Studies in patients with corticosteroid contact allergy. Understanding cross-reactivity among different steroids.	1995 Jan	7826093
Delayed generalized allergic reactions to corticosteroids.	2000	10894975
Tixocortol pivalate contact allergy in the GPMT: frequency and cross-reactivity.	2001 Jan	11156006
Exacerbation of allergic contact dermatitis from amcinonide triggered by patch testing.	2001 Oct	11683835
Patch testing with serial dilutions of budesonide, its R and S diastereomers, and potentially cross-reacting substances.	2001 Sep	11526524
Selective corticosteroid injection into the extensor pollicis brevis tenosynovium for de Quervain's disease.	2002 Jan	11811245
Angioedema and dysphagia caused by contact allergy to inhaled budesonide.	2003 Aug	14641354
Human receptor kinetics and lung tissue retention of the enhanced-affinity glucocorticoid fluticasone furoate.	2007 Jul 25	17650349
Allergic contact dermatitis to topical drugs--epidemiological risk assessment.	2008 Aug	18383004
Contact allergy to topical corticosteroids--results from the IVDK and epidemiological risk assessment.	2009 Jan	18761609

Patents

Sample Use Guides

In Vivo Use Guide

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

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

Name

Type

Language

CYCLOCORT

Preferred Name

English

AMCINONIDE

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-11?,16?,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

AMCINONIDE [USAN]

Common Name

English

AMCINONIDE [ORANGE BOOK]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C521