Amcinonide
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MedKoo CAT#: 317178

CAS#: 51022-69-6

Description: Amcinonide (trade name Cyclocort) is a topical glucocorticoid used to treat itching, redness and swelling associated with several dermatologic conditions such as atopic dermatitis and allergic contact dermatitis. Amcinonide is a synthetic glucocorticoid receptor agonist that mimics the metabolic, anti-inflammatory, and immunosuppressive activity of the natural glucocorticoids. Amcinonide interacts with specific corticosteroid receptors and was internalized, which leads to binding of DNA and modification of gene expression. This results in synthesis of anti-inflammatory mediators while inhibiting synthesis of inflammatory mediators. Consequently, an overall reduction in chronic inflammation and autoimmune reactions are achieved. Amcinonide can also be classified as a multi-functional small molecule corticosteroid, which has been approved by the FDA and is currently marketed as an ointment, lotion, or cream. It acts as both a transcription factor for responses to glucocorticoids and modulator for other transcription factors while also regulating phospholipase A2 activity.


Chemical Structure

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Amcinonide
CAS# 51022-69-6

Theoretical Analysis

MedKoo Cat#: 317178
Name: Amcinonide
CAS#: 51022-69-6
Chemical Formula: C28H35FO7
Exact Mass: 502.23668
Molecular Weight: 502.58
Elemental Analysis: C, 66.92; H, 7.02; F, 3.78; O, 22.28

Price and Availability

Size Price Availability Quantity
250.0mg USD 200.0 2 Weeks
500.0mg USD 350.0 2 Weeks
1.0g USD 550.0 2 Weeks
2.0g USD 880.0 2 Weeks
Bulk inquiry

Synonym: Amcinonide; Cyclocort; Amcinonidum; Visderm; Amcinonida; Amcinonido

IUPAC/Chemical Name: 2-((11a'R,12a'S)-6b'-fluoro-7'-hydroxy-6a',8a'-dimethyl-4'-oxo-1',2',4',6a',6b',7',8',8a',11a',12',12a',12b'-dodecahydro-8b'H-spiro[cyclopentane-1,10'-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxole]-8b'-yl)-2-oxoethyl acetate

InChi Key: ILKJAFIWWBXGDU-UVHNLHPKSA-N

InChi Code: 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

SMILES Code: CC(OCC(C([C@@](O1)([H])C[C@@]2([H])C3CCC4=CC5=O)(C2(C)CC(O)C3(F)C4(C)C=C5)OC61CCCC6)=O)=O

Appearance: White to off-white solid powder.

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 502.58 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Hong J, Kim BK, Lim H, Lee S, Lee SJ. Identification and characterization of triamcinolone acetonide, a microglial-activation inhibitor. Immunopharmacol Immunotoxicol. 2012 Dec;34(6):912-8. doi: 10.3109/08923973.2012.671332. Epub 2012 May 3. PubMed PMID: 22551518.

2: Uter W, de Pádua CM, Pfahlberg A, Nink K, Schnuch A, Lessmann H. Contact allergy to topical corticosteroids--results from the IVDK and epidemiological risk assessment. J Dtsch Dermatol Ges. 2009 Jan;7(1):34-41, 34-42. doi: 10.1111/j.1610-0387.2008.06844.x. Epub 2008 Aug 28. English, German. PubMed PMID: 18761609.

3: de Pádua CA, Schnuch A, Nink K, Pfahlberg A, Uter W. Allergic contact dermatitis to topical drugs--epidemiological risk assessment. Pharmacoepidemiol Drug Saf. 2008 Aug;17(8):813-21. doi: 10.1002/pds.1588. PubMed PMID: 18383004.

4: Pirker C, Misić A, Frosch PJ. Angioedema and dysphagia caused by contact allergy to inhaled budesonide. Contact Dermatitis. 2003 Aug;49(2):77-9. PubMed PMID: 14641354.

5: Sakai N. Selective corticosteroid injection into the extensor pollicis brevis tenosynovium for de Quervain's disease. Orthopedics. 2002 Jan;25(1):68-70. PubMed PMID: 11811245.

6: Sasseville D. Exacerbation of allergic contact dermatitis from amcinonide triggered by patch testing. Contact Dermatitis. 2001 Oct;45(4):232-3. PubMed PMID: 11683835.

7: Isaksson M, Bruze M, Lepoittevin JP, Goossens A. Patch testing with serial dilutions of budesonide, its R and S diastereomers, and potentially cross-reacting substances. Am J Contact Dermat. 2001 Sep;12(3):170-6. PubMed PMID: 11526524.

8: Frankild S, Lepoittevin JP, Kreilgaard B, Andersen KE. Tixocortol pivalate contact allergy in the GPMT: frequency and cross-reactivity. Contact Dermatitis. 2001 Jan;44(1):18-22. PubMed PMID: 11156006.

9: Bircher AJ, Bigliardi P, Zaugg T, Mäkinen-Kiljunen S. Delayed generalized allergic reactions to corticosteroids. Dermatology. 2000;200(4):349-51. PubMed PMID: 10894975.

10: Muramatsu T, Iida T, Shirai T. Pemphigoid and pemphigus foliaceus successfully treated with topical corticosteroids. J Dermatol. 1996 Oct;23(10):683-8. PubMed PMID: 8973033.

Amcinonide

250.0mg / USD 200.0