Alclomethasone-17,21-dipropionate - CAS 66734-13-2
Not Intended for Therapeutic Use. For research use only.
Category:
Inhibitor
Product Name:
Alclomethasone-17,21-dipropionate
Catalog Number:
66734-13-2
Synonyms:
(7a,11b,16a)-7-Chloro-11-hydroxy-16-methyl-17,21-bis(1-oxopropoxy)pregna-1,4-diene-3,20-dione;Pregna-1,4-diene-3,20-dione,7-chloro-11-hydroxy-16-methyl-17,21-bis(1-oxopropo;[2-[(7R,8S,9S,10R,11S,13S,14S,16R,17R)-7-chloro-11-hydroxy-10,13,16-trimethyl-3-ox
CAS Number:
66734-13-2
Description:
Alclomethasone-17,21-dipropionate is the dipropionate salt form of alclometasone, which is a synthetic corticosteroid with low to medium potency. It is used in dermatology as an anti-inflammatory, antiallergic, antipruritic, vasoconstrictive and antiproliferative agent. It is also used for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses. It was developed by Fougera Pharmaceuticals and has been listed.
Molecular Weight:
521.05
Molecular Formula:
C28H37ClO7
Quantity:
Grams to Kilograms
Quality Standard:
In-house standard
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
CCC(=O)OCC(=O)C1(C(CC2C1(CC(C3C2C(CC4=CC(=O)C=CC34C)Cl)O)C)C)OC(=O)CC
InChI:
InChI=1S/C28H37ClO7/c1-6-22(33)35-14-21(32)28(36-23(34)7-2)15(3)10-18-24-19(29)12-16-11-17(30)8-9-26(16,4)25(24)20(31)13-27(18,28)5/h8-9,11,15,18-20,24-25,31H,6-7,10,12-14H2,1-5H3/t15-,18+,19-,20+,24-,25+,26+,27+,28+/m1/s1
InChIKey:
DJHCCTTVDRAMEH-DUUJBDRPSA-N
Current Developer:
Alclomethasone-17,21-dipropionate was developed by Fougera Pharmaceuticals and has been listed.
Chemical Structure
CAS 66734-13-2 Alclomethasone-17,21-dipropionate

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Reference Reading


1.Detection of glucocorticoid receptor agonists in effluents from sewage treatment plants in Japan.
Suzuki G1, Sato K2, Isobe T3, Takigami H4, Brouwer A5, Nakayama K2. Sci Total Environ. 2015 Sep 15;527-528:328-34. doi: 10.1016/j.scitotenv.2015.05.008. Epub 2015 May 14.
Glucocorticoids (GCs) are widely used as anti-inflammatory drugs. Our previous study demonstrated that several GCs such as cortisol and dexamethasone (Dex) were frequently detected in effluents collected from Japanese sewage treatment plants (STPs) in 2012. In this study, we used the GC-Responsive Chemical-Activated LUciferase gene eXpression (GR-CALUX) assay to elucidate GC receptor (GR) agonistic activities of ten pure synthetic GCs and selected STP effluents in Japan for assessment of the risks associated with the presence of GR agonists. The tested GCs demonstrated dose-dependent agonistic effects in the GR-CALUX assay and their EC50 values were calculated for estimation of relative potencies (REPs) compared to Dex. The GR agonistic potency was in the rank of: clobetasol propionate > clobetasone butyrate > betamethasone 17-valerate > difluprednate > betamethasone 17,21-dipropionate > Dex > betamethasone > 6α-methylprednisolone > prednisolone > cortisol.
2.Selective in vivo anti-inflammatory action of the galactolipid monogalactosyldiacylglycerol.
Bruno A1, Rossi C, Marcolongo G, Di Lena A, Venzo A, Berrie CP, Corda D. Eur J Pharmacol. 2005 Nov 7;524(1-3):159-68. Epub 2005 Oct 25.
The thermophilic blue-green alga ETS-05 colonises the therapeutic thermal muds of Abano and Montegrotto, Italy. Following the isolation, purification and identification of monogalactosyldiacylglycerol (MGDG), digalactosyldiacylglycerol (DGDG), sulphoquinovosyldiacylglycerol (SQDG) and phosphatidylglycerol from ETS-05, we here examine their in vivo anti-inflammatory activities. MGDG, DGDG and SQDG inhibit croton-oil-induced ear oedema in the mouse in a dose-dependent manner. Inhibition by MGDG is greater than that of the reference drug, betamethasone 17,21-dipropionate, and is largely abrogated following acyl group saturation. SQDG is the least potent of these glycoglycerolipids, and shows an early transient effect. In the in vivo carrageenan-induced paw oedema model in the mouse, the inhibitory effects are again dose dependent, with an enhanced efficacy of MGDG over DGDG, SQDG and the reference drug, indomethacin. These compounds are all less toxic than indomethacin.
3.Partitioning of anti-inflammatory steroid drugs into phosphatidylcholine and phosphatidylcholine-cholesterol small unilamellar vesicles as studied by second-derivative spectrophotometry.
Takegami S1, Kitamura K, Funakoshi T, Kitade T. Chem Pharm Bull (Tokyo). 2008 May;56(5):663-7.
The partition coefficients (Kps) of six anti-inflammatory steroid drugs, dexamethasone (DMS), betamethasone (BMS), triamcinolone acetonide (TCLA), fluocinolone acetonide (FCLA), betamethasone 17,21-dipropionate (BMSDP), and clobetasole propionate (CBSP), for phosphatidylcholine (PC), and PC-cholesterol small unilamellar vesicles (SUVs) were determined by a second-derivative spectrophotometric method. The Kp values were obtained with a relative standard deviation of below 10% and the following order was observed: BMS< or =DMS<TCLA<FCLA<<BMSDP<CBSP. BMSDP which has a structure that the two hydroxyl groups of BMS are esterified with propionic acid showed a largely enhanced Kp value of 10.5 times that of BMS. Further, replacement of a propionate group in BMSDP with a chlorine atom resulted in the highest Kp value (CBSP) within the drugs examined, i.e., the Kp value of CBSP was 1.2 times that of BMSDP. The presence of 30 mol% cholesterol in the SUV bilayers reduced these Kp values to approximately 35-50% of those values for the PC SUVs, although the order of the Kp values remained unchanged.
4.Detection of contact hypersensitivity to corticosteroids in allergic contact dermatitis patients who do not respond to topical corticosteroids.
Gönül M1, Gül U. Contact Dermatitis. 2005 Aug;53(2):67-70.
The delayed hypersensitivity development against topical corticosteroids which are used in allergic contact dermatitis (ACD) treatment is an important clinical problem. In our study, 41 ACD patients who did not show any response to topical corticosteroid treatment were patch tested with corticosteroid series and the commercial preparations of corticosteroids and their vehicles. In corticosteroid series, there were budesonide, bethametasone-17-valerate, triamcinolone acetonide, tixocortol pivalate, alclomethasone-17-21-dipropionate, clobetasole-17-propionate, dexamethasone-21-phosphate disodium and hydrocortisone-17-butyrate. We detected positive reaction to corticosteroids in 9 of our cases (22%) (5 single and 4 multiple). The sensitivity was mostly produced by tixocortol pivalate (6 patients). This was followed by triamcinolone acetonide (2 patients) budesonide (2 patients), alclomethasone dipropionate (2 patients), dexamethasone 21 phosphate disodium (2 patients) and betamethasone-17-valerate (1 patient).