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Betamethasone Dipropionate 5593-20-4

Betamethasone Dipropionate 5593-20-4

CAS No.: 5593-20-4

Betamethasone Dipropionate (Alphatrex; BetaVal; Diprolene; SCH-11460; SCH11460; Diprolene AF; Diprosone; Luxiq; Betameth
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This product is for research use only, not for human use. We do not sell to patients.

Betamethasone Dipropionate (Alphatrex; BetaVal; Diprolene; SCH-11460; SCH11460; Diprolene AF; Diprosone; Luxiq; Betamethasone 17,21-dipropionate) is a synthetic glucocorticoid steroid with anti-inflammatory and immunosuppressive activities. It is approved as a topical cream, ointment, lotion or gel (Diprolene) to treat itching and other minor skin conditions such as eczema.



Physicochemical Properties


Molecular Formula C28H37FO7
Molecular Weight 504.59
Exact Mass 504.252
CAS # 5593-20-4
Related CAS # Betamethasone;378-44-9;Beclometasone dipropionate;5534-09-8;Beclometasone dipropionate monohydrate;77011-63-3;Betamethasone dipropionate-d10;2280940-19-2
PubChem CID 21800
Appearance White to off-white solid powder
Density 1.2±0.1 g/cm3
Boiling Point 603.2±55.0 °C at 760 mmHg
Melting Point 178 °C
Flash Point 318.6±31.5 °C
Vapour Pressure 0.0±3.9 mmHg at 25°C
Index of Refraction 1.550
LogP 4.42
Hydrogen Bond Donor Count 1
Hydrogen Bond Acceptor Count 8
Rotatable Bond Count 8
Heavy Atom Count 36
Complexity 1050
Defined Atom Stereocenter Count 8
SMILES

CCC(=O)OCC(=O)[C@]1([C@H](C[C@@H]2[C@@]1(C[C@@H]([C@]3([C@H]2CCC4=CC(=O)C=C[C@@]43C)F)O)C)C)OC(=O)CC

InChi Key CIWBQSYVNNPZIQ-XYWKZLDCSA-N
InChi Code

InChI=1S/C28H37FO7/c1-6-23(33)35-15-22(32)28(36-24(34)7-2)16(3)12-20-19-9-8-17-13-18(30)10-11-25(17,4)27(19,29)21(31)14-26(20,28)5/h10-11,13,16,19-21,31H,6-9,12,14-15H2,1-5H3/t16-,19-,20-,21-,25-,26-,27-,28-/m0/s1
Chemical Name

(8S,9R,10S,11S,13S,14S,16S,17R)-9-fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-(2-(propionyloxy)acetyl)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl propionate
Synonyms

SCH 11460;Alphatrex; BetaVal; Diprolene; SCH-11460; SCH11460;Diprolene AF; Diprosone; Luxiq
HS Tariff Code 2934.99.9001
Storage

Powder-20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Shipping Condition Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity


ln Vivo Psoriasis, dermatitis, and eczema are inflammatory skin disorders that are treated with betomethona dipropionate, an extremely strong corticosteroid. This is an artificial counterpart of adrenocortical steroids.
Efficacy in seborrhoeic dermatitis: Topical Betamethasone Dipropionate significantly improved clinical symptoms of seborrhoeic dermatitis (including erythema, scaling, pruritus, and inflammation) compared to placebo. After 2-4 weeks of treatment, the proportion of patients achieving "clear" or "markedly improved" status ranged from 65% to 82% [1]
- Superiority to milder corticosteroids: Betamethasone Dipropionate showed greater efficacy than low-potency topical corticosteroids (e.g., hydrocortisone) in reducing severe scaling and pruritus, with a mean symptom score reduction of 40-55% versus 20-30% in the low-potency group [1]
- Relapse prevention: Continuous low-dose maintenance therapy with Betamethasone Dipropionate (2-3 times weekly) reduced the relapse rate of seborrhoeic dermatitis by 38% compared to no maintenance therapy over a 12-week follow-up [1]
Toxicity/Toxicokinetics Local skin adverse effects: The most common adverse events associated with topical Betamethasone Dipropionate were mild to moderate local irritation (12-18% of patients), including burning, stinging, and dryness. These effects were usually transient and resolved after treatment discontinuation [1]
- Long-term use risks: Prolonged (≥8 weeks) continuous use of Betamethasone Dipropionate was associated with an increased risk of skin atrophy (4-6% of patients), telangiectasia (2-3%), and hypopigmentation (1-2%) [1]
- Systemic absorption risk: Minimal systemic absorption was observed with topical application; no significant changes in serum cortisol levels or systemic corticosteroid-related adverse effects (e.g., hypertension, hyperglycemia) were reported in clinical trials [1]
References Cochrane Database Syst Rev. 2013 Jan 31;1:CD007633.doi: 10.1002/14651858.CD007633.pub2.
Additional Infomation Betamethasone dipropionate is a steroid ester that is betamethasone in which the hydroxy hydrogens at positions 17 and 21 are replaced by propanoyl groups. It is used in combination with calcipotriene hydrate, a synthetic vitamin D analogue, for the topical treatment of plaque psoriasis in adult patients. It has a role as an antipsoriatic. It is a steroid ester, an 11beta-hydroxy steroid, a 20-oxo steroid, a fluorinated steroid, a propanoate ester and a 3-oxo-Delta(1),Delta(4)-steroid. It is functionally related to a betamethasone.
Betamethasone dipropionate has been reported in Dodonaea polyandra with data available.
Betamethasone Dipropionate is the 17,21-dipropionate ester of betamethasone, a synthetic glucocorticoid with metabolic, immunosuppressive and anti-inflammatory actions. Betamethasone dipropionate binds to specific intracellular glucocorticoid receptors and subsequently binds to DNA to modify gene expression. The synthesis of certain anti-inflammatory proteins is induced while the synthesis of certain inflammatory mediators is inhibited. As a result, there is an overall reduction in chronic inflammation and autoimmune reactions.
See also: Betamethasone (has active moiety); Betamethasone Dipropionate; Calcipotriene (component of); Betamethasone Dipropionate; Clotrimazole (component of) ... View More ...
Betamethasone Dipropionate is a medium-to-high potency topical corticosteroid used for the treatment of inflammatory dermatoses, including seborrhoeic dermatitis [1]
- Its therapeutic effect in seborrhoeic dermatitis is mediated by anti-inflammatory, antipruritic, and antikeratinizing properties [1]
- The Cochrane review concluded that topical Betamethasone Dipropionate is effective for short-term (2-4 weeks) treatment of moderate-to-severe seborrhoeic dermatitis, but long-term continuous use should be avoided to minimize local skin adverse effects [1]

Solubility Data


Solubility (In Vitro)
DMSO: 101 mg/mL (200.2 mM)
Water:<1 mg/mL
Ethanol: 66 mg/mL (130.8 mM)
Solubility (In Vivo) Solubility in Formulation 1: 2.75 mg/mL (5.45 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.75 mg/mL (5.45 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.9818 mL 9.9090 mL 19.8181 mL
5 mM 0.3964 mL 1.9818 mL 3.9636 mL
10 mM 0.1982 mL 0.9909 mL 1.9818 mL
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.