Alclometasone dipropionate

ChEBI: A prednisolone compound having an alpha-chloro substituent at the 7-position, an alpha-methyl substituent at the 16-position and O-propanoyl groups at the 17- and 21-positions.

Alclometasone dipropionate is a prednisolone compound having an alpha-chloro substituent at the 7-position, an alpha-methyl substituent at the 16-position and O-propanoyl groups at the 17- and 21-positions. It has a role as an anti-inflammatory drug. It is a 20-oxo steroid, an 11beta-hydroxy steroid, a glucocorticoid, a steroid ester, a propanoate ester, a 3-oxo-Delta(1),Delta(4)-steroid and a chlorinated steroid. It derives from a prednisolone.|Alclometasone Dipropionate is the dipropionate salt form of alclometasone, a synthetic corticosteroid with low to medium potency. Alclometasone dipropionate is a glucocorticoid receptor agonist that mimics the metabolic, anti-inflammatory, immunosuppressive, antipruritic, and vasoconstrictive effects of natural glucocorticoids. This drug interacts with specific intracellular receptors and binds to DNA to modify gene expression. This results in an induction of synthesis of certain proteins while inhibiting the synthesis of others. Alclometasone dipropionate is used for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses. (NCI05)

Compound (I) is dehydrogenated under the action of 2, 3-dichloro-5, 6-dicyanobenzoquinone (DDQ) to form a double bond at the 6 and 7 positions to obtain compound (II). After sodium bicarbonate hydrolyzes the 21-position ester, it reacts with triethyl orthopropionate to form the cyclic orthoformate (IV) at the 17-position and 21-position hydroxyl groups. Rearranged to the 17-position propionate (V) in acetic acid. It is then reacted with propionic anhydride to convert the 21-position hydroxyl group to propionate to obtain dipropionate (VI). Finally, it is added with hydrogen chloride to obtain aclomethasone dipropionate. The total yield is 2.678%.

Alclometasone-17,21-dipropionateis an synthetic glucocorticoid steroid used for inflammatory skin conditions. Alclometasone-17,21-dipropionate is topically used in dermatology as an anti-inflammatory, antipruritic, antiallergic, antiproliferative and vasoconstrictive agent.

Molecular Weight:521.0
XLogP3:3.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:8
Exact Mass:520.2227812
Monoisotopic Mass:520.2227812
Topological Polar Surface Area:107
Heavy Atom Count:36
Complexity:1030
Defined Atom Stereocenter Count:9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes