Alclometasone

Base Information

• Chemical Name: Alclometasone
• CAS No.: 66734-13-2
• Molecular Formula: C28H37ClO7
• Molecular Weight: 521.051
• Hs Code.: 2937220000
• UNII: 136H45TB7B
• DSSTox Substance ID: DTXSID60867277
• Nikkaji Number: J18.598A
• Wikipedia: Alclometasone
• Wikidata: Q4713192
• NCI Thesaurus Code: C65219
• RXCUI: 108088
• Metabolomics Workbench ID: 42642
• ChEMBL ID: CHEMBL1201361
• Mol file: 66734-13-2.mol

Synonyms:alclometasone;67452-97-5;Aclometasone;Alclometasone [INN:BAN];7alpha-Chloro-16alpha-methylprednisolone;UNII-136H45TB7B;Alclometasone (INN);136H45TB7B;(7R,8S,9S,10R,11S,13S,14S,16R,17R)-7-chloro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one;CHEBI:53776;ALCLOMETASONE [INN];(7alpha,11beta,16alpha)-7-chloro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione;ALCLOMETASONE [MI];D0F1EX;SCHEMBL4127;ALCLOMETASONE [VANDF];ALCLOMETASONE [WHO-DD];CHEMBL1201361;7a-hloro-16a-ethyl prednisolone;DTXSID60867277;HY-A0150;AKOS040741062;DB00240;7-alpha-chloro-16-alpha-methylprednisolone;CS-0017475;D07116;EN300-25042268;Q4713192;(1R,2R,3aS,3bS,4R,9aR,9bS,10S,11aS)-4-chloro-1,10-dihydroxy-1-(2-hydroxyacetyl)-2,9a,11a-trimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one;(1S,2R,9R,10S,11S,13R,14R,15S,17S)-9-chloro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one;(7-alpha,11-beta,16-alpha)-7-Chloro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione;(7.ALPHA.,11.BETA.,16.ALPHA.)-7-CHLORO-11,17,21-TRIHYDROXY-16-METHYLPREGNA-1,4-DIENE-3,20-DIONE;(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-11,17,21-TRIHYDROXY-16-METHYL-, (7.ALPHA.,11.BETA.,16.ALPHA.)-

Chemical Property of Alclometasone

Chemical Property:

• Vapor Pressure: 7.55E-19mmHg at 25°C
• Melting Point: 212-216°
• Refractive Index: 1.562
• Boiling Point: 636 °C at 760 mmHg
• PKA: 13.70±0.70(Predicted)
• Flash Point: 338.4 °C
• PSA: 106.97000
• Density: 1.26 g/cm³
• LogP: 3.94270
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), DMF (Slightly), Methanol (Slightly)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 408.1703517
• Heavy Atom Count: 28
• Complexity: 790

Purity/Quality:

98%,99%, ^*data from raw suppliers

Alclometasone17,21-Dipropionate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2C3C(CC4=CC(=O)C=CC4(C3C(CC2(C1(C(=O)CO)O)C)O)C)Cl
• Isomeric SMILES: C[C@@H]1C[C@H]2[C@@H]3[C@@H](CC4=CC(=O)C=C[C@@]4([C@H]3[C@H](C[C@@]2([C@]1(C(=O)CO)O)C)O)C)Cl
• Recent ClinicalTrials: Study Of Dacomitinib (PF-00299804) In Advanced NSCLC Patients (Post Chemo Or Select First Line) To Evaluate Prophylactic Intervention On Derm And GI AEs And PRO
• Description: Alclometasone dipropionate (ACM) is a synthetic nonfluorinated corticosteroid which has been marketed since 1986 for the topical treatment of inflammatory and pruritic corticosteroid-responsive dermatoses. As esterification of the hydroxyl group at positions 17 and 21 of the alclometasone molecule enhances topical anti-inflammatory activity, the dipropionate salt of alclometasone is much more potent than alclometasone itself. It reduces cutaneous anaphylaxis reactions induced by tuberculin or albumin in mice when administered topically (20 μl of a 0.1% solution). ACM also inhibits androgen-dependent cytochrome P450 activity and the O-depropylation activity of 7-alkoxy-coumarin O-dealkylase in a dose-dependent manner in male rats but has no effect on hepatic drug metabolism in female rats or mice of both sexes. Formulations containing ACM have been used to treat radiation, allergic contact dermatitis and psoriasis.
• Uses: Alclometasone dipropionate is a corticosteroid used topically for its glucocorticoid activity in the treatment of various skin disorders. It is usually used as a cream or ointment containing 0.05%. It is topically used in dermatology as an anti-inflammatory, antipruritic, antiallergic, antiproliferative and vasoconstrictive agent. Alclometasone dipropionate has been used since 1986 for the treatment of corticosteroid-responsive dermatoses. It is ranked in Group 6 based on potency and has been dassified as group D. According to the A-D grouping, patch-test reactions occur six to seven times more frequently within well-defined groups of structurally related chemicals than between corticosteroids of different groups.
• Therapeutic Function: Antiinflammatory, Antiallergic

Technology Process of Alclometasone

There total 13 articles about Alclometasone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 64.2%

16α-methyl-7,11-dihydroxy-17α,21-bispropionyloxypregna-4-ene-1,4-diene-3,20-dione → alclometasone dipropionate (66734-13-2)

Guidance literature:

With pyridine; phosphorus trichloride; In toluene; at 40 - 45 ℃; Solvent; Reagent/catalyst; Green chemistry;

Reference yield: 64.2%

(7α,11β,16α)-7-hydroxy-11-hydroxy-16-methyl-17,21-bis(1-oxopropoxy)pregna-1,4-diene-3,20-dione → alclometasone dipropionate (66734-13-2)

Guidance literature:

With pyridine; phosphorus trichloride; In toluene; at 40 - 45 ℃; Solvent; Reagent/catalyst;

Reference yield: 15.0%

16α-methyl-11β,17α,21-trihydroxy-1,4,6-pregnatriene-3,20-dione 17,21-dipropionate (67212-74-2) → alclometasone dipropionate (66734-13-2)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; for 16h; Ambient temperature;

DOI:10.1021/jm00178a015

upstream raw materials:

16α-methyl-11β,17α,21-trihydroxy-1,4,6-pregnatriene-3,20-dione 17,21-dipropionate

16α-methyl-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione 21-acetate

16α-methyl-11β,17α,21-trihydroxy-1,4,6-pregnatriene-3,20-dione

16α-methyl-11β,17α,21-trihydroxy-1,4,6-pregnatriene-3,20-dione 21-acetate

Downstream raw materials:

alclometasone

Refernces

• 1、 -. "Method for preparing etherified intermediate for alclometasone dipropionate". . . Retrieved 2019/06/07.
• 2、 Shue,Green,Berkenkoph,Monahan,Fernandez,Lutsky. "Synthesis and structure-activity studies of a series of 7α-halogeno corticosteroids". . p. 430 - 437. Retrieved 2007/10/02.