Dexamethasone

Base Information

• Chemical Name: Dexamethasone
• CAS No.: 50-02-2
• Deprecated CAS: 137098-19-2,8054-59-9,906422-84-2,1050677-47-8,906362-70-7,1050677-47-8,8054-59-9,906422-84-2
• Molecular Formula: C22H29FO5
• Molecular Weight: 392.468
• Hs Code.: HASONE DISODIUM PHOSPHATE PRODUCT IDENTIFICATION
• European Community (EC) Number: 200-003-9
• NSC Number: 34521
• UNII: 7S5I7G3JQL
• DSSTox Substance ID: DTXSID3020384
• Nikkaji Number: J1.356K
• Wikipedia: Dexamethasone
• Wikidata: Q422252
• NCI Thesaurus Code: C422
• RXCUI: 3264
• Pharos Ligand ID: M1RCMKYSB1B5
• Metabolomics Workbench ID: 43445
• ChEMBL ID: CHEMBL384467
• Mol file: 50-02-2.mol

Synonyms:Decaject;Decaject L.A.;Decaject-L.A.;Decameth;Decaspray;Dexamethasone;Dexasone;Dexpak;Hexadecadrol;Hexadrol;Maxidex;Methylfluorprednisolone;Millicorten;Oradexon

Chemical Property of Dexamethasone

Chemical Property:

• Appearance/Colour: White crystalline solid
• Vapor Pressure: 2.81E-15mmHg at 25°C
• Melting Point: 262-264 °C(lit.)
• Refractive Index: 76 ° (C=1, Dioxane)
• Boiling Point: 568.2 °C at 760 mmHg
• PKA: 12.13±0.70(Predicted)
• Flash Point: 297.5 °C
• PSA: 94.83000
• Density: 1.32 g/cm³
• LogP: 1.89570
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: ethanol: 1 mg/mL
• Water Solubility.: 10 mg/100 mL (25 ºC)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 392.19990218
• Heavy Atom Count: 28
• Complexity: 805

Purity/Quality:

98%, ^*data from raw suppliers

Dexamethasone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn,T,F
• Statements: 43-40-36/37/38-20/21/22-42/43-39/23/24/25-23/24/25-11
• Safety Statements: 36/37-45-36-26-22-16

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CC2C3CCC4=CC(=O)C=CC4(C3(C(CC2(C1(C(=O)CO)O)C)O)F)C
• Isomeric SMILES: C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)CO)O)C)O)F)C
• Recent ClinicalTrials: Intraoperative Methadone Administration for Improved Pain Control in Spinal Fusion Patients
• Recent EU Clinical Trials: Evaluation of Amivantamab Infusion Related Reaction Mitigation
• Recent NIPH Clinical Trials: Ipilimumab plus nivolumab with prophlactic dexamethasone in patients with advanced renal cell carcinoma
• Chemical Properties: Dexamethasone is a steroid compound belonging to the corticosteroid class, specifically a glucocorticoid. Dexamethasone is practically insoluble in water (鈮も??0.1 mg/mL).
• Medical Uses: Dexamethasone has been widely used to treat autoimmune diseases, allergies, ocular disorders, cancer, and COVID-19. It is utilized in the treatment of various conditions such as chronic obstructive lung disease, severe allergies, rheumatic problems, asthma, several skin conditions, brain swelling, and alongside antibiotics in tuberculosis.
• Antitumoral Effects: Dex is considered part of the chemotherapy protocol in several cancers, acting as a chemosensitizer or an anti-proliferative agent. It has been shown to exhibit anti-tumor effects in different in vitro and in vivo models of malignancy, such as breast, colon, lung, and hematological cancers.
• Challenges and Advancements in Drug Delivery: Its poor water solubility and potential severe side effects when administered systemically have led to interest in developing efficient DEX-loaded nanoformulations. Various nanoparticles have been developed to selectively deliver DEX without harming healthy cells or organs, including liposomes, polymers, hydrogels, nanofibers, silica, calcium phosphate, and hydroxyapatite.
• Synthesis of Dexamethasone: 1. Dehydration of 16尾-methylprednisolone acetate: 16尾-methylprednisolone acetate is dehydrated to produce the 9,11-dehydro derivative.; 2. Reaction with hypobromite: The 9,11-dehydro derivative is then reacted with a source of hypobromite, such as basic N-bromosuccinimide, to form the 9伪-bromo-11尾-hydrin derivative.; 3. Ring closure to an epoxide: The 9伪-bromo-11尾-hydrin derivative undergoes ring closure to form an epoxide, resulting in the synthesis of dexamethasone.; Additionally, dexamethasone-PLGA implants can be prepared by hot-melt extrusion, a process that involves mixing materials, including dexamethasone and PLGA, inside a barrel while being heated above the PLGA glass transition temperature and continuously extruded through a die until the material is exhausted.

Technology Process of Dexamethasone

There total 39 articles about Dexamethasone 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: 40.0%

C23H31FO4 → dexamethasone (50-02-2)

Guidance literature:

C₂₃H₃₁FO₄; In ethyl acetate; at 0 - 10 ℃;

With hydrogenchloride; In water; at 30 - 35 ℃; for 1h;

Reference yield: 5.0%

betamethasone (1177-87-3) → dexamethasone (50-02-2)

Guidance literature:

In ethanol; at 24 - 26 ℃; for 96h; Penicillium decumbens ATCC 10436, potato dextrose broth;

DOI:10.1016/0039-128X(95)00071-W

Reference yield:

16α-methyl-9β,11β-oxido-17α,20;20,21-bismethylenedioxy-pregna-1,4-diene-3-one (1966-25-2) → dexamethasone (50-02-2)

Guidance literature:

With hydrogen fluoride; In tetrahydrofuran; ethanol; at 0 ℃; for 20h;

DOI:10.1016/S0040-4020(01)91549-2

upstream raw materials:

16α-methyl-9β,11β-oxido-17α,20;20,21-bismethylenedioxy-pregna-1,4-diene-3-one

betamethasone

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

16α-methyl-17α,20;20,21-bismethylenedioxypregn-1,4,9(11)-triene-3-one

Downstream raw materials:

(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid

dexamethasone glyoxal

dexamethasone phosphate

17α-formyloxy-11β-hydroxy-9α-fluoro-16α-methyl-3-oxo-1,4-androstadien-17β-carboxylic acid

Refernces

• 1、 -. "Method for recycling betamethasone or dexamethasone synthetic mother liquor materials". . . Retrieved 2020/03/12.
• 2、 -. "A 17, 21 - double-hydroxy steroid derivatives of synthetic method". . . Retrieved 2018/04/02.