Dexamethasone phosphateProduct ingredient for Dexamethasone
- Name
- Dexamethasone phosphate
- Drug Entry
- Dexamethasone
Dexamethasone, or MK-125, is a corticosteroid fluorinated at position 9 used to treat endocrine, rheumatic, collagen, dermatologic, allergic, ophthalmic, gastrointestinal, respiratory, hematologic, neoplastic, edematous, and other conditions.13 Developed in 1957, it is structurally similar to other corticosteroids like hydrocortisone and prednisolone.9
Dexamethasone was granted FDA approval on 30 October 1958.11 In a press release for the Randomized Evaluation of COVID-19 Therapy (RECOVERY) trial on 16 June 2020, dexamethasone was recommended for use in COVID-19 patients with severe respiratory symptoms. Dexamethasone reduced deaths by approximately one third in patients requiring ventilation and by one fifth in those requiring oxygen.22
- Accession Number
- DBSALT001216
- Structure
- Synonyms
- Betnelan phosphate / Dexamethasone 21-phosphate / Dexamethasone-21-dihydrogen-phosphate / Wymesone
- External IDs
- EGP-437
- UNII
- 2BP70L44PR
- CAS Number
- 312-93-6
- Weight
- Average: 472.441
Monoisotopic: 472.166232653 - Chemical Formula
- C22H30FO8P
- InChI Key
- VQODGRNSFPNSQE-CXSFZGCWSA-N
- InChI
- InChI=1S/C22H30FO8P/c1-12-8-16-15-5-4-13-9-14(24)6-7-19(13,2)21(15,23)17(25)10-20(16,3)22(12,27)18(26)11-31-32(28,29)30/h6-7,9,12,15-17,25,27H,4-5,8,10-11H2,1-3H3,(H2,28,29,30)/t12-,15+,16+,17+,19+,20+,21+,22+/m1/s1
- IUPAC Name
- {2-[(1R,2R,3aS,3bS,9aS,9bR,10S,11aS)-9b-fluoro-1,10-dihydroxy-2,9a,11a-trimethyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl]-2-oxoethoxy}phosphonic acid
- SMILES
- [H][C@@]12C[C@@H](C)[C@](O)(C(=O)COP(O)(O)=O)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
- External Links
- ChemSpider
- 9030
- ChEBI
- 68637
- ChEMBL
- CHEMBL1201302
- ZINC
- ZINC000003876071
- PDBe Ligand
- 3T5
- Wikipedia
- Dexamethasone
- Predicted Properties
Property Value Source Water Solubility 2.9 mg/mL ALOGPS logP 1.21 ALOGPS logP 1.56 Chemaxon logS -2.2 ALOGPS pKa (Strongest Acidic) 1.18 Chemaxon pKa (Strongest Basic) -3.4 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 141.36 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 113.37 m3·mol-1 Chemaxon Polarizability 45.67 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon