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
ChemSpider
9030
ChEBI
68637
ChEMBL
CHEMBL1201302
ZINC
ZINC000003876071
PDBe Ligand
3T5
Wikipedia
Dexamethasone
Predicted Properties
PropertyValueSource
Water Solubility2.9 mg/mLALOGPS
logP1.21ALOGPS
logP1.56Chemaxon
logS-2.2ALOGPS
pKa (Strongest Acidic)1.18Chemaxon
pKa (Strongest Basic)-3.4Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area141.36 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity113.37 m3·mol-1Chemaxon
Polarizability45.67 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon