(1R,2S,10S,11S,13R,14R,15S,17S)-1-chloro-14-(2-chloroacetyl)-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl furan-2-carboxylate

• ChemBase ID: 73235
• Molecular Formular: C27H30Cl2O6
• Molecular Mass: 521.4295
• Monoisotopic Mass: 520.14194404
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@]2([C@H](C[C@]2([C@H]1C[C@H]([C@@]2(C(=O)CCl)OC(=O)c1ccco1)C)C)O)Cl)C
• Canonical SMILES: ClCC(=O)[C@@]1(OC(=O)c2ccco2)[C@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2CCC2=CC(=O)C=C[C@]12C)Cl
• InChI: InChI=1S/C27H30Cl2O6/c1-15-11-19-18-7-6-16-12-17(30)8-9-24(16,2)26(18,29)21(31)13-25(19,3)27(15,22(32)14-28)35-23(33)20-5-4-10-34-20/h4-5,8-10,12,15,18-19,21,31H,6-7,11,13-14H2,1-3H3/t15-,18+,19+,21+,24+,25+,26+,27+/m1/s1
• InChIKey: WOFMFGQZHJDGCX-ZULDAHANSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,10S,11S,13R,14R,15S,17S)-1-chloro-14-(2-chloroacetyl)-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl furan-2-carboxylate; (1R,2S,10S,11S,13R,14R,15S,17S)-1-chloro-14-(2-chloroacetyl)-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl furan-2-carboxylate
• IUPAC Traditional name: mometasone furoate; nasonex
• Synonyms: Mometasone furoate; (11β,16α)-9,21-Dichloro-17-[(2-furanylcarbonyl)oxy]-11-hydroxy-16-methylpregna-1,4-diene-3,20-dione; Mometasone furoate; (11β,16α)-9,21-Dichloro-17-[(2-furanylcarbonyl)oxy]-11-hydroxy-16-methyl-pregna-1,4-diene-3,20-dione; Sch-32088, Elocon, Nasonex; Twisthaler

Database IDs

• CAS Number: 83919-23-7
• MDL Number: MFCD00866003
• PubChem SID: 162038155
• PubChem CID: 441336

CALCULATED PROPERTIES

• Acid pKa: 13.836226
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 5.055208
• LogD (pH = 7.4): 5.0552077
• Log P: 5.055208
• Molar Refractivity: 132.4999 cm^3
• Polarizability: 51.422264 Å^3
• Polar Surface Area: 93.81 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL; Methanol
• Apperance: white to off-white powder; White-to-Off-White Solid
• Melting Point: 218-220°C
• Optical Rotation: [α]/D +50 to +60°, c = 0.5 in methanol

Safety Information

• Storage Condition: -20°C; -20°C Freezer, Under Inert Atmosphere
• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: furoate
• Empirical Formula (Hill Notation): C27H30Cl2O6

DETAILS

Selleck Chemicals - S1987

Research Area: Inflammation
Biological Activity:
Mometasone furoate is a glucocorticosteroid used topically to reduce inflammation of the skin or in the airways. Mometasone furoate is used in the treatment of inflammatory skin disorders (such as eczema and psoriasis), allergic rhinitis (such as hay fever), asthma for patients unresponsive to less potent corticosteroids, and penile phimosis. In terms of steroid strength, it is more potent than hydrocortisone, and less potent than dexamethasone. Mometasone furoate reduces inflammation by causing several effects: reversing the activation of inflammatory proteins, activating the secretion of anti-inflammatory proteins, stabilising cell membranes, decreasing the influx of inflammatory cells. [1]References on Mometasone furoate[1] http://en.wikipedia.org/wiki/Mometasone_furoate, ,

Sigma Aldrich - M4074

Biochem/physiol Actions
Mometasone furoate is an anti-inflammatory glucocorticoid.

Toronto Research Chemicals - M490000

A topical corticosteroid used as an anti-inflammatory.

REFERENCES

• http://en.wikipedia.org/wiki/Mometasone_furoate
• Shapiro, E.L., et al.: J. Med. Chem., 30, 1581 (1987)
• Graft, D., et al.: J. Allergy Clin. Immunol., 98, 724 (1996)