(1R,2S,10S,11S,13S,14R,15S,17S)-1-fluoro-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

• ChemBase ID: 326
• Molecular Formular: C22H29FO5
• Molecular Mass: 392.4610632
• Monoisotopic Mass: 392.19990225
• SMILES: F[C@@]12[C@H]([C@H]3[C@@]([C@](O)([C@H](C3)C)C(=O)CO)(C[C@@H]1O)C)CCC1=CC(=O)C=C[C@]21C
• Canonical SMILES: OCC(=O)[C@@]1(O)[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)F
• InChI: InChI=1S/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,17-,19-,20-,21-,22-/m0/s1
• InChIKey: UREBDLICKHMUKA-DVTGEIKXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,10S,11S,13S,14R,15S,17S)-1-fluoro-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; (1R,2S,10S,11S,13S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0?,?.0??,??]heptadeca-3,6-dien-5-one; (1R,2S,10S,11S,13S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: betamethasone
• Brand Name: Alphatrex; Bebate; Becort; Bedifos; Beta-Methasone; Beta-Methasone Alcohol; Beta-Val; Betacorlan; Betacortril; Betaderm; Betadexamethasone; Betafluorene; Betamamallet; Betametasona [INN-Spanish]; Betametasone [DCIT]; Betamethasone Alcohol; Betamethasone Base; Betamethasone Cream; Betamethasone Dipropionate; Betamethasone Sodium Phosphate; Betamethasone Valearate; Betamethasone Valerate; Betamethasone [Usan:Ban:Inn:Jan]; Betamethasonum [INN-Latin]; Betamethasonvalerat Mikron; Betamethazone; Betapredol; Betasolon; Betatrex; Betnelan; Betsolan; Celestene; Celestone; Celestone Syrup and Tablets; Cidoten; Dermabet; Desacort-Beta; Diproderm; Diprolene; Diprolene AF; Diprosone; Flubenisolone; Hormezon; Lotrisone; Luxiq; Luxiqo; Maxivate; Methazon; Rinderon; Rinderon A; Uticort; Valisone; Valnac; Visubeta
• Synonyms: Betamethasone; (11β,16β)-9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione; Sch-4831; NCS-39470; 9α-Fluoro-16 β-methyl-prednisolone; 9α-Fluoro-16 β-methyl-11β,17α, 21-trihydroxy-1,4-pregnadiene-3,20-dione; 1,4-Pregnadiene-3,20-dione-9α-fluoro-16 β-methyl-11β,17α,21-triol; Betamethasone; Betamethasone valerate impurity A (PhEur); 9α-Fluoro-11β,17α,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione; 9α-Fluoro-16β-methyl-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione; 9α-Fluoro-16β-methylprednisolone; Celestone; Betadexamethasone; Flubenisolone; Betamethasone (Celestone); 9α-氟-11β,17α,21-三羟基-16β-甲基孕甾-1,4-二烯-3,20-二酮; 9α-氟-16β-甲基-11β,17α,21-三羟基-1,4-孕甾二烯-3,20-二酮; 9α-氟-16β-甲基泼尼松龙; 倍他米松

Database IDs

• CAS Number: 378-44-9
• EC Number: 206-825-4
• MDL Number: MFCD00062969
• PubChem SID: 46505155; 24860978; 160963789; 24892150; 24278276
• PubChem CID: 9782
• CHEBI ID: 3077
• ATC CODE: H02AB01; S01CB04; D07AC01; R03BA04; S03BA03; S02BA07; C05AA05; A07EA04; S01BA06; R01AD06
• CHEMBL: 632
• Chemspider ID: 9399
• DrugBank ID: DB00443
• KEGG ID: D00244
• Unique Ingredient Identifier: 9842X06Q6M
• Wikipedia Title: Betamethasone

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.423736
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.6815696
• LogD (pH = 7.4): 1.6815655
• Log P: 1.6815697
• Molar Refractivity: 102.4929 cm^3
• Polarizability: 39.61867 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.93
• LOG S: -3.89
• Solubility (Water): 5.05e-02 g/l

PROPERTIES

Physical Property

• Solubility: Acetone; DMSO; Insoluble; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 234-236°C; 235-237 °C(lit.)
• Optical Rotation: [α]20/D +105°, c = 1 in acetone
• Hydrophobicity(logP): 1.1

Safety Information

• Storage Condition: -20°C; -20°C Freezer; Room Temperature (15-30°C)
• RTECS: TU4000000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: oral or topical
• Excretion: Renal (in urine)
• Half Life: 36-54 hours
• Metabolism: hepatic CYP3A4
• Legal Status: Rx-only
• Pregnancy Category: C (US)
• Gene Information: human ... ABCB1(5243), CYP3A4(1576), IL4(3565), IL5(3567), NR3C1(2908)mouse ... Abcb1a(18671), Abcb1b(18669), Ifng(15978), Nos2(18126), Tnf(21926)rat ... Ar(24208), Nr3c1(24413), Tnf(24835)

Product Information

• Purity: ≥95.0% (HPLC); ≥98%; 98%
• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Suitability: meets USP testing specifications
• Description: free compound
• Impurities: ≤10.0% related substances
• Shelf Life: (limited shelf life, expiry date on the label)
• Loss on Drying: ≤5.0% loss on drying
• Empirical Formula (Hill Notation): C22H29FO5

DETAILS

MP Biomedicals - 02154853

(9α-Fluoro-16β-methyl-prednisolone; 9α-Fluoro-16β-methyl-11β,17α, 21-trihydroxy-1,4-pregnadiene-3,20-dione; 1,4-Pregnadiene-3,20-dione-9α-fluoro-16β-methyl-11<

DrugBank - DB00443

• Drug Groups: approved
• Description: A glucocorticoid given orally, parenterally, by local injection, by inhalation, or applied topically in the management of various disorders in which corticosteroids are indicated. Its lack of mineralocorticoid properties makes betamethasone particularly suitable for treating cerebral edema and congenital adrenal hyperplasia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p724)
• Indication: Topical use (cream, lotion and ointment): for relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses; Topical use (foam): relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses of the scalp; Systemic use: for the treatment of edocrine disorders, rheumatic disorders, collagen diseases, dermatological diseases, allergic states, ophthalmic diseases, respiratory diseases, hematologic disorders, neoplastic diseases, edematous states, gastrointestinal diseases, tuberculous meningitis and trichinosis.
• Pharmacology: Betamethasone and its derivatives, betamethasone sodium phosphate and betamethasone acetate, are synthetic glucocorticoids. Used for its antiinflammatory or immunosuppressive properties, betamethasone is combined with a mineralocorticoid to manage adrenal insufficiency and is used in the form of betamethasone benzoate, betamethasone dipropionate, or betamethasone valerate for the treatment of inflammation due to corticosteroid-responsive dermatoses. Betamethasone and clotrimazole are used together to treat cutaneous tinea infections.
• Toxicity: Symptoms of overdose include burning, itching, irritation, dryness, folliculitis, hypertrichosis, acneiform eruptions, hypopigmentation, perioral dermatitis, allergic contact dermatitis, maceration of the skin, secondary infection, skin atrophy, striae, and miliaria.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Minimal if applied topically.
• Half Life: 5.6 hours
• Protein Binding: 64%
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1500

Research Area: Immunology
Biological Activity:
Betamethasone is a moderately potent glucocorticoid steroid with anti-inflammatory and immunosuppressive properties.Betamethasone is a corticosteroid used as a topical cream to relieve skin irritation, such as itching and flaking from eczema. Betamethasone dipropionate and salicylic acid can be used as a treatment for local psoriasis. [1]

Sigma Aldrich - B7005

包装
100, 500 mg in poly bottle

Sigma Aldrich - 34166

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - B327000

Betamethasone is a glucocorticoid used as an anti-inflammatory agent.

REFERENCES

• http://en.wikipedia.org/wiki/Betamethasone
• Ferrante, M.G., et al.: Anal. Profiles Drug Subs., 6, 43 (1977)
• Li, A., et al.: Chem. Biol. Interact., 142, 7 (1977)
• Cruz-Monteagudo, M., et al.: Eur. J. Med. Chem., 40, 1030 (1977)
• Rothfuss, A., et al.: Chem. Res. Toxicol., 19, 1313 (1977)