(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编号: 326
• 分子式: C22H29FO5
• 平均质量: 392.4610632
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: betamethasone
• 商标名: 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
• 别名: 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; 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)

登记号

• CAS号: 378-44-9
• EC号: 206-825-4
• MDL号: MFCD00062969
• PubChem SID: 46505155; 24860978; 160963789; 24892150; 24278276
• PubChem CID: 9782
• CHEBI ID: 3077
• ATC码: H02AB01; S01CB04; D07AC01; R03BA04; S03BA03; S02BA07; C05AA05; A07EA04; S01BA06; R01AD06
• CHEMBL: 632
• Chemspider ID: 9399
• DrugBank ID: DB00443
• KEGG ID: D00244
• 美国药典/FDA物质标识码: 9842X06Q6M
• 维基百科标题: Betamethasone

理论计算性质

JChem

• Acid pKa: 12.423736
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): 1.6815696
• LogD (pH = 7.4): 1.6815655
• Log P: 1.6815697
• 摩尔折射率: 102.4929 cm^3
• 极化性: 39.61867 Å^3
• 极化表面积: 94.83 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.93
• LOG S: -3.89
• 溶解度: 5.05e-02 g/l

分子性质

理化性质

• 溶解度: Acetone; DMSO; Insoluble; Methanol
• 外观: White to Off-White Solid
• 熔点: 234-236°C; 235-237 °C(lit.)
• 比旋光度: [α]20/D +105°, c = 1 in acetone
• 疏水性(logP): 1.1

安全信息

• 保存条件: -20°C; -20°C Freezer; Room Temperature (15-30°C)
• RTECS编号: TU4000000
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

药理学性质

• 给药途径: oral or topical
• 排泄: Renal (in urine)
• 半衰期: 36-54 hours
• 代谢: hepatic CYP3A4
• 法定药品分级: Rx-only
• 妊娠期药物分类: C (US)
• 相关基因信息: 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)

产品相关信息

• 纯度: ≥95.0% (HPLC); ≥98%; 98%
• 级别: VETRANAL™, analytical standard
• 成盐信息: Free Base
• 适用性: meets USP testing specifications
• 简要说明: free compound
• 杂质: ≤10.0% related substances
• 有效期: (limited shelf life, expiry date on the label)
• 干燥失重: ≤5.0% loss on drying
• Empirical Formula (Hill Notation): C22H29FO5

详细说明

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

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Toronto Research Chemicals - B327000

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

参考文献

• 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)