(1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-13,14,17-trihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one

• ChemBase编号: 502
• 分子式: C21H27FO6
• 平均质量: 394.4338832
• 单一同位素质量: 394.1791668
• SMILES: F[C@@]12[C@H]([C@H]3[C@@]([C@](O)([C@H](O)C3)C(=O)CO)(C[C@@H]1O)C)CCC1=CC(=O)C=C[C@]21C
• Canonical SMILES: OCC(=O)[C@@]1(O)[C@H](O)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/C21H27FO6/c1-18-6-5-12(24)7-11(18)3-4-13-14-8-15(25)21(28,17(27)10-23)19(14,2)9-16(26)20(13,18)22/h5-7,13-16,23,25-26,28H,3-4,8-10H2,1-2H3/t13-,14-,15+,16-,18-,19-,20-,21-/m0/s1
• InChIKey: GFNANZIMVAIWHM-OBYCQNJPSA-N

名称和登记号

名称

• IUPAC标准名: (1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-13,14,17-trihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one; (1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-13,14,17-trihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• IUPAC传统名: triamcinolone; (1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-13,14,17-trihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• 商标名: Adcortyl; Aristocort; Aristocort A; Aristocort Tablets; Aristogel; Aristospan; Azmacort; Celeste; Cinolone; Cinolone-T; Delphicort; Flutex; Kenacort; Kenacort-A; Kenacort-Ag; Kenalog; Kenalog in Orabase; Kenalog-10; Kenalog-40; Kenalog-H; Ledercort; Nasacort; Nasacort Aq; Nasacort Hfa; Omcilon; Omicilon; Oracort; Oralone; Orion; Polcortolon; Rodinolone; Sk-Triamcinolone; Tri-Nasal; Triacet; Triacort; Triam-Tablinen; Triamcet; Triamcinlon; Triamcinolon; Triatex; Tricortale; Triderm; Trymex; Vetalog; Volon; Trilone; Volon A; Tristoject; Fougera
• 别名: Kenacort; Tri-Nasal; Triaderm; Azmacort; Triamcinolone acetonide; Triamcinolone diacetate; Triamcinolone hexacetonide; Fluoxiprednisolone; Fluoxyprednisolone; Tiamcinolonum [INN-Latin]; Triamcinalone; Triamcinolona [INN-Spanish]; Triamcinolonum [INN]; Triamcinolone; Lederspan; (11β,16α)-9-Fluoro-11,16,17,21-tetrahydroxypregna-1,4-diene-3,20-dione; 9α-Fluoro-16α-Hydroxyprednisolone; Adcortyl; Aristocort; CL 19823; Triamcinlon; Triamcinolon; Tricortale; Volon; 9α-Fluoro-11β,16α,17,21-tetrahydroxy-1,4-pregnadiene-3,20-dione; 9α-Fluoro-11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dione; Triamcinolone; (8S,9R,10S,11S,13S,14S,16R,17S)-9-fluoro-11,16,17-trihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one; (1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-13,14,17-trihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,7.0^11,15]heptadeca-3,6-dien-5-one

登记号

• CAS号: 124-94-7
• EC号: 204-718-7
• MDL号: MFCD00010477
• PubChem SID: 46507950; 24278749; 24857272; 160963965
• PubChem CID: 31307
• ATC码: S01BA05; R03BA06; D07AB09; C05AA12; A01AC01; R01AD11; H02AB08
• CHEMBL: 1451
• Chemspider ID: 29046
• DrugBank ID: DB00620
• IUPHAR配体索引: 2870
• KEGG ID: D00385
• 美国药典/FDA物质标识码: 1ZK20VI6TY
• 维基百科标题: Triamcinolone

理论计算性质

JChem

• Acid pKa: 11.751343
• 质子受体: 6
• 质子供体: 4
• LogD (pH = 5.5): 0.241693
• LogD (pH = 7.4): 0.24167393
• Log P: 0.24169324
• 摩尔折射率: 99.3828 cm^3
• 极化性: 38.45974 Å^3
• 极化表面积: 115.06 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: 0.84
• LOG S: -2.67
• 溶解度: 8.47e-01 g/l

分子性质

理化性质

• 溶解度: 80 mg/L; DMSO; Methanol
• 外观: White to Off-White Solid
• 熔点: 254-256°C (dec.); 262-263 °C(lit.)
• 比旋光度: [α]25/D +69°, c = 2 in DMF
• 疏水性(logP): 0.2

安全信息

• 保存条件: -20°C; Refrigerator
• RTECS编号: TU3850000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 40
• 安全公开号: 22-36
• GHS危险品标识: GHS08
• GHS警示词: Warning
• GHS危险声明: H351
• GHS警示性声明: P281
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

药理学性质

• 给药途径: Oral, topical, IM, intra-articular, intrasynovial
• 排泄: Fecal and renal
• 半衰期: 88 minutes
• 代谢: Hepatic
• 蛋白结合率: 68%
• 法定药品分级: POM (UK); Rx-only (US)
• 妊娠期药物分类: A (Australia); C (US)
• 相关基因信息: human ... PTGS2(5743)
• 生物活性机理: ACTH antaganist; ACTH secretion inhibitor; Calcium mobilizer; Glucocorticoid; Gluconeogenesis promoter; Glycogen deposition inhibitor; Immunosuppressive; Phosphorus mobilizer

产品相关信息

• 成盐信息: Free Base
• 应用领域: Antiinflammatory agent; Immunosuppressive
• Empirical Formula (Hill Notation): C21H27FO6

详细说明

DrugBank - DB00620

• Drug Groups: approved
• Description: A glucocorticoid given, as the free alcohol or in esterified form, orally, intramuscularly, by local injection, by inhalation, or applied topically in the management of various disorders in which corticosteroids are indicated. (From Martindale, The Extra Pharmacopoeia, 30th ed, p739)
• Indication: For the treatment of perennial and seasonal allergic rhinitis.
• Pharmacology: Triamcinolone and its derivatives are synthetic glucocorticoids that are used for their antiinflammatory or immunosuppressive properties.
• Toxicity: LD₅₀=>500mg/kg (in rats)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Rapid absorption following oral administration
• Half Life: 88 minutes
• Protein Binding: 68%
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S1933

Research Area: Inflammation
Biological Activity:
Triamcinolone(Aristocort) is a glucocorticoid given, as the free alcohol or in esterified form, orally, intramuscularly, by local injection, by inhalation, or applied topically in the management of various disorders in which corticosteroids are indicated. The antiinflammatory actions of corticosteroids are thought to involve lipocortins, phospholipase A2 inhibitory proteins which, through inhibition of arachidonic acid, control the biosynthesis of prostaglandins and leukotrienes. The immune system is suppressed by corticosteroids due to a decrease in the function of the lymphatic system, a reduction in immunoglobulin and complement concentrations, the precipitation of lymphocytopenia, and interference with antigen-antibody binding. [1]

Sigma Aldrich - T6376

Biochem/physiol Actions
Triamcinolone is a synthetic glucocorticoid agonist; induces gene expression and apoptosis; inhibits prostaglandin synthesis; impairs tumor necrosis factor (TNF)-α-induced degradation of κB-α; potentiates the differentiation-inducing effects of bone morphogenetic proteins (BMP-2, -4, -6).
包装
1, 5 g in glass bottle
50, 250 mg in glass bottle

Sigma Aldrich - 287334

Biochem/physiol Actions
Triamcinolone is a synthetic glucocorticoid agonist; induces gene expression and apoptosis; inhibits prostaglandin synthesis; impairs tumor necrosis factor (TNF)-α-induced degradation of κB-α; potentiates the differentiation-inducing effects of bone morphogenetic proteins (BMP-2, -4, -6).
包装
1 g in glass bottle
250 mg in glass bottle

Toronto Research Chemicals - T767160

Triamcinolone is a glucocorticoid. Triamcinolone is used as an antiasthmatic (inhalant); antiallergic (nasal).

参考文献

• http://www.drugbank.ca/drugs/DB00620
• Bernstein, I.L., et al.: Chest, 81, 20 (1972)
• Florey, K., et al.: Anal. Profiles Drug Subs., 1, 397 (1972)
• Toft, P. et al., Can. J. Pharm. Sci., 1972, 7, 53, (ms)
• Fiegel, G., Arzneim.-Forsch., 1975, 25, 560, (rev)
• Zbinovsky, V. et al., Anal. Profiles Drug Subst., 1977, 6, 579, (rev)
• Sieh, D.H., Anal. Profiles Drug Subst., 1982, 11, 593; 615; 651, (rev)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6222; 7100; 7152
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 739
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, AQX250; AQY375; AQX500; AQX750
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 586B, (nmr)
• Bernstein, S. et al., J.A.C.S., 1956, 78, 5693, (synth)
• Fried, J. et al., J.A.C.S., 1958, 80, 2338, (synth, pharmacol)
• Florey, K., Anal. Profiles Drug Subst., 1972, 1, 367; 397; 423, (rev)