(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-16-one

• ChemBase编号: 72769
• 分子式: C24H31FO6
• 平均质量: 434.4977432
• 单一同位素质量: 434.21046693
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@]2([C@H](C[C@]2([C@H]1C[C@@H]1[C@@]2(C(=O)CO)OC(O1)(C)C)C)O)F)C
• Canonical SMILES: OCC(=O)[C@@]12OC(O[C@@H]1C[C@@H]1[C@]2(C)C[C@H](O)[C@]2([C@H]1CCC1=CC(=O)C=C[C@]21C)F)(C)C
• InChI: InChI=1S/C24H31FO6/c1-20(2)30-19-10-16-15-6-5-13-9-14(27)7-8-21(13,3)23(15,25)17(28)11-22(16,4)24(19,31-20)18(29)12-26/h7-9,15-17,19,26,28H,5-6,10-12H2,1-4H3/t15-,16-,17-,19+,21-,22-,23-,24+/m0/s1
• InChIKey: YNDXUCZADRHECN-JNQJZLCISA-N

名称和登记号

名称

• IUPAC标准名: (1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-16-one; (1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0?,?.0?,?.0??,??]icosa-14,17-dien-16-one; (1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-14,17-dien-16-one
• IUPAC传统名: nasacort AQ; (1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-14,17-dien-16-one
• 别名: 9α-氟-11β,16α,17α,21-四羟基-1,4-孕甾二烯-3,20-二酮-16,17-丙酮化合物; 9α-氟-16α-羟基波尼松龙 16α,17α-丙酮化合物; 曲安奈德; Triamcinolone acetonide; Azmacort; Triamcinolone acetonide; α-Fluoro-11β,16α,17,21-tetra-hydroxypregna-1,4-diene-3,20-dione; Aristocort; Fluoxiprednisolone; Kenacort; Lederspan; Volon

登记号

• CAS号: 76-25-5
• EC号: 200-948-7
• MDL号: MFCD00056834
• PubChem SID: 24900378; 162037690
• PubChem CID: 6436
• CHEMBL: 1504
• Chemspider ID: 6196
• 美国药典/FDA物质标识码: F446C597KA
• 维基百科标题: Triamcinolone_acetonide

理论计算性质

• Acid pKa: 13.401961
• 质子受体: 6
• 质子供体: 2
• LogD (pH = 5.5): 1.9441179
• LogD (pH = 7.4): 1.9441174
• Log P: 1.9441179
• 摩尔折射率: 111.5898 cm^3
• 极化性: 43.3673 Å^3
• 极化表面积: 93.06 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: 292°C

安全信息

• 保存条件: -20°C; Room Temperature (15-30°C)
• RTECS编号: TU3920000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 德国WGK号: 3
• 危险公开号: 61
• 安全公开号: 45
• GHS危险品标识: GHS08
• GHS警示词: Danger
• GHS危险声明: H360
• GHS警示性声明: P201-P308 + P313
• 个人保护装置: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

药理学性质

• 生物活性机理: Enhances the effect of sympatholytics-beta on cyclic-AMP production; Exact bronchodilator mechanism unknown; Glucocorticoid; May inhibit bronchoconstrictor mechanisms; May produce direct smooth muscle relaxation; Possible mechanisms: may decrease the number of inflammatory-cells; Topical admin; Vasoconstrictor

产品相关信息

• 纯度: ≥99%
• 级别: analytical standard
• 成盐信息: Free Base
• 应用领域: Antiinflammatory agent; Antiproliferative; Antipruritic

详细说明

MP Biomedicals - 02190283

Crystalline

Selleck Chemicals - S1628

Research Area: Infection ,Inflammation
Biological Activity:
Triamcinolone acetonide is a more potent type of triamcinolone, being about 8 times as effective as prednisone. It is used to treat a variety of skin conditions (e.g., eczema, dermatitis, allergies, rash). Triamcinolone reduces the swelling, itching, and redness that can occur in these types of conditions. [1]

Sigma Aldrich - T6501

Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. T6501.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

参考文献

• 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)
• Bernstein, S. et al., J.A.C.S., 1959, 81, 1689, (synth, acetonide)
• Florey, K., Anal. Profiles Drug Subst., 1972, 1, 367; 397; 423, (rev)
• 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
• van Leusen, D. et al., J.O.C., 1994, 59, 7534, (synth, acetonide)
• Jeal, W. et al., Drugs, 1997, 53, 257-280, (rev, acetonide)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, AQX250; AQY375; AQX500; AQX750