(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 ID: 72769
• Molecular Formular: C24H31FO6
• Molecular Mass: 434.4977432
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (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 Traditional name: 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
• Synonyms: Triamcinolone acetonide; Azmacort; Triamcinolone acetonide; α-Fluoro-11β,16α,17,21-tetra-hydroxypregna-1,4-diene-3,20-dione; Aristocort; Fluoxiprednisolone; Kenacort; Lederspan; Volon; 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

Database IDs

• CAS Number: 76-25-5
• EC Number: 200-948-7
• MDL Number: MFCD00056834
• PubChem SID: 24900378; 162037690
• PubChem CID: 6436
• CHEMBL: 1504
• Chemspider ID: 6196
• Unique Ingredient Identifier: F446C597KA
• Wikipedia Title: Triamcinolone_acetonide

CALCULATED PROPERTIES

• Acid pKa: 13.401961
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 1.9441179
• LogD (pH = 7.4): 1.9441174
• Log P: 1.9441179
• Molar Refractivity: 111.5898 cm^3
• Polarizability: 43.3673 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 292°C

Safety Information

• Storage Condition: -20°C; Room Temperature (15-30°C)
• RTECS: TU3920000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 61
• Safety Statements: 45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H360
• GHS Precautionary statements: P201-P308 + P313
• Personal Protective Equipment: 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

Pharmacology Properties

• Mechanism of Action: 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

Product Information

• Purity: ≥99%
• Grade: analytical standard
• Salt Data: Free Base
• Application(s): Antiinflammatory agent; Antiproliferative; Antipruritic

DETAILS

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.

REFERENCES

• 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