(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 ID: 502
• Molecular Formular: C21H27FO6
• Molecular Mass: 394.4338832
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (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 Traditional name: 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
• Brand Name: 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
• Synonyms: 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

Database IDs

• CAS Number: 124-94-7
• EC Number: 204-718-7
• MDL Number: MFCD00010477
• PubChem SID: 46507950; 24278749; 24857272; 160963965
• PubChem CID: 31307
• ATC CODE: A01AC01; R01AD11; S01BA05; D07AB09; C05AA12; H02AB08; R03BA06
• CHEMBL: 1451
• Chemspider ID: 29046
• DrugBank ID: DB00620
• IUPHAR ligand ID: 2870
• KEGG ID: D00385
• Unique Ingredient Identifier: 1ZK20VI6TY
• Wikipedia Title: Triamcinolone

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.751343
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 0.241693
• LogD (pH = 7.4): 0.24167393
• Log P: 0.24169324
• Molar Refractivity: 99.3828 cm^3
• Polarizability: 38.45974 Å^3
• Polar Surface Area: 115.06 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.84
• LOG S: -2.67
• Solubility (Water): 8.47e-01 g/l

PROPERTIES

Physical Property

• Solubility: 80 mg/L; DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 254-256°C (dec.); 262-263 °C(lit.)
• Optical Rotation: [α]25/D +69°, c = 2 in DMF
• Hydrophobicity(logP): 0.2

Safety Information

• Storage Condition: -20°C; Refrigerator
• RTECS: TU3850000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 40
• Safety Statements: 22-36
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H351
• GHS Precautionary statements: P281
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Admin Routes: Oral, topical, IM, intra-articular, intrasynovial
• Excretion: Fecal and renal
• Half Life: 88 minutes
• Metabolism: Hepatic
• Protein Bound: 68%
• Legal Status: POM (UK); Rx-only (US)
• Pregnancy Category: A (Australia); C (US)
• Gene Information: human ... PTGS2(5743)
• Mechanism of Action: ACTH antaganist; ACTH secretion inhibitor; Calcium mobilizer; Glucocorticoid; Gluconeogenesis promoter; Glycogen deposition inhibitor; Immunosuppressive; Phosphorus mobilizer

Product Information

• Salt Data: Free Base
• Application(s): Antiinflammatory agent; Immunosuppressive
• Empirical Formula (Hill Notation): C21H27FO6

DETAILS

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).
Packaging
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).

REFERENCES

• 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)