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124-94-7 molecular structure
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(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 and InChIs

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

Cite this record

CBID:502 http://www.chembase.cn/molecule-502.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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[8.7.0.02,7.011,15]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[8.7.0.02,7.011,15]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[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one
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
H02AB08
D07AB09
C05AA12
S01BA05
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 11.751343  H Acceptors
H Donor LogD (pH = 5.5) 0.241693 
LogD (pH = 7.4) 0.24167393  Log P 0.24169324 
Molar Refractivity 99.3828 cm3 Polarizability 38.45974 Å3
Polar Surface Area 115.06 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.84  LOG S -2.67 
Solubility (Water) 8.47e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
80 mg/L expand Show data source
DMSO expand Show data source
Methanol expand Show data source
Apperance
White to Off-White Solid expand Show data source
Melting Point
254-256°C (dec.) expand Show data source
262-263 °C(lit.) expand Show data source
Optical Rotation
[α]25/D +69°, c = 2 in DMF expand Show data source
Hydrophobicity(logP)
0.2 expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
RTECS
TU3850000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
40 expand Show data source
Safety Statements
22-36 expand Show data source
GHS Pictograms
GHS08 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H351 expand Show data source
GHS Precautionary statements
P281 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Admin Routes
Oral, topical, IM, intra-articular, intrasynovial expand Show data source
Excretion
Fecal and renal expand Show data source
Half Life
88 minutes expand Show data source
Metabolism
Hepatic expand Show data source
Protein Bound
68% expand Show data source
Legal Status
POM (UK) expand Show data source
Rx-only (US) expand Show data source
Pregnancy Category
A (Australia) expand Show data source
C (US) expand Show data source
Gene Information
human ... PTGS2(5743) expand Show data source
Mechanism of Action
ACTH antaganist expand Show data source
ACTH secretion inhibitor expand Show data source
Calcium mobilizer expand Show data source
Glucocorticoid expand Show data source
Gluconeogenesis promoter expand Show data source
Glycogen deposition inhibitor expand Show data source
Immunosuppressive expand Show data source
Phosphorus mobilizer expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Application(s)
Antiinflammatory agent expand Show data source
Immunosuppressive expand Show data source
Empirical Formula (Hill Notation)
C21H27FO6 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00620 external link
Item Information
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 external link
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 external link
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 external link
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 external link
Triamcinolone is a glucocorticoid. Triamcinolone is used as an antiasthmatic (inhalant); antiallergic (nasal).

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

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