Triamcinolone (CHEM003713)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (5)XML
Record Information
Version1.0
Creation Date2014-09-11 05:15:03 UTC
Update Date2016-11-09 01:09:12 UTC
Accession NumberCHEM003713
Identification
Common NameTriamcinolone
ClassSmall Molecule
DescriptionA 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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Anti-Inflammatory Agent
  • Drug
  • Ester
  • Glucocorticoid
  • Metabolite
  • Organic Compound
  • Organofluoride
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
11beta,16alpha,17alpha,21-Tetrahydroxy-9alpha-fluoro-1,4-pregnadiene-3,20-dioneChEBI
9-Fluoro-11beta,16alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dioneChEBI
9alpha-Fluoro-11beta,16alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dioneChEBI
9alpha-Fluoro-11beta,16alpha,17alpha,21-tetrahydroxypregna-1,4-diene-3,20-dioneChEBI
9alpha-Fluoro-16alpha-hydroxyprednisoloneChEBI
FluoxyprednisoloneChEBI
TriamcinolonaChEBI
TriamcinolonumChEBI
AristocortKegg
KenacortKegg
11b,16a,17a,21-Tetrahydroxy-9a-fluoro-1,4-pregnadiene-3,20-dioneGenerator
11Β,16α,17α,21-tetrahydroxy-9α-fluoro-1,4-pregnadiene-3,20-dioneGenerator
9-Fluoro-11b,16a,17,21-tetrahydroxypregna-1,4-diene-3,20-dioneGenerator
9-Fluoro-11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dioneGenerator
9a-Fluoro-11b,16a,17,21-tetrahydroxypregna-1,4-diene-3,20-dioneGenerator
9Α-fluoro-11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dioneGenerator
9a-Fluoro-11b,16a,17a,21-tetrahydroxypregna-1,4-diene-3,20-dioneGenerator
9Α-fluoro-11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dioneGenerator
9a-Fluoro-16a-hydroxyprednisoloneGenerator
9Α-fluoro-16α-hydroxyprednisoloneGenerator
FluoxiprednisoloneHMDB
TriamcinaloneHMDB
Triamcinolone acetonideHMDB
Triamcinolone diacetateHMDB
Triamcinolone hexacetonideHMDB
VolonHMDB
Chemical FormulaC21H27FO6
Average Molecular Mass394.434 g/mol
Monoisotopic Mass394.179 g/mol
CAS Registry Number124-94-7
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
Traditional 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
SMILES[H][C@@]12C[C@@H](O)[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
InChI IdentifierInChI=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
InChI KeyGFNANZIMVAIWHM-OBYCQNJPSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassHydroxysteroids
Direct Parent21-hydroxysteroids
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 21-hydroxysteroid
  • Pregnane-skeleton
  • 20-oxosteroid
  • 3-oxo-delta-1,4-steroid
  • 3-oxosteroid
  • 9-halo-steroid
  • 17-hydroxysteroid
  • 16-hydroxysteroid
  • 11-hydroxysteroid
  • 16-alpha-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Halo-steroid
  • Oxosteroid
  • Delta-1,4-steroid
  • Alpha-hydroxy ketone
  • Cyclic alcohol
  • Tertiary alcohol
  • Fluorohydrin
  • Cyclic ketone
  • Halohydrin
  • Secondary alcohol
  • Ketone
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Primary alcohol
  • Alkyl halide
  • Organofluoride
  • Alcohol
  • Alkyl fluoride
  • Organohalogen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point270°C
Boiling PointNot Available
Solubility80 mg/L (at 25°C)
Predicted Properties
PropertyValueSource
Water Solubility0.85 g/LALOGPS
logP0.84ALOGPS
logP0.24ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)11.75ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area115.06 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity99.38 m³·mol⁻¹ChemAxon
Polarizability39.8 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05q9-4958000000-8d5e298bc84911e269f1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-014i-1304009000-a6db8dfa34bd6ccf8bd6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-006t-3970000000-70c8dcf068945a18ecddSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-006t-3970000000-70c8dcf068945a18ecddSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-002b-0009000000-139556289d74866f2be3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a70-0296000000-07efad54f91e2f4f8da9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004j-0019000000-2a242af1cc09f059e525Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-8c3845c2bd0bb91f6658Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-00mo-2910000000-8b5e71de002c589e636aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-020a-0490000000-0f3f7ce5872fa7f7533aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0592-0790000000-f2eacbf26900597c87ffSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-471ea538b5d986e0c4dfSpectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-00dj-1960000000-5d9e6e746dc765305042Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0002-0009000000-ce41bd6a5080c4c10c1cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0592-0960000000-cd971a61830ca6619b63Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-00dj-1960000000-b64d7111d5289725129bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-01rj-0491000000-c7e04bfdda68e0cbc0a7Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-0009000000-a7af8c93633183e5865eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-002b-0009000000-9f249447972141b9bcebSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0592-0960000000-a77f2165c6e21f53b6c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0a4r-0279000000-2f221b536c1c36be4e8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0009000000-7c85eb6f9e8e9630084dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-6039000000-53d51d2a92776995454cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ap0-2194000000-072453c8d1ed2f28f6f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000f-0009000000-35cd67a7424fc78754b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-4009000000-2aa7a537a1470cde7169Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aou-6049000000-68d446beab8eb3cdcbccSpectrum
MSMass Spectrum (Electron Ionization)splash10-00di-2931000000-ee37afbf8c285181a340Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureRapid absorption following oral administration
Mechanism of ToxicityThe 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. Firstly, however, these glucocorticoids bind to the glucocorticoid receptors which translocate into the nucleus and bind DNA (GRE) and change genetic expression both positively and negatively. 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.
MetabolismHepatic. Half Life: 88 minutes
Toxicity ValuesLD50=>500mg/kg (in rats)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of perennial and seasonal allergic rhinitis.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00620
HMDB IDHMDB0014758
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTriamcinolone
Chemspider ID29046
ChEBI ID9667
PubChem Compound ID31307
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Abu Alam, “Triamcinolone formulations and methods for their preparation and use.” U.S. Patent US20040186084, issued September 23, 2004.

MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11583068
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15305946
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19668443
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22846803
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23151875
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23337526
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23370580
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23440982
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23449717
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23473287
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23562859
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=7509503
13. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
14. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
15. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
16. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
17. The lipid handbook with CD-ROM