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Record Information
Version4.0
Creation Date2012-09-06 15:16:50 UTC
Update Date2017-09-27 08:27:41 UTC
HMDB IDHMDB0014758
Secondary Accession Numbers
  • HMDB14758
Metabolite Identification
Common NameTriamcinolone
DescriptionTriamcinolone is only found in individuals that have used or taken this drug. It 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. (From Martindale, The Extra Pharmacopoeia, 30th ed, p739)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. 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.
Structure
Thumb
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
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
AristocortMeSH
VolonMeSH
Chemical FormulaC21H27FO6
Average Molecular Weight394.4339
Monoisotopic Molecular Weight394.179166801
IUPAC Name(1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-13,14,17-trihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one
Traditional Nametriamcinolone
CAS Registry Number124-94-7
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 Identifier
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
InChI KeyGFNANZIMVAIWHM-OBYCQNJPSA-N
Chemical Taxonomy
DescriptionThis compound 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
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Route of exposure:

  Enteral:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Biological role:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point274 - 278 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.85 g/LNot Available
LogP0.2Not Available
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
Polarizability39.79 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-006t-3970000000-70c8dcf068945a18ecddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0009000000-7c85eb6f9e8e9630084dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-6039000000-53d51d2a92776995454cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ap0-2194000000-072453c8d1ed2f28f6f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot AvailableView in JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-00di-2931000000-ee37afbf8c285181a340View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00620 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00620 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-3 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-1 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00620
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID29046
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTriamcinolone
METLIN IDNot Available
PubChem Compound31307
PDB IDNot Available
ChEBI ID481691
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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. [PubMed:16902246 ]
  3. 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. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]