Triamcinolone acetonide (CHEM016433)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:31:35 UTC
Update Date2016-11-09 01:15:23 UTC
Accession NumberCHEM016433
Identification
Common NameTriamcinolone acetonide
ClassSmall Molecule
DescriptionA synthetic glucocorticoid that is the 16,17-acetonide of triamcinolone. Used to treat various skin infections.
Contaminant Sources
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(11beta,16alpha)-9-Fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dioneChEBI
9-Fluoro-11beta,16alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione-16,17-acetonideChEBI
9alpha-Fluoro-11beta,21-dihydroxy-16alpha,17-isopropylidenedioxy-1,4-pregnadiene,3,20-dioneChEBI
9alpha-Fluoro-11beta,21-dihydroxy-16alpha,17alpha-isopropylidenedioxypregna-1,4-diene-3,20-dioneChEBI
9alpha-Fluoro-16alpha-17alpha-isopropyledenedioxyprednisoloneChEBI
9alpha-Fluoro-16alpha-17alpha-isopropylidenedioxy-Delta-1-hydrocortisoneChEBI
9alpha-Fluoro-16alpha-hydroxyprednisolone 16alpha,17alpha-acetonideChEBI
Triamcinolone 16,17-acetonideChEBI
AzmacortKegg
KenalogKegg
NasacortKegg
(11b,16a)-9-Fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dioneGenerator
(11Β,16α)-9-fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dioneGenerator
9-Fluoro-11b,16a,17,21-tetrahydroxypregna-1,4-diene-3,20-dione-16,17-acetonideGenerator
9-Fluoro-11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dione-16,17-acetonideGenerator
9a-Fluoro-11b,21-dihydroxy-16a,17-isopropylidenedioxy-1,4-pregnadiene,3,20-dioneGenerator
9Α-fluoro-11β,21-dihydroxy-16α,17-isopropylidenedioxy-1,4-pregnadiene,3,20-dioneGenerator
9a-Fluoro-11b,21-dihydroxy-16a,17a-isopropylidenedioxypregna-1,4-diene-3,20-dioneGenerator
9Α-fluoro-11β,21-dihydroxy-16α,17α-isopropylidenedioxypregna-1,4-diene-3,20-dioneGenerator
9a-Fluoro-16a-17a-isopropyledenedioxyprednisoloneGenerator
9Α-fluoro-16α-17α-isopropyledenedioxyprednisoloneGenerator
9a-Fluoro-16a-17a-isopropylidenedioxy-delta-1-hydrocortisoneGenerator
9Α-fluoro-16α-17α-isopropylidenedioxy-δ-1-hydrocortisoneGenerator
9a-Fluoro-16a-hydroxyprednisolone 16a,17a-acetonideGenerator
9Α-fluoro-16α-hydroxyprednisolone 16α,17α-acetonideGenerator
Tricort-40MeSH
Kenacort aMeSH
Tricort 40MeSH
Acetonide, triamcinoloneMeSH
CinonideMeSH
Tricort40MeSH
Kenalog 40MeSH
9a-fluoro-16a-17a-Isopropylidenedioxy-δ-1-hydrocortisoneGenerator
40, KenalogMeSH
Triamcinolone acetonideMeSH
a, KenacortMeSH
Chemical FormulaC24H31FO6
Average Molecular Mass434.504 g/mol
Monoisotopic Mass434.210 g/mol
CAS Registry Number76-25-5
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[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosa-14,17-dien-16-one
Traditional Namenasacort AQ
SMILES[H][C@@]12C[C@@]3([H])[C@]4([H])CCC5=CC(=O)C=C[C@]5(C)[C@@]4(F)[C@@]([H])(O)C[C@]3(C)[C@@]1(OC(C)(C)O2)C(=O)CO
InChI IdentifierInChI=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
InChI KeyYNDXUCZADRHECN-JNQJZLCISA-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
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • 9-halo-steroid
  • Oxosteroid
  • Halo-steroid
  • Delta-1,4-steroid
  • Ketal
  • Meta-dioxolane
  • Alpha-hydroxy ketone
  • Cyclic alcohol
  • Cyclic ketone
  • Fluorohydrin
  • Secondary alcohol
  • Halohydrin
  • Ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl fluoride
  • Organooxygen compound
  • Organofluoride
  • Alcohol
  • Organohalogen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.042 g/LALOGPS
logP2.31ALOGPS
logP1.94ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)13.4ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity111.59 m³·mol⁻¹ChemAxon
Polarizability44.82 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-029b-0596100000-ab38daf7db6d31055f43Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-05fr-3970000000-f386333d26c1abd0ba2fSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-029b-0596100000-ab38daf7db6d31055f43Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-05fr-3970000000-f386333d26c1abd0ba2fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0012900000-98d03ac5b7b415602b57Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0699-2159700000-8828392e139b2c45ef71Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abd-1292100000-e1d078cd10c385ad5b17Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1005900000-26d5be72895ff36914abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0api-2006900000-eb15967669727d92c2adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-5019000000-ac002e934e5e8db444a0Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDBSALT000860
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTriamcinolone_acetonide
Chemspider IDNot Available
ChEBI ID71418
PubChem Compound ID6436
Kegg Compound IDC08183
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available