CHEBI:9667 - triamcinolone

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ChEBI Name triamcinolone
ChEBI ID CHEBI:9667
Definition A C21-steroid hormone that is 1,4-pregnadiene-3,20-dione carrying four hydroxy substituents at positions 11β, 16α, 17α and 21 as well as a fluoro substituent at position 9. Used in the form of its 16,17-acetonide to treat various skin infections.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB1734678, eMolecules:31267429, eMolecules:494883, Selleckchem:Triamcinolone(Aristocort), ZINC000003882036
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Triamcinolone is a glucocorticoid used to treat certain skin diseases, allergies, and rheumatic disorders among others. It is also used to prevent worsening of asthma and chronic obstructive pulmonary disease (COPD). It can be taken in various ways including by mouth, injection into a muscle, and inhalation. Common side effects with long-term use include osteoporosis, cataracts, thrush, and muscle weakness. Serious side effects may include psychosis, increased risk of infections, adrenal suppression, and bronchospasm. Use in pregnancy is generally safe. It works by decreasing inflammation and immune system activity. Triamcinolone was patented in 1956 and came into medical use in 1958. It is available as a generic medication. In 2022, it was the 102nd most commonly prescribed medication in the United States, with more than 6 million prescriptions.
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Formula C21H27FO6
Net Charge 0
Average Mass 394.43390
Monoisotopic Mass 394.17917
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
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
Roles Classification
Biological Role(s): hormone
Originally referring to an endogenous compound that is formed in specialized organ or group of cells and carried to another organ or group of cells, in the same organism, upon which it has a specific regulatory function, the term is now commonly used to include non-endogenous, semi-synthetic and fully synthetic analogues of such compounds.
(via steroid hormone )
Application(s): anti-allergic agent
A drug used to treat allergic reactions.
anti-inflammatory drug
A substance that reduces or suppresses inflammation.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing triamcinolone (CHEBI:9667) has parent hydride pregnane (CHEBI:8386)
triamcinolone (CHEBI:9667) has role anti-allergic agent (CHEBI:50857)
triamcinolone (CHEBI:9667) has role anti-inflammatory drug (CHEBI:35472)
triamcinolone (CHEBI:9667) is a 11β-hydroxy steroid (CHEBI:35346)
triamcinolone (CHEBI:9667) is a 16α-hydroxy steroid (CHEBI:16799)
triamcinolone (CHEBI:9667) is a 17α-hydroxy steroid (CHEBI:35342)
triamcinolone (CHEBI:9667) is a 20-oxo steroid (CHEBI:36885)
triamcinolone (CHEBI:9667) is a 21-hydroxy steroid (CHEBI:35344)
triamcinolone (CHEBI:9667) is a 3-oxo-Δ4 steroid (CHEBI:47909)
triamcinolone (CHEBI:9667) is a C21-steroid hormone (CHEBI:64600)
triamcinolone (CHEBI:9667) is a fluorinated steroid (CHEBI:50830)
triamcinolone (CHEBI:9667) is a glucocorticoid (CHEBI:24261)
triamcinolone (CHEBI:9667) is a primary α-hydroxy ketone (CHEBI:139590)
triamcinolone (CHEBI:9667) is a tertiary α-hydroxy ketone (CHEBI:139592)
Incoming triamcinolone acetonide (CHEBI:71418) has functional parent triamcinolone (CHEBI:9667)
IUPAC Name
(11β,16α)-9-fluoro-11,16,17,21-tetrahydroxypregna-1,4-diene-3,20-dione
INNs Sources
triamcinolona DrugBank
triamcinolone KEGG DRUG
triamcinolone WHO MedNet
triamcinolonum DrugBank
Synonyms Sources
11β,16α,17α,21-tetrahydroxy-9α-fluoro-1,4-pregnadiene-3,20-dione ChemIDplus
9-fluoro-11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dione ChemIDplus
9α-fluoro-11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dione ChemIDplus
9α-fluoro-11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione NIST Chemistry WebBook
9α-fluoro-16α-hydroxyprednisolone ChemIDplus
Fluoxyprednisolone ChemIDplus
Manual Xrefs Databases
2725 DrugCentral
D00385 KEGG DRUG
DB00620 DrugBank
HMDB0014758 HMDB
Triamcinolone Wikipedia
WO2005028495 Patent
View more database links
Registry Numbers Types Sources
124-94-7 CAS Registry Number NIST Chemistry WebBook
124-94-7 CAS Registry Number ChemIDplus
2341955 Reaxys Registry Number Reaxys
Citations Waiting for Citations
Last Modified
07 February 2018