Triamcinolone

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 COPD. It can be taken in various ways including by mouth, injection into a muscle, and inhalation.

Triamcinolone

Clinical data
Trade names	Kenalog, Nasacort, Adcortyl, others
Other names	Click show to see (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
AHFS/Drugs.com	Monograph
MedlinePlus	a601122
License data	US DailyMed: Triamcinolone
Pregnancy category	AU: A
Routes of administration	By mouth, topical, intranasal, intramuscular, intra-articular, intra-synovial
ATC code	A01AC01 (WHO) C05AA12 (WHO), D07AB09 (WHO), H02AB08 (WHO), R01AD11 (WHO), R03BA06 (WHO), S01BA05 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) / S3 UK: POM (Prescription only) / P US: ℞-only / OTC (Nasacort, intranasal) In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	>90%
Protein binding	68%
Metabolism	Liver
Onset of action	(2–)24(–48) hours
Elimination half-life	200–300 minutes (plasma), up to 36 hours (total)
Excretion	Urine (75%) and faeces (25%)
Identifiers
IUPAC name (11β,16α)-9-Fluoro-11,16,17,21-tetrahydroxypregna-1,4-diene-3,20-dione
CAS Number	124-94-7 Y
PubChem CID	31307
IUPHAR/BPS	2870
DrugBank	DB00620 Y
ChemSpider	29046 Y
UNII	1ZK20VI6TY
KEGG	D00385 Y
ChEBI	CHEBI:9667 N
ChEMBL	ChEMBL1451 Y
CompTox Dashboard (EPA)	DTXSID1040742
ECHA InfoCard	100.004.290
Chemical and physical data
Formula	C21H27FO6
Molar mass	394.439 g·mol−1
3D model (JSmol)	Interactive image
Specific rotation	${\displaystyle [\alpha ]_{D}^{20}}$ +65° to +72°
Melting point	260 to 271 °C (500 to 520 °F)
Solubility in water	2
SMILES O=C(CO)[C@]3(O)[C@]2(C[C@H](O)[C@]4(F)[C@@]/1(\C(=C/C(=O)\C=C\1)CC[C@H]4[C@@H]2C[C@H]3O)C)C
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 Y Key:GFNANZIMVAIWHM-OBYCQNJPSA-N Y
NY (what is this?)  (verify)

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 2021, it was the 104th most commonly prescribed medication in the United States, with more than 6 million prescriptions.