Triamcinolone

Triamcinolone

Systematic (IUPAC) name
(11β,16α)-9-Fluoro-11,16,17,21-tetrahydroxypregna-1,4-diene-3,20-dione
Clinical data
Trade names	Kenalog Nasacort
AHFS/Drugs.com	monograph
Pregnancy category	AU: A US: C (Risk not ruled out)
Legal status	UK: POM (Prescription only) US: ℞-only
Routes of administration	Oral, topical, IM, intra-articular, intrasynovial
Pharmacokinetic data
Protein binding	68%
Metabolism	Hepatic
Biological half-life	88 minutes
Excretion	Fecal and renal
Identifiers
CAS Number	124-94-7 Y
ATC code	A01AC01 (WHO) C05AA12, D07AB09, H02AB08, R01AD11, R03BA06, S01BA05
PubChem	CID: 31307
IUPHAR/BPS	2870
DrugBank	DB00620 Y
ChemSpider	29046 Y
UNII	1ZK20VI6TY Y
KEGG	D00385 Y
ChEBI	CHEBI:9667 N
ChEMBL	CHEMBL1451 Y
Synonyms	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
Chemical data
Formula	C21H27FO6
Molecular mass	394.434 g/mol
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)

Triamcinolone is a long-acting synthetic corticosteroid given orally, by injection, by inhalation, or as a topical ointment or cream.

Uses

Triamcinolone is used to treat a number of different medical conditions, such as eczema, psoriasis, arthritis, allergies, ulcerative colitis, lupus, sympathetic ophthalmia, temporal arteritis, uveitis, ocular inflammation, Urushiol-induced contact dermatitis, aphthous ulcers (usually as triamcinolone acetonide), visualization during vitrectomy and the prevention of asthma attacks. It will not treat an asthma attack once it has already begun. It has also been used off-label for macular degeneration.

Prior to 2007 it was sold under the name Azmacort as a corticosteroid inhaler for asthma long-term care.

In 2010, TEVA and Perrigo launched the first generic inhalable triamcinolone.

Triamcinolone is used to alleviate infection-induced eczema in fungal skin infections in the combination drug of econazole/triamcinolone.

The derivative triamcinolone acetonide is one of the ingredients of Ledermix, an endodontic (tooth's root canal) lotion used between sessions, and Sanofi sold it under the brand name Nasacort. Triamcinolone acetonide is also used as intra lesional steroid injection to treat keloids and hypertrophic scars.

Forms

Different triamcinolone derivatives are available, including acetonide, benetonide, furetonide, hexacetonide and diacetate.

Triamcinolone acetonide is a more potent type of triamcinolone, being about eight times as effective as prednisone.

Side effects

Side effects of triamcinolone include sore throat, nosebleeds, increased coughing, headache, and runny nose. White patches in the throat or nose indicate a serious side effect. Symptoms of an allergic reaction include rash, itch, swelling, severe dizziness, trouble breathing. An additional side effect for women is a prolonged menstrual cycle.

Trade names

Trade names for triamcinolone include Aristocort (Sandoz, now Novartis), Kenacort (Bristol-Myers Squibb), Kenalog (Bristol-Myers Squibb), Tricort (Cadila), Triaderm (Schering-Plough), Azmacort (KOS), Trilone, Volon A, Tristoject, Tricortone and Ratio-Triacomb.

See also

• Glucocorticoid (a chart comparing various glucocorticoids)
• Triamcinolone acetonide

References

Aristocort (triamcinolone) topical cream

Kenalog (triamcinolone) IM injection

External links

• Triamcinolone Topical | MedlinePlus
• Triamcinolone (Topical Application Route) | MayoClinic