Chemistry:Triamcinolone acetonide

Short description: Medicinal chemical compound, steroid

Triamcinolone acetonide

Clinical data
Trade names	Kenalog, Nasacort, Xipere, others
AHFS/Drugs.com	Monograph
MedlinePlus	a601124
License data	US DailyMed: Triamcinolone
Pregnancy category	AU: B3/ A
Routes of administration	Topical, joint injection, nasal
ATC code	A01AC01 (WHO) D07AB09 (WHO), H02AB08 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) / S3 / S2 CA: ℞-only / OTC UK: POM (Prescription only) / GSL US: ℞-only / OTC EU: Rx-only
Pharmacokinetic data
Metabolism	Liver
Excretion	Urine (75%) and feces (25%)
Identifiers
IUPAC name (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS)-4b-fluoro-6b-glycoloyl-5-hydroxy-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one
CAS Number	76-25-5 Y
PubChem CID	6436
IUPHAR/BPS	2867
DrugBank	DBSALT000860
ChemSpider	6196 Y
UNII	F446C597KA
KEGG	D00983
ChEBI	CHEBI:71418 N
ChEMBL	ChEMBL1504 Y
PDB ligand	1TA (PDBe, RCSB PDB)
Chemical and physical data
Formula	C24H31FO6
Molar mass	434.504 g·mol−1
3D model (JSmol)	Interactive image
Melting point	290 to 294 °C (554 to 561 °F)
SMILES C[C@]12C[C@@H]([C@]3([C@H]([C@@H]1C[C@@H]4[C@]2(OC(O4)(C)C)C(=O)CO)CCC5=CC(=O)C=C[C@@]53C)F)O
InChI InChI=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 Y Key:YNDXUCZADRHECN-JNQJZLCISA-N Y
NY (what is this?)  (verify)

Triamcinolone acetonide, sold under the brand name Kenalog among others, is a synthetic corticosteroid medication used topically to treat various skin conditions, to relieve the discomfort of mouth sores, and by injection into joints to treat various joint conditions. It is also injected into lesions to treat inflammation in some parts of the body, particularly the skin. In nasal spray form, it is used to treat allergic rhinitis. It is used for the treatment of macular edema associated with uveitis. It is a more potent derivative of triamcinolone, and is about eight times as potent as prednisone.

Most forms of triamcinolone acetonide are prescription drugs. In 2014, the U.S. Food and Drug Administration (FDA) made triamcinolone acetonide an over-the-counter drug in the United States in nasal spray form under the brand name Nasacort. It is available as a generic medication.

Medical uses

Triamcinolone acetonide as an intra-articular injectable has been used to treat a variety of musculoskeletal conditions. When applied to the skin as a topical ointment, it is used to mitigate blistering from poison ivy, oak, and sumac. When combined with nystatin, it is used to treat skin infections with discomfort from fungus, though it should not be used on the eyes. It provides relatively immediate relief and is used before using oral prednisone. Oral and dental paste preparations are used for treating aphthous ulcers.

As an intravitreal injection, triamcinolone acetonide has been used to treat various eye diseases and has been found useful in reducing macular edema. Drug trials have found it to be as efficient as anti-VEGF drugs in eyes with artificial lenses over a two-year period. A systematic review did not find any evidence of any benefit in preventing vision loss in eyes treated with triamcinolone acetonide over placebo, for patients with age-related macular degeneration.

Triamcinolone acetonide is also administered via intralesional injection in the treatment of hypertrophic and keloid scars.

Contraindications

Evidence suggests that usage of triamcinolone acetonide or other steroids to treat macular edema increases the risk of increasing intraocular pressure in patients.

Triamcinolone acetonide should not be used by those with tuberculosis or untreated fungal, bacterial, systemic viral or herpes simplex infections without consulting a doctor first.

Pharmacology

Pharmacodynamics

Further information: Glucocorticoid § Mechanism of action

Triamcinolone acetonide is a corticosteroid. It is specifically a glucocorticoid, or an agonist of the glucocorticoid receptor, that is about five times as potent as cortisol. It has very little mineralocorticoid effects. The affinities of triamcinolone acetonide for the androgen and estrogen receptors are both <0.1% (relative to testosterone and estradiol). However, triamcinolone acetonide has 15% of the affinity of progesterone for the progesterone receptor. In relation to this, triamcinolone acetonide can produce endocrine side effects like ovulation inhibition and menstrual irregularities.

Chemistry

Triamcinolone acetonide, also known as 9α-fluoro-16α-hydroxyprednisolone 16α,17α-acetonide or as 9α-fluoro-11β,16α-17α,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with acetone, is a synthetic halogenated cyclic ketal pregnane corticosteroid. It is the C16α,17α acetonide of triamcinolone.

Veterinary use

Triamcinolone acetonide is also used in veterinary medicine as an ingredient in topical ointments and in topical sprays for control of pruritus in dogs.

A series of injections with triamcinolone acetonide or another corticosteroid may reduce keloid size and irritation. It is used as a preinductor and/or inductor of birth in cows. It was also used in the horse racing industry, but it is now a banned substance if found in a horse's system on race day.

External links

• "Triamcinolone acetonide". Drug Information Portal. U.S. National Library of Medicine. https://druginfo.nlm.nih.gov/drugportal/name/triamcinolone%20acetonide. 
• "Triamcinolone". https://medlineplus.gov/druginfo/meds/a601122.html. 
• "Triamcinolone Nasal Spray". https://medlineplus.gov/druginfo/meds/a682791.html.