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: Rx-only, OTC (Nasacort, Intranasal)
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 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[8.7.0.0^2,7.0^11,15]heptadeca-3,6-dien-5-one
Chemical data
Formula	C₂₁H₂₇FO₆
Molar 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.^[1]^[2]^[3] It has also been used off-label for macular degeneration.^[4]

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.^[5]

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.^[6] 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.

References

Aristocort (triamcinolone) topical cream

Kenalog (triamcinolone) IM injection

External links

Glucocorticoids and antiglucocorticoids (H02)

Glucocorticoids

Pregnene	Cortisone

Pregnenedione	Hydrocortisone (cortisol)^# (Hydrocortisone aceponate Hydrocortisone buteprate Hydrocortisone butyrate) Budesonide Ciclesonide Deflazacort Medrysone Tixocortol Halogenated at 6: Cloprednol Halogenated, with FG at 16: Halcinonide

Pregnadiene	Rimexolone Halogenated, with FG at 16: Flunisolide Triamcinolone Amcinonide Fluocinolone acetonide (Fluocinonide)

Pregnadienediol	Prednisone (Meprednisone) Halogenated at 9: Fluorometholone Halogenated, with FG at 16: Fluocortolone (Clocortolone Diflucortolone Fluocortin) Desoximetasone

Pregnadienetriol	Prednisolone^# (Methylprednisolone Methylprednisolone aceponate Prednicarbate Prednylidene) Desonide Halogenated: Fluprednisolone (Difluprednate Fluperolone) Halogenated, with FG at 16: Dexamethasone^# Betamethasone (Clobetasol Clobetasone Diflorasone Halometasone Ulobetasol) Beclometasone Paramethasone Alclometasone Fluclorolone acetonide Flumetasone Fluprednidene

Pregnatriene	Cortivazol

Androstene	Halogenated, with FG at 16: Fluticasone (Fluticasone propionate Fluticasone furoate)

Others/unsorted	Halogenated: Loteprednol Halogenated, with FG at 16: Fludroxycortide Formocortal Mometasone furoate Promestriene

Antiglucocorticoids

SGRMs: Dagrocorat^§
Fosdagrocorat^§
Mapracorat^†

Antagonists: Ketoconazole
Mifepristone

Synthesis modifiers

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Stomatological preparations (A01)

Caries prophylaxis	Dectaflur Olaflur Sodium fluoride Sodium monofluorophosphate Stannous fluoride

Infection and antiseptics	Amphotericin B Benzoxonium chloride Chlorhexidine Chlortetracycline Clotrimazole Domiphen bromide Doxycycline Eugenol Hexetidine Hydrogen peroxide Mepartricin Metronidazole Miconazole Minocycline Natamycin Neomycin Oxyquinoline Polynoxylin Sodium perborate Tetracycline Tibezonium iodide

Corticosteroids (Glucocorticoids)	Dexamethasone Hydrocortisone Triamcinolone

Other	Amlexanox Acetylsalicylic acid Becaplermin Benzydamine Epinephrine/Adrenalone

Decongestants and other nasal preparations (R01)

Topical

Sympathomimetics, plain	Cyclopentamine Ephedrine Epinephrine Fenoxazoline Levomethamphetamine Metizoline Naphazoline Oxymetazoline Phenylephrine Propylhexedrine Tetryzoline Tramazoline Tuaminoheptane Tymazoline Xylometazoline

Antiallergic agents, excluding corticosteroids	Spaglumic acid histamine antagonists (Levocabastine Antazoline Thonzylamine) mast cell stabilizer (some are also antihistamines) (Cromoglicic acid Nedocromil Azelastine Olopatadine Lodoxamide)

Corticosteroids	Beclometasone dipropionate Betamethasone Budesonide Ciclesonide Dexamethasone Flunisolide Fluticasone Mometasone furoate Prednisolone Tixocortol Triamcinolone

Other nasal preparations	Cafaminol Calcium hexamine thiocyanate Eucalyptus oil Framycetin Hexamidine Hyaluronan Ipratropium bromide Mupirocin Retinol Ritiometan Saline water

Systemic use:
Sympathomimetics

Drugs for obstructive airway diseases: asthma/COPD (R03)

Adrenergics, inhalants

Short-acting β₂ agonists	Bitolterol Carbuterol Fenoterol Pirbuterol Procaterol Reproterol Rimiterol Salbutamol (albuterol)^#/Levosalbutamol (levalbuterol) Terbutaline Tulobuterol

Long-acting β₂ agonists (LABA)	Bambuterol Clenbuterol Formoterol/Arformoterol Salmeterol Salmefamol

Ultra-long-acting β₂ agonists	Indacaterol Olodaterol Vilanterol

Other	Epinephrine^# Hexoprenaline Isoprenaline (isoproterenol) Orciprenaline (metaproterenol)

Glucocorticoids

Anticholinergics/
muscarinic antagonist

Mast cell stabilizers

Xanthines

Eicosanoid inhibition

Leukotriene antagonists	Montelukast Pranlukast Zafirlukast

Arachidonate 5-lipoxygenase inhibitors	Baicalein^§ Caffeic acid^§ Curcumin^§ Hyperforin^§ Meclofenamate sodium^§ St John's wort^§ Zileuton

Thromboxane receptor antagonists	Ramatroban Seratrodast

Non-xanthine PDE4 inhibitors	Ibudilast Roflumilast

Others/unknown

Combination products

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Glucocorticoid signaling

Receptor
(ligands)

Agonists	5α-Dihydrocorticosterone 11-Deoxycorticosterone (desoxycortone, cortexone) 11-Deoxycortisol (cortodoxone, cortexolone)) 15β-Hydroxycyproterone acetate 17-Hydroxyprogesterone 21-Deoxycortisol Acrocinonide Alclometasone Amcinafal Amcinafide Amcinonide Amebucort Amelometasone Amicinonide Anecortave AZD5423 Beclometasone Beclometasone dipropionate Betamethasone Betamethasone acibutate Betamethasone dipropionate Budesonide Butixocort Chlormadinone acetate Chloroprednisone Ciclesonide Cicortonide Ciprocinonide Clobetasol Clobetasol propionate Clobetasone Clocortolone Cloprednol Cloticasone Cormetasone Corticosterone Cortisone Cortisuzol Cortivazol Cyproterone Cyproterone acetate Deflazacort Deprodone Descinolone Desonide Desoximetasone Dexbudesonide Dexamethasone Dexamethasone acefurate Dexamethasone cipecilate Dexamethasone isonicotinate Dichlorisone Diflorasone Difluocortolone Difluocortolone valerate Difluprednate Domoprednate Doxibetasol Drocinonide Etiprednol dicloacetate Fluazacort Fluclorolone Fluclorolone (flucloronide) Fludrocortisone Fludroxycortide Flumoxonide Flumetasone Flunisolide Fluocinolone Fluocinolone acetonide Fluocinonide Fluocortin Fluocortolone Fluorometholone Fluperolone Fluperolone acetate Fluprednidene Fluprednidene acetate Fluprednisolone Fluticasone Fluticasone furoate Fluticasone propionate Formocortal GSK-9027 Halcinonide Halocortolone Halometasone Halopredone Hydrocortamate Hydrocortisone (cortisol) Hydrocortisone aceponate Hydrocortisone buteprate Hydrocortisone-17-butyrate Hydrocortisone-21-butyrate Icometasone enbutate Isoflupredone Isoprednidene Itrocinonide Locicortolone dicibate Loteprednol Mazipredone Meclorisone Medroxyprogesterone acetate Megestrol acetate Medrysone Meprednisone Methylprednisolone Methylprednisolone aceponate Methylprednisolone suleptanate Mometasone Mometasone furoate Naflocort Nestorone Nicocortonide Nivacortol Oxisopred Paramethasone Prednazate Prednazoline Prednicarbate Prednimustine Prednisolamate Prednisolone Prednisolone steaglate Prednisone Prednylidene Procinonide Progesterone Promestriene Resocortol Rimexolone Rofleponide Tetrahydrocorticosterone Tetrahydrogestrinone Timobesone Tipredane Tixocortol Tixocortol pivalate Tralonide Triamcinolone Triamcinolone acetonide Triamcinolone benetonide Triamcinolone furetonide Triamcinolone hexacetonide Triclonide Ulobetasol (halobetasol)

Mixed (SEGRAs)	Dagrocorat Fosdagrocorat Mapracorat

Antagonists	3α-Hydroxytibolone 3β-Hydroxytibolone Aglepristone Asoprisnil C108297 C113176 CORT-108297 Cyproterone acetate Guggulsterone Ketoconazole Lilopristone LLY-2707 Miconazole Mifepristone Onapristone ORG-34116 ORG-34517 (SCH-900636) ORG-34850 Pregnenolone 16α-carbonitrile Spironolactone Telapristone Tibolone Toripristone Ulipristal acetate

Enzyme

Modulators	See here instead (modulators of 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, 11β-HSD, 21-hydroxylase, 11β-hydroxylase, and 18-hydroxylase).

Others

Precursors	Cholesterol 22R-Hydroxycholesterol 20α,22R-Dihydroxycholesterol Pregnenolone Pregnenolone sulfate 17-Hydroxypregnenolone Progesterone 17-Hydroxyprogesterone 11-Deoxycorticosterone

Indirect	ACTH (corticotropin) CRH DHEA DHEA sulfate Plasma proteins (albumin, transcortin) Vasopressin

See also: Androgenics • Estrogenics • Mineralocorticoids • Progestogenics

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