Triamcinolone
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Systematic (IUPAC) name |
(11β,16α)-9-fluoro-11,16,17,21-tetrahydroxypregna-1,4-diene-3,20-dione |
Clinical data |
Trade names |
Kenalog |
AHFS/Drugs.com |
monograph |
Pregnancy cat. |
A (AU) C (US) |
Legal status |
POM (UK) ℞-only (US) |
Routes |
Oral, topical, IM, intra-articular, intrasynovial |
Pharmacokinetic data |
Protein binding |
68% |
Metabolism |
Hepatic |
Half-life |
88 minutes |
Excretion |
Fecal and renal |
Identifiers |
CAS number |
124-94-7 |
ATC code |
A01AC01 C05AA12, D07AB09, H02AB08, R01AD11, R03BA06, S01BA05 |
PubChem |
CID 31307 |
IUPHAR ligand |
2870 |
DrugBank |
DB00620 |
ChemSpider |
29046 Y |
UNII |
1ZK20VI6TY Y |
KEGG |
D00385 Y |
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
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Chemical data |
Formula |
C21H27FO6 |
Mol. 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
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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
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Y (what is this?) (verify)
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Triamcinolone (trade names Aristocort, Kenacort, Tri-Nasal, Triaderm, Azmacort, Trilone, Volon A, Tristoject, and Tricortone) is a long-acting synthetic corticosteroid given orally, by injection, inhalation, or as a topical ointment or cream.
Contents
- 1 Uses
- 2 Forms
- 3 Side effects
- 4 References
- 5 External links
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Uses
Triamcinolone is used to treat several different medical conditions, such as eczema, psoriasis, arthritis, allergies, ulcerative colitis, lupus, sympathetic ophthalmia, temporal arteritis, uveitis, ocular inflammation, visualization during vitrectomy and the prevention of asthma attacks. It will not treat an asthma attack once it has already begun.[1][2][3]
Prior to 2007 it was manufactured under the name Azmacort as a corticosteroid inhaler for asthma long-term care. The patent holder, Sanofi, sold it under the brand name Nasacort.
In 2010, TEVA and Perrigo launched the first generic inhalable triamcinolone.[4]
Triamcinolone is used to alleviate infection-induced eczema in fungal skin infections in the combination drug of econazole/triamcinolone.
Triamcinolone acetonide is one of the ingredients of Ledermix - an endodontic (tooth's root canal) lotion used between sessions.
Forms
Different triamcinolone salts 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.[5] An additional side effect for women is a prolonged menstrual cycle.
References
Aristocort (triamcinolone) topical cream
Kenalog (triamcinolone) IM injection
- ^ Triamcinolone - Drugs.com
- ^ Triamcinolone Inhalation - Drugs.com
- ^ Alcon Receives FDA Approval of Triesence Injectable Triamcinolone Suspension for Use in Eye Surgery - Drugs.com
- ^ Perrigo Announces Launch Of Generic Version Of Nasacort AQ - CBS Detroit
- ^ "Drugs and Treatments - Nasacort AQ Nasl - Patient Handout". WebMD. http://www.webmd.com/drugs/drug-16244-Nasacort+AQ.aspx?drugid=16244&drugname=Nasacort%20AQ. Retrieved 2008-03-24.
External links
- Triamcinolone Topical | MedlinePlus
- Triamcinolone (Topical Application Route) | MayoClinic
Stomatological preparations (A01)
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Caries prophylactic agents |
- Dectaflur
- Olaflur
- Sodium fluoride
- Sodium monofluorophosphate
- Stannous fluoride
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Anti-infectives 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
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Corticosteroids (Glucocorticoids) |
- Dexamethasone
- Hydrocortisone
- Triamcinolone
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Other |
- Amlexanox
- Acetylsalicylic acid
- Becaplermin
- Benzydamine
- Epinephrine/Adrenalone
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noco/cofa(c)/cogi/tumr, sysi
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Decongestants and other nasal preparations (R01)
|
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Topical |
Sympathomimetics, plain
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- Cyclopentamine
- Ephedrine
- Phenylephrine
- Oxymetazoline
- Tetryzoline
- Xylometazoline
- Naphazoline
- Tramazoline
- Metizoline
- Tuaminoheptane
- Fenoxazoline
- Tymazoline
- Epinephrine
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Antiallergic agents,
excluding corticosteroids
|
- histamine antagonists (Levocabastine
- Antazoline
- Thonzylamine)
- mast cell stabilizer (some are also antihistamines) (Cromoglicic acid
- Nedocromil
- Azelastine
- Olopatadine
- Lodoxamide)
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Corticosteroids
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- Beclometasone
- Prednisolone
- Dexamethasone
- Flunisolide
- Budesonide
- Betamethasone
- Tixocortol
- Fluticasone
- Mometasone furoate
- Triamcinolone
- Ciclesonide
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Other nasal preparations
|
- Cafaminol
- Calcium hexamine thiocyanate
- Retinol
- Ipratropium bromide
- Ritiometan
- Mupirocin
- Hexamidine
- Framycetin
- Hyaluronic acid
- Eucalyptus oil
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Systemic use:
Sympathomimetics |
- Phenylpropanolamine
- Pseudoephedrine (+loratadine)
- Phenylephrine
- Phenylpropylamine
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anat(n, x, l, c)/phys/devp
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noco(c, p)/cong/tumr, sysi/epon, injr
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Drugs for obstructive airway diseases: asthma/COPD (R03)
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Adrenergics, inhalants |
Short acting β2-agonists
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Salbutamol#/Levosalbutamol • Fenoterol • Terbutaline • Pirbuterol • Procaterol • Bitolterol • Rimiterol • Carbuterol • Tulobuterol • Reproterol
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Long acting β2-agonists (LABA)
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Arformoterol • Bambuterol • Clenbuterol • Formoterol • Salmeterol Ultra LABA: Indacaterol
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other
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Epinephrine# • Hexoprenaline • Isoprenaline (Isoproterenol) • Orciprenaline (Metaproterenol)
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Glucocorticoids |
Beclometasone# • Budesonide • Ciclesonide • Fluticasone • Mometasone • Flunisolide • Betamethasone • Triamcinolone
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Anticholinergics/
muscarinic antagonist |
Aclidinium bromide • Ipratropium bromide# • Oxitropium bromide • Tiotropium bromide
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Mast cell stabilizers |
Cromoglicate • Nedocromil
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Xanthines |
Doxofylline • Enprofylline • Theobromine • Theophylline/Aminophylline/Choline theophyllinate
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Eicosanoid inhibition |
Leukotriene antagonists
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Montelukast • Pranlukast • Zafirlukast
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Lipoxygenase inhibitor
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Zileuton
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Thromboxane receptor antagonists
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Ramatroban • Seratrodast
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Combination products |
Budesonide/formoterol • Fluticasone/salmeterol • Ipratropium bromide/salbutamol • Mometasone/formoterol
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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anat(n, x, l, c)/phys/devp
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noco(c, p)/cong/tumr, sysi/epon, injr
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Corticosteroids – glucocorticoids and mineralocorticoids (H02)
(also A07EA, C05AA, D07, D10AA, R01AD, R03BA, S01BA, S02B, and S03B)
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Mineralocorticoids
(3-one, 4-ene,
no FG at 16) |
- Pregnenedione: ALDOSTERONE
- 11-DEOXYCORTICOSTERONE
- HALOGENATED AT 9: Fludrocortisone
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Glucocorticoids
(3-one, 4-ene,
11-FG,
17-hydroxy) |
Pregnene
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Pregnenedione
(+20-one)
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- HYDROCORTISONE/CORTISOL# (Hydrocortisone aceponate
- Hydrocortisone buteprate
- Hydrocortisone butyrate)
- Budesonide
- Ciclesonide
- Deflazacort
- Medrysone
- Tixocortol
- HALOGENATED AT 6: Cloprednol
- HALOGENATED, WITH FG AT 16: Halcinonide
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Pregnadiene (+1-ene)
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- Rimexolone
- HALOGENATED, WITH FG AT 16: Flunisolide
- Triamcinolone
- Amcinonide
- Fluocinolone acetonide (Fluocinonide)
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Pregnadienediol
(+21-hydroxy)
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- Prednisone (Meprednisone)
- HALOGENATED AT 9: Fluorometholone
- HALOGENATED, WITH FG AT 16: Fluocortolone (Clocortolone
- Diflucortolone
- Fluocortin)
- Desoximetasone
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Pregnadienetriol
(+11-hydroxy)
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- 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
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Pregnatriene
(+2-ene)
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Androstene
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- HALOGENATED, WITH FG AT 16: Fluticasone (Fluticasone propionate
- Fluticasone furoate)
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Other/ungrouped
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- HALOGENATED: Loteprednol
- HALOGENATED, WITH FG AT 16: Fludroxycortide
- Formocortal
- Mometasone furoate
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Aldosterone antagonists |
- Spironolactone
- Eplerenone
- Potassium canrenoate
- Canrenone
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Synthesis modifiers |
- Trilostane
- Carbenoxolone
- Aminoglutethimide
- Metyrapone
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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noco(d)/cong/tumr, sysi/epon
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proc, drug (A10/H1/H2/H3/H5)
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Glucocorticoids
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Receptor |
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Enzyme
(inhibitors) |
20,22-Desmolase
|
- 22-ABC
- 3,3′-Dimethoxybenzidine
- 3-Methoxybenzidine
- Aminoglutethimide
- Cyanoketone
- Danazol
- Etomidate
- Mitotane
- Trilostane
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17α-Hydroxylase,
17,20-Lyase
|
- 22-ABC
- 22-Oxime
- Abiraterone
- Bifonazole
- Clotrimazole
- Cyanoketone
- Cyproterone
- Danazol
- Econazole
- Galeterone
- Gestrinone
- Isoconazole
- Ketoconazole
- L-39
- Liarozole
- LY-207,320
- MDL-27,302
- Miconazole
- Mifepristone
- Orteronel
- Pioglitazone
- Rosiglitazone
- Spironolactone
- Stanozolol
- SU-10,603
- TGF-β
- Tioconazole
- Troglitazone
- VN/87-1
- YM116
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3β-HSD
|
- 4-MA
- Azastene
- Cyanoketone
- Danazol
- Epostane
- Genistein
- Gestrinone
- Metyrapone
- Norethisterone
- Oxymetholone
- Pioglitazone
- Rosiglitazone
- Trilostane
- Troglitazone
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21-Hydroxylase
|
- Aminoglutethimide
- Amphenone B
- Bifonazole
- Clotrimazole
- Diazepam
- Econazole
- Genistein
- Isoconazole
- Ketoconazole
- Metyrapone
- Miconazole
- Midazolam
- Tioconazole
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11β-Hydroxylase
|
- Aminoglutethimide
- Canrenone
- Etomidate
- Fadrozole
- FETO
- Ketoconazole
- Metomidate
- Metyrapone
- Mitotane
- Potassium canrenoate
- Spironolactone
- Trilostane
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18-Hydroxylase
|
- Aminoglutethimide
- Canrenone
- FAD286
- Fadrozole
- Ketoconazole
- LCI699
- Metyrapone
- Mespirenone
- Potassium canrenoate
- Spironolactone
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Other |
Endogenous
|
- Glucocorticoids: Corticosterone
- Cortisone
- Cortodoxone/Deoxycortisol
- Hydrocortisone/Cortisol
- Antiglucocorticoids: 17-Hydroxyprogesterone
- Deoxycorticosterone
- Pregnenolone
- Progesterone
- Precursors: Cholesterol
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- Pregnenolone
- 17-Hydroxypregnenolone
- 17-Hydroxyprogesterone
- Progesterone
- Deoxycorticosterone
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Indirect
|
- ACTH/Corticotropin
- CRH
- DHEA
- DHEA sulfate
- Plasma proteins (Transcortin, Albumin)
- Vasopressin
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Procedures
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- Adrenalectomy
- Hypophysectomy
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