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: Prescription-only (POM)
- 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 Registry 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[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one
|
Chemical data |
Formula |
C21H27FO6 |
Molecular mass |
394.434 g/mol |
SMILES
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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
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Key:GFNANZIMVAIWHM-OBYCQNJPSA-N Y
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N (what is this?) (verify) |
Triamcinolone is a long-acting synthetic corticosteroid given orally, by injection, by inhalation, or as a topical ointment or cream.
Contents
- 1 Uses
- 2 Forms
- 3 Side effects
- 4 Trade names
- 5 See also
- 6 References
- 7 External links
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.[citation needed] 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.
See also
- Glucocorticoid (a chart comparing various glucocorticoids)
- Triamcinolone acetonide
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
- ^ Age-Related Macular Degeneration (AMD) Treatment
- ^ Perrigo Announces Launch Of Generic Version Of Nasacort AQ - CBS Detroit
- ^ "Drugs and Treatments - Nasacort AQ Nasl - Patient Handout". WebMD. Retrieved 2008-03-24.
External links
- Triamcinolone Topical | MedlinePlus
- Triamcinolone (Topical Application Route) | MayoClinic
Glucocorticoids and antiglucocorticoids (H02)
|
|
Agonists |
Pregnene |
|
|
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 |
|
|
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
|
|
|
Antagonists /
SGRMs |
- Antagonists: Ketoconazole
- Mifepristone
|
|
Synthesis modifiers |
- Acetoxolone
- Aminoglutethimide
- Carbenoxolone
- Enoxolone
- Ketoconazole
- Metyrapone
- Mitotane
- Trilostane
|
|
-
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
|
Index of hormones
|
|
Description |
- Glands
- Hormones
- thyroid
- mineralocorticoids
- Physiology
- Development
|
|
Disease |
- Diabetes
- Congenital
- Neoplasms and cancer
- Other
- Symptoms and signs
|
|
Treatment |
- Procedures
- Drugs
- calcium balance
- corticosteroids
- oral hypoglycemics
- pituitary and hypothalamic
- thyroid
|
|
|
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
|
|
Index of the mouth
|
|
Description |
|
|
Disease |
- Congenital
- face and neck
- cleft
- digestive system
- Neoplasms and cancer
- Other
- Symptoms and signs
|
|
Treatment |
|
|
|
Decongestants and other nasal preparations (R01)
|
|
Topical |
Sympathomimetics, plain
|
- Cyclopentamine
- Ephedrine
- Epinephrine
- Fenoxazoline
- Metizoline
- Naphazoline
- Oxymetazoline
- Phenylephrine
- Tetryzoline
- Tramazoline
- Tuaminoheptane
- Tymazoline
- Xylometazoline
|
|
Antiallergic agents,
excluding corticosteroids
|
- 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 |
- Phenylephrine
- Phenylpropanolamine
- Phenylpropylamine
- Pseudoephedrine (+loratadine)
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|
Index of the respiratory system
|
|
Description |
- Anatomy
- Physiology
- Development
|
|
Disease |
- Congenital
- Neoplasms and cancer
- Chest trauma
- Infection
- common cold
- pneumonia
- tuberculosis
- Other
- Symptoms and signs
|
|
Treatment |
- Procedures
- Drugs
- nasal
- throat
- obstructive airway diseases
- cough and cold
- histaminergics
- pulmonary arterial hypertension
- other
- Surgery
|
|
|
Drugs for obstructive airway diseases: asthma/COPD (R03)
|
|
Adrenergics, inhalants |
Short acting β2-agonists |
- Bitolterol
- Carbuterol
- Fenoterol
- Pirbuterol
- Procaterol
- Reproterol
- Rimiterol
- Salbutamol#/Levosalbutamol
- Terbutaline
- Tulobuterol
|
|
Long acting β2-agonists (LABA) |
- Arformoterol
- Bambuterol
- Clenbuterol
- Formoterol
- Salmeterol
- Salmefamol
- Ultra LABA: Indacaterol, Olodaterol, Vilanterol
|
|
other |
- Epinephrine#
- Hexoprenaline
- Isoprenaline (Isoproterenol)
- Orciprenaline (Metaproterenol)
|
|
|
Glucocorticoids |
- Beclometasone#
- Betamethasone
- Budesonide
- Ciclesonide
- Flunisolide
- Fluticasone
- Mometasone
- Triamcinolone
|
|
Anticholinergics/
muscarinic antagonist |
- Aclidinium bromide
- Glycopyrronium bromide
- Ipratropium bromide#
- Oxitropium bromide
- Tiotropium bromide
- Umeclidinium bromide
|
|
Mast cell stabilizers |
|
|
Xanthines |
- Acefylline
- Ambuphylline
- Bamifylline
- Doxofylline
- Enprofylline
- Etamiphylline
- Proxyphylline
- Theobromine
- Theophylline/Aminophylline/Choline theophyllinate
|
|
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 |
|
|
Non-xanthine PDE4 inhibitors |
|
|
|
Others/unknown |
- Amlexanox
- Eprozinol
- Fenspiride
- Omalizumab
|
|
Combination products |
- Aclidinium/formoterol
- Budesonide/formoterol
- Fluticasone furoate/vilanterol
- Fluticasone/salmeterol
- Indacaterol/glycopyrrolate
- Ipratropium bromide/salbutamol
- Mometasone/formoterol
- Umeclidinium bromide/vilanterol
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
Index of the respiratory system
|
|
Description |
- Anatomy
- Physiology
- Development
|
|
Disease |
- Congenital
- Neoplasms and cancer
- Chest trauma
- Infection
- common cold
- pneumonia
- tuberculosis
- Other
- Symptoms and signs
|
|
Treatment |
- Procedures
- Drugs
- nasal
- throat
- obstructive airway diseases
- cough and cold
- histaminergics
- pulmonary arterial hypertension
- other
- Surgery
|
|
|
Glucocorticoid signaling
|
|
Receptor
(ligands) |
GR
|
Agonists
|
|
|
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 34850
- Pregnenolone 16α-carbonitrile
- 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).
|
|
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Others |
Precursors/prohormones
|
- Cholesterol
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- Pregnenolone
- Pregnenolone sulfate
- 17-Hydroxypregnenolone
- Progesterone
- 17-Hydroxyprogesterone
- 11-Deoxycorticosterone
|
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Indirect
|
- ACTH (corticotropin)
- CRH
- DHEA
- DHEA sulfate
- Plasma proteins (albumin, transcortin)
- Vasopressin
|
|
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See also: Androgenics • Estrogenics • Mineralocorticoids • Progestogenics
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