Triamcinolone acetonide
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Clinical data |
Routes of
administration |
Topical, joint injection |
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
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Synonyms |
9α-Fluoro-16α-17α-isopropyledenedioxyprednisolone; 9α-Fluoro-16α-hydroxyprednisolone 16α,17α-acetonide; 9α-Fluoro-11β,16α-17α,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with acetone; 9α-Fluoro-11β,21-dihydroxy-16α,17α-isopropylidenedioxypregna-1,4-diene,3,20-dione |
CAS Number |
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PubChem CID |
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IUPHAR/BPS |
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ChemSpider |
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UNII |
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ChEBI |
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ChEMBL |
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ECHA InfoCard |
100.000.863 |
Chemical and physical data |
Formula |
C24H31FO6 |
Molar mass |
434.504 g/mol |
3D model (JSmol) |
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SMILES
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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
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InChI
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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
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Key:YNDXUCZADRHECN-JNQJZLCISA-N Y
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NY (what is this?) (verify) |
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Triamcinolone acetonide is a synthetic corticosteroid used topically to treat various skin conditions, to relieve the discomfort of mouth sores and intra-articularly by proceduralists to treat various joint conditions.[1] In nasal spray form, it is used to treat allergic rhinitis. It is a more potent derivative of triamcinolone, and is about eight times as potent as prednisone.[2]
It is also known under the brand names Kenalog (topical) and Volon A as an injection, to treat allergies, arthritis, eye diseases, intestinal problems, and skin diseases. There are possible risks from an injection. It has been known to cause fat and muscle loss at an injection site, leaving a large divot bone deep.[3]
In 2014, the FDA made triamcinolone acetonide an over-the-counter drug in the United States in nasal spray form under the brand name Nasacort.[4]
Contents
- 1 Medical uses
- 2 Contraindications
- 3 Chemistry
- 4 Veterinary use
- 5 See also
- 6 References
Medical uses
Triamcinolone acetonide as an intra-articular injectable has been used to treat a variety of musculoskeletal conditions. When applied as a topical ointment, applied to the skin, it is used to mitigate blistering from poison ivy, oak, and sumac,[citation needed]. When combined with Nystatin, it is used to treat skin infections with and discomfort from fungus, though it should not be used on the eyes, mouth, or genital area.[5] 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.[6] 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.[7]
Uncommonly, intramuscular injection of triamcinolone acetonide may be indicated for the control of severe or incapacitating allergic states for which conventional treatments have failed, such as asthma, atopic dermatitis, contact dermatitis, perennial or seasonal allergic rhinitis, serum sickness, and transfusion and drug hypersensitivity reactions.
Contraindications
As with all immunosuppressant drugs, triamcinolone acetonide should not be taken by persons suffering from infectious diseases, either currently or in recuperation or soon thereafter. Contact with infectious persons should be avoided during the entire course of treatment. Users who contract an infection during their regimen should contact their doctors to discuss whether to discontinue triamcinolone acetonide.
Triamcinolone acetonide should not be taken if the patient is also taking any other steroid or immunosuppressant, or if they have recently undergone any medical procedures involving the administration of steroids (e.g. nerve block).[citation needed]
Evidence suggests that usage of traimcinolone acetonide or other steroids to treat macular edema increases the risk of increasing intraocular pressure in patients.[8]
Many drugs have been demonstrated to increase triamcinolone acetonide concentration in the blood to well above the intended level. Patients should inform doctors about any other drugs they are taking.[citation needed]
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.
Chemistry
See also: List of corticosteroids
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.[9] It is the C16α,17α acetonide of triamcinolone.[9]
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.[10] 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 is also used in the horse racing industry, it being a banned substance if found in a horse's system on race day.[11]
See also
- Topical steroid relative strength groupings list
References
- ^ Triamcinolone Acetonide Drug information from MedLine Plus
- ^ Nasacort medication leaflet
- ^ "Kenalog injection," Web M.D.
- ^ Nasacort.com
- ^ "Nystatin And Triamcinolone (Topical Route)". mayoclinic.org. Mayo Foundation for Medical Education and Research. Retrieved 18 May 2016.
- ^ Grover DA, Li T, Chong CCW (2008). "Intravitreal steroids for macular edema in diabetes". Cochrane Database Syst Rev (1): CD005656. PMID 18254088. doi:10.1002/14651858.CD005656.pub2.
- ^ Geltzer A, Turalba A, Vedula SS (2013). "Surgical implantation of steroids with antiangiogenic characteristics for treating neovascular age-related macular degeneration". Cochrane Database Syst Rev (1): CD005022. PMID 23440797. doi:10.1002/14651858.CD005022.pub3.
- ^ Gewaily D, Muthuswamy K, Greenberg PB (2015). "Intravitreal steroids versus observation for macular edema secondary to central retinal vein occlusion". Cochrane Database Syst Rev. 9 (9): CD007324. PMC 4733851 . PMID 26352007. doi:10.1002/14651858.CD007324.pub3.
- ^ a b J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1228–. ISBN 978-1-4757-2085-3.
- ^ GENESIS® (triamcinolone acetonide) Topical Spray Drug information
- ^ Champion Hurdle favourite Yanworth failed drug test
Glucocorticoids and antiglucocorticoids (H02)
|
Glucocorticoids |
Natural |
- Cortisone
- Cortodoxone (cortexolone, 11-deoxycortisol)
- Desoxycortone (deoxycortone, cortexone, 11-deoxycorticosterone)
- Hydrocortisone (cortisol)#
- Prebediolone acetate
- Pregnenolone
- Pregnenolone acetate
- Pregnenolone succinate
|
Synthetic |
- Cortisol-like and related (16-unsubstituted): Chloroprednisone
- Cloprednol
- Difluprednate
- Fludrocortisone
- Flugestone acetate (flurogestone acetate)
- Fluocinolone
- Fluorometholone
- Fluperolone
- Fluprednisolone
- Loteprednol
- Medrysone
- Methylprednisolone
- Methylprednisolone esters
- Prednicarbate
- Prednisolone
- Prednisone
- Tixocortol
- Methasones and related (16-substituted): Alclometasone
- Beclometasone
- Betamethasone
- Clobetasol
- Clobetasone
- Clocortolone
- Cortivazol
- Desoximetasone
- Dexamethasone
- Diflorasone
- Diflucortolone
- Fluclorolone
- Flumetasone
- Fluocortin
- Fluocortolone
- Fluprednidene acetate
- Fluticasone
- Fluticasone furoate
- Fluticasone propionate
- Halometasone
- Meprednisone
- Mometasone
- Paramethasone
- Prednylidene
- Rimexolone
- Triamcinolone
- Ulobetasol (halobetasol)
- Cyclic ketals (16,17-cyclized): Amcinonide
- Budesonide
- Ciclesonide
- Deflazacort
- Desonide
- Fluclorolone acetonide (flucloronide)
- Fludroxycortide (flurandrenolone, flurandrenolide)
- Flunisolide
- Fluocinolone acetonide
- Fluocinonide
- Formocortal (fluoroformylone)
- Halcinonide
- Triamcinolone acetonide
- Triamcinolone acetonide esters
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|
Antiglucocorticoids |
- Antagonists: Aglepristone
- Ketoconazole
- Mifepristone
- Ulipristal acetate
|
Synthesis modifiers |
- Acetoxolone
- Aminoglutethimide
- Carbenoxolone
- Enoxolone
- Ketoconazole
- Metyrapone
- Mitotane
- Trilostane
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
See also: Androgens and antiandrogens • Estrogens and antiestrogens • Progestogens and antiprogestogens • Mineralocorticoids and antimineralocorticoids
|
Glucocorticoid receptor modulators
|
GR |
Agonists |
- Cortisol-like and related (16-unsubstituted): 3α,5α-Tetrahydrocorticosterone
- 5α-Dihydrocorticosterone
- 9α-Fluorocortisone (alfluorone)
- 11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)
- 11-Dehydrocorticosterone acetate
- 11-Deoxycorticosterone (desoxycortone, deoxycortone, desoxycorticosterone)
- 11-Deoxycortisol (cortodoxone, cortexolone)
- Cortifen (cortiphen, kortifen)
- Cortodoxone acetate
- 21-Deoxycortisol
- Δ7-Prednisolone
- Δ7-Prednisolone 21-acetate
- Amebucort
- Chloroprednisone
- Cloprednol
- Corticosterone
- Corticosterone acetate
- Corticosterone benzoate
- Cortisol (hydrocortisone)
- Benzodrocortisone (hydrocortisone benzoate)
- Hydrocortamate (hydrocortisone diethylaminoacetate)
- Hydrocortisone esters
- Cortisone
- Deprodone
- Dichlorisone
- Dichlorisone acetate
- Dichlorisone diacetate
- Difluprednate
- Endrisone (endrysone)
- Etiprednol
- Etiprednol dicloacetate (etiprednol dichloroacetate)
- Fludrocortisone (fludrocortone)
- Fluorometholone
- Fluperolone
- Fluprednisolone
- Halopredone
- Halopredone acetate (halopredone diacetate)
- Isoflupredone (9α-fluoroprednisolone)
- Loteprednol
- Mazipredone (depersolone)
- Medrysone
- Methylprednisolone
- Methylprednisolone esters
- Prebediolone
- Prednisolone
- Prednazate
- Prednazoline
- Prednicarbate (prednisolone ethylcarbonate propionate)
- Prednimustine
- Prednisolamate (prednisolone diethylaminoacetate)
- Prednisolone esters
- Prednisone
- Pregnenolone
- Pregnenolone acetate
- Pregnenolone succinate (pregnenolone hemisuccinate)
- Resocortol
- Tipredane
- Tixocortol
- Butixocort (tixocortol butyrate)
- Tixocortol pivalate
- Methasones and related (16-substituted): 16α-Methyl-11-oxoprednisolone
- Alclometasone
- Alclometasone dipropionate
- Amelometasone
- Beclometasone (beclomethasone)
- Betamethasone (betametasone)
- Betamethasone esters
- Cortobenzolone (betamethasone salicylate)
- Ciclometasone (ciclomethasone, cyclomethasone)
- Clobetasol
- Clobetasone
- Clocortolone
- Cloticasone
- Cormetasone (cormethasone)
- Descinolone
- Desoximetasone (desoxymethasone)
- Dexamethasone (dexametasone)
- Diflorasone
- Diflucortolone
- Diflucortolone pivalate
- Diflucortolone valerate
- Dimesone
- Doxibetasol (doxybetasol)
- Fluclorolone
- Flumetasone (flumethasone)
- Flumetasone acetate
- Flumetasone pivalate
- Fluocinolone
- Fluocortin
- Fluocortin butyl (fluocortin butylate)
- Fluocortolone
- Fluprednidene (fluprednylidene)
- Fluticasone
- Fluticasone furoate
- Fluticasone propionate
- Halocortolone
- Halometasone
- Icometasone
- Icometasone enbutate (icometasone butyrate acetate)
- Isoprednidene
- Locicortolone (locicortone)
- Locicortolone dicibate (locicortone dicibate)
- Meclorisone
- Meprednisone (methylprednisone)
- Meprednisone acetate
- Meprednisone hydrogen succinate (methylprednisone hemisuccinate)
- Mometasone
- Paramethasone
- Paramethasone acetate
- Paramethasone disodium phosphate
- Paramethasone phosphate
- Prednylidene
- Prednylidene diethylaminoacetate
- Rimexolone
- Ticabesone
- Timobesone
- Triamcinolone
- Ulobetasol (halobetasol)
- Vamorolone
- Cyclic ketals (16,17-cyclized): Acrocinonide (triamcinolone acroleinide)
- Amcinafal (triamcinolone pentanonide)
- Amcinafide (triamcinolone acetophenide)
- Amcinonide (triamcinolone acetate cyclopentanonide)
- Budesonide
- Ciclesonide
- Cicortonide
- Deflazacort (azacort)
- Descinolone acetonide
- Desonide (hydroxyprednisolone acetonide)
- Desonide disodium phosphate
- Desonide pivalate
- Dexbudesonide
- Drocinonide
- Fluazacort
- Fluclorolone acetonide (flucloronide)
- Fludroxycortide (flurandrenolone, flurandrenolide)
- Flumoxonide
- Flunisolide
- Fluocinolone acetonide
- Ciprocinonide (fluocinolone acetonide cyclopropylcarboxylate)
- Fluocinonide (fluocinolide, fluocinolone acetonide acetate)
- Procinonide (fluocinolone acetonide propionate)
- Formocortal
- Halcinonide
- Itrocinonide
- Rofleponide
- Tralonide
- Triamcinolone acetonide
- Flupamesone (triamcinolone acetonide metembonate)
- Triamcinolone acetonide esters
- Triamcinolone aminobenzal benzamidoisobutyrate (TBI-PAB)
- Triclonide
- Others/atypical (other expanded steroid ring systems, homosteroids, and non-pregnane steroids): Cortisuzol
- Cortivazol
- Domoprednate
- Naflocort
- Nicocortonide
- Nivacortol (nivazol)
- Oxisopred
- RU-28362
- Non-corticosteroids with some glucocorticoid activity: 15β-Hydroxycyproterone acetate
- 17α-Hydroxyprogesterone
- Chlormadinone acetate
- Cyproterone
- Cyproterone acetate
- Delmadinone acetate
- Flugestone
- Flugestone acetate (flurogestone acetate)
- Fluoxymesterone
- Gestodene
- Medrogestone
- Medroxyprogesterone acetate
- Megestrol acetate
- Metribolone
- Norgestomet
- Osaterone acetate
- Progesterone
- Promegestone
- Quingestrone
- Segesterone acetate (nestorone)
- Tetrahydrogestrinone
- Nonsteroidal glucocorticoids: AZD-5423
- GSK-9027
|
Mixed (SEGRMs) |
- Dagrocorat
- Fosdagrocorat
- Mapracorat
|
Antagonists |
- 7α-Hydroxy-DHEA
- 17α-Methylprogesterone
- Aglepristone
- Asoprisnil
- Asoprisnil ecamate
- 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
- RTI 3021–012
- RTI 3021–022
- Telapristone
- Tibolone
- Toripristone
- Ulipristal acetate
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- See also
- Receptor/signaling modulators
- Androgenics
- Estrogenics
- Mineralocorticoidics
- Progestogenics
- Steroid metabolism modulators
- List of corticosteroids
|