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Triamcinolone acetonide
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Names |
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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Identifiers |
CAS Number
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76-25-5 Y |
3D model (Jmol) |
Interactive image |
ChEBI |
CHEBI:71418 N |
ChEMBL |
ChEMBL1504 Y |
ChemSpider |
6196 Y |
ECHA InfoCard |
100.000.863 |
IUPHAR/BPS
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2867 |
PubChem |
6436 |
UNII |
F446C597KA Y |
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
Key: YNDXUCZADRHECN-JNQJZLCISA-N Y
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InChI=1/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
Key: YNDXUCZADRHECN-JNQJZLCIBL
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SMILES
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O=C\1\C=C5/[C@@](/C=C/1)(C)[C@]2(F)[C@H]([C@H]3[C@](C[C@@H]2O)([C@@]4(OC(O[C@@H]4C3)(C)C)C(=O)CO)C)CC5
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Properties |
Chemical formula
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C24H31FO6 |
Molar mass |
434.50 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N verify (what is YN ?) |
Infobox references |
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Triamcinolone acetonide is a synthetic corticosteroid used to treat various skin conditions, and to relieve the discomfort of mouth sores.[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 use
- 2 Contraindications
- 3 Veterinary use
- 4 See also
- 5 References
Medical use
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. Drug trials have found it to be as efficient as anti-VEGF drugs in eyes with artificial lenses over a two-year period.
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.[6]
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.
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.[7] A series of injections with triamcinolone acetonide or another corticosteroid may reduce keloid size and irritation. It is also used as a preinductor and/or inductor of birth in cows.
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.
- ^ 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. doi:10.1002/14651858.CD007324.pub3. PMC 4733851. PMID 26352007.
- ^ GENESIS® (triamcinolone acetonide) Topical Spray Drug information
Glucocorticoids and antiglucocorticoids (H02)
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Glucocorticoids |
Natural |
- Cortisone
- Cortodoxone (cortexolone, 11-deoxycortisol)
- Desoxycortone (deoxycortone, cortexone, 11-deoxycorticosterone)
- Hydrocortisone (cortisol)#
- Hydrocortisone aceponate
- Hydrocortisone buteprate
- Hydrocortisone butyrate
- Prebediolone acetate
- Pregnenolone
- Pregnenolone acetate
- Pregnenolone succinate
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Synthetic |
- Cortisol-like and related (16-unsubstituted): Chloroprednisone
- Cloprednol
- Difluprednate
- Fludrocortisone
- Flugestone acetate (flurogestone acetate)
- Fluocinolone
- Fluorometholone
- Fluperolone
- Fluprednisolone
- Loteprednol
- Medrysone
- Methylprednisolone
- Methylprednisolone aceponate
- Methylprednisolone acetate
- Methylprednisolone suleptanate
- Prednicarbate
- Prednisolone
- Prednisone
- Tixocortol
- Methasones and related (16-substituted): Alclometasone
- Beclometasone
- Beclometasone dipropionate
- Betamethasone
- Betamethasone dipropionate
- Clobetasol
- Clobetasone
- Clocortolone
- Cortivazol
- Desoximetasone
- Dexamethasone
- Dexamethasone acefurate
- Dexamethasone isonicotinate
- Diflorasone
- Difluocortolone
- Fluclorolone
- Flumetasone
- Fluocortin
- Fluocortolone
- Fluprednidene
- Fluticasone
- Fluticasone furoate
- Fluticasone propionate
- Halometasone
- Meprednisone
- Mometasone
- Paramethasone
- Prednylidene
- Rimexolone
- Triamcinolone
- Ulobetasol (halobetasol)
- Acetonides and related (16,17-cyclized): Amcinonide
- Budesonide
- Ciclesonide
- Deflazacort
- Desonide
- Fluclorolone acetonide (flucloronide)
- Fludroxycortide (flurandrenolone, flurandrenolide)
- Flunisolide
- Fluocinolone acetonide
- Fluocinonide
- Formocortal (fluoroformylone)
- Halcinonide
- Triamcinolone acetonide
- Triamcinolone benetonide
- Triamcinolone furetonide
- Triamcinolone hexacetonide
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Antiglucocorticoids |
- SGRMs: Dagrocorat§
- Fosdagrocorat§
- Mapracorat†
- Antagonists: Ketoconazole
- Mifepristone
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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
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Glucocorticoid receptor modulators
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GR |
Agonists
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- 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)
- Desoxycortone acetate
- Desoxycortone cypionate (desoxycortone cyclopentanepropionate)
- Desoxycortone enanthate (desoxycortone heptanoate)
- Desoxycortone glucoside
- Desoxycortone pivalate
- 11-Deoxycortisol (cortodoxone, cortexolone)
- Cortifen (cortiphen, kortifen)
- Cortodoxone acetate
- 21-Deoxycortisol
- Δ7-Prednisolone
- Δ7-Prednisolone 21-acetate
- Amebucort
- Butixocort
- Chloroprednisone
- Cloprednol
- Corticosterone
- Corticosterone acetate
- Corticosterone benzoate
- Cortisol (hydrocortisone)
- Hydrocortamate (hydrocortisone diethylaminoacetate)
- Hydrocortisone aceponate (hydrocortisone acetate propionate)
- Hydrocortisone acetate
- Hydrocortisone bendazac
- Hydrocortisone buteprate (hydrocortisone butyrate propionate)
- Hydrocortisone cypionate (hydrocortisone cipionate)
- Hydrocortisone hemisuccinate (hydrocortisone hydrogen succinate)
- Hydrocortisone phosphate
- Hydrocortisone sodium phosphate
- Hydrocortisone sodium succinate
- Hydrocortisone tebutate
- Hydrocortisone valerate
- Hydrocortisone xanthogenate
- Hydrocortisone 17α-butyrate
- Hydrocortisone 21-butyrate
- Cortisone
- Deprodone
- Dichlorisone
- Dichlorisone acetate
- Dichlorisone diacetate
- Difluprednate
- Endrisone (endrysone)
- Etiprednol
- Etiprednol dicloacetate (etiprednol dichloroacetate)
- Fludrocortisone (fludrocortone)
- Fluorometholone
- Fluperolone
- Fluprednisolone
- Fluprednisolone acetate
- Fluprednisolone hemisuccinate
- Fluprednisolone sodium hemisuccinate
- Fluprednisolone valerate
- Halopredone
- Halopredone acetate (halopredone diacetate)
- Isoflupredone (9α-fluoroprednisolone)
- Loteprednol
- Mazipredone (depersolone)
- Medrysone
- Methylprednisolone
- Methylprednisolone aceponate (methylprednisolone acetate propionate)
- Methylprednisolone acetate
- Methylprednisolone hemisuccinate (methylprednisolone hydrogen succinate)
- Methylprednisolone sodium phosphate
- Methylprednisolone sodium succinate
- Methylprednisolone suleptanate
- Prebediolone
- Prednisolone
- Prednazate
- Prednazoline
- Prednicarbate (prednisolone ethylcarbonate propionate)
- Prednimustine
- Prednisolamate (prednisolone diethylaminoacetate)
- Prednisolone acetate
- Prednisolone disodium phosphate
- Prednisolone hydrogen tetrahydrophthalate
- Prednisolone meta-sulfobenzoate
- Prednisolone sodium meta-sulfobenzoate
- Prednisolone palmitate
- Prednisolone phosphate
- Prednisolone piperidinoacetate
- Prednisolone pivalate
- Prednisolone sodium phosphate
- Prednisolone sodium succinate
- Prednisolone sodium sulfate
- Prednisolone sodium tetrahydrophthalate
- Prednisolone steaglate (prednisolone stearoylglycolate)
- Prednisolone succinate (prednisolone hemisuccinate)
- Prednisolone sulfate
- Prednisolone tebutate
- Prednisolone valerate
- Prednisolone valeroacetate (prednisolone valerate acetate)
- Prednisone
- Prednisone acetate
- Prednisone palmitate
- Prednisone succinate
- Pregnenolone
- Pregnenolone acetate
- Pregnenolone succinate (pregnenolone hemisuccinate)
- Resocortol
- Tipredane
- Tixocortol
- Methasones and related (16-substituted): 16α-Methyl-11-oxoprednisolone
- Alclometasone
- Alclometasone dipropionate
- Amelometasone
- Beclometasone (beclomethasone)
- Beclometasone dipropionate
- Beclometasone salicylate
- Beclometasone valeroacetate (beclometasone valerate acetate)
- Betamethasone (betametasone)
- Betamethasone acetate
- Betamethasone acibutate (betamethasone acetate isobutyrate)
- Betamethasone adamantoate
- Betamethasone benzoate
- Betamethasone dipropionate
- Betamethasone divalerate
- Betamethasone phosphate
- Betamethasone salicylate
- Betamethasone sodium phosphate
- Betamethasone succinate
- Betamethasone valerate
- Betamethasone valeroacetate (betamethasone valerate acetate)
- Ciclometasone (ciclomethasone, cyclomethasone)
- Clobetasol
- Clobetasone
- Clocortolone
- Clocortolone acetate
- Clocortolone caproate
- Clocortolone pivalate
- Cloticasone
- Cormetasone (cormethasone)
- Cyclomethasone (ciclometasone)
- Descinolone
- Desoximetasone (desoxymethasone)
- Dexamethasone (dexametasone)
- Dexamethasone acefurate (dexamethasone acetate furoate)
- Dexamethasone acetate
- Dexamethasone cipecilate (dexamethasone cyclopropylcarbonate cyclohexanecarboxylate)
- Dexamethasone diethylaminoacetate
- Dexamethasone dipropionate
- Dexamethasone isonicotinate
- Dexamethasone linoleate
- Dexamethasone meta-sulphobenzoate
- Dexamethasone palmitate
- Dexamethasone phenylpropionate
- Dexamethasone phosphate
- Dexamethasone pivalate
- Dexamethasone sodium meta-sulphobenzoate
- Dexamethasone sodium phosphate
- Dexamethasone sodium sulfate
- Dexamethasone succinate
- Dexamethasone sulfate
- Dexamethasone tebutate
- Dexamethasone troxundate
- Dexamethasone 17α-valerate
- Dexamethasone 21-valerate
- Diflorasone
- Diflucortolone
- Diflucortolone pivalate
- Diflucortolone valerate
- Dimesone
- Doxibetasol (doxybetasol)
- Fluclorolone
- Flumetasone (flumethasone)
- Flumetasone acetate
- Flumetasone pivalate
- Fluocinolone
- Fluocortin
- Fluocortin butyl (fluocortin butylate)
- Fluocortolone
- Fluocortolone acetate
- Fluocortolone caproate
- Fluocortolone pivalate
- 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
- Acetonides and related (16,17-cyclized): Acrocinonide (triamcinolone acroleinide)
- Amcinafal (triamcinolone pentanonide)
- Amcinafide (triamcinolone acetophenide)
- Amcinonide (triamcinolone acetate cyclopentanonide)
- Budesonide
- Ciclesonide
- Cicortonide
- Ciprocinonide (fluocinolone acetonide)
- Deflazacort (azacort)
- Descinolone acetonide
- Desonide (hydroxyprednisolone acetonide)
- Desonide disodium phosphate
- Desonide phosphate
- Desonide pivalate
- Dexbudesonide
- Drocinonide
- Fluazacort
- Fluclorolone acetonide (flucloronide)
- Fludroxycortide (flurandrenolone, flurandrenolide)
- Flumoxonide
- Flunisolide
- Fluocinolone acetonide
- Fluocinonide (fluocinolide, fluocinolone acetonide acetate)
- Procinonide (fluocinolone acetonide propionate)
- Flupamesone (triamcinolone acetonide metembonate)
- Formocortal
- Halcinonide
- Itrocinonide
- Rofleponide
- Tralonide
- Triamcinolone acetonide
- Triamcinolone acetonide dipotassium phosphate
- Triamcinolone acetonide hemisuccinate
- Triamcinolone acetonide phosphate
- Triamcinolone acetonide sodium phosphate
- Triamcinolone benetonide
- Triamcinolone furetonide
- Triamcinolone hexacetonide
- 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
- Non-steroidal glucocorticoids: AZD5423
- GSK-9027
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Mixed (SEGRAs)
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- Dagrocorat
- Fosdagrocorat
- Mapracorat
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Antagonists
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- 7α-Hydroxy-DHEA
- 17α-Methylprogesterone
- Aglepristone
- Asoprisnil
- C108297
- C113176
- CORT-108297
- Cyproterone acetate
- Formebolone
- Guggulsterone
- Ketoconazole
- Lilopristone
- LLY-2707
- Miconazole
- Mifepristone
- Onapristone
- ORG-34116
- ORG-34517 (SCH-900636)
- ORG-34850
- Pregnenolone 16α-carbonitrile
- Telapristone
- Tibolone
- Toripristone
- Ulipristal acetate
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See also: Androgenics • Estrogenics • Mineralocorticoidics • Progestogenics • Steroid hormone metabolism modulators
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