Triamcinolone

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

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, D07XB02, H02AB08, R01AD11, R03BA06, S01BA05

PubChem CID 31307

DrugBank APRD00422

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[8.7.0.0^2,7.0^11,15]heptadeca-3,6-dien-5-one

Chemical data

Formula C₂₁H₂₇F O₆

Mol. mass 394.434 g/mol

SMILES eMolecules & PubChem

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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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

Uses

Triamcinolone is used to treat several different medical conditions, such as eczema, psoriasis, arthritis, allergies, ulcerative colitis, lupus, sympathetic ophthalmia, temporal arteritis, uveitis, and 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 (AU)

Kenalog (triamcinolone) IM injection (SCO)

^ 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

v · d · eStomatological preparations (A01)

Caries prophylactic agents
Dectaflur • Olaflur • Sodium fluoride • Sodium monofluorophosphate • Stannous fluoride

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

Corticosteroids (Glucocorticoids)
Dexamethasone • Hydrocortisone • Triamcinolone

Other
Amlexanox • Acetylsalicylic acid • Becaplermin • Benzydamine • Epinephrine/Adrenalone

M: MOU

anat/devp

noco/cofa(c)/cogi/tumr, sysi

proc (peri), drug (A1)

v · d · eDecongestants and other nasal preparations (R01)

Topical

Sympathomimetics, plain

Cyclopentamine • Ephedrine • Phenylephrine • Oxymetazoline • Tetryzoline • Xylometazoline • Naphazoline • Tramazoline • Metizoline • Tuaminoheptane • Fenoxazoline • Tymazoline • Epinephrine

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 • Prednisolone • Dexamethasone • Flunisolide • Budesonide • Betamethasone • Tixocortol • Fluticasone • Mometasone furoate • Triamcinolone • Ciclesonide

Other nasal preparations

Cafaminol • Calcium hexamine thiocyanate • Retinol • Ipratropium bromide • Ritiometan • Mupirocin • Hexamidine • Framycetin • Hyaluronic acid • Eucalyptus oil

Systemic use:
Sympathomimetics
Phenylpropanolamine • Pseudoephedrine (+loratadine) • Phenylephrine • Phenylpropylamine

M: RES

anat(n, x, l, c)/phys/devp

noco(c, p)/cong/tumr, sysi/epon, injr

proc, drug(R1/2/3/5/6/7)

v · d · eCorticosteroids – glucocorticoids and mineralocorticoids (H02)
(also A07EA, C05AA, D07, D10AA, R01AD, R03BA, S01BA, S02B, and S03B)

Mineralocorticoids
(3-one, 4-ene,
no FG at 16)
Pregnenedione: ALDOSTERONE • 11-DEOXYCORTICOSTERONE • HALOGENATED AT 9: Fludrocortisone

Glucocorticoids
(3-one, 4-ene,
11-FG,
17-hydroxy)

Pregnene

CORTISONE

Pregnenedione
(+20-one)

HYDROCORTISONE/CORTISOL^# (Hydrocortisone aceponate, Hydrocortisone buteprate, Hydrocortisone butyrate) • Budesonide • Ciclesonide • Deflazacort • Medrysone • Tixocortol • HALOGENATED AT 6: Cloprednol • HALOGENATED, WITH FG AT 16: Halcinonide

Pregnadiene (+1-ene)

Rimexolone • HALOGENATED, WITH FG AT 16: Flunisolide • Triamcinolone • Amcinonide • Fluocinolone acetonide (Fluocinonide)

Pregnadienediol
(+21-hydroxy)

Prednisone (Meprednisone) • HALOGENATED AT 9: Fluorometholone • HALOGENATED, WITH FG AT 16: Fluocortolone (Clocortolone, Diflucortolone, Fluocortin) • Desoximetasone

Pregnadienetriol
(+11-hydroxy)

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 • Flumetasone • Fluprednidene

Pregnatriene
(+2-ene)

Cortivazol

Androstene

HALOGENATED, WITH FG AT 16: Fluticasone (Fluticasone propionate, Fluticasone furoate)

Other/ungrouped

HALOGENATED: Loteprednol • HALOGENATED, WITH FG AT 16: Fludroxycortide • Formocortal • Mometasone furoate

Aldosterone antagonists
Spironolactone • Eplerenone • Potassium canrenoate • Canrenone

Synthesis modifiers
Trilostane • Carbenoxolone • Aminoglutethimide • Metyrapone

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

M: END

anat/phys/devp/horm

noco(d)/cong/tumr, sysi/epon

proc, drug (A10/H1/H2/H3/H5)

v · d · eDrugs for obstructive airway diseases: asthma/COPD (R03)

Adrenergics, inhalants

Short acting β₂-agonists

Salbutamol^#/Levosalbutamol • Fenoterol • Terbutaline • Pirbuterol • Procaterol • Bitolterol • Rimiterol • Carbuterol • Tulobuterol • Reproterol

Long acting β₂-agonists (LABA)

Arformoterol • Bambuterol • Clenbuterol • Formoterol • Salmeterol Ultra LABA: Indacaterol

other

Epinephrine^# • Hexoprenaline • Isoprenaline (Isoproterenol) • Orciprenaline (Metaproterenol)

Glucocorticoids
Beclometasone^# • Budesonide • Ciclesonide • Fluticasone • Mometasone • Flunisolide • Betamethasone • Triamcinolone

Anticholinergics/
muscarinic antagonist
Ipratropium bromide^# • Oxitropium bromide • Tiotropium bromide

Mast cell stabilizers
Cromoglicate • Nedocromil

Xanthines
Doxofylline • Enprofylline • Theobromine • Theophylline/Aminophylline/Choline theophyllinate

Eicosanoid inhibition

Leukotriene antagonists

Montelukast • Pranlukast • Zafirlukast

Lipoxygenase inhibitor

Zileuton

Thromboxane receptor antagonists

Ramatroban • Seratrodast

Combination products
Budesonide/formoterol • Fluticasone/salmeterol • Ipratropium bromide/salbutamol • Mometasone/formoterol

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

M: RES

anat(n, x, l, c)/phys/devp

noco(c, p)/cong/tumr, sysi/epon, injr

proc, drug(R1/2/3/5/6/7)

Categories:
Glucocorticoids
Sanofi
Organofluorides

Triamcinolone

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, D07XB02, H02AB08, R01AD11, R03BA06, S01BA05
PubChem	CID 31307
DrugBank	APRD00422
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[8.7.0.0^2,7.0^11,15]heptadeca-3,6-dien-5-one
Chemical data
Formula	C₂₁H₂₇F O₆
Mol. mass	394.434 g/mol
SMILES	eMolecules & PubChem
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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triamcinolone — ● triamcinolone nom féminin Dérivé fluoré de la prednisolone, doué d une activité anti inflammatoire six fois supérieure à celle de la cortisone … Encyclopédie Universelle
Triamcinolone acetonide — Chembox new ImageFile=Triamcinolone acetonide.png ImageSize=200px IUPACName= OtherNames= Section1= Chembox Identifiers CASNo= PubChem=6436 SMILES=CC1(OC2CC3C4CCC5=CC(=O)C=CC5(C4(C(CC3(C2(O1)C(=O)CO)C)O)F)C)C Section2= Chembox Properties… … Wikipedia
triamcinolone acetonide — [USP] an ester of triamcinolone; applied topically to the skin or oral mucosa as an antiinflammatory, and administered by inhalation for the chronic treatment of asthma, intranasally in the treatment of allergic rhinitis and other inflammatory… … Medical dictionary
triamcinolone diacetate — [USP] the diacetate ester of triamcinolone, having actions similar to those of the base and used as an antiinflammatory and immunosuppressant in a wide variety of disorders; administered orally and by intra articular, intrasynovial, intralesional … Medical dictionary
triamcinolone hexacetonide — [USP] an ester of triamcinolone having actions similar to those of the base and used as an antiinflammatory and immunosuppressant in a wide variety of disorders; administered by intra articular, intralesional, or sublesional injection … Medical dictionary
triamcinolone — noun Etymology: tri + amcin (alteration of American Cyanimid Company) + 1 ol + one Date: 1957 a glucocorticoid drug C21H27FO6 used chiefly in the form of its acetal or acetate derivatives especially in treating skin disorders, asthma, and… … New Collegiate Dictionary
triamcinolone — /truy am sin euh lohn /, n. Pharm. a synthetic glucocorticoid drug, C21H27FO6, used in the symptomatic treatment of inflammation. [1955 60; triamcin (of unexplained derivation) + (PREDNIS)OLONE] * * * … Universalium
triamcinolone — noun A certain synthetic corticosteroid … Wiktionary
triamcinolone — A glucocorticoid with actions and uses similar to those of prednisolone. t. acetonide a potent glucocorticoid for topical treatment of dermatoses. t. diacetate an anti inflammatory and antiallergic agent for parenteral use. * … Medical dictionary
triamcinolone — tri·am·cin·o·lone … English syllables

Academic Dictionaries and Encyclopedias

Triamcinolone

Contents

Uses

Forms

Side effects

References

External links

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Triamcinolone

Contents

Uses

Forms

Side effects

References

External links

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