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Triamcinolone acetonide

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/01/06 21:26:17」(JST)

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Triamcinolone acetonide

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
Identifiers
CAS Number	76-25-5 Y
ChEBI	CHEBI:71418 N
ChEMBL	ChEMBL1504 Y
ChemSpider	6196 Y
IUPHAR/BPS	2867
Jmol interactive 3D	Image
PubChem	6436
UNII	F446C597KA Y
InChI 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 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
SMILES 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
Properties
Chemical formula	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).
N verify (what is YN ?)
Infobox references

Triamcinolone acetonide is a synthetic corticosteroid used to treat various skin conditions, to relieve the discomfort of mouth sores, and in nasal spray form, to treat allergic rhinitis. It is a more potent derivative of triamcinolone, and is about eight times as potent as prednisone.

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. In 2014, the FDA made triamcinolone acetonide an over-the-counter drug in the USA in nasal spray form under the brand name Nasacort.

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, it is used for blistering from poison ivy, oak, and sumac, applied to the skin, avoiding eyes, mouth, and genital area. 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).

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.

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. 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.

References

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English Journal

• Comparison of the flow properties of aqueous suspension corticosteroid nasal sprays under differing sampling conditions.

• Sharpe SA, Sandweiss V, Tuazon J, Giordano M, Witchey-Lakshmanan L, Hart J, Sequeira J.SourceSchering-Plough Research Institute, Kenilworth, New Jersey 07033-0530, USA. stefan.sharpe@spcorp.com
• Drug development and industrial pharmacy.Drug Dev Ind Pharm.2003 Oct;29(9):1005-12.
• Many aqueous suspension corticosteroid nasal sprays become less viscous when shaken and sprayed, then return to a more viscous state after application. This time-dependent, reversible loss of viscosity under shear (e.g., shaking or spraying) can be quantified in the rheological property of thixotrop
• PMID 14606664

• A new solution-based intranasal triamcinolone acetonide formulation in patients with perennial allergic rhinitis: how does the pharmacokinetic/pharmacodynamic profile for cortisol suppression compare with an aqueous suspension-based formulation?

• Hochhaus G, González MA, Dockhorn RJ, Shilstone J, Karafilidis J.SourceDepartment of Pharmaceutics, College of Pharmacy, University of Florida, Gainesville 32610, USA.
• Journal of clinical pharmacology.J Clin Pharmacol.2002 Jun;42(6):662-9.
• The present study was undertaken to describe the pharmacokinetics of a new solution-based intranasal triamcinolone acetonideformulation (Tri-Nasal) in patients with perennial allergic rhinitis and to use a pharmacokinetic/pharmacodynamic (PK/PD) simulation approach to compare the potential effects o
• PMID 12043955

• The use of a capillary rheometer to determine the shear and extensional flow behaviour of nasal spray suspensions.

• Eccleston GM, Hudson NE.SourceDepartment of Pharmaceutical Sciences, University of Strathclyde, Glasgow, UK.
• The Journal of pharmacy and pharmacology.J Pharm Pharmacol.2000 Oct;52(10):1223-32.
• The rheological profiles of four commercial nasal spray suspensions (Beconase, Flixonase, Nasacort and Nasonex) were compared using rotational viscometry. Two of the nasal sprays (Beconase and Nasonex) were further examined in both shear and extension using a capillary rheometer under conditions sim
• PMID 11092566

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