TRIAMCINOLONE ACETONIDE

First approved in 1958

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H31FO6
Molecular Weight	434.4977
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12C[C@@]3([H])[C@]4([H])CCC5=CC(=O)C=C[C@]5(C)[C@@]4(F)[C@@H](O)C[C@]3(C)[C@@]1(OC(C)(C)O2)C(=O)CO

InChI

InChIKey=YNDXUCZADRHECN-JNQJZLCISA-N

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

HIDE SMILES / InChI

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022223,022048lbl.pdf
Curator's Comment: description was created based on several sources, including

Triamcinolone acetonide is a synthetic corticosteroid used to treat various skin conditions, and to relieve the discomfort of mouth sores. 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. TRIESENCE™ is a synthetic corticosteroid indicated for: sympathetic ophthalmia, temporal arteritis, uveitis, and ocular inflammatory conditions unresponsive to topical corticosteroids. Triamcinolone acetonide is a synthetic fluorinated corticosteroid with approximately 8 times the potency of prednisone in animal models of inflammation. Although the precise mechanism of corticosteroid antiallergic action is unknown, corticosteroids have been shown to have a wide range of actions on multiple cell types (e.g., mast cells, eosinophils, neutrophils, macrophages, lymphocytes) and mediators (e.g., histamine, eicosanoids, leukotrienes, cytokines) involved in inflammation.

Originator

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Sympathetic ophthalmia 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022223,022048lbl.pdf	Primary	Approved 8429	TRIESENCE Approved Use 1.1. Ophthalmic Diseases TRIESENCE™ (triamcinolone acetonide injectable suspension) 40 mg/mL is indicated for: • sympathetic ophthalmia, • temporal arteritis, • uveitis, and • ocular inflammatory conditions unresponsive to topical corticosteroids. 1.2 Visualization during Vitrectomy TRIESENCE™ is indicated for visualization during vitrectomy.
Temporal arteritis 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022223,022048lbl.pdf	Primary	Approved 8429	TRIESENCE Approved Use 1.1. Ophthalmic Diseases TRIESENCE™ (triamcinolone acetonide injectable suspension) 40 mg/mL is indicated for: • sympathetic ophthalmia, • temporal arteritis, • uveitis, and • ocular inflammatory conditions unresponsive to topical corticosteroids. 1.2 Visualization during Vitrectomy TRIESENCE™ is indicated for visualization during vitrectomy.
Uveitis 27 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022223,022048lbl.pdf	Primary	Approved 8429	TRIESENCE Approved Use 1.1. Ophthalmic Diseases TRIESENCE™ (triamcinolone acetonide injectable suspension) 40 mg/mL is indicated for: • sympathetic ophthalmia, • temporal arteritis, • uveitis, and • ocular inflammatory conditions unresponsive to topical corticosteroids. 1.2 Visualization during Vitrectomy TRIESENCE™ is indicated for visualization during vitrectomy.
Perennial allergic rhinitis 47 Sources: https://www.drugs.com/nasacort.html	Primary	Approved 8429	Nasacort Approved Use NASACORT AQ Nasal Spray is indicated for the treatment of the nasal symptoms of seasonal and perennial allergic rhinitis in adults and children 2 years of age and older. Launch Date 1996
Seasonal allergic rhinitis 64 Sources: https://www.drugs.com/nasacort.html	Primary	Approved 8429	Nasacort Approved Use NASACORT AQ Nasal Spray is indicated for the treatment of the nasal symptoms of seasonal and perennial allergic rhinitis in adults and children 2 years of age and older. Launch Date 1996

C_max

Value	Dose	Co-administered	Analyte	Population
10.5 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7608322	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:		TRIAMCINOLONE ACETONIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
30.4 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7608322	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:		TRIAMCINOLONE ACETONIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.6 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7608322	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:		TRIAMCINOLONE ACETONIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2 h EXPERIMENT https://www.jacionline.org/article/S0091-6749(98)70156-3/pdf	, respiratory		TRIAMCINOLONE ACETONIDE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
29% EXPERIMENT https://www.jacionline.org/article/S0091-6749(98)70156-3/pdf	, respiratory		TRIAMCINOLONE ACETONIDE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
120 mg 1 times / day multiple, intramuscular Highest studied dose Dose: 120 mg, 1 times / day Route: intramuscular Route: multiple Dose: 120 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9392980 Page: p.323	unhealthy, 37-70 n = 12 Health Status: unhealthy Condition: Chronic asthma Age Group: 37-70 Sex: M+F Population Size: 12 Sources: https://pubmed.ncbi.nlm.nih.gov/9392980 Page: p.323	Sources: https://pubmed.ncbi.nlm.nih.gov/9392980 Page: p.323
200 mg single, intrabursal Overdose Dose: 200 mg Route: intrabursal Route: single Dose: 200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/10667036 Page: p.13	unhealthy, 46 n = 1 Health Status: unhealthy Condition: Bursitis of the hip Age Group: 46 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/10667036 Page: p.13	Disc. AE: Cushing's syndrome... AEs leading to discontinuation/dose reduction: Cushing's syndrome Sources: https://pubmed.ncbi.nlm.nih.gov/10667036 Page: p.13

AEs

AE	Significance	Dose	Population
Cushing's syndrome	Disc. AE	200 mg single, intrabursal Overdose Dose: 200 mg Route: intrabursal Route: single Dose: 200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/10667036 Page: p.13	unhealthy, 46 n = 1 Health Status: unhealthy Condition: Bursitis of the hip Age Group: 46 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/10667036 Page: p.13

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:71418	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:71418
ChemicalBook	CB4186553	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4186553
MolPort	MolPort-002-529-154	https://www.molport.com/shop/molecule-link/MolPort-002-529-154
Selleck Chemicals	Triamcinolone-Acetonide	http://www.selleckchem.com/products/Triamcinolone-Acetonide.html
ZINC	ZINC000003875481	http://zinc15.docking.org/substances/ZINC000003875481
eMolecules	31590384	https://www.emolecules.com/cgi-bin/more?vid=31590384
eMolecules	36754828	https://www.emolecules.com/cgi-bin/more?vid=36754828
eMolecules	594687	https://www.emolecules.com/cgi-bin/more?vid=594687

PubMed

Title	Date	PubMed
Therapeutic options for a 53-year-old black woman with concomitant glaucoma, uveitis, and cataract.	2001 Aug	11558825
Regression of neovascular iris vessels by intravitreal injection of crystalline cortisone.	2001 Aug	11558812
Cost analysis of the use of inhaled corticosteroids in the treatment of asthma: a 1-year follow-up.	2001 Dec	11778798
The painful shoulder.	2001 Dec	11771220
Periodontal response to two intracanal medicaments in replanted monkey incisors.	2001 Dec	11766092
Selective nerve root blocks for the treatment of sciatica: evaluation of injection site and effectiveness--a study with patients and cadavers.	2001 Dec	11719666
Intravitreal injection of crystalline cortisone as treatment of pre-phthisical ocular hypotony.	2001 Jul	11561798
Improved asthma control after changing from low-to-medium doses of other inhaled corticosteroids to low-dose fluticasone propionate.	2001 Jun 8	11549975
Intralesional cryosurgery using lumbar puncture and/or hypodermic needles for large, bulky, recalcitrant keloids.	2001 May	11555001
[Post-corticoid atrophy].	2001 Nov	11908181
Three methods of treatment of chalazia in children.	2001 Nov	11744967
The misconception of using floating patterns as an accurate means of measuring the contents of metered-dose inhaler devices.	2001 Nov	11730185
[Intravitreal injection of triamcinolone acetonide in non infectious uveitis].	2001 Nov	11715104
Once-daily vs twice-daily triamcinolone acetonide cream for psoriasis.	2001 Nov	11708967
Presence of lichen planus during a course of interferon alpha-2a therapy for a viral chronic C hepatitis.	2001 Nov-Dec	11694869
Intralesional steroids reduce inflammation from extravasated chemotherapeutic agents.	2001 Oct	11703309
Markers of allergic inflammation in peripheral blood of children with asthma after treatment with inhaled triamcinolone acetonide.	2001 Oct	11686425
Fas mediates apoptosis in steroid-induced myopathy of rats.	2001 Oct	11679091
Intracanal use of a corticosteroid-antibiotic compound for the management of posttreatment endodontic pain.	2001 Oct	11598580
[Immunological regulations of dendritic cell in abnormal scarring tissue].	2001 Sep	11767704
[Comparative efficacy of glucocorticoid preparations in the local therapy of inflammatory degenerative diseases of the locomotor apparatus].	2001 Sep	11668794
The role of ultrasonography in the diagnosis and management of idiopathic plantar fasciitis.	2001 Sep	11561110
Bone loss accompanying medical therapies.	2001 Sep 27	11575293
Effects of inhaled glucocorticoids on bone density in premenopausal women.	2001 Sep 27	11575285
[Experience gained with the use of local administration of medicinal remedies in rheumatic diseases].	2001 Sep-Dec	11881370
[Ropivacaine (naropin), local anesthetic of choice for epidural blockade].	2001 Sep-Oct	11757299
Aerosol characterization of nebulized intranasal glucocorticoid formulations.	2001 Summer	11681655
The effect of scatter and attenuation on aerosol deposition as determined by gamma scintigraphy.	2001 Summer	11681649
Deposition and pharmacokinetics of an HFA formulation of triamcinolone acetonide delivered by pressurized metered dose inhaler.	2001 Summer	11681648
Local atrophy following steroid injection.	2002 Apr	11936086
A prospective evaluation of subconjunctival injection of triamcinolone acetonide for resistant anterior scleritis.	2002 Apr	11927443
Angiostatic effects of corticosteroid on wound healing of the rabbit ear.	2002 Feb	11901762
Subcutaneous steroid injection as treatment for chalazion: prospective case series.	2002 Feb	11861988
Combination therapy with inhaled long-acting beta2-agonists and inhaled corticosteroids: a paradigm shift in asthma management.	2002 Feb	11837559
Dermopathy of Graves' disease (pretibial myxedema): long-term outcome.	2002 Feb	11836263
Intravitreal triamcinolone acetonide for macular oedema due to central retinal vein occlusion.	2002 Feb	11815359
Subtenon's depot corticosteroid injections in patients with a history of corticosteroid-induced intraocular pressure elevation.	2002 Feb	11812422
Experiences with neurotomies.	2002 Feb 1	11805702
Synthesis, pharmacokinetics, efficacy, and rat retinal toxicity of a novel mitomycin C-triamcinolone acetonide conjugate.	2002 Feb 28	11855992
Development of a topical suspension containing three active ingredients.	2002 Jan	11858522
A meta-analysis of the dose-response relationship of inhaled corticosteroids in adolescents and adults with mild to moderate persistent asthma.	2002 Jan	11833824
Macrophage migration inhibitory factor in patients with juvenile idiopathic arthritis.	2002 Jan	11817596
Adult-onset limbal juvenile xanthogranuloma.	2002 Jan	11786069
Correction of the soft tissue pollybeak using triamcinolone injection.	2002 Jan-Mar	11843673
Stealth triamcinolone acetonide in a phytocosmetic cream.	2002 Mar	11952564
Prolonged childhood Cushing's syndrome secondary to intralesional triamcinolone acetonide.	2002 Mar	11926057
Multiple-center study of reduced-concentration triamcinolone topical solution for the treatment of dogs with known or suspected allergic pruritus.	2002 Mar	11911576
Short-term use of intranasal corticosteroids: lack of systemic effects.	2002 Mar	11898010
Release of triamcinolone acetonide from mucoadhesive polymer composed of chitosan and poly(acrylic acid) in vitro.	2002 Mar	11829436
[Steroid sprays in non-infectious rhinitis and sinusitis. Proper and regular spraying does not damage the nasal mucosa].	2002 Mar 7	11928263

Patents

Sample Use Guides

In Vivo Use Guide

40 mg/mL

Route of Administration: Other

In Vitro Use Guide

In chondrocyte cultures, triamcinolone acetonide (TA) reduced chondrocyte viability in a concentration-dependent manner. Low-molecular-weight hyaluronan (LMWHA) 2.5 mg/ml combined with TA at IC20 (0.09 mg/ml) could increase the viability of normal chondrocytes when compared with TA-treated alone. TA at IC20 induced down-regulation of ACAN and induced up-regulation of ADAMTS5 in canine normal chondrocytes. TA at IC20 (0.11 mg/ml) up-regulated ADAMTS5, MMP2, MMP3, MMP13, and ACAN expression in canine OA chondrocytes. In explant culture, TA at 1.25, 2.5, and 5 mg/ml increased the severity of structural damage, chondrocyte loss and cluster formation, and proteoglycan loss in OA cartilage.

Name

Type

Language

TRIAMCINOLONE ACETONIDE

Common Name

English

XIPERE

Brand Name

English

TRIAMCINOLONE ACETONIDE [ORANGE BOOK]

Common Name

English

TRIAMCINOLONE HEXACETONIDE IMPURITY A [EP IMPURITY]

Common Name

English

TRIAMCINOLONE ACETONIDE COMPONENT OF MYTREX F

Common Name

English

VOLON A

Brand Name

English

TRIAMCINOLONE ACETONIDE [EP MONOGRAPH]

Common Name

English

TRIACET

Brand Name

English

KENALOG

Brand Name

English

ZILRETTA

Brand Name

English

TRIESENCE

Brand Name

English

CLS-1001

Common Name

English

NSC-21916

Code

English

TRIAMCINOLONE ACETONIDE COMPONENT OF MYCOLOG

Common Name

English

TRIAM

Brand Name

English

TRIAMCINOLONE ACETONIDE [JAN]

Common Name

English

TRIAMCINOLONE ACETONIDE [USP-RS]

Common Name

English

TRIAMCINOLONE ACETONIDE [GREEN BOOK]

Common Name

English

MYTREX F COMPONENT TRIAMCINOLONE ACETONIDE

Common Name

English

TRIAMCINOLONE ACETONIDE [MART.]

Common Name

English

NASACORT

Brand Name

English

FLUOCINOLONE ACETONIDE IMPURITY H

Common Name

English

PREGNA-1,4-DIENE-3,20-DIONE, 9-FLUORO-11,21-DIHYDROXY-16,17-((1-METHYLETHYLIDENE)BIS(OXY))-, (11.BETA.,16.ALPHA.)-

Common Name

English

TRIAMCINOLONE ACETONIDE [MI]

Common Name

English

ORALONE

Brand Name

English

RESPICORT

Brand Name

English

DELPHICORT

Brand Name

English

TRIAMCINOLONE ACETONIDE [USP MONOGRAPH]

Common Name

English

MYCOLOG COMPONENT TRIAMCINOLONE ACETONIDE

Common Name

English

EXTRACORT

Brand Name

English

SOLODELF

Brand Name

English

RINETON

Brand Name

English

TRIAMCINOLONE ACETONIDE [VANDF]

Common Name

English

TRIAMCINOLONE ACETONIDE COMPONENT OF MYKACET

Common Name

English

TRAMACIN

Brand Name

English

KENACORT-A

Brand Name

English

ADCORTYL

Brand Name

English

CLS1001

Common Name

English

LEDERCORT CREAM

Brand Name

English

FTOROCORT

Brand Name

English

TRIDERM

Brand Name

English

TRIAMCINOLONE ACETONIDE COMPONENT OF MYTREX A

Common Name

English

VOLONIMAT

Brand Name

English

TRICINOLON

Brand Name

English

MYTREX A COMPONENT TRIAMCINOLONE ACETONIDE

Common Name

English

MYKACET COMPONENT TRIAMCINOLONE ACETONIDE

Common Name

English

Triamcinolone acetonide [WHO-DD]

Common Name

English

AZMACORT

Brand Name

English

VETALOG

Brand Name

English

9-Fluoro-11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with acetone

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C521