U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of TRIAMCINOLONE ACETONIDE

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

Molecular Formula C24H31FO6
Molecular Weight 434.4977
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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.
Primary
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.
Primary
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.
Primary
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

8.3246403E11
Primary
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

8.3246403E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
10.5 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
30.4 ng × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.6 h
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
, respiratory
TRIAMCINOLONE ACETONIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
29%
, respiratory
TRIAMCINOLONE ACETONIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse 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: 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: Page: p.323
200 mg single, intrabursal
Overdose
Dose: 200 mg
Route: intrabursal
Route: single
Dose: 200 mg
Sources: Page: p.13
unhealthy, 46
n = 1
Health Status: unhealthy
Condition: Bursitis of the hip
Age Group: 46
Sex: F
Population Size: 1
Sources: Page: p.13
Disc. AE: Cushing's syndrome...
AEs leading to
discontinuation/dose reduction:
Cushing's syndrome
Sources: Page: p.13
AEs

AEs

AESignificanceDosePopulation
Cushing's syndrome Disc. AE
200 mg single, intrabursal
Overdose
Dose: 200 mg
Route: intrabursal
Route: single
Dose: 200 mg
Sources: Page: p.13
unhealthy, 46
n = 1
Health Status: unhealthy
Condition: Bursitis of the hip
Age Group: 46
Sex: F
Population Size: 1
Sources: Page: p.13
PubMed

PubMed

TitleDatePubMed
Regulation of the action of hydrocortisone in airway epithelial cells by 11beta-hydroxysteroid dehydrogenase.
1999 Sep
Inhibition of GM-CSF secretion by topical corticosteroids and nedocromil sodium. A comparison study using nasal polyp epithelial cells.
2000 May
A study comparing the clinical pharmacokinetics, pharmacodynamics, and tolerability of triamcinolone acetonide HFA-134a metered-dose inhaler and budesonide dry-powder inhaler following inhalation administration.
2000 May
Induction of rat hepatic aryl sulfotransferase (SULT1A1) gene expression by triamcinolone acetonide: impact on minoxidil-mediated hypotension.
2000 May 1
Analysis of corticosteroids in equine urine by liquid chromatography-mass spectrometry.
2001 Apr 15
[Reducing the dosage by new technology].
2001 Jan
Sampling and analysis of airborne particulate matter and aerosols using in-needle trap and SPME fiber devices.
2001 Jan 1
Inhibitory effects of anti-inflammatory drugs on interleukin-6 bioactivity.
2001 Jun
Second thoughts on a common treatment for COPD.
2001 Jun
In vitro permeation studies of triamcinolone acetonide mouthwashes.
2001 Jun 4
[Treatment of therapy refractory chronic otitis externa by local injection of triamcinolone acetate crystalline suspension. Initial experiences].
2001 Mar
Nonpigmenting solitary fixed drug eruption after skin testing and intra-articular injection of triamcinolone acetonide.
2001 Mar
[Post-corticoid atrophy].
2001 Nov
Once-daily vs twice-daily triamcinolone acetonide cream for psoriasis.
2001 Nov
Intralesional steroids reduce inflammation from extravasated chemotherapeutic agents.
2001 Oct
Markers of allergic inflammation in peripheral blood of children with asthma after treatment with inhaled triamcinolone acetonide.
2001 Oct
Treatment of childhood phimosis with a moderately potent topical steroid.
2001 Sep
[Experience gained with the use of local administration of medicinal remedies in rheumatic diseases].
2001 Sep-Dec
[Ropivacaine (naropin), local anesthetic of choice for epidural blockade].
2001 Sep-Oct
Aerosol characterization of nebulized intranasal glucocorticoid formulations.
2001 Summer
The effect of scatter and attenuation on aerosol deposition as determined by gamma scintigraphy.
2001 Summer
Deposition and pharmacokinetics of an HFA formulation of triamcinolone acetonide delivered by pressurized metered dose inhaler.
2001 Summer
Local atrophy following steroid injection.
2002 Apr
A prospective evaluation of subconjunctival injection of triamcinolone acetonide for resistant anterior scleritis.
2002 Apr
Angiostatic effects of corticosteroid on wound healing of the rabbit ear.
2002 Feb
Subcutaneous steroid injection as treatment for chalazion: prospective case series.
2002 Feb
Combination therapy with inhaled long-acting beta2-agonists and inhaled corticosteroids: a paradigm shift in asthma management.
2002 Feb
Dermopathy of Graves' disease (pretibial myxedema): long-term outcome.
2002 Feb
Intravitreal triamcinolone acetonide for macular oedema due to central retinal vein occlusion.
2002 Feb
Subtenon's depot corticosteroid injections in patients with a history of corticosteroid-induced intraocular pressure elevation.
2002 Feb
Adult-onset limbal juvenile xanthogranuloma.
2002 Jan
Stealth triamcinolone acetonide in a phytocosmetic cream.
2002 Mar
Prolonged childhood Cushing's syndrome secondary to intralesional triamcinolone acetonide.
2002 Mar
Multiple-center study of reduced-concentration triamcinolone topical solution for the treatment of dogs with known or suspected allergic pruritus.
2002 Mar
Short-term use of intranasal corticosteroids: lack of systemic effects.
2002 Mar
[Steroid sprays in non-infectious rhinitis and sinusitis. Proper and regular spraying does not damage the nasal mucosa].
2002 Mar 7
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020468s024lbl.pdf
40 mg/mL
Route of Administration: Other
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 14:58:48 UTC 2023
Edited
by admin
on Fri Dec 15 14:58:48 UTC 2023
Record UNII
F446C597KA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRIAMCINOLONE ACETONIDE
EP   GREEN BOOK   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
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
Created by admin on Fri Dec 15 14:58:48 UTC 2023 , Edited by admin on Fri Dec 15 14:58:48 UTC 2023
NDF-RT N0000175576
Created by admin on Fri Dec 15 14:58:48 UTC 2023 , Edited by admin on Fri Dec 15 14:58:48 UTC 2023
EU-Orphan Drug EU/3/15/1490
Created by admin on Fri Dec 15 14:58:48 UTC 2023 , Edited by admin on Fri Dec 15 14:58:48 UTC 2023
Code System Code Type Description
CAS
76-25-5
Created by admin on Fri Dec 15 14:58:48 UTC 2023 , Edited by admin on Fri Dec 15 14:58:48 UTC 2023
PRIMARY
DRUG BANK
DBSALT000860
Created by admin on Fri Dec 15 14:58:48 UTC 2023 , Edited by admin on Fri Dec 15 14:58:48 UTC 2023
PRIMARY
SMS_ID
100000090386
Created by admin on Fri Dec 15 14:58:48 UTC 2023 , Edited by admin on Fri Dec 15 14:58:48 UTC 2023
PRIMARY
RXCUI
10761
Created by admin on Fri Dec 15 14:58:48 UTC 2023 , Edited by admin on Fri Dec 15 14:58:48 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID6021371
Created by admin on Fri Dec 15 14:58:48 UTC 2023 , Edited by admin on Fri Dec 15 14:58:48 UTC 2023
PRIMARY
EVMPD
SUB04936MIG
Created by admin on Fri Dec 15 14:58:48 UTC 2023 , Edited by admin on Fri Dec 15 14:58:48 UTC 2023
PRIMARY
PUBCHEM
6436
Created by admin on Fri Dec 15 14:58:48 UTC 2023 , Edited by admin on Fri Dec 15 14:58:48 UTC 2023
PRIMARY
MESH
D014222
Created by admin on Fri Dec 15 14:58:48 UTC 2023 , Edited by admin on Fri Dec 15 14:58:48 UTC 2023
PRIMARY
RS_ITEM_NUM
1677002
Created by admin on Fri Dec 15 14:58:48 UTC 2023 , Edited by admin on Fri Dec 15 14:58:48 UTC 2023
PRIMARY
MERCK INDEX
m11028
Created by admin on Fri Dec 15 14:58:48 UTC 2023 , Edited by admin on Fri Dec 15 14:58:48 UTC 2023
PRIMARY Merck Index
DAILYMED
F446C597KA
Created by admin on Fri Dec 15 14:58:48 UTC 2023 , Edited by admin on Fri Dec 15 14:58:48 UTC 2023
PRIMARY
CHEBI
71418
Created by admin on Fri Dec 15 14:58:48 UTC 2023 , Edited by admin on Fri Dec 15 14:58:48 UTC 2023
PRIMARY
WIKIPEDIA
TRIAMCINOLONE ACETONIDE
Created by admin on Fri Dec 15 14:58:48 UTC 2023 , Edited by admin on Fri Dec 15 14:58:48 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-948-7
Created by admin on Fri Dec 15 14:58:48 UTC 2023 , Edited by admin on Fri Dec 15 14:58:48 UTC 2023
PRIMARY
NCI_THESAURUS
C48027
Created by admin on Fri Dec 15 14:58:48 UTC 2023 , Edited by admin on Fri Dec 15 14:58:48 UTC 2023
PRIMARY
FDA UNII
F446C597KA
Created by admin on Fri Dec 15 14:58:48 UTC 2023 , Edited by admin on Fri Dec 15 14:58:48 UTC 2023
PRIMARY
ChEMBL
CHEMBL1504
Created by admin on Fri Dec 15 14:58:48 UTC 2023 , Edited by admin on Fri Dec 15 14:58:48 UTC 2023
PRIMARY
NSC
21916
Created by admin on Fri Dec 15 14:58:48 UTC 2023 , Edited by admin on Fri Dec 15 14:58:48 UTC 2023
PRIMARY
DRUG CENTRAL
2726
Created by admin on Fri Dec 15 14:58:48 UTC 2023 , Edited by admin on Fri Dec 15 14:58:48 UTC 2023
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
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