Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C33H35FO8 |
| Molecular Weight | 578.6246 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 8 / 8 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
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)COC(=O)C6=CC7=C(O6)C=CC=C7
InChI
InChIKey=OSWKQSQWSQSPQH-GNFRAIDCSA-N
InChI=1S/C33H35FO8/c1-29(2)41-27-15-22-21-10-9-19-14-20(35)11-12-30(19,3)32(21,34)25(36)16-31(22,4)33(27,42-29)26(37)17-39-28(38)24-13-18-7-5-6-8-23(18)40-24/h5-8,11-14,21-22,25,27,36H,9-10,15-17H2,1-4H3/t21-,22-,25-,27+,30-,31-,32-,33+/m0/s1
| Molecular Formula | C33H35FO8 |
| Molecular Weight | 578.6246 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 8 / 8 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | TRIESENCE Approved Use1.1. 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 Use1.1. 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 Use1.1. 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 UseNASACORT 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 Date1996 |
|||
| Primary | Nasacort Approved UseNASACORT 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 Date1996 |
Cmax
| 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 |
T1/2
| 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 |
, respiratory |
TRIAMCINOLONE ACETONIDE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
29% |
, 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: 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
| 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: 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
| Title | Date | PubMed |
|---|---|---|
| Therapeutic options for a 53-year-old black woman with concomitant glaucoma, uveitis, and cataract. | 2001 Aug |
|
| Regression of neovascular iris vessels by intravitreal injection of crystalline cortisone. | 2001 Aug |
|
| Apoptosis of skeletal muscle on steroid-induced myopathy in rats. | 2001 Aug |
|
| Nail lichen planus in children: clinical features, response to treatment, and long-term follow-up. | 2001 Aug |
|
| The painful shoulder. | 2001 Dec |
|
| Selective nerve root blocks for the treatment of sciatica: evaluation of injection site and effectiveness--a study with patients and cadavers. | 2001 Dec |
|
| Intravitreal injection of crystalline cortisone as treatment of pre-phthisical ocular hypotony. | 2001 Jul |
|
| Pain-relieving effect of local steroid injection in uvulopalatopharyngoplasty. | 2001 Jun |
|
| Improved asthma control after changing from low-to-medium doses of other inhaled corticosteroids to low-dose fluticasone propionate. | 2001 Jun 8 |
|
| [Fear of dying after intra-keloid injection of triamcinolone acetonide and lidocaine: Hoigne's syndrome]. | 2001 Jun-Jul |
|
| Intralesional cryosurgery using lumbar puncture and/or hypodermic needles for large, bulky, recalcitrant keloids. | 2001 May |
|
| [Post-corticoid atrophy]. | 2001 Nov |
|
| Three methods of treatment of chalazia in children. | 2001 Nov |
|
| [Intravitreal injection of triamcinolone acetonide in non infectious uveitis]. | 2001 Nov |
|
| Once-daily vs twice-daily triamcinolone acetonide cream for psoriasis. | 2001 Nov |
|
| Presence of lichen planus during a course of interferon alpha-2a therapy for a viral chronic C hepatitis. | 2001 Nov-Dec |
|
| 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 |
|
| Fas mediates apoptosis in steroid-induced myopathy of rats. | 2001 Oct |
|
| Intracanal use of a corticosteroid-antibiotic compound for the management of posttreatment endodontic pain. | 2001 Oct |
|
| [Comparative efficacy of glucocorticoid preparations in the local therapy of inflammatory degenerative diseases of the locomotor apparatus]. | 2001 Sep |
|
| The role of ultrasonography in the diagnosis and management of idiopathic plantar fasciitis. | 2001 Sep |
|
| Intravitreal triamcinolone for refractory cystoid macular edema secondary to birdshot retinochoroidopathy. | 2001 Sep |
|
| Intraocular injection of crystalline cortisone as adjunctive treatment of diabetic macular edema. | 2001 Sep |
|
| Treatment of childhood phimosis with a moderately potent topical steroid. | 2001 Sep |
|
| Patch testing with serial dilutions of budesonide, its R and S diastereomers, and potentially cross-reacting substances. | 2001 Sep |
|
| Bone loss accompanying medical therapies. | 2001 Sep 27 |
|
| Effects of inhaled glucocorticoids on bone density in premenopausal women. | 2001 Sep 27 |
|
| [Experience gained with the use of local administration of medicinal remedies in rheumatic diseases]. | 2001 Sep-Dec |
|
| 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 |
|
| Experiences with neurotomies. | 2002 Feb 1 |
|
| A meta-analysis of the dose-response relationship of inhaled corticosteroids in adolescents and adults with mild to moderate persistent asthma. | 2002 Jan |
|
| Macrophage migration inhibitory factor in patients with juvenile idiopathic arthritis. | 2002 Jan |
|
| Adult-onset limbal juvenile xanthogranuloma. | 2002 Jan |
|
| Correction of the soft tissue pollybeak using triamcinolone injection. | 2002 Jan-Mar |
|
| 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 |
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
Edited
Fri Dec 15 16:09:57 GMT 2023
by
admin
on
Fri Dec 15 16:09:57 GMT 2023
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| Record UNII |
O49NOC9ROC
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
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Official Name | English | ||
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Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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NCI_THESAURUS |
C521
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225-650-4
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C77007
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