| Identification |
|---|
| Name |
Triamcinolone |
| Accession Number |
DB00620
(APRD00422)
|
| Type |
small molecule |
| Groups |
approved |
| Description |
A glucocorticoid given, as the free alcohol or in esterified form, orally, intramuscularly, by local injection, by inhalation, or applied topically in the management of various disorders in which corticosteroids are indicated. (From Martindale, The Extra Pharmacopoeia, 30th ed, p739) |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
| Fluoxiprednisolone |
| Fluoxyprednisolone |
| Tiamcinolonum [INN-Latin] |
| Triamcinalone |
| Triamcinolona [INN-Spanish] |
| Triamcinolone acetonide |
| Triamcinolone diacetate |
| Triamcinolone hexacetonide |
| Triamcinolonum [INN] |
|
| Salts |
Not Available |
| Brand names |
| Name |
Company |
| Adcortyl |
|
| Aristocort |
|
| Aristocort A |
|
| Aristocort Tablets |
|
| Aristogel |
|
| Aristospan |
|
| Azmacort |
|
| Celeste |
|
| Cinolone |
|
| Cinolone-T |
|
| Delphicort |
|
| Flutex |
|
| Fougera |
|
| Kenacort |
|
| Kenacort-Ag |
|
| Kenalog |
|
| Kenalog in Orabase |
|
| Kenalog-10 |
|
| Kenalog-40 |
|
| Kenalog-H |
|
| Ledercort |
|
| Nasacort |
|
| Nasacort Aq |
|
| Nasacort Hfa |
|
| Omcilon |
|
| Omicilon |
|
| Oracort |
|
| Oralone |
|
| Orion |
|
| Rodinolone |
|
| Sk-Triamcinolone |
|
| Tri-Nasal |
|
| Triacet |
|
| Triacort |
|
| Triam-Tablinen |
|
| Triamcet |
|
| Triamcinlon |
|
| Triamcinolon |
|
| Triatex |
|
| Tricortale |
|
| Triderm |
|
| Trilone |
|
| Tristoject |
|
| Trymex |
|
| Volon |
|
| Volon A |
|
|
| Brand mixtures |
| Brand Name |
Ingredients |
| Aristoform R Crm 0.1% |
Clioquinol + Triamcinolone Acetonide |
| Derma-4 Ont |
Neomycin Sulfate + Nystatin + Thiostrepton (Antibiotic of a Streptomyces Species) + Triamcinolone Acetonide |
| Kenacomb Cream |
Gramicidin + Neomycin Sulfate + Nystatin + Triamcinolone Acetonide |
| Kenacomb Mild Cream |
Gramicidin + Neomycin Sulfate + Nystatin + Triamcinolone Acetonide |
| Kenacomb Mild Ointment |
Gramicidin + Neomycin Sulfate + Nystatin + Triamcinolone Acetonide |
| Kenacomb Ointment |
Gramicidin + Neomycin Sulfate + Nystatin + Triamcinolone Acetonide |
| Kenacomb Ont |
Gramicidin + Neomycin (Neomycin Sulfate) + Nystatin + Triamcinolone Acetonide |
| Mecomb Crm 0.1% |
Gramicidin + Neomycin (Neomycin Sulfate) + Nystatin + Triamcinolone Acetonide |
| Oribiotic Ointment |
Bacitracin + Lidocaine + Neomycin (Neomycin Sulfate) + Nystatin + Triamcinolone Acetonide |
| Panolog Cream |
Neomycin (Neomycin Sulfate) + Nystatin + Thiostrepton (Antibiotic of a Streptomyces Species) + Triamcinolone Acetonide |
| Panolog Ointment |
Neomycin (Neomycin Sulfate) + Nystatin + Thiostrepton (Antibiotic of a Streptomyces Species) + Triamcinolone Acetonide |
| Ratio-Triacomb Regular Cream |
Gramicidin + Neomycin (Neomycin Sulfate) + Nystatin + Triamcinolone Acetonide |
| Solvaderm Ointment |
Neomycin (Neomycin Sulfate) + Nystatin + Thiostrepton (Antibiotic of a Streptomyces Species) + Triamcinolone Acetonide |
| Theraderm Cream |
Gramicidin + Neomycin (Neomycin Sulfate) + Nystatin + Triamcinolone Acetonide |
| Viaderm Kc Crm |
Gramicidin + Neomycin (Neomycin Sulfate) + Nystatin + Triamcinolone Acetonide |
| Viaderm Kc Ont |
Gramicidin + Neomycin (Neomycin Sulfate) + Nystatin + Triamcinolone Acetonide |
|
| Categories |
- Anti-inflammatory Agents
- Adrenergic Agents
- Glucocorticoids
|
| CAS number |
124-94-7 |
| Weight |
Average: 394.4339
Monoisotopic: 394.179166801
|
| Chemical Formula |
C21H27FO6 |
| InChI Key |
InChIKey=GFNANZIMVAIWHM-OBYCQNJPSA-N |
| 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
Plain Text
|
| IUPAC Name |
(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
|
| SMILES |
[H][C@@]12C[C@@H](O)[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
Plain Text
|
| Mass Spec |
show (9.24 KB)
|
| Taxonomy |
|---|
| Kingdom |
Organic |
| Classes |
- Steroids and Steroid Derivatives
|
| Substructures |
- Steroids and Steroid Derivatives
- Hydroxy Compounds
- Alkanes and Alkenes
- Alkyl Halides
- Alcohols and Polyols
- Ketones
|
| Pharmacology |
|---|
| Indication |
For the treatment of perennial and seasonal allergic rhinitis. |
| Pharmacodynamics |
Triamcinolone and its derivatives are synthetic glucocorticoids that are used for their antiinflammatory or immunosuppressive properties. |
| Mechanism of action |
The antiinflammatory actions of corticosteroids are thought to involve lipocortins, phospholipase A2 inhibitory proteins which, through inhibition of arachidonic acid, control the biosynthesis of prostaglandins and leukotrienes. Firstly, however, these glucocorticoids bind to the glucocorticoid receptors which translocate into the nucleus and bind DNA (GRE) and change genetic expression both positively and negatively. The immune system is suppressed by corticosteroids due to a decrease in the function of the lymphatic system, a reduction in immunoglobulin and complement concentrations, the precipitation of lymphocytopenia, and interference with antigen-antibody binding. |
| Absorption |
Rapid absorption following oral administration |
| Volume of distribution |
Not Available |
| Protein binding |
68% |
| Metabolism |
Hepatic. |
| Route of elimination |
Not Available |
| Half life |
88 minutes |
| Clearance |
Not Available |
| Toxicity |
LD50=>500mg/kg (in rats) |
| Affected organisms |
|
| Pathways |
Not Available |
| Pharmacoeconomics |
|---|
| Manufacturers |
- Astellas pharma us inc
- Bristol myers squibb co
- Barr laboratories inc
- Impax laboratories inc
- Ivax pharmaceuticals inc sub teva pharmaceuticals usa
- Mylan pharmaceuticals inc
- Purepac pharmaceutical co
- Roxane laboratories inc
- Sandoz inc
- Teva pharmaceuticals usa inc
- Watson laboratories inc
- Abbott laboratories
- Sanofi aventis us llc
- Ivax pharmaceuticals inc
- Apothecon inc div bristol myers squibb
- Solvay pharmaceuticals
- Actavis mid atlantic llc
- Alpharma us pharmaceuticals division
- Altana inc
- Ambix laboratories div organics corp america
- G and w laboratories inc
- Morton grove pharmaceuticals inc
- Perrigo new york inc
- Pharmaderm div altana inc
- Pharmafair inc
- Taro pharmaceuticals inc
- Taro pharmaceuticals usa inc
- Topiderm inc
- Vintage pharmaceuticals llc
- Del ray laboratories inc
- Savage laboratories inc div altana inc
- Parnell pharmaceuticals inc
- Sandoz canada inc
- Allergan inc
- Alcon inc
- Bristol myers squibb co pharmaceutical research institute
- Wockhardt eu operations (swiss) ag
- Carolina medical products co
- Lyne laboratories inc
- Lupin atlantis holding sa switzerland
- Ranbaxy laboratories inc
- Akorn inc
|
| Packagers |
|
| Dosage forms |
| Form |
Route |
Strength |
| Aerosol, metered |
Nasal |
|
| Cream |
Topical |
|
| Liquid |
Intramuscular |
|
| Ointment |
Topical |
|
| Paste |
Dental |
|
| Spray |
Nasal |
|
| Suspension |
Intra-articular |
|
| Suspension |
Intramuscular |
|
| Suspension |
Intrasynovial |
|
|
| Prices |
| Unit description |
Cost |
Unit |
| Triesence 40 mg/ml vial |
148.8 USD |
ml |
| Kenalog Aerosol 63 gm Can |
118.99 USD |
can |
| Nasacort AQ 55 mcg/act Aerosol (Nasal Spray) |
118.74 USD |
inhaler |
| Triamcinolone Acetonide 0.1% Paste 5 gm Tube |
71.7 USD |
tube |
| Kenalog 0.5% Cream 20 gm Tube |
54.99 USD |
tube |
| Kenalog 0.1% Lotion 60ml Bottle |
51.99 USD |
bottle |
| Kenalog 0.025% Lotion 60ml Bottle |
46.99 USD |
bottle |
| Triamcinolone Acetonide 0.025% Lotion 60ml Bottle |
40.99 USD |
bottle |
| Triamcinolone diacetate powder |
26.01 USD |
g |
| Triamcinolone powder |
20.29 USD |
g |
| Kenalog 0.1% Cream 15 gm Tube |
18.99 USD |
tube |
| Triamcinolone Acetonide 0.1% Ointment 80 gm Tube |
18.99 USD |
tube |
| Triamcinolone Acetonide 0.5% Ointment 15 gm Tube |
14.99 USD |
tube |
| Aristospan 20 mg/ml vial |
14.19 USD |
ml |
| Oralone 0.1% paste |
13.57 USD |
g |
| Triamcinolone Acetonide 0.025% Cream 80 gm Tube |
12.99 USD |
tube |
| Triamcinolone Acetonide 0.1% Cream 80 gm Tube |
12.99 USD |
tube |
| Triamcinolone Acetonide 0.5% Cream 15 gm Tube |
12.99 USD |
tube |
| Triamcinolone Acetonide 0.025% Cream 15 gm Tube |
11.99 USD |
tube |
| Triamcinolone Acetonide 0.025% Ointment 80 gm Tube |
11.99 USD |
tube |
| Triamcinolone Acetonide 0.1% Cream 15 gm Tube |
11.99 USD |
tube |
| Triamcinolone Acetonide 0.1% Ointment 15 gm Tube |
11.99 USD |
tube |
| Kenalog-40 40 mg/ml vial |
8.99 USD |
ml |
| Triamcinolone acet 40 mg/ml sus |
8.42 USD |
ml |
| Kenalog-40 40 mg/ml |
7.53 USD |
ml |
| Nasacort aq nasal spray |
6.99 USD |
g |
| Triamcinolone 0.1% paste |
6.4 USD |
g |
| Triamcinolone Acetonide 40 mg/ml |
6.29 USD |
ml |
| Triamcinolone Acetonide Usp 40 mg/ml |
5.76 USD |
ml |
| Aristospan 5 mg/ml vial |
3.54 USD |
ml |
| Kenalog-10 10 mg/ml |
3.24 USD |
ml |
| Triamcinolone Acetonide 10 mg/ml |
2.71 USD |
ml |
| Kenalog-10 10 mg/ml vial |
2.32 USD |
ml |
| Triamcinolone acet 10 mg/ml sus |
2.18 USD |
ml |
| Aristocort C 0.5 % Cream |
1.3 USD |
g |
| Oracort 0.1 % Paste |
1.19 USD |
g |
| Triderm 0.1% cream |
0.47 USD |
g |
| Triamcinolone 0.5% cream |
0.22 USD |
g |
| Aristocort R 0.1 % Cream |
0.15 USD |
g |
| Aristocort R 0.1 % Ointment |
0.15 USD |
g |
| Triamcinolone Acetonide 0.1% Cream |
0.07 USD |
gm |
| Triaderm Regular 0.1 % Cream |
0.07 USD |
g |
| Triamcinolone 0.025% cream |
0.06 USD |
g |
| Triamcinolone Acetonide 0.1% Ointment |
0.05 USD |
gm |
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational
purposes only.
|
| Patents |
| Country |
Patent Number |
Approved |
Expires (estimated) |
| United States |
6395294 |
2000-01-13 |
2020-01-13 |
| United States |
5976573 |
1996-07-03 |
2016-07-03 |
| Canada |
2268927 |
2003-09-23 |
2017-07-02 |
|
| Properties |
|---|
| State |
solid |
| Experimental Properties |
| Property |
Value |
Source |
| melting point |
270 °C |
PhysProp |
| water solubility |
80 mg/L (at 25 °C) |
YALKOWSKY,SH & DANNENFELSER,RM (1992) |
| logP |
1.16 |
HANSCH,C ET AL. (1995) |
| logS |
-3.69 |
ADME Research, USCD |
|
| Predicted Properties |
|
| References |
|---|
| Synthesis Reference |
Not Available
|
| General Reference |
Not Available
|
| External Links |
|
| ATC Codes |
- A01AC01
- D07AB09
- D07XB02
- H02AB08
- R01AD11
- R03BA06
- S01BA05
- C05AA12
|
| AHFS Codes |
- 52:08.08
- 84:06.00
- 68:04.00
|
| PDB Entries |
Not Available |
| FDA label |
show (150 KB)
|
| MSDS |
show (72.6 KB)
|
| Interactions |
|---|
| Drug Interactions |
| Drug |
Interaction |
| Acenocoumarol |
The corticosteroid, triamcinolone, alters the anticoagulant effect, acenocoumarol. |
| Acetylsalicylic acid |
The corticosteroid, triamcinolone, may decrease the effect of the salicylate, acetylsalicylic acid. |
| Ambenonium |
The corticosteroid, triamcinolone, may decrease the effect of the anticholinesterase, ambenonium. |
| Amobarbital |
The barbiturate, amobarbital, may decrease the effect of the corticosteroid, triamcinolone. |
| Anisindione |
The corticosteroid, triamcinolone, alters the anticoagulant effect of anisindione. |
| Aprobarbital |
The barbiturate, aprobarbital, may decrease the effect of the corticosteroid, triamcinolone. |
| Bismuth Subsalicylate |
The corticosteroid, triamcinolone, may decrease the effect of the salicylate, bismuth subsalicylate. |
| Butabarbital |
The barbiturate, butabarbital, may decrease the effect of the corticosteroid, triamcinolone. |
| Butalbital |
The barbiturate, butalbital, may decrease the effect of the corticosteroid, triamcinolone. |
| Butethal |
The barbiturate, butethal, may decrease the effect of the corticosteroid, triamcinolone. |
| Dicumarol |
The corticosteroid, triamcinolone, alters the anticoagulant effect of dicumarol. |
| Dihydroquinidine barbiturate |
The barbiturate, dihydroquinidine barbiturate, may decrease the effect of the corticosteroid, triamcinolone. |
| Edrophonium |
The corticosteroid, triamcinolone, may decrease the effect of the anticholinesterase, edrophonium. |
| Ethotoin |
The enzyme inducer, ethotoin, may decrease the effect of the corticosteroid, triamcinolone. |
| Fosphenytoin |
The enzyme inducer, fosphenytoin, may decrease the effect of the corticosteroid, triamcinolone. |
| Heptabarbital |
The barbiturate, heptabarbital, may decrease the effect of the corticosteroid, triamcinolone. |
| Hexobarbital |
The barbiturate, hexobarbital, may decrease the effect of the corticosteroid, triamcinolone. |
| Magnesium salicylate |
The corticosteroid, triamcinolone, may decrease the effect of magnesium salicylate. |
| Mephenytoin |
The enzyme inducer, mephenytoin, may decrease the effect of the corticosteroid, triamcinolone. |
| Methohexital |
The barbiturate, methohexital, may decrease the effect of the corticosteroid, triamcinolone. |
| Methylphenobarbital |
The barbiturate, methylphenobarbital, may decrease the effect of the corticosteroid, triamcinolone. |
| Midodrine |
Increased arterial pressure |
| Neostigmine |
The corticosteroid, triamcinolone, may decrease the effect of the anticholinesterase, neostigmine. |
| Pentobarbital |
The barbiturate, pentobarbital, may decrease the effect of the corticosteroid, triamcinolone. |
| Phenobarbital |
The barbiturate, phenobarbital, may decrease the effect of the corticosteroid, triamcinolone. |
| Phenytoin |
The enzyme inducer, phenytoin, may decrease the effect of the corticosteroid, triamcinolone. |
| Primidone |
The barbiturate, primidone, may decrease the effect of the corticosteroid, triamcinolone. |
| Pyridostigmine |
The corticosteroid, triamcinolone, may decrease the effect of the anticholinesterase, pyridostigmine. |
| Quinidine barbiturate |
The barbiturate, quinidine barbiturate, may decrease the effect of the corticosteroid, triamcinolone. |
| Rifampin |
The enzyme inducer, rifampin, may decrease the effect of the corticosteroid, triamcinolone. |
| Salicylate-sodium |
The corticosteroid, triamcinolone, may decrease the effect of the salicylate, salicylate-sodium. |
| Salsalate |
The corticosteroid, triamcinolone, may decrease the effect of the salicylate, salsalate. |
| Secobarbital |
The barbiturate, secobarbital, may decrease the effect of the corticosteroid, triamcinolone. |
| Tacrine |
Tacrine and Triamcinolone may independently exacerbate muscle weakness in myasthenia gravis patients. Monitor for additive muscle weakness effects. |
| Talbutal |
The barbiturate, talbutal, may decrease the effect of the corticosteroid, triamcinolone. |
| Trastuzumab |
Trastuzumab may increase the risk of neutropenia and anemia. Monitor closely for signs and symptoms of adverse events. |
| Trisalicylate-choline |
The corticosteroid, triamcinolone, may decrease the effect of the salicylate, trisalicylate-choline. |
| Vecuronium |
Vecuronium may increase the adverse neuromuscular effects of systemic corticosteroids, such as Triamcinolone. Monitor for increased muscle weakness and signs of polyneuropathies and myopathy. |
| Warfarin |
The corticosteroid, triamcinolone, alters the anticoagulant effect of warfarin. |
|
| Food Interactions |
Not Available |
