DrugBank: Triamcinolone (DB00620)

targets (1) carriers (1)

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]

Brand names

Adcortyl
Aristocort
Aristocort A
Aristocort Tablets
Aristogel
Aristospan
Azmacort
Celeste
Cinolone
Cinolone-T
Delphicort
Flutex
Fougera
Kenacort
Kenacort-A
Kenacort-Ag
Kenalog
Kenalog in Orabase
Kenalog-10
Kenalog-40
Kenalog-H
Ledercort
Nasacort
Nasacort Aq
Nasacort Hfa
Omcilon
Omicilon
Oracort
Oralone
Orion
Polcortolon
Rodinolone
Sk-Triamcinolone
Tri-Nasal
Triacet
Triacort
Triam-Tablinen
Triamcet
Triamcinlon
Triamcinolon
Triatex
Tricortale
Triderm
Trilone
Tristoject
Trymex
Vetalog
Volon
Volon A

Brand name mixtures

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 (9.2 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

Humans and other mammals

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

Patents

Country	Patent Number	Approved	Expires
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

Melting point

274 - 278 oC

Experimental Properties

Property	Value	Source
water solubility	80 mg/L	PhysProp
logP	0.2	PhysProp
logS	-3.69 [ADME Research, USCD]	PhysProp

Predicted Properties

Property	Value	Source
water solubility	8.47e-01 g/l	ALOGPS
logP	0.84	ALOGPS
logP	0.24	ChemAxon Molconvert
logS	-2.67	ALOGPS
pKa	13.40	ChemAxon Molconvert
hydrogen acceptor count	6	ChemAxon Molconvert
hydrogen donor count	4	ChemAxon Molconvert
polar surface area	115.06	ChemAxon Molconvert
rotatable bond count	2	ChemAxon Molconvert
refractivity	99.38	ChemAxon Molconvert
polarizability	39.79	ChemAxon Molconvert

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
KEGG Drug	D00385
PubChem Compound	31307
PubChem Substance	46507950
ChemSpider	29046
Therapeutic Targets Database	DAP000417
PharmGKB	PA451748
Drug Product Database	2229540
RxList	http://www.rxlist.com/cgi/generic/triamaer.htm
Drugs.com	http://www.drugs.com/cdi/triamcinolone-spray.html
PDRhealth	http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/azm1044.shtml
Wikipedia	http://en.wikipedia.org/wiki/Triamcinolone

ATC Codes

A01AC01
D07AB09
D07XB02
H02AB08
R01AD11
R03BA06
S01BA05

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

Not Available

Food Interactions

Not Available

Targets
1. Glucocorticoid receptor Pharmacological action: yes Actions: agonist Receptor for glucocorticoids (GC). Has a dual mode of action:as a transcription factor that binds to glucocorticoid response elements (GRE) and as a modulator of other transcription factors. Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Could act as a coactivator for STAT5-dependent transcription upon growth hormone (GH) stimulation and could reveal an essential role of hepatic GR in the control of body growth Organism class: human UniProt ID: P04150 Gene: NR3C1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Nehme A, Lobenhofer EK, Stamer WD, Edelman JL: Glucocorticoids with different chemical structures but similar glucocorticoid receptor potency regulate subsets of common and unique genes in human trabecular meshwork cells. BMC Med Genomics. 2009 Sep 10;2:58. Pubmed Issar M, Sahasranaman S, Buchwald P, Hochhaus G: Differences in the glucocorticoid to progesterone receptor selectivity of inhaled glucocorticoids. Eur Respir J. 2006 Mar;27(3):511-6. Pubmed Shahin V, Ludwig Y, Schafer C, Nikova D, Oberleithner H: Glucocorticoids remodel nuclear envelope structure and permeability. J Cell Sci. 2005 Jul 1;118(Pt 13):2881-9. Pubmed

Targets

1. Glucocorticoid receptor

Pharmacological action: yes
Actions: agonist

Receptor for glucocorticoids (GC). Has a dual mode of action:as a transcription factor that binds to glucocorticoid response elements (GRE) and as a modulator of other transcription factors. Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Could act as a coactivator for STAT5-dependent transcription upon growth hormone (GH) stimulation and could reveal an essential role of hepatic GR in the control of body growth

Organism class: human
UniProt ID: P04150 Link_out

Gene: NR3C1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Nehme A, Lobenhofer EK, Stamer WD, Edelman JL: Glucocorticoids with different chemical structures but similar glucocorticoid receptor potency regulate subsets of common and unique genes in human trabecular meshwork cells. BMC Med Genomics. 2009 Sep 10;2:58. Pubmed
Issar M, Sahasranaman S, Buchwald P, Hochhaus G: Differences in the glucocorticoid to progesterone receptor selectivity of inhaled glucocorticoids. Eur Respir J. 2006 Mar;27(3):511-6. Pubmed
Shahin V, Ludwig Y, Schafer C, Nikova D, Oberleithner H: Glucocorticoids remodel nuclear envelope structure and permeability. J Cell Sci. 2005 Jul 1;118(Pt 13):2881-9. Pubmed

Carriers
1. Corticosteroid-binding globulin Actions: binder Major transport protein for glucocorticoids and progestins in the blood of almost all vertebrate species UniProt ID: P08185 Gene: SERPINA6 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed Groyer A, Le Bouc Y, Joab I, Radanyi C, Renoir JM, Robel P, Baulieu EE: Chick oviduct glucocorticosteroid receptor. Specific binding of the synthetic steroid RU 486 and immunological studies with antibodies to chick oviduct progesterone receptor. Eur J Biochem. 1985 Jun 3;149(2):445-51. Pubmed Svec F, Harrison RW: Conditions affecting AtT-20 cell glucocorticoid uptake. Steroids. 1981 Feb;37(2):143-56. Pubmed Eisen HJ: An antiserum to the rat liver glucocorticoid receptor. Proc Natl Acad Sci U S A. 1980 Jul;77(7):3893-7. Pubmed Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Carriers

1. Corticosteroid-binding globulin

Actions: binder

Major transport protein for glucocorticoids and progestins in the blood of almost all vertebrate species

UniProt ID: P08185 Link_out

Gene: SERPINA6 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
Groyer A, Le Bouc Y, Joab I, Radanyi C, Renoir JM, Robel P, Baulieu EE: Chick oviduct glucocorticosteroid receptor. Specific binding of the synthetic steroid RU 486 and immunological studies with antibodies to chick oviduct progesterone receptor. Eur J Biochem. 1985 Jun 3;149(2):445-51. Pubmed
Svec F, Harrison RW: Conditions affecting AtT-20 cell glucocorticoid uptake. Steroids. 1981 Feb;37(2):143-56. Pubmed
Eisen HJ: An antiserum to the rat liver glucocorticoid receptor. Proc Natl Acad Sci U S A. 1980 Jul;77(7):3893-7. Pubmed
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Comments

Drug created on June 13, 2005 07:24 / Updated on November 10, 2010 13:41

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.