Triamcinolone hexacetonide

Structural formula
General
Non-proprietary name	Triamcinolone hexacetonide
other names	9 α -Fluor-11 β , 16 α , 17,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with acetone 21- (3,3-dimethylbutyrate); 2 - [(1 S , 2 S , 4 R , 8 S , 9 S , 11 S , 12 R , 13 S ) -12-fluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo -5,7-dioxapentacyclo [10.8.0.0 2.9 .0 4.8 .0 13.18 ] icosa-14,17-dien-8-yl] -2-oxoethyl-3,3-dimethylbutanoate ( IUPAC );
Molecular formula	C 30 H 41 FO 7
Brief description	white to almost white, crystalline powder
External identifiers / databases
EC number	227-031-4
ECHA InfoCard	100,024,575
PubChem	21826
Wikidata	Q1593246
Drug information
ATC code	H02 AB08
Drug class	Glucocorticoid
Mechanism of action	Corticoid binds to the corresponding cytosolic glucocorticoid receptor
properties
Molar mass	532.64 g · mol -1
Physical state	firmly
Melting point	295 ° C
solubility	practically insoluble in water, slightly soluble in anhydrous ethanol and in methanol
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 302 + 312 + 332-371
	P: 260-261-280-309 + 311-405-501
Toxicological data	420 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Triamcinolone hexacetonide is an artificially produced chemical compound from the group of steroids . Due to multiple esterification , it is a very fat-soluble glucocorticoid that is used as a medicinal substance for the treatment of inflammatory processes in joints (for example arthritis ).

Clinical information

Application areas (indications)

Intra-articular injections

Persistent inflammation in one or a few joints after general treatment for chronic inflammatory joint diseases
Arthritis in pseudogout / chondrocalcinosis
Activated osteoarthritis
Post-traumatic, non-bacterial arthritis

Infiltration therapy

Non-bacterial tendovaginitis (strict indication) and bursitis
Periarthopathies
Insertion tendopathies
Enthesopathies in inflammatory rheumatic systemic diseases

Sub- and intralesional injection

Isolated psoriatic foci
Lichen planus , lichen simplex chronicus (neurodermatitis circumscripta)
Alopecia areata
Lupus erythematosus chronicus discoides
Keloids

Special areas of application

Applications in juvenile idiopathic arthritis (JIA)

First choice for intra-articular steroid therapy in children
Triamcinolone hexacetonide (TH) is more effective than triamcinolone acetonide (TA), even when TA is given in higher doses

Applications in radiosynoviorthesis (RSO)

for the " polyethylene disease " after knee replacement surgery ( total endo prosthesis )
with persistent synovitis in the ankle
in rheumatoid arthritis in medium-sized and small joints
with synovial hypertrophy in DIP joints

dosage

The dosage for intra-articular therapy depends on the size of the joint and the severity of the findings. The following dosage information can serve as a guide: large joints 10–20 mg, medium joints 5–10 mg, small joints 2–5 mg triamcinolone hexacetonide.

Contraindications (contraindications)

If you are hypersensitive to triamcinolone hexacetonide, this drug should not be used.

Use during pregnancy and breastfeeding

The use of triamcinolone in the first five months of pregnancy should be avoided. In the case of long-term use, intrauterine growth disorders cannot be ruled out. In late pregnancy treatment, the fetus is at risk of adrenal atrophy. Glucocorticoids are excreted in breast milk. If treatment with higher doses or long-term treatment is required, breastfeeding should be discontinued.

Adverse effects (side effects)

Triamcinolone hexacetonide has fewer systemic side effects for the patient than other glucocorticoids, as the high corticoid concentration at the site of action results in a lower corticoid plasma level.

Pharmacological properties

Mechanism of action (pharmacodynamics)

Triamcinolone hexacetonide is released from the crystalline depot and then converted by tissue enzymes ( esterases ) into triamcinolone acetonide with a higher receptor affinity. The corticoid binds to the corresponding cytosolic glucocorticoid receptor and causes its conformational change. The activated receptor can now influence gene expression by reducing the synthesis of pro-inflammatory mediators and increasing the formation of anti-inflammatory proteins. The inflammatory process in the joints is thus suppressed and the pain is reduced.

Trade names

Triamcinolone hexacetonide is marketed as a monopreparation under the trade name Lederlon ^® in the form of ampoules for injection .

Individual evidence

↑ ^a ^b ^c ^d data sheet TRIAMCINOLONE HEXACETONIDE CRS (PDF) at EDQM , accessed on February 20, 2010.
↑ ^a ^b Triamcinolone Hexacetonide ( Memento from October 31, 2016 in the Internet Archive )
↑ J. Neidel: The intra-articular steroid therapy for inflammatory rheumatic diseases of children and adolescents. In: Orthopedics. 31, 2002, pp. 1175-1178.
^ F. Zulian, G. Martini, D. Gobber, M. Plebani, F. Zacchello, P. Manners: Triamcinolone acetonide and hexacetonide intra-articular treatment of symmetrical joints in juvenile idiopathic arthritis: a double blind trial. In: Rheumatology . 43, 2004, pp. 1288-1291.
↑ G. Mödder, R. Mödder-Reese: Radiosynoviorthesis after knee endoprostheses: Effective therapy in "Polyethylene disease". In: The nuclear medicine. 24, No. 2, 2001, pp. 97-103.
↑ FM van der Zant, ZN Jahangier, JD Moolenburgh, W. van der Zee, RO Boer, JW Jacobs: Radiation synovectomy of the ankle with 75 MBq colloidal 186rhenium-sulfide: effect, leakage, and radiation consideration. In: J Rheumatol . 31 (5), 2004, pp. 896-901.
↑ D. Göbel, S. Gratz, T. von Rothkirch, W. Becker: Chronic polyarthritis and radiosynoviorthesis: a prospective, controlled study of injection therapy with erbium 169 and rhenium 186. In: Z Rheumatol. 56 (4), 1997, pp. 207-213.
↑ G. Mödder: Radiosynoviorthesis for activated finger polyarthrosis. In: The nuclear medicine. 29, 2006, pp. 21-27.
↑ Yellow list : Lederlon® 5 crystal suspension. ( Memento from August 4, 2012 in the web archive archive.today )

[Ph._Eur.-1] ta sheet TRIAMCINOLONE HEXACETONIDE CRS (PDF) at EDQM , accessed on February 20, 2010.

[lgcstandards-2] Triamcinolone Hexacetonide ( Memento from October 31, 2016 in the Internet Archive )

[Neidel-3] J. Neidel: The intra-articular steroid therapy for inflammatory rheumatic diseases of children and adolescents. In: Orthopedics. 31, 2002, pp. 1175-1178.

[Zulian-4] F. Zulian, G. Martini, D. Gobber, M. Plebani, F. Zacchello, P. Manners: Triamcinolone acetonide and hexacetonide intra-articular treatment of symmetrical joints in juvenile idiopathic arthritis: a double blind trial. In: Rheumatology . 43, 2004, pp. 1288-1291.

[Mödder-5] G. Mödder, R. Mödder-Reese: Radiosynoviorthesis after knee endoprostheses: Effective therapy in "Polyethylene disease". In: The nuclear medicine. 24, No. 2, 2001, pp. 97-103.

[van_der_Zant-6] FM van der Zant, ZN Jahangier, JD Moolenburgh, W. van der Zee, RO Boer, JW Jacobs: Radiation synovectomy of the ankle with 75 MBq colloidal 186rhenium-sulfide: effect, leakage, and radiation consideration. In: J Rheumatol . 31 (5), 2004, pp. 896-901.

[Göbel-7] D. Göbel, S. Gratz, T. von Rothkirch, W. Becker: Chronic polyarthritis and radiosynoviorthesis: a prospective, controlled study of injection therapy with erbium 169 and rhenium 186. In: Z Rheumatol. 56 (4), 1997, pp. 207-213.

[Mödder_G-8] G. Mödder: Radiosynoviorthesis for activated finger polyarthrosis. In: The nuclear medicine. 29, 2006, pp. 21-27.

[9] Yellow list : Lederlon® 5 crystal suspension. ( Memento from August 4, 2012 in the web archive archive.today )