Triamcinolone

Triamcinolone
Clinical data
Trade names	Kenalog, Nasacort, Adcortyl, others
Other names	Click show to see (8S,9R,10S,11S,13S,14S,16R,17S)-9-fluoro-11,16,17-trihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one; (1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-13,14,17-trihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one
AHFS/Drugs.com	Monograph
MedlinePlus	a601122
License data	US DailyMed: Triamcinolone;
Pregnancy; category	AU: A;
Routes of; administration	By mouth, topical, intranasal, intramuscular, intra-articular, intra-synovial
ATC code	A01AC01 (WHO) C05AA12 (WHO), D07AB09 (WHO), H02AB08 (WHO), R01AD11 (WHO), R03BA06 (WHO), S01BA05 (WHO);
Legal status
Legal status	AU: S4 (Prescription only) / S3; UK: POM (Prescription only) / P; US: ℞-only / OTC (Nasacort, intranasal); In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	>90%
Protein binding	68%
Metabolism	Liver
Onset of action	(2–)24(–48) hours
Elimination half-life	200–300 minutes (plasma), up to 36 hours (total)
Excretion	Urine (75%) and faeces (25%)
Identifiers
	IUPAC name (11β,16α)-9-Fluoro-11,16,17,21-tetrahydroxypregna-1,4-diene-3,20-dione;
CAS Number	124-94-7 ;
PubChem CID	31307;
IUPHAR/BPS	2870;
DrugBank	DB00620 ;
ChemSpider	29046 ;
UNII	1ZK20VI6TY;
KEGG	D00385 ;
ChEBI	CHEBI:9667 ;
ChEMBL	ChEMBL1451 ;
CompTox Dashboard (EPA)	DTXSID1040742 ;
ECHA InfoCard	100.004.290
Chemical and physical data
Formula	C21H27FO6
Molar mass	394.439 g·mol−1
3D model (JSmol)	Interactive image;
Specific rotation	+65° to +72°
Melting point	260 to 271 °C (500 to 520 °F)
Solubility in water	2
	SMILES O=C(CO)[C@]3(O)[C@]2(C[C@H](O)[C@]4(F)[C@@]/1(\C(=C/C(=O)\C=C\1)CC[C@H]4[C@@H]2C[C@H]3O)C)C;
	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 ; Key:GFNANZIMVAIWHM-OBYCQNJPSA-N ;
	(what is this?) (verify)

Triamcinolone is a glucocorticoid used to treat certain skin diseases, allergies, and rheumatic disorders among others.^[6] It is also used to prevent worsening of asthma and chronic obstructive pulmonary disease (COPD).^[6] It can be taken in various ways including by mouth, injection into a muscle, and inhalation.^[6]

Common side effects with long-term use include osteoporosis, cataracts, thrush, and muscle weakness.^[6] Serious side effects may include psychosis, increased risk of infections, adrenal suppression, and bronchospasm.^[6] Use in pregnancy is generally safe.^[7] It works by decreasing inflammation and immune system activity.^[6]

Triamcinolone was patented in 1956 and came into medical use in 1958.^[8] It is available as a generic medication.^[9] In 2022, it was the 102nd most commonly prescribed medication in the United States, with more than 6 million prescriptions.^[10]^[11]

^ "Kenalog Intra-articular / Intramuscular Injection - Summary of Product Characteristics (SmPC)". (emc). 10 June 2020. Retrieved 20 August 2020.
^ "Nasacort Allergy 55 micrograms/dose Nasal Spray suspension - Summary of Product Characteristics (SmPC)". (emc). 30 August 2018. Archived from the original on 23 December 2022. Retrieved 20 August 2020.
^ "Adcortyl Intra-Articular/Intradermal Injection 10mg/ml - Summary of Product Characteristics (SmPC)". (emc). 11 December 2017. Retrieved 20 August 2020.
^ ^a ^b ^c ^d Dinnendahl V, Fricke U, eds. (2004). Arzneistoff-Profile (in German). Vol. 10 (19 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. Triamcinolon. ISBN 978-3-7741-9846-3.
^ ^a ^b Cite error: The named reference PPA was invoked but never defined (see the help page).
^ ^a ^b ^c ^d ^e ^f "Triamcinolone Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019.
^ "Triamcinolone Use During Pregnancy". Drugs.com. Retrieved 3 March 2019.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 486. ISBN 978-3-527-60749-5.
^ Vallerand AH (2018). Davis's Drug Guide for Nurses. F.A. Davis. p. 365. ISBN 978-0-8036-7000-6.
^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
^ "Triamcinolone Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.

[1] "Kenalog Intra-articular / Intramuscular Injection - Summary of Product Characteristics (SmPC)". (emc). 10 June 2020. Retrieved 20 August 2020.

[2] "Nasacort Allergy 55 micrograms/dose Nasal Spray suspension - Summary of Product Characteristics (SmPC)". (emc). 30 August 2018. Archived from the original on 23 December 2022. Retrieved 20 August 2020.

[3] "Adcortyl Intra-Articular/Intradermal Injection 10mg/ml - Summary of Product Characteristics (SmPC)". (emc). 11 December 2017. Retrieved 20 August 2020.

[Dinnendahl-4] Dinnendahl V, Fricke U, eds. (2004). Arzneistoff-Profile (in German). Vol. 10 (19 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. Triamcinolon. ISBN 978-3-7741-9846-3.

[PPA-5] Cite error: The named reference PPA was invoked but never defined (see the help page).

[AHFS2019-6] ^ ^a ^b ^c ^d ^e ^f "Triamcinolone Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019.

[Preg2019-7] "Triamcinolone Use During Pregnancy". Drugs.com. Retrieved 3 March 2019.

[Fis2006-8] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 486. ISBN 978-3-527-60749-5.

[9] Vallerand AH (2018). Davis's Drug Guide for Nurses. F.A. Davis. p. 365. ISBN 978-0-8036-7000-6.

[10] "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.

[11] "Triamcinolone Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]