Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Triamcinolone: Difference between pages

{{Short description|Steroid medication}}

{{Use dmy dates|date=October 2022}}

{{Infobox drug

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 470612980

| image = Triamcinolone.svg

| width = 200

| alt =

| image2 = Triamcinolone ball-and-stick animation.gif

| width2 = 200

| alt2 =

| caption =

<!-- Clinical data -->

| pronounce =

| tradename = Kenalog, Nasacort, Adcortyl, others

| MedlinePlus = a601122

| DailyMedID = Triamcinolone

| pregnancy_AU_comment =

| pregnancy_category=

| routes_of_administration = [[Oral administration|By mouth]], [[Topical administration|topical]], [[intranasal]], [[intramuscular]], [[intra-articular]], intra-[[Synovial fluid|synovial]]

| class =

| ATC_prefix = A01

| ATC_suffix = AC01

| ATC_supplemental = {{ATC|C05|AA12}}, {{ATC|D07|AB09}}, {{ATC|H02|AB08}}, {{ATC|R01|AD11}}, {{ATC|R03|BA06}}, {{ATC|S01|BA05}}

<!-- Legal status -->

| legal_AU = S4

| legal_AU_comment = /&nbsp;S3

| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->

| legal_BR_comment =

| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->

| legal_CA_comment =

| legal_DE = <!-- Anlage I, II, III or Unscheduled -->

| legal_DE_comment =

| legal_NZ = <!-- Class A, B, C -->

| legal_NZ_comment =

| legal_UK_comment = /&nbsp;P<ref>{{cite web | title=Kenalog Intra-articular / Intramuscular Injection - Summary of Product Characteristics (SmPC) | website=(emc) | date=10 June 2020 | url=https://www.medicines.org.uk/emc/product/6748/smpc | access-date=20 August 2020}}</ref><ref>{{cite web | title=Nasacort Allergy 55 micrograms/dose Nasal Spray suspension - Summary of Product Characteristics (SmPC) | website=(emc) | date=30 August 2018 | url=https://www.medicines.org.uk/emc/product/6501/smpc | access-date=20 August 2020}}</ref><ref>{{cite web | title=Adcortyl Intra-Articular/Intradermal Injection 10mg/ml - Summary of Product Characteristics (SmPC) | website=(emc) | date=11 December 2017 | url=https://www.medicines.org.uk/emc/product/1410/smpc | access-date=20 August 2020}}</ref>

| legal_US_comment = /&nbsp;[[Over-the-counter drug|OTC]] (Nasacort, intranasal)

| legal_EU =

| legal_EU_comment =

| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->

| legal_UN_comment =

| legal_status = Rx-only

<!-- Pharmacokinetic data -->

| bioavailability = >90%<ref name="Dinnendahl">{{cite book|title=Arzneistoff-Profile| veditors = Dinnendahl V, Fricke U |publisher=Govi Pharmazeutischer Verlag|location=Eschborn, Germany|date=2004|edition=19|volume=10|at=Triamcinolon|isbn=978-3-7741-9846-3|language=German}}</ref>

| protein_bound = 68%{{fact|date=August 2020}}

| metabolism = [[Liver]]<ref name="Dinnendahl" />

| metabolites =

| onset = (2–)24(–48) hours<ref name="Dinnendahl" /><ref name="PPA" />

| elimination_half-life = 200–300 minutes ([[blood plasma|plasma]]), up to 36 hours (total)<ref name="Dinnendahl" />

| duration_of_action =

| excretion = Urine (75%) and faeces (25%)<ref name="PPA" />

<!-- Identifiers -->

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_supplemental =

| IUPHAR_ligand = 2870

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 9667

| NIAID_ChemDB =

| PDB_ligand =

| synonyms = {{hidden|Click ''show'' to see|<small>(8''S'',9''R'',10''S'',11''S'',13''S'',14''S'',16''R'',17''S'')-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-3''H''-cyclopenta[''a'']phenanthren-3-one; (1''R'',2''S'',10''S'',11''S'',13''R'',14''S'',15''S'',17''S'')-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</small>}}

<!-- Chemical and physical data -->

| IUPAC_name = (11β,16α)-9-Fluoro-11,16,17,21-tetrahydroxypregna-1,4-diene-3,20-dione

| C=21 | H=27 | F=1 | O=6

| 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

| StdInChI_comment =

| density =

| density_notes =

| melting_point = 260

| melting_high = 271

| melting_notes =

| boiling_point =

| boiling_notes =

| solubility = 2

| sol_units =

| specific_rotation = <math>[\alpha]_D^{20}</math> +65° to +72°

<!-- Definition and medical uses -->

'''Triamcinolone''' is a [[glucocorticoid]] used to treat certain [[skin diseases]], allergies, and [[rheumatic disorder]]s among others.<ref name=AHFS2019 /> It is also used to prevent worsening of [[asthma]] and [[chronic obstructive pulmonary disease]] (COPD).<ref name="AHFS2019" /> It can be taken in various ways including [[by mouth]], [[intramuscular|injection into a muscle]], and [[inhalation]].<ref name=AHFS2019 />

<!-- Side effects and mechanisms -->

Common side effects with long-term use include [[osteoporosis]], [[cataracts]], [[oral candidiasis|thrush]], and [[muscle weakness]].<ref name=AHFS2019 /> Serious side effects may include [[psychosis]], increased risk of infections, [[adrenal suppression]], and [[bronchospasm]].<ref name=AHFS2019 /> Use in [[pregnancy]] is generally safe.<ref name=Preg2019>{{cite web |title=Triamcinolone Use During Pregnancy |url=https://www.drugs.com/pregnancy/triamcinolone.html |website=Drugs.com |access-date=3 March 2019 }}</ref> It works by decreasing [[inflammation]] and [[immune system]] activity.<ref name=AHFS2019>{{cite web |title=Triamcinolone Monograph for Professionals |url=https://www.drugs.com/monograph/triamcinolone.html |website=Drugs.com |publisher=American Society of Health-System Pharmacists |access-date=3 March 2019 }}</ref>

<!-- Society and culture -->

Triamcinolone was patented in 1956 and came into medical use in 1958.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=978-3-527-60749-5 |page=486 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA486 }}</ref> It is available as a [[generic medication]].<ref>{{cite book | vauthors = Vallerand AH |title=Davis's Drug Guide for Nurses |date=2018 |publisher=F.A. Davis |isbn=978-0-8036-7000-6 |page=365 |url=https://books.google.com/books?id=WbdeDwAAQBAJ&pg=PA365 }}</ref> In 2022, it was the 102nd most commonly prescribed medication in the United States, with more than 6{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Triamcinolone Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Triamcinolone | access-date = 30 August 2024 }}</ref>

== Medical uses ==

Triamcinolone is used to treat many different medical conditions, such as [[eczema]], [[alopecia areata]], [[lichen sclerosus]], [[psoriasis]], [[arthritis]], [[allergies]], [[ulcerative colitis]], [[lupus]], [[sympathetic ophthalmia]], [[temporal arteritis]], [[uveitis]], [[human eye|ocular]] [[inflammation]], [[keloid]]s, [[urushiol-induced contact dermatitis]], [[aphthous ulcers]] (usually as [[triamcinolone acetonide]]), [[central retinal vein occlusion]], visualization during [[vitrectomy]] and the prevention of [[asthma]] attacks.<ref>{{Cite web|url=https://www.drugs.com/triamcinolone.html|title=Triamcinolone: Uses, Dosage, Side Effects, Warnings|website=Drugs.com}}</ref><ref>{{Cite web|url=https://www.drugs.com/azmacort.html|title=Azmacort Inhaler: Side Effects, Dosage & Uses|website=Drugs.com}}</ref><ref>{{Cite web|url=https://www.drugs.com/newdrugs/alcon-receives-fda-approval-triesence-injectable-triamcinolone-suspension-eye-surgery-731.html|title=Alcon Receives FDA Approval of Triesence Injectable Triamcinolone Suspension for Use in Eye Surgery|website=Drugs.com}}</ref>

The [[derivative (chemistry)|derivative]] [[triamcinolone acetonide]] is the active ingredient in various topical skin preparations (cream, lotion, ointment, aerosol spray) designed to treat skin conditions such as rash, inflammation, redness, or intense itching due to [[eczema]]<ref>{{cite journal | vauthors = Chong M, Fonacier L | title = Treatment of Eczema: Corticosteroids and Beyond | journal = Clinical Reviews in Allergy & Immunology | volume = 51 | issue = 3 | pages = 249–262 | date = December 2016 | pmid = 25869743 | doi = 10.1007/s12016-015-8486-7 | s2cid = 44337035 }}</ref> and [[dermatitis]].<ref>{{cite journal | vauthors = Eichenfield LF, Tom WL, Berger TG, Krol A, Paller AS, Schwarzenberger K, Bergman JN, Chamlin SL, Cohen DE, Cooper KD, Cordoro KM, Davis DM, Feldman SR, Hanifin JM, Margolis DJ, Silverman RA, Simpson EL, Williams HC, Elmets CA, Block J, Harrod CG, Smith Begolka W, Sidbury R | display-authors = 6 | title = Guidelines of care for the management of atopic dermatitis: section 2. Management and treatment of atopic dermatitis with topical therapies | journal = Journal of the American Academy of Dermatology | volume = 71 | issue = 1 | pages = 116–132 | date = July 2014 | pmid = 24813302 | pmc = 4326095 | doi = 10.1016/j.jaad.2014.03.023 | quote = Topical corticosteroids (TCS) are used in the management of AD in both adults and children and are the mainstay of anti-inflammatory therapy. }}</ref>

== Contraindications ==

Contraindications for [[Systemic administration|systemic]] triamcinolone are similar to those of other corticoids. They include systemic [[mycoses]] (fungal infections) and [[parasitic disease]]s, as well as eight weeks before and two weeks after application of [[live vaccine]]s. For long-term treatment, the drug is also contraindicated in people with [[peptic ulcer]]s, severe [[osteoporosis]], severe [[myopathy]], certain [[viral infection]]s, [[glaucoma]], and [[metastasizing]] tumours.<ref name="AC">{{cite book|title=Austria-Codex| veditors = Haberfeld H |at=Volon 4 mg-Tabletten|publisher=Österreichischer Apothekerverlag|location=Vienna|year=2020|language=German}}</ref>

There are no contraindications for use in [[emergency medicine]].<ref name="Dinnendahl" />

== Side effects ==

{{see|Glucocorticoid#Side effects}}

The side effects of triamcinolone are similar to other corticosteroids. In short-term treatment of up to ten days, it has very few adverse effects; however, sometimes [[gastrointestinal bleeding]] is seen, as well as acute infections (mainly [[viral infection|viral]]) and impaired [[glucose tolerance]].<ref name="Dinnendahl" />

Side effects of triamcinolone long-term treatment may include coughing (up to [[bronchospasm]]s), [[sinusitis]], [[metabolic syndrome]]–like symptoms such as [[high blood sugar]] and [[Hypercholesterolemia|cholesterol]], [[weight gain]] due to [[Edema|water retention]], and [[electrolyte imbalance]], as well as [[cataract]], [[oral candidiasis|thrush]], [[osteoporosis]], [[reduced muscle mass]], and [[psychosis]].<ref name="PPA">Triamcinolone (systemic) {{drugs.com|PPA|triamcinolone-systemic}}. Accessed 19 August 2020.</ref><ref name=AHFS2019 /><ref name="AC" /> Triamcinolone injections can cause bruising and joint swelling.<ref name="PPA" /> Symptoms of an [[allergic reaction]] include [[rash]], [[itch]], [[Edema|swelling]], severe [[dizziness]], [[Shortness of breath|trouble breathing]],<ref>{{cite web| title = Drugs and Treatments – Nasacort AQ Nasl – Patient Handout| publisher = [[WebMD]]| url = http://www.webmd.com/drugs/drug-16244-Nasacort+AQ.aspx?drugid=16244&drugname=Nasacort%20AQ| access-date = 24 March 2008}}</ref> and [[anaphylaxis]].<ref name="AC" />

== Overdose ==

No acute [[overdosing]] of triamcinolone has been described.<ref name="AC" />

== Interactions ==

[[Drug interactions]] are mainly pharmacodynamic, that is, they result from other drugs either adding to triamcinolone's corticosteroid side effects or working against its desired effects. They include:<ref name="Dinnendahl" /><ref name="AC" />

* [[Atropine]] and other [[anticholinergic]]s can substantially [[ocular hypertension|increase pressure in the eyes]].

* [[Antidiabetic drug]]s can become less effective because triamcinolone causes diabetes-like symptoms.

* [[Aspirin]] and other [[NSAID]]s, as well as [[anticoagulants]] such as [[warfarin]], add to the risk of gastrointestinal bleeding.

* [[Diuretic]]s that excrete [[potassium]] (such as [[loop diuretic]]s and [[thiazide]]s) can increase the risk of [[hypokalemia]] and thus lead to [[arrhythmia|abnormal heart rhythm]].

* [[Cardiac glycoside]]s may have more adverse effects due to reduced potassium levels in the blood.

* The risk for [[blood count]] changes is increased when combining triamcinolone with [[ACE inhibitor]]s.

Triamcinolone and other drugs can also influence each other's concentrations in the body, amounting to pharmacokinetic interactions such as:<ref name="Dinnendahl" /><ref name="AC" />

* [[Rifampicin]], [[phenytoin]], [[carbamazepine]] and other inducers of the liver enzyme [[CYP3A4]]<ref name="pmid23143891">{{cite journal | vauthors = Moore CD, Roberts JK, Orton CR, Murai T, Fidler TP, Reilly CA, Ward RM, Yost GS | display-authors = 6 | title = Metabolic pathways of inhaled glucocorticoids by the CYP3A enzymes | journal = Drug Metabolism and Disposition | volume = 41 | issue = 2 | pages = 379–389 | date = February 2013 | pmid = 23143891 | pmc = 3558858 | doi = 10.1124/dmd.112.046318 }}</ref> speed up metabolization of triamcinolone and can therefore reduce its effectiveness.

* Conversely, CYP3A4 inhibitors such as [[ketoconazole]] and [[itraconazole]] can increase its concentrations in the body and the risk for adverse effects.

* Blood concentrations of [[ciclosporin]] can be increased.

== Pharmacology ==

{{main|Glucocorticoid#Pharmacology}}

=== Mechanism of action ===

{{see|Glucocorticoid#Mechanism of action}}

Triamcinolone is a glucocorticoid that is about five times as potent as [[cortisol]] but has very few [[mineralocorticoid]] effects.<ref name="Dinnendahl" />

=== Pharmacokinetics ===

When taken by mouth, the drug's [[bioavailability]] is over 90%. It reaches its highest concentrations in the [[blood plasma]] after one to two hours and is bound to [[plasma protein]]s to about 80%. The [[biological half-life]] from the plasma is 200 to 300 minutes; due to stable complexes of triamcinolone and [[Glucocorticoid receptor|its receptor]] in the [[intracellular fluid]], the total half-life is significantly longer at about 36 hours.<ref name="Dinnendahl" /><ref name="PPA" />

A small fraction of the substance is metabolized to 6-hydroxy- and 20-dihydro-triamcinolone; most of it probably undergoes [[glucuronidation]], and a smaller part [[sulfation]]. Three-quarters are excreted via the urine, and the rest via the faeces.<ref name="Dinnendahl" /><ref name="AC" />

Due to corticoids' mechanism of action, the effects are delayed as compared to plasma concentrations. Depending on the route of administration and the treated condition, the onset of action can be from two hours up to one or two days after application; and the drug can act much longer than its elimination half-life would suggest.<ref name="Dinnendahl" /><ref name="PPA" />

== Chemistry ==

Triamcinolone is a [[synthetic compound|synthetic]] [[pregnane]] [[corticosteroid]] and [[chemical derivative|derivative]] of [[cortisol]] (hydrocortisone) and is also known as 1-dehydro-9α-fluoro-16α-hydroxyhydrocortisone or 9α-fluoro-16α-hydroxyprednisolone as well as 9α-fluoro-11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione.<ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA1228|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=1228–}}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA1054|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=1054–}}</ref>

The substance is a light-sensitive, white to off-white, crystalline powder, or has the form of colourless, matted crystals. It has no odour or is nearly odourless. Information on the melting point varies, partly due to the substance's [[polymorphism (materials science)|polymorphism]]: {{convert|260 to 263|C|F}}, {{convert|264 to 268|C|F}}, or {{convert|269 to 271|C|F}} can be found in the literature.<ref name="Dinnendahl" />

[[Solubility]] is 1:500 in water and 1:240 in [[ethanol]]; it is slightly soluble in [[methanol]], very slightly soluble in [[chloroform]] and [[diethylether]], and practically insoluble in [[dichloromethane]]. The [[specific rotation]] is <math>[\alpha]_D^{20}</math> +65° to +72° cm³/dm·g (1% in [[dimethylformamide]]).<ref name="Dinnendahl" />

== Society and culture ==

In 2010, [[Teva Pharmaceuticals|Teva]] and [[Perrigo]] launched the first generic inhalable triamcinolone.<ref>{{Cite web|url=https://detroit.cbslocal.com/2011/06/15/perrigo-announces-launch-of-generic-version-of-nasacort-aq/|title=Perrigo Announces Launch Of Generic Version Of Nasacort AQ|date=15 June 2011}}</ref>

According to Chang et al. (2014), "Triamcinolone acetonide (TA) is classified as an S9 [[glucocorticoid]] in the 2014 Prohibited List published by the [[World Anti-Doping Agency]], which caused it to be prohibited in international athletic competition when administered orally, intravenously, intramuscularly or rectally".<ref>{{cite journal | vauthors = Chang CW, Huang TY, Tseng YC, Chang-Chien GP, Lin SF, Hsu MC | title = Positive doping results caused by the single-dose local injection of triamcinolone acetonide | journal = Forensic Science International | volume = 244 | pages = 1–6 | date = November 2014 | pmid = 25126738 | doi = 10.1016/j.forsciint.2014.07.024 | doi-access = free }}</ref>

== References ==

{{Reflist}}

== External links ==

* {{cite web | title=Triamcinolone Topical | website=MedlinePlus | url=https://medlineplus.gov/druginfo/meds/a601124.html }}

* {{cite web | title=Triamcinolone Nasal Spray | website=MedlinePlus | url=https://medlineplus.gov/druginfo/meds/a682791.html }}

{{Glucocorticoids}}

{{Stomatological preparations}}

{{Nasal preparations}}

{{Drugs for obstructive airway diseases}}

{{Glucocorticoidics}}

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