Triamcinolone

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Triamcinolone
Triamcinolone.svg
Triamcinolone ball-and-stick animation.gif
Clinical data
Trade names Kenalog, Nasacort, Adcortyl, others
Other names
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(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
Pregnancy
category
  • AU:A
Routes of
administration 		By mouth, topical, intranasal, intramuscular, intra-articular, intra-synovial
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)/ S3
  • UK: POM (Prescription only)/ P [1] [2] [3]
  • US: ℞-only /  OTC (Nasacort, intranasal)
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability >90% [4]
Protein binding 68%[ citation needed ]
Metabolism Liver [4]
Onset of action (2–)24(–48) hours [4] [5]
Elimination half-life 200–300 minutes (plasma), up to 36 hours (total) [4]
Excretion Urine (75%) and faeces (25%) [5]
Identifiers
  • (11β,16α)-9-Fluoro-11,16,17,21-tetrahydroxypregna-1,4-diene-3,20-dione
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.004.290 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C21H27FO6
Molar mass 394.439 g·mol−1
3D model (JSmol)
Specific rotation +65° to +72°
Melting point 260 to 271 °C (500 to 520 °F)
Solubility in water 2
  • 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=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 Yes check.svgY
  • Key:GFNANZIMVAIWHM-OBYCQNJPSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (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]

Contents

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]

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, ocular inflammation, keloids, urushiol-induced contact dermatitis, aphthous ulcers (usually as triamcinolone acetonide), central retinal vein occlusion, visualization during vitrectomy and the prevention of asthma attacks. [12] [13] [14]

The 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 [15] and dermatitis. [16]

Contraindications

Contraindications for systemic triamcinolone are similar to those of other corticoids. They include systemic mycoses (fungal infections) and parasitic diseases, as well as eight weeks before and two weeks after application of live vaccines. For long-term treatment, the drug is also contraindicated in people with peptic ulcers, severe osteoporosis, severe myopathy, certain viral infections, glaucoma, and metastasizing tumours. [17]

There are no contraindications for use in emergency medicine. [4]

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) and impaired glucose tolerance. [4]

Side effects of triamcinolone long-term treatment may include coughing (up to bronchospasms), sinusitis, metabolic syndrome–like symptoms such as high blood sugar and cholesterol, weight gain due to water retention, and electrolyte imbalance, as well as cataract, thrush, osteoporosis, reduced muscle mass, and psychosis. [5] [6] [17] Triamcinolone injections can cause bruising and joint swelling. [5] Symptoms of an allergic reaction include rash, itch, swelling, severe dizziness, trouble breathing, [18] and anaphylaxis. [17]

Overdose

No acute overdosing of triamcinolone has been described. [17]

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: [4] [17]

Triamcinolone and other drugs can also influence each other's concentrations in the body, amounting to pharmacokinetic interactions such as: [4] [17]

Pharmacology

Mechanism of action

Triamcinolone is a glucocorticoid that is about five times as potent as cortisol but has very few mineralocorticoid effects. [4]

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 proteins to about 80%. The biological half-life from the plasma is 200 to 300 minutes; due to stable complexes of triamcinolone and its receptor in the intracellular fluid, the total half-life is significantly longer at about 36 hours. [4] [5]

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. [4] [17]

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. [4] [5]

Chemistry

Triamcinolone is a synthetic pregnane corticosteroid and 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. [20] [21]

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: 260 to 263 °C (500 to 505 °F), 264 to 268 °C (507 to 514 °F), or 269 to 271 °C (516 to 520 °F) can be found in the literature. [4]

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 +65° to +72° cm3/dm·g (1% in dimethylformamide). [4]

Society and culture

In 2010, Teva and Perrigo launched the first generic inhalable triamcinolone. [22]

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". [23]

Related Research Articles

<span class="mw-page-title-main">Corticosteroid</span> Class of steroid hormones

Corticosteroids are a class of steroid hormones that are produced in the adrenal cortex of vertebrates, as well as the synthetic analogues of these hormones. Two main classes of corticosteroids, glucocorticoids and mineralocorticoids, are involved in a wide range of physiological processes, including stress response, immune response, and regulation of inflammation, carbohydrate metabolism, protein catabolism, blood electrolyte levels, and behavior.

<span class="mw-page-title-main">Cortisone</span> Corticosteroid precursor and metabolite of cortisol

Cortisone is a pregnene (21-carbon) steroid hormone. It is a naturally-occurring corticosteroid metabolite that is also used as a pharmaceutical prodrug. Cortisol is converted by the action of the enzyme corticosteroid 11-beta-dehydrogenase isozyme 2 into the inactive metabolite cortisone, particularly in the kidneys. This is done by oxidizing the alcohol group at carbon 11. Cortisone is converted back to the active steroid cortisol by stereospecific hydrogenation at carbon 11 by the enzyme 11β-Hydroxysteroid dehydrogenase type 1, particularly in the liver.

<span class="mw-page-title-main">Dexamethasone</span> Corticosteroid medication

Dexamethasone is a fluorinated glucocorticoid medication used to treat rheumatic problems, a number of skin diseases, severe allergies, asthma, chronic obstructive pulmonary disease (COPD), croup, brain swelling, eye pain following eye surgery, superior vena cava syndrome, and along with antibiotics in tuberculosis. In adrenocortical insufficiency, it may be used in combination with a mineralocorticoid medication such as fludrocortisone. In preterm labor, it may be used to improve outcomes in the baby. It may be given by mouth, as an injection into a muscle, as an injection into a vein, as a topical cream or ointment for the skin or as a topical ophthalmic solution to the eye. The effects of dexamethasone are frequently seen within a day and last for about three days.

A decongestant, or nasal decongestant, is a type of pharmaceutical drug that is used to relieve nasal congestion in the upper respiratory tract. The active ingredient in most decongestants is either pseudoephedrine or phenylephrine. Intranasal corticosteroids can also be used as decongestants and antihistamines can be used to alleviate runny nose, nasal itch, and sneezing.

<span class="mw-page-title-main">Hydrocortisone</span> Glucocorticoid and Mineralocorticoid hormone Cortisol supplied as a medication

Hydrocortisone is the name for the hormone cortisol when supplied as a medication. It is a corticosteroid and works as an anti-inflammatory and by immune suppression. Uses include conditions such as adrenocortical insufficiency, adrenogenital syndrome, high blood calcium, thyroiditis, rheumatoid arthritis, dermatitis, asthma, and COPD. It is the treatment of choice for adrenocortical insufficiency. It can be given by mouth, topically, or by injection. Stopping treatment after long-term use should be done slowly.

<span class="mw-page-title-main">Glucocorticoid</span> Class of corticosteroids

Glucocorticoids are a class of corticosteroids, which are a class of steroid hormones. Glucocorticoids are corticosteroids that bind to the glucocorticoid receptor that is present in almost every vertebrate animal cell. The name "glucocorticoid" is a portmanteau and is composed from its role in regulation of glucose metabolism, synthesis in the adrenal cortex, and its steroidal structure.

<span class="mw-page-title-main">Prednisolone</span> Corticosteroid medication

Prednisolone is a corticosteroid, a steroid hormone used to treat certain types of allergies, inflammatory conditions, autoimmune disorders, and cancers. Some of these conditions include adrenocortical insufficiency, high blood calcium, rheumatoid arthritis, dermatitis, eye inflammation, asthma, and multiple sclerosis. It can be taken by mouth, injected into a vein, used topically as a skin cream, or as eye drops. It differs from the similarly named prednisone in having a hydroxyl at the 11th carbon instead of a ketone.

<span class="mw-page-title-main">Pimecrolimus</span> Immunosuppressive drug

Pimecrolimus is an immunosuppressant drug of the calcineurin inhibitor class used in the treatment of atopic dermatitis (eczema).

<span class="mw-page-title-main">Nasal spray</span> Spray that delivers medications locally in the nasal cavities or systemically

Nasal sprays are used to deliver medications locally in the nasal cavities or systemically. They are used locally for conditions such as nasal congestion and allergic rhinitis. In some situations, the nasal delivery route is preferred for systemic therapy because it provides an agreeable alternative to injection or pills. Substances can be assimilated extremely quickly and directly through the nose. Many pharmaceutical drugs exist as nasal sprays for systemic administration. Other applications include hormone replacement therapy, treatment of Alzheimer's disease and Parkinson's disease. Nasal sprays are seen as a more efficient way of transporting drugs with potential use in crossing the blood–brain barrier.

<span class="mw-page-title-main">Methylprednisolone</span> Corticosteroid medication

Methylprednisolone is a synthetic glucocorticoid, primarily prescribed for its anti-inflammatory and immunosuppressive effects. It is either used at low doses for chronic illnesses or used concomitantly at high doses during acute flares. Methylprednisolone and its derivatives can be administered orally or parenterally.

<span class="mw-page-title-main">Fluticasone propionate</span> Medication

Fluticasone propionate, sold under the brand names Flovent and Flonase among others, is a glucocorticoid steroid medication. When inhaled it is used for the long term management of asthma and COPD. In the nose it is used for hay fever and nasal polyps. It can also be used for mouth ulcers. It works by decreasing inflammation.

<span class="mw-page-title-main">Betamethasone dipropionate</span> Glucocorticoid steroid (chemical compound)

Betamethasone dipropionate is a glucocorticoid steroid with anti-inflammatory and immunosuppressive properties. It is applied as a topical cream, ointment, lotion or gel (Diprolene) to treat itching and other skin conditions such as eczema. Minor side effects include dry skin and mild, temporary stinging when applied. Betamethasone dipropionate is a "super high potency" corticosteroid used to treat inflammatory skin conditions such as dermatitis, eczema and psoriasis. It is a synthetic analog of the adrenal corticosteroids. Although its exact mechanism of action is not known, it is effective when applied topically to cortico-responsive inflammatory dermatoses. It is available as a generic medication.

<span class="mw-page-title-main">Triamcinolone acetonide</span> Medicinal chemical compound, steroid

Triamcinolone acetonide, sold under the brand name Kenalog among others, is a synthetic corticosteroid medication used topically to treat various skin conditions, to relieve the discomfort of mouth sores, and by injection into joints to treat various joint conditions. It is also injected into lesions to treat inflammation in some parts of the body, particularly the skin. In nasal spray form, it is used to treat allergic rhinitis. It is used for the treatment of macular edema associated with uveitis. It is a more potent derivative of triamcinolone, and is about eight times as potent as prednisone.

<span class="mw-page-title-main">Fluocinonide</span> Chemical compound

Fluocinonide is a potent glucocorticoid used topically as an anti-inflammatory agent for the treatment of skin disorders such as eczema and seborrhoeic dermatitis. It relieves itching, redness, dryness, crusting, scaling, inflammation, and discomfort.

<span class="mw-page-title-main">Mometasone</span> Steroid medication

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<span class="mw-page-title-main">Amcinonide</span> Chemical compound

Amcinonide is a topical glucocorticoid used to treat itching, redness and swelling associated with several dermatologic conditions such as atopic dermatitis and allergic contact dermatitis. Amcinonide can also be classified as a multi-functional small molecule corticosteroid, which has been approved by the FDA and is currently marketed as an ointment, lotion, or cream. It acts as both a transcription factor for responses to glucocorticoids and modulator for other transcription factors while also regulating phospholipase A2 activity.

Topical steroids are the topical forms of corticosteroids. Topical steroids are the most commonly prescribed topical medications for the treatment of rash and eczema. Topical steroids have anti-inflammatory properties and are classified based on their skin vasoconstrictive abilities. There are numerous topical steroid products. All the preparations in each class have the same anti-inflammatory properties but essentially differ in base and price.

<span class="mw-page-title-main">Topical glucocorticoids</span>

Topical glucocorticoids are the topical forms of glucocorticoids. Topical glucocorticoids are used in the treatment of many skin conditions. They provide anti-inflammatory, antimitotic, and immune-system suppressing actions through various mechanisms.

Anti-allergic agents are medications used to treat allergic reactions. Anti-allergic agents have existed since 3000 B.C in countries such as China and Egypt. It was not until 1933 when antihistamines, the first type of anti-allergic agents, were developed. Common allergic diseases include allergic rhinitis, allergic asthma and atopic dermatitis with varying symptoms, including runny nose, watery eyes, itchiness, coughing, and shortness of breath. More than one-third of the world's population is currently being affected by one or more allergic conditions.

References

  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. 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.
  4. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 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.
  5. 1 2 3 4 5 6 Triamcinolone (systemic) Professional Drug Facts . Accessed 19 August 2020.
  6. 1 2 3 4 5 6 7 "Triamcinolone Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019.
  7. ↑ "Triamcinolone Use During Pregnancy". Drugs.com. Retrieved 3 March 2019.
  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.
  12. ↑ "Triamcinolone: Uses, Dosage, Side Effects, Warnings". Drugs.com.
  13. ↑ "Azmacort Inhaler: Side Effects, Dosage & Uses". Drugs.com.
  14. ↑ "Alcon Receives FDA Approval of Triesence Injectable Triamcinolone Suspension for Use in Eye Surgery". Drugs.com.
  15. ↑ Chong M, Fonacier L (December 2016). "Treatment of Eczema: Corticosteroids and Beyond". Clinical Reviews in Allergy & Immunology. 51 (3): 249–262. doi:10.1007/s12016-015-8486-7. PMID   25869743. S2CID   44337035.
  16. ↑ Eichenfield LF, Tom WL, Berger TG, Krol A, Paller AS, Schwarzenberger K, et al. (July 2014). "Guidelines of care for the management of atopic dermatitis: section 2. Management and treatment of atopic dermatitis with topical therapies". Journal of the American Academy of Dermatology. 71 (1): 116–132. doi:10.1016/j.jaad.2014.03.023. PMC   4326095 . PMID   24813302. Topical corticosteroids (TCS) are used in the management of AD in both adults and children and are the mainstay of anti-inflammatory therapy.
  17. 1 2 3 4 5 6 7 Haberfeld H, ed. (2020). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Volon 4 mg-Tabletten.
  18. ↑ "Drugs and Treatments – Nasacort AQ Nasl – Patient Handout". WebMD . Retrieved 24 March 2008.
  19. ↑ Moore CD, Roberts JK, Orton CR, Murai T, Fidler TP, Reilly CA, et al. (February 2013). "Metabolic pathways of inhaled glucocorticoids by the CYP3A enzymes". Drug Metabolism and Disposition. 41 (2): 379–389. doi:10.1124/dmd.112.046318. PMC   3558858 . PMID   23143891.
  20. ↑ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1228–. ISBN   978-1-4757-2085-3.
  21. ↑ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 1054–. ISBN   978-3-88763-075-1.
  22. ↑ "Perrigo Announces Launch Of Generic Version Of Nasacort AQ". 15 June 2011.
  23. ↑ Chang CW, Huang TY, Tseng YC, Chang-Chien GP, Lin SF, Hsu MC (November 2014). "Positive doping results caused by the single-dose local injection of triamcinolone acetonide". Forensic Science International. 244: 1–6. doi: 10.1016/j.forsciint.2014.07.024 . PMID   25126738.
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