Budesonide

Budesonide
Clinical data
Trade names Pulmicort, Rhinocort, Entocort, others
Synonyms 11β,21-Dihydroxy-16α,17α-(butylidenebis(oxy))pregna-1,4-diene-3,20-dione
AHFS/Drugs.com Monograph
MedlinePlus a608007
License data
Pregnancy
category
  • US: B (No risk in non-human studies)
    Routes of
    administration    		 By mouth, nasal, tracheal, rectal
    ATC code
    Legal status
    Legal status
    Pharmacokinetic data
    Bioavailability 10-20% (first pass effect)
    Protein binding 85-90%
    Metabolism Hepatic CYP3A4
    Elimination half-life 2.0-3.6 hours
    Excretion Urine, feces
    Identifiers
    CAS Number
    PubChem CID
    DrugBank
    ChemSpider
    UNII
    KEGG
    ChEMBL
    PDB ligand
    ECHA InfoCard 100.051.927 Edit this at Wikidata
    Chemical and physical data
    Formula C25H34O6
    Molar mass 430.534 g/mol
    3D model (JSmol)
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    Budesonide (BUD), sold under the brand name Pulmicort among others, is a medication of the corticosteroid type.[1] It is available as an inhaler, pill, nasal spray, and rectal forms.[1][2] The inhaled form is used in the long-term management of asthma and chronic obstructive pulmonary disease (COPD).[1][3][4] The nasal spray is used for allergic rhinitis and nasal polyps.[2][5] The pills in a delayed release form and rectal forms may be used for inflammatory bowel disease including Crohn's disease, ulcerative colitis and microscopic colitis.[6][7][8]

    Common side effects with the inhaled form include respiratory infections, cough, and headaches.[1] Common side effects with the pills include feeling tired, vomiting, and joint pains.[1] Serious side effects include an increased risk of infection, loss of bone strength, and cataracts.[1] Long-term use of the pill form may cause adrenal insufficiency.[1] Stopping the pills suddenly following long-term use may therefore be dangerous.[1] The inhaled form is generally safe in pregnancy.[1] Budesonide is mainly acting as a glucocorticoid.[1]

    Budesonide was initially patented in 1973.[9] Commercial use as an asthma medication began in 1981.[10] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[11] Some forms are available as a generic medication.[12] The wholesale price in the developing world for an inhaler containing 200 doses is about US$5 to US$7 as of 2014.[13] As of 2015 the cost for a typical month of the inhaler medication in the United States is US$100 to US$200.[12]

    Medical uses

    Asthma

    Budesonide is nebulized for maintenance and prophylactic treatment of asthma including patients who require oral corticosteroids and those who may benefit from a systemic dose reduction.[14]

    Inflammatory bowel disease

    Formulations of delayed-release Budesonide are an effective treatment for mild-to-moderately active Crohn's disease involving the ileum and/or ascending colon.[15] A Cochrane review found evidence for up to 3 months (but not longer) of maintenance of remission Crohn's disease.[16]

    Budesonide assists in the induction of remission in people with active ulcerative colitis.[17]

    Budesonide is highly effective and recommended as the drug of choice in microscopic colitis, for induction and maintenance of remission, and for both the lymphocytic colitis and collagenous colitis forms.[18]

    Allergic rhinitis

    Nasal spray budesonide is a treatment for allergic rhinitis.[19]

    Side effects

    Budesonide may cause:[20]

    • Nose irritation or burning
    • Bleeding or sores in the nose
    • Lightheadedness
    • Upset stomach
    • Cough
    • Hoarseness
    • Dry mouth
    • Rash
    • Sore throat
    • Bad taste in mouth
    • Change in mucus
    • Blurred vision [21]

    In addition, the following symptoms should be reported immediately:

    • Difficulty breathing or swelling of the face
    • White patches in the throat, mouth, or nose
    • Irregular menstrual periods
    • Severe acne
    • On rare occasions, behavioral changes (mostly affecting children)[20]

    Contraindications

    Budesonide is contraindicated as a primary treatment of status asthmaticus or other acute episode of asthma where intensive measures are required.[22] It is also contraindicated for patients who have hypersensitivity to budesonide.[23]

    Interactions

    Those taking tablets or capsules orally should avoid grapefruit juice and echinacea.

    Also, high fat meals delay absorption but do not impede absorption.

    Pharmacology

    Budesonide is an agonist of glucocorticoid receptors. Among its effects are:

    • Controls the rate of protein synthesis.
    • Depresses the migration of polymorphonuclear leukocytes and fibroblasts.
    • Reverses capillary permeability and lysosomal stabilization at the cellular level to prevent or control inflammation.
    • Has a potent glucocorticoid activity and weak mineralocorticoid activity.

    Pharmacokinetics

    • Onset of action: Nebulization: 2–8 days; Inhalation: 24 hours
    • Peak effect: Nebulization: 4–6 weeks; Inhalation: 1–2 weeks
    • Distribution: 2.2-3.9 L/kg
    • Protein binding: 85% to 90%
    • Metabolism: Hepatic via CYP3A4 to two metabolites: 16 alpha-hydroxyprednisolone and 6 beta-hydroxybudesonide; minor activity
    • Bioavailability: Limited by high first-pass effect; Capsule: 9% to 21%; Nebulization: 6%; Inhalation: 6% to 13%
    • Half-life elimination: 2-3.6 hours
    • Time to peak: Capsule: 0.5–10 hours (variable in Crohn's disease); Nebulization: 10–30 minutes; Inhalation: 1–2 hours; Tablet: 7.4-19.2 hours
    • Excretion: Urine (60%) and feces as metabolites.

    Chemistry

    Budesonide, also known as 11β,21-dihydroxy-16α,17α-(butylidenebis(oxy))pregna-1,4-diene-3,20-dione, is a synthetic pregnane steroid and non-halogenated cyclic ketal corticosteroid.[24][25] It is the C16α hydroxyl, C16α,17α cyclic ketal with butyraldehyde derivative of prednisolone (11β,17α,21-trihydroxypregna-1,4-diene-3,20-dione).[24][25]

    Stereoisomerism

    Budesonide
    (2 stereoisomers)

    (22R)-configuration
    (22S)-configuration

    Society and culture

    Brand names

    Inhaler for a powder based in budesonide and formoterol

    Aeronide (TH); Aquacort (DE); B Cort (CO); Bronex (PH); Budair (MY); Budecort DP (MY); Budenofalk (DE, GB, HK, KP, PH, SG); Budeson (AR); Budeson Aqua (AR); BudeSpray (TH); Budiair (KP); Budicort Respules (IL); Budinide (KSA); Bunase (TH); Clebudan (CN); Cycortide (HK); Denecort (PH); Duasma (TW); Eltair (MY); Entocort (AR, AT, BE, BR, CH, CZ, DK, FI, FR, GB, HK, IE, IL, IT, KP, NL, NO, PL, PT, SE, TR); Giona Easyhaler (MY, SG, TH); Inflammide (PE); Miflonid (CZ); Miflonide (BE, DE, IL, IT, NZ, PT); Neumocort (PY); Novopulmon (DE, FR); Pulmicon Susp for Nebulizer (KP); Pulmicort (AT, BE, BG, BR, CH, CL, CN, CO, CR, CZ, DE, DK, DO, EE, FI, FR, GB, GR, GT, HN, ID, IN, NI, NL, NO, PA, PK, PL, PT, RU, SE, SV, TR, TW, UY, VE, ZA); Pulmicort Nasal Turbohaler (CL, KE, MU, NG); Pulmicort Turbuhaler (KE, MU, NG); Rafton (FR); Rhinocort (AU); Rhinocort Aqua (HK); Rhinoside (GR); Symbicort (FR, US, ZA) Uceris (US)

    See also

    References

    1. 1 2 3 4 5 6 7 8 9 10 "Budesonide". The American Society of Health-System Pharmacists. Archived from the original on 2015-11-28. Retrieved Dec 2, 2015.
    2. 1 2 "Budesonide eent". The American Society of Health-System Pharmacists. Archived from the original on 2015-12-08. Retrieved Dec 2, 2015.
    3. ↑ De Coster, DA; Jones, M (2014). "Tailoring of corticosteroids in COPD management". Current Respiratory Care Reports. 3 (3): 121–132. doi:10.1007/s13665-014-0084-2. PMC 4113685. PMID 25089228.
    4. ↑ Christophi, GP; Rengarajan, A; Ciorba, MA (2016). "Rectal budesonide and mesalamine formulations in active ulcerative proctosigmoiditis: efficacy, tolerance, and treatment approach". Clinical and Experimental Gastroenterology. 9: 125–30. doi:10.2147/CEG.S80237. PMC 4876845. PMID 27274301.
    5. ↑ Rudmik, L; Schlosser, RJ; Smith, TL; Soler, ZM (July 2012). "Impact of topical nasal steroid therapy on symptoms of nasal polyposis: a meta-analysis". The Laryngoscope. 122 (7): 1431–7. doi:10.1002/lary.23259. PMID 22410935.
    6. ↑ Silverman J, Otley A (2011). "Budesonide in the treatment of inflammatory bowel disease". Expert Rev Clin Immunol. 7 (4): 419–28. doi:10.1586/eci.11.34. PMID 21790284.
    7. ↑ Pardi DS, Tremaine WJ, Carrasco-Labra A (2016). "American Gastroenterological Association Institute Technical Review on the Medical Management of Microscopic Colitis". Gastroenterology. 150 (1): 247–274.e11. doi:10.1053/j.gastro.2015.11.006. PMID 26584602.
    8. ↑ British national formulary : BNF 58 (58 ed.). British Medical Association. 2009. pp. 56–57. ISBN 9780857111562.
    9. ↑ Domeij, Bengt (2000). Pharmaceutical patents in Europe. The Hague: Kluwer Law International. p. 278. ISBN 9789041113481. Archived from the original on 2015-12-08.
    10. ↑ Hamley, Peter (2015). Small Molecule Medicinal Chemistry: Strategies and Technologies. John Wiley & Sons. p. 390. ISBN 9781118771693. Archived from the original on 2015-12-08.
    11. ↑ "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Archived (PDF) from the original on 13 December 2016. Retrieved 8 December 2016.
    12. 1 2 Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 451. ISBN 9781284057560.
    13. ↑ "Budesonide". International Drug Price Indicator Guide. Retrieved 5 December 2015.
    14. ↑ Global Strategy for Asthma Management and Prevention, Global Initiative for Asthma (GINA) 2011. Available at http://www.ginasthma.org Archived 2013-10-14 at the Wayback Machine.
    15. ↑ Lichtenstein GR, Hanauer SB, Sandborn WJ (2009). "Management of Crohn's Disease in Adults". Am J Gastroenterol. 104 (2): 465–83. doi:10.1038/ajg.2008.168. PMID 19174807.
    16. ↑ Kuenzig ME, Rezaie A, Seow CH, Otley AR, Steinhart AH, Griffiths AM, et al. (2014). "Budesonide for maintenance of remission in Crohn's disease". Cochrane Database Syst Rev. 8 (8): CD002913. doi:10.1002/14651858.CD002913.pub3. PMID 25141071.
    17. ↑ Habal FM, Huang VW (2012). "Review Article: A Decision-Making Algorithm For the Management of Pregnancy in the Inflammatory Bowel Disease Patient". Aliment Pharmacol Ther. 35 (5): 501–15. doi:10.1111/j.1365-2036.2011.04967.x. PMID 22221203.
    18. ↑ Pardi, Darrell (2016). "American Gastroenterological Association Institute Technical Review on the Medical Management of Microscopic Colitis". www.gastrojournal.org.
    19. ↑ Stanaland, BE (April 2004). "Once-daily budesonide aqueous nasal spray for allergic rhinitis: a review". Clinical Therapeutics. 26 (4): 473–92. doi:10.1016/s0149-2918(04)90050-1. PMID 15189745.
    20. 1 2 BUDESONIDE - NASAL AEROSOL INHALER (Rhinocort) side effects, medical uses, and drug interactions Archived November 6, 2008, at the Wayback Machine.
    21. ↑ "Budesonide: CMDh scientific conclusions and grounds for variation, amendments to the product information and timetable for the implementation - PSUSA/00000449/201604" (pdf). European Medicines Agency (EMA). March 10, 2017. Archived (PDF) from the original on 8 September 2017. Retrieved 19 May 2017.
    22. ↑ Todd GR, Acerini CL, Buck JJ, Murphy NP, Ross-Russell R, Warner JT, McCance DR (2002). "Acute Adrenal Crisis in Asthmatics Treated With High-Dose Fluticasone Propionate". Eur Respir J. 19 (6): 1207–9. doi:10.1183/09031936.02.00274402. PMID 12108877.
    23. ↑ Todd GR, Acerini CL, Ross-Russell R, Zahra S, Warner JT, McCance D (2002). "Survey of Adrenal Crisis Associated With Inhaled Corticosteroids in the United Kingdom". Arch Dis Child. 87 (6): 457–61. doi:10.1136/adc.87.6.457. PMC 1755820. PMID 12456538.
    24. 1 2 J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 186, 1011. ISBN 978-1-4757-2085-3. Archived from the original on 8 September 2017.
    25. 1 2 Thomas L. Lemke; David A. Williams (2008). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 1253–. ISBN 978-0-7817-6879-5. Archived from the original on 2017-09-08.
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