Budesonide

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Budesonide
250px
Budesonide ball-and-stick.png
Systematic (IUPAC) name
11β,21-Dihydroxy-16α,17α-[butane-1,1-diylbis(oxy)]pregna-1,4-diene-3,20-dione
Clinical data
Trade names Pulmicort, Rhinocort, Entocort, others
AHFS/Drugs.com monograph
MedlinePlus a608007
Licence data EMA:Link, US Daily Med:link
Pregnancy
category
  • AU: A / B3
  • US: B (No risk in non-human studies)
Legal status
  • AU: S2 (Pharmacy only) / S4
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: OTC / Rx-only
  • EU: Rx-only
Routes of
administration		 By mouth, nasal, tracheal, rectal, inhalation
Pharmacokinetic data
Bioavailability 10-20% (first pass effect)
Protein binding 85-90%
Metabolism Liver CYP3A4
Biological half-life 2.0-3.6 hours
Excretion Urine, feces
Identifiers
CAS Number 51333-22-3 YesY
ATC code A07EA06 (WHO) D07AC09, R01AD05, R03BA02
PubChem CID: 40000
DrugBank DB01222 YesY
ChemSpider 4444479 N
UNII Q3OKS62Q6X YesY
KEGG D00246 YesY
ChEMBL CHEMBL1370 N
PDB ligand ID 8W5 (PDBe, RCSB PDB)
Chemical data
Formula C25H34O6
Molecular mass 430.54 g·mol−1
  • CCCC1O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@@]5([C@H]4[C@H](C[C@@]3([C@@]2(O1)C(=O)CO)C)O)C
  • InChI=1S/C25H34O6/c1-4-5-21-30-20-11-17-16-7-6-14-10-15(27)8-9-23(14,2)22(16)18(28)12-24(17,3)25(20,31-21)19(29)13-26/h8-10,16-18,20-22,26,28H,4-7,11-13H2,1-3H3/t16-,17-,18-,20+,21?,22+,23-,24-,25+/m0/s1 N
  • Key:VOVIALXJUBGFJZ-KWVAZRHASA N
 NYesY (what is this?)  (verify)

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.[11] Some forms are available as a generic medication.[12] In 2019, generic budesonide was listed as involved in Teva's price fixing scheme in the United States.[13] In 2017, it was the 190th most commonly prescribed medication in the United States, with more than three million prescriptions.[14][15]

During the 2020 COVID-19 pandemic, doctors and researchers observed that patients already prescribed inhaled corticosteroids appeared to develop less serious illness when diagnosed with COVID-19, despite often having conditions such as asthma that might be thought to lead to more serious illness.[citation needed] In June 2020, UK and Australian researchers began a UK-based trial of budesonide as an early-intervention treatment for COVID-19, with results expected in September of that year.[citation needed]

Medical uses

Asthma

Budesonide is given by metered-dose inhaler or nebulizer for maintenance and prophylactic treatment of asthma, including patients who require oral corticosteroids and those who may benefit from a systemic dose reduction.[16]

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.[17] A Cochrane review found evidence for up to three months (but not longer) of maintenance of remission in Crohn's disease.[18]

Budesonide assists in the induction of remission in people with active ulcerative colitis.[19]

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.[20]

Allergic rhinitis

Budesonide in the form of nasal sprays is a treatment for allergic rhinitis.[21]

Eosinophilic esophagitis

Topical budesonide has considerable effects in eosinophilic esophagitis.[22] For this use, it is formulated as a tablet that disperses in the mouth, and sold under the trade name Jorveza.[23]

Side effects

Budesonide may cause:[24][25]

  • 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[26]

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)[24]

Contraindications

Budesonide is contraindicated as a primary treatment of status asthmaticus or other acute episode of asthma where intensive measures are required.[27] It is also contraindicated for patients who have hypersensitivity to budesonide.[28]

Interactions

Those taking tablets or capsules orally should avoid grapefruit and grapefruit juice[29][30] and echinacea.[31]

Also, high-fat meals delay absorption but do not impede absorption.[32]

Pharmacology

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

Pharmacokinetics

  • Onset of action: Nebulization: 2–8 days; Inhalation: 24 hours; Nasal: 10 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.[medical citation needed]

Chemistry

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See also: List of corticosteroids and List of corticosteroid cyclic ketals

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.[35][36] It is the C16α hydroxyl, C16α,17α cyclic ketal with butyraldehyde derivative of prednisolone (11β,17α,21-trihydroxypregna-1,4-diene-3,20-dione).[35][36]

Stereoisomerism

Budesonide
(2 stereoisomers)
(R)-Budesonid
(22R)-configuration		 (S)-Budesonid
(22S)-configuration

Society and culture

Brand names

File:Budesonide and formoterol inhaler.jpg
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); Cortiment (GB); 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);[37] 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);[37] Pulmicort Nasal Turbohaler (CL, KE, MU, NG); Pulmicort Turbuhaler (KE, MU, NG); Rafton (FR); Rhinocort (AU); Rhinocort Aqua (HK);[38] Rhinoside (GR); Symbicort (FR, US, ZA) Uceris (US).

Research

COVID-19

During the 2020 COVID-19 pandemic, doctors and researchers observed that patients already prescribed inhaled corticosteroids appeared to develop less serious illness when diagnosed with COVID-19, despite often having conditions such as asthma that might be thought to lead to more serious illness.[39][40] Subsequently, the drug was explored as a possible treatment for the disease.[41] In June 2020, UK and Australian researchers began a UK-based trial of budesonide as an early-intervention treatment for COVID-19, with results expected in September of that year.[42]

See also

References

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External links

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  16. ↑ Global Strategy for Asthma Management and Prevention, Global Initiative for Asthma (GiNA) 2011. Available at https://www.ginasthma.org Archived 2013-10-14 at the Wayback Machine
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  29. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  30. ↑ Theodore M. Bayless, Stephen B. Hanauer (2014). Advanced Therapy of Inflammatory Bowel Disease, Volume 2, IBD and Crohn's Disease
  31. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  32. ↑ Carol K. Taketomo, Jane Hurlburt Hodding, Donna M. Kraus (2009). Pediatric Dosage Handbook; Including Neonatal Dosing, Drug Administration & Extemporaneous Preparations
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  38. ↑ H. Winter Griffith (2014). Complete Guide to Prescription and Nonprescription Drugs 2015; Features an A-Z List of Conditions and the Drugs Most Commonly Used, 2015 Edition
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