Budesonide

Last updated

Budesonide
Budesonide skeletal.svg
Budesonide ball-and-stick.png
Clinical data
Trade names Pulmicort, Rhinocort, Entocort, others
Other namesBUD
AHFS/Drugs.com Monograph
MedlinePlus a608007
License data
Pregnancy
category
  • AU:A/ B3
Routes of
administration 		By mouth, nasal, tracheal, rectal, inhalation
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 10-20% (first pass effect)
Protein binding 85-90%
Metabolism Liver CYP3A4
Elimination half-life 2.0-3.6 hours
Excretion Urine, feces
Identifiers
  • 11β,21-Dihydroxy-16α,17α-[butane-1,1-diylbis(oxy)]pregna-1,4-diene-3,20-dione
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard 100.051.927 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C25H34O6
Molar mass 430.541 g·mol−1
3D model (JSmol)
  • 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 X mark.svgN
  • Key:VOVIALXJUBGFJZ-KWVAZRHASA X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Budesonide, sold under the brand name Pulmicort, among others, is a steroid medication. [8] It is available as an inhaler, nebulization solution, pill, nasal spray, and rectal forms. [8] [9] The inhaled form is used in the long-term management of asthma and chronic obstructive pulmonary disease (COPD). [8] [10] [11] The nasal spray is used for allergic rhinitis and nasal polyps. [9] [12] Modified-release pills or capsules and rectal forms may be used for inflammatory bowel disease including Crohn's disease, ulcerative colitis, and microscopic colitis. [13] [14] [15]

Contents

Common side effects with the inhaled form include respiratory infections, cough, and headaches. [16] Common side effects with the pills include feeling tired, vomiting, and joint pains. [16] Serious side effects include an increased risk of infection, loss of bone strength, and cataracts. [16] Long-term use of the pill form may cause adrenal insufficiency. [16] Stopping the pills suddenly following long-term use may therefore be dangerous. [16] The inhaled form is generally safe in pregnancy. [16] Budesonide chiefly acts as a glucocorticoid. [16]

Budesonide was initially patented in 1973. [17] Commercial use as an asthma medication began in 1981. [18] It is on the World Health Organization's List of Essential Medicines. [19] Some forms are available as a generic medication. [20] [21] In 2021, it was the 185th most commonly prescribed medication in the United States, with more than 2 million prescriptions. [22] [23]

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. [24]

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. [25] A Cochrane review found evidence for up to three months (but not longer) of maintenance of remission in Crohn's disease. [26]

Budesonide assists in the induction of remission in people with active ulcerative colitis. [27]

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. [28] [29]

Allergic rhinitis

Budesonide in the form of nasal sprays is a treatment for allergic rhinitis. [30]

Eosinophilic esophagitis

Topical budesonide has considerable effects in eosinophilic esophagitis. [31] For this use, it is formulated as a tablet that disperses in the mouth, and sold under the brand name Jorveza. [32]

Berger's disease

Budesonide (Tarpeyo (US); Kinpeygo (EU, UK)) is indicated to reduce proteinuria (increased protein levels in the urine) in adults with primary immunoglobulin A (IgA) nephropathy (Berger's disease) at risk of rapid disease progression. [3] [33] [7]

Side effects

Nasal budesonide inhalers have been associated with a number of side effects. [34] [35] These include 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, and blurred vision. [36] Other symptoms which should be reported immediately include difficulty in breathing, swelling of the face, white patches in the throat, mouth, or nose, irregular menstrual periods, severe acne, and on rare occasions, behavioral changes (mostly affecting children). [34]

Overdose

Acute toxicity from an overdose of Budesonide is significantly more rare than an overdosing of budesonide over a prolonged period of therapy, however both can can cause systemic toxicity that manifests as hypercortisolism. [37] Symptoms of an overdose include more specific symptoms such as darkening and thinning of the skin, changes in body fat around the face, neck, back, and waist, increased acne or facial hair, menstrual problems, impotence, or loss of interest in sex, as well as some less specific symptoms such as diarrhea, dizziness, loss of appetite, mental depression, nausea, skin rash, unusual tiredness or weakness, or vomiting. [38] [39]

Contraindications

Budesonide is contraindicated in people with:

In Canada, there are additional contraindications labeled for Budesonide for people with:

Interactions

Budesonide is mainly metabolized in the liver by the enzyme CYP3A4. [43] [44] Drugs that are CYP3A4 inhibitors such as ketoconazole, clarithromycin, ritonavir, and nefazodone, among many others, may inhibit the metabolism of Budesonide, prolonging its elimination and leading to possible increased rates of corticosteroid adverse effects due to unwanted drug accumulation. [43] [45] Grapefruit is also a potent inhibitor of CYP3A4, and therefore its consumption is not recommended while on budesonide treatment. [43] [46]

Pharmacology

Mechanism of action

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

Pharmacokinetics

Different pharmacokinetic proprieties can be seen in the absorption of budesonide depending on how it is formulated. When taken as an extended-release oral capsule, budesonide has an oral bioavailability of 9–21% and reaches peak plasma concentrations (Cmax) within 2–8 hours. [50] A high fat meal when taken with the capsule can lengthen the time it takes to reach Cmax by another 2.3 hours, but will not have any other affects on the pharmacokinetics properties of budesonide. [51] When inhaled through an metered dose inhaler, 34% of budesonide is deposited in the lung with a bioavailability of 39% and reaches Cmax within 10 minutes. [51] [52] When nebulized, budesonide has an bioavailability of 6% and reaches Cmax within 1–3 hours. [52] [51] When formulated as a rectal foam, budesonide has an bioavailability of 3% to 27% and reaches Cmax around 1.5 hours. [53]

The plasma protein binding of budesonide is around 85-90%, with an apparent volume of distribution of 2.2-3.9L/kg. [51] [50] Budesonide is 80-90% metabolized at first pass in the liver by the hepatocytic cytochrome P450 isoenzyme 3A4 (CYP3A4) into two metabolites: 16 alpha-hydroxyprednisolone and 6 beta-hydroxybudesonide. Both of these metabolites have a negligible glucocorticoid activity of less than 1% compared to the parent compound budesonide. [51] 60% of budesonide is excreted is through the urine as its metabolites, no unchanged budesonide is detectable in urine. [51] The average elimination half-life in plasma is between 2-3.6 hours. [51]

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. [54] [55] It is the C16α hydroxyl, C16α,17α cyclic ketal with butyraldehyde derivative of prednisolone (11β,17α,21-trihydroxypregna-1,4-diene-3,20-dione). [54] [55]

Stereoisomerism

Budesonide
(2 stereoisomers)
22R-Budesonid V4.svg
(22R)-configuration		 22S-Budesonid V4.svg
(22S)-configuration

Society and culture

Dry powder inhaler that contains a combination of budesonide and formoterol. Budesonide and formoterol inhaler.jpg
Dry powder inhaler that contains a combination of budesonide and formoterol.

Brand names

Budesonide is a drug that is marketed under various brand and generic names internationally, some notable examples for each formulation are listed here;

Inhalation: Pulmicort; Pulmicort Flexhaler, Pulmicort Nebuamp, Pulmicort Turbuhaler, TARO-Budesonide, TEVA-Budesonide, Novolizer budesonid meda, Budenova. [56] [57]

Systemic (oral pills): Tarpeyo, Uceris, Eohilia, Cortiment, Entocort Jorveza. [58] [57]

Nasal: MYLAN-Budesonide AQ, Rhinocort Aqua, Formancis. [59] [57]

Topical: Entocort, Uceris, Budenofalk. [60] [57]

Economics

In 2019, generic budesonide was listed as being involved in Teva's price fixing scheme in the United States. [61]

In May 2022, the Committee for Medicinal Products for Human Use (CHMP) of the European Medicines Agency (EMA) adopted a positive opinion, recommending the granting of a conditional marketing authorization for the medicinal product Kinpeygo, intended for the treatment of primary immunoglobulin A nephropathy. [62] The applicant for this medicinal product is Calliditas Therapeutics AB. [62] Kinpeygo is a hybrid medicine of Entocort which has been authorised in the EU since 2 April 1992. [62] Kinpeygo contains the same active substance as Entocort but has a different formulation and a different indication. [62] Kinpeygo was approved for medical use in the European Union in July 2022. [7] [63]

Research

COVID-19

Budesonide was recommended in April 2021 by the UK's NHS to treat COVID-19 on a case-by-case basis for those aged 50 years of age and older. [64] After a University of Oxford research team found in a trial with 1,700 patients that budesonide could benefit many people over 50 with COVID-19 symptoms, it was recommended from 12 April 2021, by the National Health Service in the UK for general practitioners (GPs) to treat COVID-19 on a case-by-case basis. [65] [66] Results of a large-scale trial published in August 2021 suggest that inhaled budesonide improves the time of recovery and people's well-being during the recovery process. [67] [68] Inhalational budesonide was added to the recommended treatment for cases of COVID-19 in India in April 2021. [69] [70] The NIH recommendation was withdrawn in December 2021 citing the need for more research. [71] [72]

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">Salbutamol</span> Short-acting bronchodilator used for acute asthma

Salbutamol, also known as albuterol and sold under the brand name Ventolin among others, is a medication that opens up the medium and large airways in the lungs. It is a short-acting β2 adrenergic receptor agonist that causes relaxation of airway smooth muscle. It is used to treat asthma, including asthma attacks and exercise-induced bronchoconstriction, as well as chronic obstructive pulmonary disease (COPD). It may also be used to treat high blood potassium levels. Salbutamol is usually used with an inhaler or nebulizer, but it is also available in a pill, liquid, and intravenous solution. Onset of action of the inhaled version is typically within 15 minutes and lasts for two to six hours.

<span class="mw-page-title-main">Ipratropium bromide</span> Type of anticholinergic

Ipratropium bromide, sold under the trade name Atrovent among others, is a type of anticholinergic medication which is applied by different routes: inhaler, nebulizer, or nasal spray, for different reasons.

<span class="mw-page-title-main">Nicotine replacement therapy</span> Treatment for tobacco use disorder

Nicotine replacement therapy (NRT) is a medically approved way to treat people with tobacco use disorder by taking nicotine through means other than tobacco. It is used to help with quitting smoking or stopping chewing tobacco. It increases the chance of quitting tobacco smoking by about 55%. Often it is used along with other behavioral techniques. NRT has also been used to treat ulcerative colitis. Types of NRT include the adhesive patch, chewing gum, lozenges, nose spray, and inhaler. The use of multiple types of NRT at a time may increase effectiveness.

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

Salmeterol is a long-acting β2 adrenergic receptor agonist (LABA) used in the maintenance and prevention of asthma symptoms and maintenance of chronic obstructive pulmonary disease (COPD) symptoms. Symptoms of bronchospasm include shortness of breath, wheezing, coughing and chest tightness. It is also used to prevent breathing difficulties during exercise.

<span class="mw-page-title-main">Budesonide/formoterol</span> Medication for asthma & chronic obstructive pulmonary disease

Budesonide/formoterol, sold under the brand name Symbicort among others, is a fixed-dose combination medication used in the management of asthma or chronic obstructive pulmonary disease (COPD). It contains budesonide, a steroid and formoterol, a long-acting β2-agonist (LABA). The product monograph does not support its use for sudden worsening or treatment of active bronchospasm. However, a 2020 review of the literature does support such use. It is used by breathing in the medication.

<span class="mw-page-title-main">Formoterol</span> Bronchiodilator Drug

Formoterol, also known as eformoterol, is a long-acting β2 agonist (LABA) used as a bronchodilator in the management of asthma and chronic obstructive pulmonary disease (COPD). Formoterol has an extended duration of action compared to short-acting β2 agonists such as salbutamol (albuterol), which are effective for 4 h to 6 h. Formoterol has a relatively rapid onset of action compared to other LABAs, and is effective within 2-3 minutes. The 2022 Global Initiative for Asthma report recommends a combination formoterol/inhaled corticosteroid inhaler as both a preventer and reliever treatment for asthma in adults. In children, a short-acting β2 adrenergic agonist is still recommended.

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

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<span class="mw-page-title-main">Inhaler</span> Medical device used to deliver medicines into lungs

An inhaler is a medical device used for delivering medicines into the lungs through the work of a person's breathing. This allows medicines to be delivered to and absorbed in the lungs, which provides the ability for targeted medical treatment to this specific region of the body, as well as a reduction in the side effects of oral medications. There are a wide variety of inhalers, and they are commonly used to treat numerous medical conditions with asthma and chronic obstructive pulmonary disease (COPD) being among the most notable.

Beta<sub>2</sub>-adrenergic agonist Compounds that bind to and activate adrenergic beta-2 receptors

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

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

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<span class="mw-page-title-main">Metered-dose inhaler</span> Device that helps deliver a specific amount of medication to the lungs

A metered-dose inhaler (MDI) is a device that delivers a specific amount of medication to the lungs in the form of a short burst of aerosolized medicine that is usually self-administered by the patient via inhalation. It is the most commonly used delivery system for treating asthma, chronic obstructive pulmonary disease (COPD) and other respiratory diseases. The medication in a metered dose inhaler is most commonly a bronchodilator, corticosteroid or a combination of both for treating asthma and COPD. Other medications less commonly used but also administered by MDI are mast cell stabilizers, such as cromoglicate or nedocromil.

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

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

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

Indacaterol is an ultra-long-acting beta-adrenoceptor agonist developed by Novartis. It needs to be taken only once a day, unlike the related drugs formoterol and salmeterol. It is licensed only for the treatment of chronic obstructive pulmonary disease (COPD). It is delivered as an aerosol formulation through a dry powder inhaler.

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<span class="mw-page-title-main">Tiotropium bromide</span> Long-acting bronchodilator in the maintenance of COPD and asthma

Tiotropium bromide, sold under the brand name Spiriva among others, is a long-acting bronchodilator used in the management of chronic obstructive pulmonary disease (COPD) and asthma. Specifically it is used during periods of breathing difficulty to prevent them from getting worse, rather than to prevent them from happening. It is used by inhalation through the mouth. Onset typically begins within half an hour and lasts for 24 hours.

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Salbutamol/budesonide, sold under the brand name Airsupra, is a fixed-dose combination medication for the treatment of bronchoconstriction and asthma. It is a combination of salbutamol sulfate, a short-acting beta2-adrenergic agonist, and budesonide, an inhaled corticosteroid. It is inhaled using a pressurized metered-dose inhaler.

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