Budesonide
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MedKoo CAT#: 300250

CAS#: 51333-22-3

Description: Budesonide is a glucocorticoid steroid for the treatment of asthma, non-infectious rhinitis (including hay fever and other allergies), and for treatment and prevention of nasal polyposis. Additionally, it is used for Crohn's disease (inflammatory bowel disease). It is marketed by AstraZeneca as a nasal inhalant under the brand name Rhinocort (in Denmark, as Rhinosol), as an oral inhalant under the brand name Pulmicort (in Israel, Budicort), and as either an enema or a modified release oral capsule under the brand name Entocort. It is also sold in combination with formoterol (Oxis) in a single inhaler, under the brand name Symbicort.


Chemical Structure

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Budesonide
CAS# 51333-22-3

Theoretical Analysis

MedKoo Cat#: 300250
Name: Budesonide
CAS#: 51333-22-3
Chemical Formula: C25H34O6
Exact Mass: 430.23554
Molecular Weight: 430.53
Elemental Analysis: C, 69.74; H, 7.96; O, 22.30

Price and Availability

Size Price Availability Quantity
100.0mg USD 250.0 Ready to ship
200.0mg USD 450.0 Ready to ship
500.0mg USD 650.0 Ready to ship
1.0g USD 950.0 Ready to ship
2.0g USD 1650.0 Ready to ship
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Synonym: S 1320; S-1320; S1320; Spirocort; Rhinocort; Budesonide;

IUPAC/Chemical Name: (6aR,6bS,7S,8aS,8bS,11aR,12aS,12bS)-7-hydroxy-8b-(2-hydroxyacetyl)-6a,8a-dimethyl-10-propyl-6a,6b,7,8,8a,8b,11a,12,12a,12b-decahydro-1H-naphtho[2',1':4,5] indeno[1,2-d][1,3]dioxol-4(2H)-one

InChi Key: VOVIALXJUBGFJZ-KWVAZRHASA-N

InChi Code: 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

SMILES Code: O=C(C=C[C@@]12C)C=C1CC[C@@]([C@]2([H])[C@@H](O)C[C@@]34C)([H])[C@]3([H])C[C@]5([H])[C@@]4(C(CO)=O)OC(CCC)O5

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO.

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Biological target: Budesonide, an inhaled glucocortical steroid, is an orally active glucocorticoid receptor agonist.
In vitro activity: In vitro studies were performed on normal CHO-K1 cells that were treated with budesonide at concentrations of 0.5 μM - 45 μM. After 48 hours of incubation with the test agent, the samples were prepared for optical microscopy using the H&E method and transmission electron microscopy. Comparison of cells exposed to budesonide with control cells (without addition of test agent) revealed vacuolization changes with autophagy. Apoptotic changes have also been demonstrated, which occured to a lesser extent than vacuolization. The changes observed after budesonide treatment in the cytological picture of patients with allergic rhinitis indicate the therapeutic effect of this drug. On the other hand, the changes observed in the cytoplasm of epithelial cells, such as autophagy (clearly promoted in CHO-K1 cells) and leucophagocytosis, may indicate an additional mechanism of action for budesonide. Reference: J Physiol Pharmacol. 2017 Dec;68(6):907-919. http://www.jpp.krakow.pl/journal/archive/12_17/pdf/907_12_17_article.pdf
In vivo activity: To assess the effects of budesonide on the survival of mice with ALI, a lethal dose of LPS (40 mg/kg) was injected (i.t.), which resulted in about 70% death within 72 h (Figure 5, P < 0.01). The mortality rate dropped to 25% in the budesonide-treated group (Figure 5, P < 0.01). These findings suggested that budesonide improved the survival of ALI mice. The results showed that the components of the NLRP3 inflammasome, including NLRP3, pro-caspase-1, pro-IL-1β, and pro-IL-18, were significantly increased in the lungs of mice with LPS-induced ALI (Figures 6(a)–6(g), P < 0.01). Budesonide pretreatment partially restored these effects, indicating inhibition of the NLRP3 inflammasome (Figures 6(a)–6(g), P < 0.05). Additionally, budesonide also dramatically reduced NLRP3 inflammasome activation by modulating the expression of caspase-1 p20 and the secretion of IL-1β and IL-18 (Figures 6(c), 6(e), and 6(h)–6(i); P < 0.05). Taken together, these data indicated that inhibition of NLRP3 inflammasome activation contributed to the protective effects of budesonide against LPS-induced ALI in mice. Reference: J Immunol Res. 2019 Feb 27;2019:7264383. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/30937316/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 25.0 58.1

Preparing Stock Solutions

The following data is based on the product molecular weight 430.53 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
In vitro protocol: 1. Trybus E, Krol G, Obarzanowski T, Trybus W, Kopacz-Bednarska A, Obarzanowski M, Krol T. In vivo and in vitro studies on multidirectional mechanism of anti-allergic activity of budesonide. J Physiol Pharmacol. 2017 Dec;68(6):907-919. PMID: 29550803. 2. Dong L, Zhu YH, Liu DX, Li J, Zhao PC, Zhong YP, Chen YQ, Xu W, Zhu ZQ. Intranasal Application of Budesonide Attenuates Lipopolysaccharide-Induced Acute Lung Injury by Suppressing Nucleotide-Binding Oligomerization Domain-Like Receptor Family, Pyrin Domain-Containing 3 Inflammasome Activation in Mice. J Immunol Res. 2019 Feb 27;2019:7264383. doi: 10.1155/2019/7264383. PMID: 30937316; PMCID: PMC6415278.
In vivo protocol: 1. Dong L, Zhu YH, Liu DX, Li J, Zhao PC, Zhong YP, Chen YQ, Xu W, Zhu ZQ. Intranasal Application of Budesonide Attenuates Lipopolysaccharide-Induced Acute Lung Injury by Suppressing Nucleotide-Binding Oligomerization Domain-Like Receptor Family, Pyrin Domain-Containing 3 Inflammasome Activation in Mice. J Immunol Res. 2019 Feb 27;2019:7264383. doi: 10.1155/2019/7264383. PMID: 30937316; PMCID: PMC6415278.

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 1: Haghi M, Hittinger M, Zeng Q, Oliver B, Traini D, Young PM, Huwer H, Schneider-Daum N, Lehr CM. Mono- and Cocultures of Bronchial and Alveolar Epithelial Cells Respond Differently to Proinflammatory Stimuli and Their Modulation by Salbutamol and Budesonide. Mol Pharm. 2015 Jul 6. [Epub ahead of print] PubMed PMID: 26147243.

2: Wang L, Zhang B, Li Z, Li J, Liu Q, Sun W. Budesonide mitigates pathological changes in animal model Of COPD through reducing neutrophil elastase expression. Int J Clin Exp Med. 2015 Apr 15;8(4):5227-35. eCollection 2015. PubMed PMID: 26131096; PubMed Central PMCID: PMC4483969.

3: Zhang C, Shang YX, Wei B, Xiang Y, Zhang H. [Expression of leptin and its receptor in lungs of asthmatic BALB/c mice and effect of budesonide on their expression]. Zhongguo Dang Dai Er Ke Za Zhi. 2015 Jun;17(6):623-8. Chinese. PubMed PMID: 26108327.

4: Lichtenstein GR, Travis S, Danese S, D'Haens G, Moro L, Jones R, Huang M, Ballard ED, Bagin R, Hardiman Y, Collazo R, Sandborn WJ. Budesonide MMX® for the induction of remission of mild to moderate ulcerative colitis: a pooled safety analysis. J Crohns Colitis. 2015 Jun 20. pii: jjv101. [Epub ahead of print] PubMed PMID: 26094251.

5: Razi CH, Akelma AZ, Harmanci K, Kocak M, Kuras Can Y. The Addition of Inhaled Budesonide to Standard Therapy Shortens the Length of Stay in Hospital for Asthmatic Preschool Children: A Randomized, Double-Blind, Placebo-Controlled Trial. Int Arch Allergy Immunol. 2015;166(4):297-303. doi: 10.1159/000430443. Epub 2015 May 30. PubMed PMID: 26044872.

6: Chrystyn H, Safioti G, Keegstra JR, Gopalan G. Effect of inhalation profile and throat geometry on predicted lung deposition of budesonide and formoterol (BF) in COPD: an in-vitro comparison of Spiromax with Turbuhaler. Int J Pharm. 2015 Jun 1. pii: S0378-5173(15)00505-0. doi: 10.1016/j.ijpharm.2015.05.076. [Epub ahead of print] PubMed PMID: 26043823.

7: Weisfeld L, Shu Y, Shah TP. Bioequivalence of budesonide plus formoterol (BF) Spiromax® and BF Turbohaler® (with and without charcoal block) in healthy volunteers. Int J Clin Pharmacol Ther. 2015 Jul;53(7):593-602. doi: 10.5414/CP202238. PubMed PMID: 26042485.

8: Rezaie A, Kuenzig ME, Benchimol EI, Griffiths AM, Otley AR, Steinhart AH, Kaplan GG, Seow CH. Budesonide for induction of remission in Crohn's disease. Cochrane Database Syst Rev. 2015 Jun 3;6:CD000296. doi: 10.1002/14651858.CD000296.pub4. PubMed PMID: 26039678.

9: Li Z, Geng M. [Effect of budesonide on the expression of IL-12 in animal model of minimal persistent inflammation of allergic rhinitis in rats]. Lin Chung Er Bi Yan Hou Tou Jing Wai Ke Za Zhi. 2015 Feb;29(3):270-4. Chinese. PubMed PMID: 26012304.

10: Bachmann O, Nitschmann S. [Budesonide foam for ulcerative proctitis and proctosigmoiditis]. Internist (Berl). 2015 Jun;56(6):713-5. doi: 10.1007/s00108-015-3721-0. German. PubMed PMID: 25991492.

Budesonide

100.0mg / USD 250.0


Additional Information

Budesonide, the active component of PULMICORT RESPULES®, is a corticosteroid designated chemically as (RS)-11β, 16α, 17, 21-tetrahydroxypregna-1, 4-diene-3, 20dione cyclic 16, 17-acetal with butyraldehyde. Budesonide is provided as a mixture of two epimers (22R and 22S). The empirical formula of budesonide is C25H34O6 and its molecular weight is 430.5.
Budesonide is a white to off-white, tasteless, odorless powder that is practically insoluble in water and in heptane, sparingly soluble in ethanol, and freely soluble in chloroform. Its partition coefficient between octanol and water at pH 7.4 is 1.6 x 103.
 
Mechanism of Action: Budesonide is an anti-inflammatory corticosteroid that exhibits potent glucocorticoid activity and weak mineralocorticoid activity. In standard in vitro and animal models, budesonide has approximately a 200-fold higher affinity for the glucocorticoid receptor and a 1000-fold higher topical anti-inflammatory potency than cortisol (rat croton oil ear edema assay). As a measure of systemic activity, budesonide is 40 times more potent than cortisol when administered subcutaneously and 25 times more potent when administered orally in the rat thymus involution assay. The clinical significance of these findings is unknown. The therapeutic effects of conventional doses of orally inhaled budesonide are largely explained by its direct local action on the respiratory tract. To confirm that systemic absorption is not a significant factor in the clinical efficacy of inhaled budesonide, a clinical study in adult patients with asthma was performed comparing 400 mcg budesonide administered via a pressurized metered dose inhaler with a tube spacer to 1400 mcg of oral budesonide and placebo. The study demonstrated the efficacy of inhaled budesonide but not orally administered budesonide, even though systemic budesonide exposure was comparable for both treatments, indicating that the inhaled treatment is working locally in the lung. Thus, the therapeutic effect of conventional doses of orally inhaled budesonide are largely explained by its direct action on the respiratory tract. Improvement in the control of asthma symptoms following inhalation of PULMICORT RESPULES can occur within 2-8 days of beginning treatment, although maximum benefit may not be achieved for 4-6 weeks.
Mechanism of Action: Budesonide is an anti-inflammatory corticosteroid that exhibits potent glucocorticoid activity and weak mineralocorticoid activity. In standard in vitro and animal models, budesonide has approximately a 200-fold higher affinity for the glucocorticoid receptor and a 1000-fold higher topical anti-inflammatory potency than cortisol (rat croton oil ear edema assay). As a measure of systemic activity, budesonide is 40 times more potent than cortisol when administered subcutaneously and 25 times more potent when administered orally in the rat thymus involution assay. The clinical significance of these findings is unknown. The therapeutic effects of conventional doses of orally inhaled budesonide are largely explained by its direct local action on the respiratory tract. To confirm that systemic absorption is not a significant factor in the clinical efficacy of inhaled budesonide, a clinical study in adult patients with asthma was performed comparing 400 mcg budesonide administered via a pressurized metered dose inhaler with a tube spacer to 1400 mcg of oral budesonide and placebo. The study demonstrated the efficacy of inhaled budesonide but not orally administered budesonide, even though systemic budesonide exposure was comparable for both treatments, indicating that the inhaled treatment is working locally in the lung. Thus, the therapeutic effect of conventional doses of orally inhaled budesonide are largely explained by its direct action on the respiratory tract. Improvement in the control of asthma symptoms following inhalation of PULMICORT RESPULES can occur within 2-8 days of beginning treatment, although maximum benefit may not be achieved for 4-6 weeks.