Budesonide

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WARNING: This product is for research use only, not for human or veterinary use.

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.

Price and Availability

Budesonide, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.

Chemical Structure

Theoretical Analysis

MedKoo Cat#: 300250Name: BudesonideCAS#: 51333-22-3Chemical Formula: C25H34O6Exact Mass: 430.23554Molecular Weight: 430.53386Elemental Analysis:C, 69.74; H, 7.96; O, 22.30

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

Technical Data

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.

References

 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 theinduction 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 InhaledBudesonide 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.