Budesonide | CAS#51333-22-3 | glucocorticoid steroid

MedKoo Cat#: 300250 | Name: Budesonide

Description:

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

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

Budesonide

CAS#51333-22-3 (free base)

Theoretical Analysis

MedKoo Cat#: 300250

Name: Budesonide

CAS#: 51333-22-3 (free base)

Chemical Formula: C25H34O6

Exact Mass: 430.2355

Molecular Weight: 430.53

Elemental Analysis: C, 69.74; H, 7.96; O, 22.30

Price and Availability

Size	Price	Availability
100mg	USD 90.00	Ready to ship
200mg	USD 150.00	Ready to ship
500mg	USD 250.00	Ready to ship
1g	USD 400.00	Ready to ship
2g	USD 650.00	Ready to ship
5g	USD 1,250.00	Ready to ship

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Related CAS #

43229-80-7 (fumarate) 51333-22-3 (free base)

Synonym

S 1320; S-1320; S1320; TAK 721; TAK721; TAK-721; Spirocort; Rhinocort; Budesonide; Pulmicort; Preferid;

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

More Info

Budesonide, the active component of PULMICORT RESPULESÂ®, 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.

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#A21T04K30

QC Data

View QC data: current batch, Lot#A21T04K30

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

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/

	Solvent	mg/mL	mM
Solubility
	DMSO	25.0	58.10

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

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

Formulation protocol:

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.

1: Hintong T, Chongvisal S, Pipanmekaporn T, Unchiti K. A Randomized Comparison of Effects of Budesonide Spray and K-Y Gel as an Endotracheal Tube Cuff Lubricant on Incidence of Postoperative Sore Throat. J Perianesth Nurs. 2023 Jan 5:S1089-9472(22)00546-9. doi: 10.1016/j.jopan.2022.10.003. Epub ahead of print. PMID: 36610870. 2: Zhang M, Li Q, Li L, Guo X, Wang X, Han X, Liang L, Miao M, Zhang F, Wang J, Wu Y, Yu C. The Efficacy of N-Acetylcysteine Combined With Budesonide/Formoterol in the Treatment of Stable Chronic Obstructive Pulmonary Disease. Am J Ther. 2022 Nov-Dec 01;29(6):e687-e690. doi: 10.1097/MJT.0000000000001290. Epub 2021 Jan 29. PMID: 36608067. 3: D'Amico V, Arduino I, Vacca M, Iacobazzi RM, Altamura D, Lopalco A, Rizzi R, Cutrignelli A, Laquintana V, Massimo F, De Angelis M, Denora N, Lopedota AA. Colonic budesonide delivery by multistimuli alginate/Eudragit® FS 30D/inulin- based microspheres as a paediatric formulation. Carbohydr Polym. 2023 Feb 15;302:120422. doi: 10.1016/j.carbpol.2022.120422. Epub 2022 Nov 30. PMID: 36604084. 4: Daferera N, Nyström S, Hjortswang H, Ignatova S, Jenmalm MC, Ström M, Münch A. Mucosa associated invariant T and natural killer cells in active and budesonide treated collagenous colitis patients. Front Immunol. 2022 Dec 15;13:981740. doi: 10.3389/fimmu.2022.981740. PMID: 36591297; PMCID: PMC9798420. 5: Bafadhel M, Rabe KF, Martinez FJ, Singh D, Darken P, Jenkins M, Aurivillius M, Patel M, Dorinsky P. Benefits of Budesonide/Glycopyrronium/Formoterol Fumarate Dihydrate on COPD Exacerbations, Lung Function, Symptoms, and Quality of Life Across Blood Eosinophil Ranges: A Post-Hoc Analysis of Data from ETHOS. Int J Chron Obstruct Pulmon Dis. 2022 Dec 6;17:3061-3073. doi: 10.2147/COPD.S374670. PMID: 36510486; PMCID: PMC9738173. 6: Gummlich BPM, Seif Amir Hosseini A, Schwörer H. Budesonide with Low-Dose 6-Mercaptopurine as a Possible New Treatment for IgG4-Related Sclerosing Cholangitis and Systemic IgG4-Related Disease: A Case Report. Am J Case Rep. 2022 Dec 8;23:e938272. doi: 10.12659/AJCR.938272. PMID: 36476942; PMCID: PMC9745840. 7: Mishra RK, Ahmad A, Kanika, Kumar A, Vyawahare A, Sakla R, Nadeem A, Siddiqui N, Raza SS, Khan R. Caffeic Acid-Conjugated Budesonide-Loaded Nanomicelle Attenuates Inflammation in Experimental Colitis. Mol Pharm. 2023 Jan 2;20(1):172-182. doi: 10.1021/acs.molpharmaceut.2c00558. Epub 2022 Dec 6. PMID: 36472567. 8: Olszanecka-Glinianowicz M, Chudek J, Urcus A, Almgren-Rachtan A. Factors affecting the choice of budesonide in the therapy of croup, asthma and chronic obstructive pulmonary disease. Postepy Dermatol Alergol. 2022 Oct;39(5):893-901. doi: 10.5114/ada.2022.120883. Epub 2022 Nov 9. PMID: 36457671; PMCID: PMC9704461. 9: Kothiwala M, Samdani S, Grover M, Gurjar V. Efficacy of Topical High Volume Budesonide Nasal Irrigation in Post FESS Patients of Chronic Rhinosinusitis With or Without Nasal Polyposis. Indian J Otolaryngol Head Neck Surg. 2022 Oct;74(Suppl 2):1399-1407. doi: 10.1007/s12070-021-02509-9. Epub 2021 Apr 15. PMID: 36452810; PMCID: PMC9702420. 10: de Nigris E, Treharne C, Brighton N, Holmgren U, Walker A, Haughney J. Cost- Effectiveness of Triple Therapy with Budesonide/Glycopyrronium/Formoterol Fumarate Dihydrate versus Dual Therapies in Moderate-to-Very Severe Chronic Obstructive Pulmonary Disease: United Kingdom Analysis Using the ETHOS Study. Int J Chron Obstruct Pulmon Dis. 2022 Nov 22;17:2987-3000. doi: 10.2147/COPD.S381138. PMID: 36444374; PMCID: PMC9700475. 11: Moraes LHA, Coelho RMD, Neves Dos Santos Beozzo GP, Yoshida RAM, de Albuquerque Diniz EM, de Carvalho WB. Use of budesonide associated with a pulmonary surfactant to prevent bronchopulmonary dysplasia in premature newborns - A systematic review. J Pediatr (Rio J). 2022 Nov 25:S0021-7557(22)00124-3. doi: 10.1016/j.jped.2022.10.007. Epub ahead of print. PMID: 36436670. 12: Warzecha J, Dziekiewicz M, Bieńkowska-Tokarczyk A, Małecki M, Banaszkiewicz A. A New Viscous Budesonide Formulation for the Treatment of Eosinophilic Esophagitis in Children: A Preliminary Experience and Review of the Literature. J Clin Med. 2022 Nov 14;11(22):6730. doi: 10.3390/jcm11226730. PMID: 36431208; PMCID: PMC9694526. 13: Trigueros JA, Garin N, Baloira A, Aceituno S, Calvo A, Prades M, Touron C, Martínez A, Torres C. Cost-Effectiveness Analysis of Triple Therapy with Budesonide/ Glycopyrronium/ Formoterol Fumarate versus Dual Therapy in Patients with Chronic Obstructive Pulmonary Disease in Spain. Int J Chron Obstruct Pulmon Dis. 2022 Nov 15;17:2905-2917. doi: 10.2147/COPD.S384591. PMID: 36411773; PMCID: PMC9675425. 14: Lopez-Martinez M, Torres I, Bermejo S, Moreso F, Garcia-Carro C, Vergara A, Ramos N, Perello M, Gabaldon A, Azancot MA, Bolufer M, Toapanta N, Bestard O, Agraz-Pamplona I, Soler MJ. Enteric Budesonide in Transplant and Native IgA Nephropathy: Real-World Clinical Practice. Transpl Int. 2022 Oct 14;35:10693. doi: 10.3389/ti.2022.10693. PMID: 36311259; PMCID: PMC9613952. 15: Ali Ibrahim A, Kenyon V, Fasano A, Leonard MM. Budesonide and the Gluten Containing Elimination Diet as Treatments for Non-responsive Celiac Disease in Children. J Pediatr Gastroenterol Nutr. 2022 Nov 1;75(5):616-622. doi: 10.1097/MPG.0000000000003596. Epub 2022 Aug 22. PMID: 36305882; PMCID: PMC9627632. 16: Li Y, Yu H, Lv M, Li Q, Zou K, Lv S. Combination therapy with budesonide and N-acetylcysteine ameliorates LPS-induced ALI by attenuating neutrophil recruitment through the miR-196b-5p/Socs3 molecular axis. BMC Pulm Med. 2022 Oct 26;22(1):388. doi: 10.1186/s12890-022-02185-7. PMID: 36289489; PMCID: PMC9608916. 17: Zyryanov SK, Dyakov IN, Aisanov ZR. [Pharmacoeconomics analysis of using a fixed combination of budesonide/formoterol in patients with asthma in the health care system of the Russian Federation]. Ter Arkh. 2022 Aug 12;94(7):850-858. Russian. doi: 10.26442/00403660.2022.07.201715. PMID: 36286942. 18: Barratt J, Lafayette R, Kristensen J, Stone A, Cattran D, Floege J, Tesar V, Trimarchi H, Zhang H, Eren N, Paliege A, Rovin BH; NefIgArd Trial Investigators. Results from part A of the multi-center, double-blind, randomized, placebo- controlled NefIgArd trial, which evaluated targeted-release formulation of budesonide for the treatment of primary immunoglobulin A nephropathy. Kidney Int. 2022 Oct 19:S0085-2538(22)00836-5. doi: 10.1016/j.kint.2022.09.017. Epub ahead of print. PMID: 36270561. 19: Feng W, Chen H, Lu Y, Liu R, Yuan MY, An J, Li M, Chua LS, Kait JA, Xin L. Comparing the efficacy and safety of atomization of traditional Chinese medicine Kai Hou Jian and budesonide suspension in adult acute laryngitis: a randomized control trial. Ann Transl Med. 2022 Sep;10(18):1019. doi: 10.21037/atm-22-4305. PMID: 36267766; PMCID: PMC9577730. 20: Hussain N, Robert M, Al-Bawardy B. Open-Capsule Budesonide for the Treatment of Isolated Immune Checkpoint Inhibitor-Induced Enteritis. ACG Case Rep J. 2022 Oct 7;9(10):e00882. doi: 10.14309/crj.0000000000000882. PMID: 36237281; PMCID: PMC9553371.