budesonide   Click here for help

GtoPdb Ligand ID: 7434

Synonyms: Entocort® | Eohilia® (budesonide oral suspension) | Jorveza® | Pulmicort® | S-1320 | Uceris®
Approved drug Immunopharmacology Ligand
budesonide is an approved drug (FDA (1997), EMA (2018))
Compound class: Synthetic organic
Comment: Budesonide is a glucocorticoid steroid. The INN document specifies that the approved drug consists of a racemic mixture of two epimers, based on the stereocentre of the carbon where the butyl chain meets the rest of the molecule. Our structure does not specify strereochemistry at this point and represents the mixture. The two epimers are represented by CID 40000 and CID 63006.

COVID-19: Results from a Phase 2 clinical trial have shown that a short duration administration of budesonide in the early phase of SARS-CoV-2 infection reduces both the likelihood of needing urgent medical care and time to recovery [5].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 93.06
Molecular weight 430.24
XLogP 1.91
No. Lipinski's rules broken 0
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Canonical SMILES CCCC1OC2C(O1)(C(=O)CO)C1(C(C2)C2CCC3=CC(=O)C=CC3(C2C(C1)O)C)C
Isomeric SMILES CCCC1O[C@H]2[C@](O1)(C(=O)CO)[C@@]1([C@@H](C2)[C@@H]2CCC3=CC(=O)C=C[C@@]3([C@H]2[C@H](C1)O)C)C
InChI 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
1. Habal FM, Huang VW. (2012)
Review article: a decision-making algorithm for the management of pregnancy in the inflammatory bowel disease patient.
Aliment Pharmacol Ther, 35 (5): 501-15. [PMID:22221203]
2. Hemmerling M, Nilsson S, Edman K, Eirefelt S, Russell W, Hendrickx R, Johnsson E, Kärrman Mårdh C, Berger M, Rehwinkel H et al.. (2017)
Selective Nonsteroidal Glucocorticoid Receptor Modulators for the Inhaled Treatment of Pulmonary Diseases.
J Med Chem, 60 (20): 8591-8605. [PMID:28937774]
3. Lichtenstein GR, Hanauer SB, Sandborn WJ, Practice Parameters Committee of American College of Gastroenterology. (2009)
Management of Crohn's disease in adults.
Am J Gastroenterol, 104 (2): 465-83; quiz 464, 484. [PMID:19174807]
4. Millan DS, Ballard SA, Chunn S, Dybowski JA, Fulton CK, Glossop PA, Guillabert E, Hewson CA, Jones RM, Lamb DJ et al.. (2011)
Design and synthesis of long acting inhaled corticosteroids for the treatment of asthma.
Bioorg Med Chem Lett, 21 (19): 5826-30. [PMID:21880489]
5. Ramakrishnan S, Nicolau Jr DV, Langford B, Mahdi M, Jeffers H, Mwasuku C, Krassowska K, Fox R, Binnian I, Glover V et al.. (2021)
Inhaled budesonide in the treatment of early COVID-19 (STOIC): a phase 2, open-label, randomised controlled trial.
Lancet Respir Med, 9 (7): 763-772. [PMID:33844996]