Sonidegib (LDE-225)
Sonidegib, also known as, erismodegib, LDE225, NVP-LDE225, is an orally bioavailable small-molecule Smoothened (Smo) antagonist with potential antineoplastic activity. Erismodegib selectively binds to the Hedgehog (Hh)-ligand cell surface receptor Smo, which may result in the suppression of the Hh signaling pathway and, so, the inhibition of tumor cells in which this pathway is abnormally activated. It was approved by the FDA for treating basal cell carcinoma in July 2015.
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Chemical Information
| Name | Sonidegib (LDE-225) |
|---|---|
| Iupac Chemical Name | N-(6-((2R,6S)-2,6-dimethylmorpholino)pyridin-3-yl)-2-methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carboxamide |
| Synonyms | LDE225; LDE 225; LDE-225; NVP-LDE225; NVP-LDE-225; NVP LDE225; Erismodegib; Sonidegib; Odomzo. |
| Molecular Formula | C26H26F3N3O3 |
| Molecular Weight | 485.49815 |
| Smile | O=C(C1=C(C)C(C2=CC=C(OC(F)(F)F)C=C2)=CC=C1)NC3=CC=C(N4C[C@@H](C)O[C@@H](C)C4)N=C3 |
| InChiKey | VZZJRYRQSPEMTK-CALCHBBNSA-N |
| InChi | InChI=1S/C26H26F3N3O3/c1-16-14-32(15-17(2)34-16)24-12-9-20(13-30-24)31-25(33)23-6-4-5-22(18(23)3)19-7-10-21(11-8-19)35-26(27,28)29/h4-13,16-17H,14-15H2,1-3H3,(H,31,33)/t16-,17+ |
| CAS Number | 956697-53-3 |
| Related CAS |
Ordering Information
| Packaging | Price | Availability | Purity | Shipping Time |
|---|---|---|---|---|
| Bulk | Enquiry | Enquiry | Enquiry |
| Formulation | Solid powder |
|---|---|
| Purity | 98% Min. |
| Storage | 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 |
| Handling | |
| 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. |
| HS Code |
| Targets | |
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| Mechanism | |
| Cell study | |
| Animal study | |
| Clinical study |
1: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012-. Available from http://www.ncbi.nlm.nih.gov/books/NBK548922/ PubMed PMID: 31644228.
2: Li Y, Song Q, Day BW. Phase I and phase II sonidegib and vismodegib clinical trials for the treatment of paediatric and adult MB patients: a systemic review and meta-analysis. Acta Neuropathol Commun. 2019 Jul 30;7(1):123. doi: 10.1186/s40478-019-0773-8. Review. PubMed PMID: 31362788; PubMed Central PMCID: PMC6668073.
3: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006-. Available from http://www.ncbi.nlm.nih.gov/books/NBK500869/ PubMed PMID: 29999928.
4: Sonidegib for basal cell carcinoma. Aust Prescr. 2018 Jun;41(3):94. doi: 10.18773/austprescr.2018.025. Epub 2018 May 15. Review. PubMed PMID: 29922006; PubMed Central PMCID: PMC6003011.
5: Jain S, Song R, Xie J. Sonidegib: mechanism of action, pharmacology, and clinical utility for advanced basal cell carcinomas. Onco Targets Ther. 2017 Mar 16;10:1645-1653. doi: 10.2147/OTT.S130910. eCollection 2017. Review. PubMed PMID: 28352196; PubMed Central PMCID: PMC5360396.
6: Wahid M, Jawed A, Dar SA, Mandal RK, Haque S. Differential pharmacology and clinical utility of sonidegib in advanced basal cell carcinoma. Onco Targets Ther. 2017 Jan 24;10:515-520. doi: 10.2147/OTT.S97713. eCollection 2017. Review. PubMed PMID: 28182134; PubMed Central PMCID: PMC5279825.
7: Doan HQ, Silapunt S, Migden MR. Sonidegib, a novel smoothened inhibitor for the treatment of advanced basal cell carcinoma. Onco Targets Ther. 2016 Sep 14;9:5671-5678. eCollection 2016. Review. PubMed PMID: 27695345; PubMed Central PMCID: PMC5028081.
8: Collier NJ, Ali FR, Lear JT. The safety and efficacy of sonidegib for the treatment of locally advanced basal cell carcinoma. Expert Rev Anticancer Ther. 2016 Oct;16(10):1011-8. doi: 10.1080/14737140.2016.1230020. Epub 2016 Sep 22. Review. PubMed PMID: 27636236.
9: Ramelyte E, Amann VC, Dummer R. Sonidegib for the treatment of advanced basal cell carcinoma. Expert Opin Pharmacother. 2016 Oct;17(14):1963-8. doi: 10.1080/14656566.2016.1225725. Epub 2016 Aug 29. Review. PubMed PMID: 27538055.
10: Chen L, Silapunt S, Migden MR. Sonidegib for the treatment of advanced basal cell carcinoma: a comprehensive review of sonidegib and the BOLT trial with 12-month update. Future Oncol. 2016 Sep;12(18):2095-105. doi: 10.2217/fon-2016-0118. Epub 2016 May 18. Review. PubMed PMID: 27189494.
11: Sonidegib (Odomzo) for basal cell carcinoma. Med Lett Drugs Ther. 2016 Feb 29;58(1489):31-2. Review. PubMed PMID: 26938701.
12: Burness CB, Scott LJ. Sonidegib: A Review in Locally Advanced Basal Cell Carcinoma. Target Oncol. 2016 Apr;11(2):239-46. doi: 10.1007/s11523-016-0418-9. Review. PubMed PMID: 26867946.
13: Wahid M, Jawed A, Mandal RK, Dar SA, Khan S, Akhter N, Haque S. Vismodegib, itraconazole and sonidegib as hedgehog pathway inhibitors and their relative competencies in the treatment of basal cell carcinomas. Crit Rev Oncol Hematol. 2016 Feb;98:235-41. doi: 10.1016/j.critrevonc.2015.11.006. Epub 2015 Nov 21. Review. PubMed PMID: 26614022.
14: Burness CB. Sonidegib: First Global Approval. Drugs. 2015 Sep;75(13):1559-66. doi: 10.1007/s40265-015-0458-y. Review. PubMed PMID: 26323341.
Chemical Structure
