Sonidegib phosphate | LDE225 | Erismodegib | CAS#1218778-77-8 | 956697-53-3 | Hedgehog inhibitor

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

MedKoo CAT#: 100942

CAS#: 1218778-77-8 (phosphate)

Description: Sonidegib (also known as erismodegib, LDE225, and 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.

Chemical Structure

Sonidegib phosphate

CAS# 1218778-77-8 (phosphate)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 100942
Name: Sonidegib phosphate
CAS#: 1218778-77-8 (phosphate)
Chemical Formula: C26H32F3N3O11P2
Exact Mass: 0.00
Molecular Weight: 681.490
Elemental Analysis: C, 45.82; H, 4.73; F, 8.36; N, 6.17; O, 25.82; P, 9.09

Price and Availability

Size	Price	Availability
5mg	USD 250	2 Weeks
10mg	USD 420	2 Weeks
50mg	USD 600	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 956697-53-3 (free base)

Synonym: LDE225 phosphate; LDE 225 phosphate; LDE-225 phosphate; NVP-LDE225 phosphate; NVP-LDE-225 phosphate; NVP LDE225 phosphate; Erismodegib; Sonidegib phosphate; Odomzo phosphate; Sonidegib diphosphate; Erismodegib diphosphate; LDE225 diphosphate; NVP-LDE225 diphosphate

IUPAC/Chemical Name: N-(6-((2R,6S)-2,6-dimethylmorpholino)pyridin-3-yl)-2-methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carboxamide bis(phosphate)

InChi Key: RWIVSVMMGFFZIJ-VWDRLOGHSA-N

InChi Code: InChI=1S/C26H26F3N3O3.2H3O4P/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;2*1-5(2,3)4/h4-13,16-17H,14-15H2,1-3H3,(H,31,33);2*(H3,1,2,3,4)/t16-,17+;;

SMILES Code: 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.O=P(O)(O)O.O=P(O)(O)O

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 and water

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: Related CAS# CAS# 956697-53-3 (Sonidegib free base). CAS# 1218778-77-8 (Sonidegib phosphate)

Product Data:

Product Data

Instruction:

View handling instruction

Biological target:	Sonidegib is a Smo antagonist with IC50 of 1.3 nM (mouse) and 2.5 nM (human) in cell-free assays.
In vitro activity:	Sonidegib may have potential therapeutic use in melanoma, even without BRAF(V600E). Inhibition of SONIC HEDGEHOG (SHH)-GLI pathway by the novel small molecule inhibitor of smoothened sonidegib was followed by inhibition of cell growth and induction of apoptosis in human melanoma cell lines, interestingly with both BRAF(V600E) and BRAF(Wild Type) status. Sonidegib was potent in reducing cell proliferation in vitro, and these effects were superior to cyclopamine. Reference: PLoS One. 2013 Jul 30;8(7):e69064. https://pubmed.ncbi.nlm.nih.gov/23935925/
In vivo activity:	Sonideib has therapeutic potential in the treatment of locally advanced basal cell carcinoma. Eleven patients, including four with Basal Cell Naevus syndrome, received sonidegib. Results showed 50% achieved complete remission, 37.5% had partial response, and 12.5% had stable disease. No signs of progression were observed. All four patients suffering from Basal Cell Naevus syndrome achieved disease control by being treated with sonidegib. Reference: Cancers (Basel). 2023 Jul 14;15(14):3621. https://pubmed.ncbi.nlm.nih.gov/37509282/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	100.0	146.74
	Water	0.3	0.37

Preparing Stock Solutions

The following data is based on the product molecular weight 681.49 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:	1. Jalili A, Mertz KD, Romanov J, Wagner C, Kalthoff F, Stuetz A, Pathria G, Gschaider M, Stingl G, Wagner SN. NVP-LDE225, a potent and selective SMOOTHENED antagonist reduces melanoma growth in vitro and in vivo. PLoS One. 2013 Jul 30;8(7):e69064. doi: 10.1371/journal.pone.0069064. Erratum in: PLoS One. 2013;8(9). doi:10.1371/annotation/ddd22094-5d8d-43ef-ad81-b95afe392ec7. PMID: 23935925; PMCID: PMC3728309. 2. Irvine DA, Zhang B, Kinstrie R, Tarafdar A, Morrison H, Campbell VL, Moka HA, Ho Y, Nixon C, Manley PW, Wheadon H, Goodlad JR, Holyoake TL, Bhatia R, Copland M. Deregulated hedgehog pathway signaling is inhibited by the smoothened antagonist LDE225 (Sonidegib) in chronic phase chronic myeloid leukaemia. Sci Rep. 2016 May 9;6:25476. doi: 10.1038/srep25476. PMID: 27157927; PMCID: PMC4860619. 3. Cantisani C, Musolff N, Longo C, Di Guardo A, Rovaldi E, Rossi G, Sasso F, Farnetani F, Rega F, Bánvölgyiv A, Azzella G, Paolino G, Pellacani G. Dynamic optical coherence tomography evaluation in locally advanced basal cell carcinoma during sonidegib treatment. J Eur Acad Dermatol Venereol. 2024 Jan 25. doi: 10.1111/jdv.19806. Epub ahead of print. PMID: 38270330. 4. Nazzaro G, Benzecry V, Mattioli MA, Denaro N, Beltramini GA, Marzano AV, Passoni E. Sonidegib in Locally Advanced Basal Cell Carcinoma: A Monocentric Retrospective Experience and a Review of Published Real-Life Data. Cancers (Basel). 2023 Jul 14;15(14):3621. doi: 10.3390/cancers15143621. PMID: 37509282; PMCID: PMC10377077.
In vitro protocol:	1. Jalili A, Mertz KD, Romanov J, Wagner C, Kalthoff F, Stuetz A, Pathria G, Gschaider M, Stingl G, Wagner SN. NVP-LDE225, a potent and selective SMOOTHENED antagonist reduces melanoma growth in vitro and in vivo. PLoS One. 2013 Jul 30;8(7):e69064. doi: 10.1371/journal.pone.0069064. Erratum in: PLoS One. 2013;8(9). doi:10.1371/annotation/ddd22094-5d8d-43ef-ad81-b95afe392ec7. PMID: 23935925; PMCID: PMC3728309. 2. Irvine DA, Zhang B, Kinstrie R, Tarafdar A, Morrison H, Campbell VL, Moka HA, Ho Y, Nixon C, Manley PW, Wheadon H, Goodlad JR, Holyoake TL, Bhatia R, Copland M. Deregulated hedgehog pathway signaling is inhibited by the smoothened antagonist LDE225 (Sonidegib) in chronic phase chronic myeloid leukaemia. Sci Rep. 2016 May 9;6:25476. doi: 10.1038/srep25476. PMID: 27157927; PMCID: PMC4860619.
In vivo protocol:	1. Cantisani C, Musolff N, Longo C, Di Guardo A, Rovaldi E, Rossi G, Sasso F, Farnetani F, Rega F, Bánvölgyiv A, Azzella G, Paolino G, Pellacani G. Dynamic optical coherence tomography evaluation in locally advanced basal cell carcinoma during sonidegib treatment. J Eur Acad Dermatol Venereol. 2024 Jan 25. doi: 10.1111/jdv.19806. Epub ahead of print. PMID: 38270330. 2. Nazzaro G, Benzecry V, Mattioli MA, Denaro N, Beltramini GA, Marzano AV, Passoni E. Sonidegib in Locally Advanced Basal Cell Carcinoma: A Monocentric Retrospective Experience and a Review of Published Real-Life Data. Cancers (Basel). 2023 Jul 14;15(14):3621. doi: 10.3390/cancers15143621. PMID: 37509282; PMCID: PMC10377077.

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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.

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