MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 205510 | Name: Sonidegib (LDE-225)
Featured New

Description:

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

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.

Chemical Structure

Sonidegib (LDE-225)
Sonidegib (LDE-225)
CAS#956697-53-3 (free base)

Theoretical Analysis

MedKoo Cat#: 205510

Name: Sonidegib (LDE-225)

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

Chemical Formula: C26H26F3N3O3

Exact Mass: 485.1926

Molecular Weight: 485.50

Elemental Analysis: C, 64.32; H, 5.40; F, 11.74; N, 8.66; O, 9.89

Price and Availability

Size Price Availability Quantity
25mg USD 90.00 Ready to ship
50mg USD 150.00 Ready to ship
100mg USD 250.00 Ready to ship
200mg USD 450.00 Ready to ship
500mg USD 950.00 Ready to ship
1g USD 1,650.00 Ready to ship
2g USD 2,950.00 Ready to ship
Show More
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
1218778-77-8 (phosphate) 956697-53-3 (free base)
Synonym
LDE225; LDE 225; LDE-225; NVP-LDE225; NVP-LDE-225; NVP LDE225; Erismodegib; Sonidegib; Odomzo.
IUPAC/Chemical Name
N-(6-((2R,6S)-2,6-dimethylmorpholino)pyridin-3-yl)-2-methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carboxamide
InChi Key
VZZJRYRQSPEMTK-CALCHBBNSA-N
InChi Code
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+
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
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 ethanol
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)
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/
Solvent mg/mL mM
Solubility
DMSO 73.5 151.39
Ethanol 48.0 98.87
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 485.50 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.

Recalculate based on batch purity %
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.
1: Gutzmer R, Leiter U, Mohr P, Kähler KC, Ascierto PA, Scalvenzi M, Peris K, Pérez-Pastor GM, Fernández-de-Misa R, Botella-Estrada R, Hunger RE, Martelli S, Güneli N, Arntz R, Hauschild A. Interim analysis of the multinational, post- authorization safety study (NISSO) to assess the long-term safety of sonidegib in patients with locally advanced basal cell carcinoma. BMC Cancer. 2024 Nov 14;24(1):1401. doi: 10.1186/s12885-024-13101-z. PMID: 39538176; PMCID: PMC11562082. 2: Pierce CM, Wang RJ, Howe R, Burgess BA, Owen JL. Secondary cutaneous malignancy after treatment of basal cell carcinoma with hedgehog pathway inhibitor: a systematic review. Arch Dermatol Res. 2024 Oct 26;316(10):716. doi: 10.1007/s00403-024-03471-6. PMID: 39460789. 3: Truong K, Peera M, Liu R, Wijaya M, Jones-Caballero M, Araujo RR, Fernandez- Penas P. Real-world data on the efficacy and safety of hedgehog pathway inhibitors in patients with basal cell carcinoma: Experience of a tertiary Australian centre. Australas J Dermatol. 2024 Oct 25. doi: 10.1111/ajd.14373. Epub ahead of print. PMID: 39451045. 4: Moreno-Arrones OM, Béa-Ardebol S, Galiano-Mejías S, Turrión-Merino L, de Perosanz-Lobo D, Perez-Brocal V, Moya A, Rios-Buceta L. Locally advanced basal cell carcinoma associated with distinct gut microbiome signature. J Dtsch Dermatol Ges. 2024 Oct 15. doi: 10.1111/ddg.15588. Epub ahead of print. PMID: 39410728. 5: Proietti I, Filippi L, Bagni O, Potenza C. Metabolic Imaging of Advanced Basal Cell Carcinoma Treated with Sonidegib: A Retrospective Case Series Study. J Clin Med. 2024 Aug 27;13(17):5087. doi: 10.3390/jcm13175087. PMID: 39274300; PMCID: PMC11396429. 6: Khayyat A, Pour ME, Nasrollahi H, Mehrabi MM, Zohouri SA, Geramizadeh B. A case of basal cell carcinoma of skin with bone metastasis: a case report. J Med Case Rep. 2024 Sep 14;18(1):428. doi: 10.1186/s13256-024-04755-1. PMID: 39272192; PMCID: PMC11401265. 7: Deshpande A, Munoz J, Kurzrock R. Images in Immunotherapy and Precision Oncology: Advanced Basal Cell Carcinoma. J Immunother Precis Oncol. 2024 Aug 19;7(3):201-204. doi: 10.36401/JIPO-23-47. PMID: 39219994; PMCID: PMC11361336. 8: Attal ZG, Shalata W, Soklakova A, Tourkey L, Shalata S, Abu Saleh O, Abu Salamah F, Alatawneh I, Yakobson A. Advanced and Metastatic Non-Melanoma Skin Cancer: Epidemiology, Risk Factors, Clinical Features, and Treatment Options. Biomedicines. 2024 Jun 28;12(7):1448. doi: 10.3390/biomedicines12071448. PMID: 39062023; PMCID: PMC11274597. 9: Wofford W, Kim J, Kim D, Janneh AH, Lee HG, Atilgan FC, Oleinik N, Kassir MF, Saatci O, Chakraborty P, Tokat UM, Gencer S, Howley B, Howe P, Mehrotra S, Sahin O, Ogretmen B. Alterations of ceramide synthesis induce PD-L1 internalization and signaling to regulate tumor metastasis and immunotherapy response. Cell Rep. 2024 Aug 27;43(8):114532. doi: 10.1016/j.celrep.2024.114532. Epub 2024 Jul 23. PMID: 39046874; PMCID: PMC11404065. 10: Wladis EJ, Aakalu VK, Vagefi MR, Tao JP, McCulley TJ, Freitag SK, Foster JA, Kim SJ. Oral Hedgehog Inhibitor, Vismodegib, for Locally Advanced Periorbital and Orbital Basal Cell Carcinoma: A Report by the American Academy of Ophthalmology. Ophthalmology. 2024 Nov;131(11):1339-1344. doi: 10.1016/j.ophtha.2024.06.007. Epub 2024 Jul 10. PMID: 39001766. 11: Baczynski A, Cahn B, Worley B, Haber R, Alam M. Oral smoothened inhibitors for Gorlin syndrome: A clinical review. J Am Acad Dermatol. 2024 Oct;91(4):706-711. doi: 10.1016/j.jaad.2024.06.047. Epub 2024 Jun 29. PMID: 38950707. 12: Murgia G, Valtellini L, Denaro N, Nazzaro G, Bortoluzzi P, Benzecry V, Passoni E, Marzano AV. Gorlin Syndrome-Associated Basal Cell Carcinomas Treated with Vismodegib or Sonidegib: A Retrospective Study. Cancers (Basel). 2024 Jun 7;16(12):2166. doi: 10.3390/cancers16122166. PMID: 38927872; PMCID: PMC11201977. 13: Nair B, Kamath AJ, Pradeep G, Devan AR, Sethi G, Nath LR. Unveiling the role of the Hedgehog signaling pathway in chronic liver disease: Therapeutic insights and strategies. Drug Discov Today. 2024 Aug;29(8):104064. doi: 10.1016/j.drudis.2024.104064. Epub 2024 Jun 18. PMID: 38901671. 14: Farberg AS, Portela D, Sharma D, Kheterpal M. Evaluation of the Tolerability of Hedgehog Pathway Inhibitors in the Treatment of Advanced Basal Cell Carcinoma: A Narrative Review of Treatment Strategies. Am J Clin Dermatol. 2024 Sep;25(5):779-794. doi: 10.1007/s40257-024-00870-3. Epub 2024 Jun 19. PMID: 38896403; PMCID: PMC11358199. 15: Sachse MM, Kähler KC. Alopezie durch Chemotherapeutika, Hedgehog- Inhibitoren, zielgerichtete Antikörpertherapien und Immuncheckpointinhibitoren : Pathogenese, Klinik, Diagnostik und Prophylaxe [Alopecia due to chemotherapeutics, hedgehog inhibitors, targeted antibody therapies and immune checkpoint inhibitors : Pathogenesis, clinical picture, diagnostics and prophylaxis]. Dermatologie (Heidelb). 2024 Jun;75(6):459-465. German. doi: 10.1007/s00105-024-05352-5. Epub 2024 May 23. PMID: 38780777. 16: Li J, Li J, Chen J, Cao W, Chen B. Comprehensive analysis of ATP6V1s family member, ATP6V1C2, with prognostic and drug development values in colorectal cancer. Pathol Res Pract. 2024 Jun;258:155357. doi: 10.1016/j.prp.2024.155357. Epub 2024 May 20. PMID: 38772116. 17: Mason E, Pascucci E, Schena D, Girolomoni G. Fast and safe clinical response to sonidegib in a 98-year old woman affected by locally advanced basal cell carcinoma. Dermatol Online J. 2024 Mar 15;30(1). doi: 10.5070/D330163292. PMID: 38762862. 18: Zhang S, Ran M. Deceptive pigment changes in neoadjuvant sonidegib therapy for basal cell carcinoma. Br J Dermatol. 2024 Aug 14;191(3):472-473. doi: 10.1093/bjd/ljae187. PMID: 38703062. 19: Patel S, Armbruster H, Pardo G, Archambeau B, Kim NH, Jeter J, Wu R, Kendra K, Contreras CM, Spaccarelli N, Dulmage B, Pootrakul L, Carr DR, Verschraegen C. Hedgehog pathway inhibitors for locally advanced and metastatic basal cell carcinoma: A real-world single-center retrospective review. PLoS One. 2024 Apr 30;19(4):e0297531. doi: 10.1371/journal.pone.0297531. PMID: 38687774; PMCID: PMC11060576. 20: Spallone G, Carbone A, Sperati F, Frascione P, Eibenschutz L. Clinical determinants of clinical response to Sonidegib in advanced basal cell carcinoma: a monocenter experience. Eur Rev Med Pharmacol Sci. 2024 Apr;28(7):2923-2928. doi: 10.26355/eurrev_202404_35923. PMID: 38639529.