Sonidegib diphosphate - ≥99% , Smoothened homolog inhibitor, CAS No.1218778-77-8, Smoothened homolog inhibitor

CAS: 1218778-77-8 Cat. No.: S649283 Peso molecular: 681.5 PubChem CID: 45138699
Disponible para pedir
GRADE & PURITY ≥99%
Synonyms
CHEBI:90864 | N-(6-((2R,6S)-2,6-Dimethylmorpholino)pyridin-3-yl)-2-methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carboxamide bis(phosphate) | Sonidegib phosphate | SONIDEGIB PHOSPHATE [USAN] | Erismodegib phosphate | NVP-LDE 225 diphosphateSonidegib diph
Storage
Store at 2-8°C,Desiccated
Shipped In
Wet ice
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S649283-5mg
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Why this grade

≥99% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.

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Storage & shipping

Store at 2-8°C,Desiccated Ships Wet ice Check lot-specific COA for exact specifications.

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Quality documents

SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.

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Literature proof

Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.

Descripción general

Sonidegib diphosphate (Erismodegib diphosphate) is a potent and selective Smo antagonist with IC 50 of 1.3 nM and 2.5 nM for mouse and human Smo in binding assay, respectively

In Vitro

The IC 50 values for Sonidegib (NVP-LDE225) for the major human CYP450 drug metabolizing enzymes is greater than 10 μM. Sonidegib (LDE225), a small molecule, clinically investigated SMO inhibitor, used alone and in combination with Nilotinib, inhibits the Hh pathway in CD34 + chronic phase (CP)-chronic myeloid leukaemia (CML) cells, reducing the number and self-renewal capacity of CML leukaemia stem cell (LSC). Sonidegib interacts directly with SMO, in a similar fashion to cyclopamine, to reduce expression of downstream Hh signaling targets. Primary CD34 + CP-CML cells are cultured in serum free media (SFM)±Sonidegib for 6, 24 and 72 hours (h). At 72 h, while there is variability between the biological samples, GLI1 is significantly downregulated following exposure to Sonidegib (10 nM; 0.78-fold and 100 nM; 0.73-fold, respectively (p<0.01). MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Sonidegib (NVP-LDE225) is a weak base with a measured pK a of 4.2 and exhibits relatively poor aqueous solubility. In the subcutaneous Ptch +/- p53 -/- medulloblastoma allograft mouse model, Sonidegib demonstrates dose-related antitumor activity after 10 days of oral administration of a suspension of the diphosphate salt. At a dose of 5 mg/kg/day qd, Sonidegib significantly inhibits tumor growth, corresponding to a T/C value of 33% (p<0.05 as compared to vehicle controls). When dosed at 10 and 20 mg/kg/day qd, Sonidegib affords 51 and 83% regression, respectively . Bone marrow cells and spleen cells from a subset of treated mice are transplanted into secondary recipient mice. Transplantation of either bone marrow (BM) or spleen cells from mice treated with Sonidegib (LDE225)+Nilotinib results in reduced white cell count (WCC) and reduces leukaemia development in secondary recipients compared to Sonidegib or Nilotinib alone. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Cell Assay

CD34 + CP-CML cells are seeded in SFM alone±Sonidegib±Nilotinib and cultured for 24-72 h prior to assessment. Proliferation is measured using colorimetric assessment of BrDU incorporation. Proportion of viable cells versus those in early and late apoptosis is assessed by flow cytometry using annexin V-FITC and 7-amino-actinomycin D (7-AAD, Via-Probe solution). Cell cycle status is assessed using Ki67 (FITC) expression and 7-AAD incorporation. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Animal administration

Mice The transgenic EGFP + /SCLtTA/TRE-BCR-ABL mouse model is used to investigate the effect of Sonidegib treatment on CML LSC in vivo. Scl-tTa-BCR-ABL mice in the FVB/N background are crossed with transgenic GFP-expressing mice. Bone marrow cells are obtained 4 weeks post induction, GFP + cells are selected by flow cytometry and transplanted by tail vein injection (10 6 cells/mouse) into wild-type FVB/N recipient mice, irradiated at 900 cGy, generating a large cohort of mice with similar time of onset of leukemia. Blood samples obtained 4 weeks post transplantation confirmed a neutrophilic leukocytosis in recipient mice. Mice are treated with Nilotinib (50 mg/kg by gavage, daily), Sonidegib (80 mg/kg by gavage, daily), Sonidegib+Nilotinib, or with vehicle alone (control). After 3 weeks of treatment, animals are euthanised and marrow content of femurs and tibiae, spleen cells and blood obtained. Total white cell count (WCC), GFP-expressing WCC, myeloid cells, and GFP+ progenitors and stem cells are measured by flow cytometry. Survival is assessed in a subset of mice for 120d post discontinuation of treatment. Spleen and BM cells from a subset of mice in each arm are pooled and 5×10 6 cells/mouse (8 mice/condition) are transplanted into wild-type FVB/N recipient mice irradiated at 900 cGy. Engraftment is monitored by drawing peripheral blood (PB) every 4 weeks. The percentage of GFP + cells in PB is analyzed by flow cytometry. aladdin has not independently confirmed the accuracy of these methods. They are for reference only.

Form:Solid

IC50& Target:IC50: 1.3 nM (mSmo), 2.5 nM (hSmo)

Specifications

Sinónimos
CHEBI:90864 | N-(6-((2R, 6S)-2, 6-Dimethylmorpholino)pyridin-3-yl)-2-methyl-4'-(trifluoromethoxy)-[1, 1'-biphenyl]-3-carboxamide bis(phosphate) | Sonidegib phosphate | SONIDEGIB PHOSPHATE [USAN] | Erismodegib phosphate | NVP-LDE 225 diphosphateSonidegib diph
Especificaciones y pureza
≥99%
Mecanismos bioquímicos y fisiológicos
Sonidegib diphosphate (Erismodegib diphosphate) is a potent and selective Smo antagonist with IC 50 of 1.3 nM and 2.5 nM for mouse and human Smo in binding assay, respectively.
Condiciones de almacenamiento de almacenamiento
Store at 2-8°C, Desiccated
Enviado en
Wet ice
Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.
Tipo de acción
INHIBITOR
Mecanismo de acción
Smoothened homolog inhibitor
Pureza
≥99%
Nombres e identificadores
Sonrisas canónicasCC1CN(CC(O1)C)C2=NC=C(C=C2)NC(=O)C3=CC=CC(=C3C)C4=CC=C(C=C4)OC(F)(F)F.OP(=O)(O)O.OP(=O)(O)O
IUPAC NameN-[6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]pyridin-3-yl]-2-methyl-3-[4-(trifluoromethoxy)phenyl]benzamide;phosphoric acid
InChIKeyRWIVSVMMGFFZIJ-VWDRLOGHSA-N
INCHI1S/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+;;
Isómeros SMILES C[C@@H]1CN(C[C@@H](O1)C)C2=NC=C(C=C2)NC(=O)C3=CC=CC(=C3C)C4=CC=C(C=C4)OC(F)(F)F.OP(=O)(O)O.OP(=O)(O)O
PubChem CID 45138699
Peso molecular 681.5

Documentation

📋 Safety Data Sheet (SDS)

Comprehensive hazard, handling, storage, and regulatory compliance document.

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✅ Certificate of Analysis (COA)

Lot-specific quality data. Enter your lot number to retrieve the exact COA.

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📊 Datasheet

Quick-reference summary of product specifications and applications.

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🔬 Specification Sheet

Full quality attributes and acceptance criteria for this grade.

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Advanced Data

Taxonomic Classification

Taxonomy Tree

KingdomOrganic compounds
SuperclassBenzenoids
ClaseBenzene and substituted derivatives
SubclassBiphenyls and derivatives
Intermediate Tree Nodes Not available
Direct ParentBiphenyls and derivatives
Alternative Parents o-Toluamides  Benzamides  Phenoxy compounds  Phenol ethers  Benzoyl derivatives  Dialkylarylamines  Aminopyridines and derivatives  Organic phosphoric acids and derivatives  Morpholines  Imidolactams  Heteroaromatic compounds  Trihalomethanes  Secondary carboxylic acid amides  Oxacyclic compounds  Azacyclic compounds  Dialkyl ethers  Organofluorides  Organopnictogen compounds  Alkyl fluorides  Organic oxides  Hydrocarbon derivatives  
Molecular FrameworkAromatic heteromonocyclic compounds
Substituents Biphenyl - Benzamide - Benzoic acid or derivatives - O-toluamide - Toluamide - Phenoxy compound - Benzoyl - Phenol ether - Dialkylarylamine - Aminopyridine - Toluene - Morpholine - Organic phosphoric acid derivative - Oxazinane - Pyridine - Imidolactam - Heteroaromatic compound - Secondary carboxylic acid amide - Trihalomethane - Carboxamide group - Azacycle - Oxacycle - Organoheterocyclic compound - Carboxylic acid derivative - Dialkyl ether - Ether - Alkyl fluoride - Halomethane - Organohalogen compound - Hydrocarbon derivative - Organofluoride - Organonitrogen compound - Organooxygen compound - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Alkyl halide - Aromatic heteromonocyclic compound
DescripciónThis compound belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
External Descriptors Not available
Estructura 3D
Modelo de Estructura Química Interactiva





Certificados (CoA, COO, BSE/TSE y tabla de análisis)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propiedades químicas y físicas
SolubilidadDMSO : 100 mg/mL (146.74 mM; Need ultrasonic) H2O : 0.25 mg/mL (0.37 mM; Need ultrasonic)
Peso molecular681.500 g/mol
XLogP3
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count16
Rotatable Bond Count5
Exact Mass681.146 Da
Monoisotopic Mass681.146 Da
Topological Polar Surface Area219.000 Ų
Heavy Atom Count45
Formal Charge0
Complexity741.000
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
The total count of all stereochemical bonds0
Covalently-Bonded Unit Count3
Preguntas frecuentes y artículos
Calculadoras de soluciones
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