Dasatinib
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MedKoo CAT#: 574900

CAS#: 302962-49-8 (free)

Description: Dasatinib is a potent inhibitor of the non-receptor tyrosine kinases Abl and Src as well as other members of the Src family. Dasatinib may have therapeutic value in fibrotic diseases characterized by elevated levels of Abl and Src kinases.


Chemical Structure

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Dasatinib
CAS# 302962-49-8 (free)

Theoretical Analysis

MedKoo Cat#: 574900
Name: Dasatinib
CAS#: 302962-49-8 (free)
Chemical Formula: C22H26ClN7O2S
Exact Mass: 487.1557
Molecular Weight: 488.01
Elemental Analysis: C, 54.15; H, 5.37; Cl, 7.26; N, 20.09; O, 6.56; S, 6.57

Price and Availability

Size Price Availability Quantity
500.0mg USD 150.0 Ready to ship
1.0g USD 250.0 Ready to ship
2.0g USD 450.0 Ready to ship
5.0g USD 750.0 Ready to ship
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Related CAS #: 863127-77-9 (hydrate)   302962-49-8 (free)   2112837-79-1 (cabaldehyde)   910297-52-8 (N-oxide)    

Synonym: BMS 354825, Dasatinib, Sprycel

IUPAC/Chemical Name: N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5-thiazolecarboxamide

InChi Key: ZBNZXTGUTAYRHI-UHFFFAOYSA-N

InChi Code: InChI=1S/C22H26ClN7O2S/c1-14-4-3-5-16(23)20(14)28-21(32)17-13-24-22(33-17)27-18-12-19(26-15(2)25-18)30-8-6-29(7-9-30)10-11-31/h3-5,12-13,31H,6-11H2,1-2H3,(H,28,32)(H,24,25,26,27)

SMILES Code: O=C(NC1=C(Cl)C=CC=C1C)C(S2)=CN=C2NC3=NC(C)=NC(N4CCN(CCO)CC4)=C3

Appearance: A crystalline solid

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

Shelf Life: >3 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

Biological target: Dasatinib (BMS-354825) is an ATP competitive, dual Src/Bcr-Abl inhibitor (IC50s of <1.0 nM and 0.5 nM) with potent antitumor activity and Ki’s of 16 pM and 30 pM for Src and Bcr-Abl, respectively.
In vitro activity: Dasatinib inhibited tyrosine kinase and induced eryptosis in human erythrocytes with early denature of esterase, cell shrinkage, loss of membrane integrity with inside-out phosphatidylserine, increase in the cytosolic Ca2+ ion concentration ([Ca2+]i), caspase-3 activation and change in cellular redox state. Mechanistically, the rise of [Ca2+]i seems to be a key mediator in the dasatinib-mediated eryptosis because depletion of external Ca2+ could suppress the eryptotic effects. Also, dasatinib was able to reduce membrane fluidity in human RBCs. For the direct action on membrane, dasatinib permeabilized RBC ghosts in a way similar to digitonin. Dasatinib inhibited tyrosine kinase and induced eryptosis in human erythrocytes through Ca2+ loading and membrane permeabilization. Reference: Toxicol Lett. 2018 Oct 1;295:10-21. https://www.sciencedirect.com/science/article/abs/pii/S0378427418302273?via%3Dihub
In vivo activity: In vivo effects of Dasatinib treatment on the occurrence of skeletal metastases were tested in a xenograft mouse model after intracardiac injection of osteotropic MDA-MB-231-cells. Mice which received an intra-peritoneal treatment with Dasatinib showed significantly less skeletal metastases in bioluminescence scans. Moreover, a pronounced increase in bone volume was observed in the treatment group, as detected by µ-Computed Tomography. Dasatinib treatment also led to a greater increase in bone density in tibiae without metastatic affection, which was accompanied by reduced recruitment of osteoclasts. Reference: Arch Gynecol Obstet. 2020 Jun;301(6):1493-1502. https://link.springer.com/article/10.1007%2Fs00404-020-05496-4

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 49.0 100.41

Preparing Stock Solutions

The following data is based on the product molecular weight 488.01 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. Sheng LX, Wang JP, Lai YL, Wu H, Sun YC, Zhou M, Ouyang GF, Huang H. [Effects of Dasatinib on the Expansion, Subsets, Receptor Expression and Cytotoxic Function of NK Cells in Vitro]. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2020 Oct;28(5):1762- 1768. Chinese. doi: 10.19746/j.cnki.issn.1009-2137.2020.05.055. PMID: 33067987. 2. Chan WY, Lau PM, Yeung KW, Kong SK. The second generation tyrosine kinase inhibitor dasatinib induced eryptosis in human erythrocytes-An in vitro study. Toxicol Lett. 2018 Oct 1;295:10-21. doi: 10.1016/j.toxlet.2018.05.030. Epub 2018 May 24. PMID: 29803841. 3. Abdelgalil AA, Alam MA, Raish M, Mohammed IE, Hassan Mohammed AE, Ansari MA, Al Jenoobi FI. Dasatinib significantly reduced in vivo exposure to cyclosporine in a rat model: The possible involvement of CYP3A induction. Pharmacol Rep. 2019 Apr;71(2):201-205. doi: 10.1016/j.pharep.2018.10.018. Epub 2018 Oct 31. PMID: 30785057. 4. Heilmann T, Rumpf AL, Roscher M, Tietgen M, Will O, Gerle M, Damm T, Borzikowsky C, Maass N, Glüer CC, Tiwari S, Trauzold A, Schem C. Dasatinib prevents skeletal metastasis of osteotropic MDA-MB-231 cells in a xenograft mouse model. Arch Gynecol Obstet. 2020 Jun;301(6):1493-1502. doi: 10.1007/s00404-020-05496-4. Epub 2020 Mar 14. PMID: 32170411.
In vitro protocol: 1. Sheng LX, Wang JP, Lai YL, Wu H, Sun YC, Zhou M, Ouyang GF, Huang H. [Effects of Dasatinib on the Expansion, Subsets, Receptor Expression and Cytotoxic Function of NK Cells in Vitro]. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2020 Oct;28(5):1762- 1768. Chinese. doi: 10.19746/j.cnki.issn.1009-2137.2020.05.055. PMID: 33067987. 2. Chan WY, Lau PM, Yeung KW, Kong SK. The second generation tyrosine kinase inhibitor dasatinib induced eryptosis in human erythrocytes-An in vitro study. Toxicol Lett. 2018 Oct 1;295:10-21. doi: 10.1016/j.toxlet.2018.05.030. Epub 2018 May 24. PMID: 29803841.
In vivo protocol: 1. Abdelgalil AA, Alam MA, Raish M, Mohammed IE, Hassan Mohammed AE, Ansari MA, Al Jenoobi FI. Dasatinib significantly reduced in vivo exposure to cyclosporine in a rat model: The possible involvement of CYP3A induction. Pharmacol Rep. 2019 Apr;71(2):201-205. doi: 10.1016/j.pharep.2018.10.018. Epub 2018 Oct 31. PMID: 30785057. 2. Heilmann T, Rumpf AL, Roscher M, Tietgen M, Will O, Gerle M, Damm T, Borzikowsky C, Maass N, Glüer CC, Tiwari S, Trauzold A, Schem C. Dasatinib prevents skeletal metastasis of osteotropic MDA-MB-231 cells in a xenograft mouse model. Arch Gynecol Obstet. 2020 Jun;301(6):1493-1502. doi: 10.1007/s00404-020-05496-4. Epub 2020 Mar 14. PMID: 32170411.

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1. Lombardo, L.J., Lee, F.Y., Chen, P., et al. Discovery of N-(2-chloro-6-methyl-phenyl)-2-(6-(4-(2-hydroxyethyl)-piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-carboxamide (BMS-354825),a dual Src/Abl kinase inhibitor with potent antitumor activity in preclinical assays. Journal of Medicinal Chemistry 47(27), 6658-6661 (2004).

2. Das, J., Chen, P., Norris, D., et al. 2-aminothiazole as a novel kinase inhibitor template. Structure-activity relationship studies toward the discovery of N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl)]-2-methyl-4-pyrimidinyl]amino)]-1,3-thiazole-5-carboxamide (Dasatinib, BMS-354825) as a potent pan-Src kinase inhibitor. Journal of Medicinal Chemistry 49(23), 6819-6823 (2006).

3. Davis, M.I., Hunt, J.P., Herrgard, S., et al. Comprehensive analysis of kinase inhibitor selectivity. Nat.Biotechnol. 29(11), 1046-1051 (2011).

4. Carter, T.A., Wodicka, L.M., Shah, N.P., et al. Inhibition of drug-resistant mutants of ABL, KIT, and EGF receptor kinases. Proceedings of the National Academy of Sciences of the United States of America 102(31), 11011-11016 (2005).

5. El-Amm, J., Freeman, A., Patel, N., et al. Bone-targeted therapies in metastatic castration-resistant prostate cancer: Evolving paradigms. Prostate Cancer 2013, 1-10 (2013).

6. Distler, J.H.W., and Distler, O. Intracellular tyrosine kinases as novel targets for anti-fibrotic therapy in systemic sclerosis. Rheumatology 47, 10-11 (2008).

7. McFarland, K.L., and Wetzstein, G.A. Chronic myeloid leukemia therapy: Focus on second-generation tyrosine kinase inhibitors. Cancer Control 16(2), 132-140 (2009).

Dasatinib

500.0mg / USD 150.0