WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 100230
CAS#: 863127-77-9 (hydrate)
Description: Dasatinib, also known as BMS-354825, is an orally bioavailable synthetic small molecule-inhibitor of SRC-family protein-tyrosine kinases. Dasatinib binds to and inhibits the growth-promoting activities of these kinases. Apparently because of its less stringent binding affinity for the BCR-ABL kinase, dasatinib has been shown to overcome the resistance to imatinib of chronic myeloid leukemia (CML) cells harboring BCR-ABL kinase domain point mutations.
MedKoo Cat#: 100230
Name: Dasatinib monohydrate
CAS#: 863127-77-9 (hydrate)
Chemical Formula: C22H28ClN7O3S
Exact Mass: 487.15572
Molecular Weight: 506.02
Elemental Analysis: C, 52.22; H, 5.58; Cl, 7.01; N, 19.38; O, 9.49; S, 6.34
Related CAS #: 302962-49-8 (free form) 863127-77-9 (hydrate)
Synonym: BMS-354825; BMS 354825; BMS354825; Dasatinib; US brand name: Sprycel.
IUPAC/Chemical Name: N-(2-chloro-6-methylphenyl)-2-((6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-yl)amino)thiazole-5-carboxamide monohydrate.
InChi Key: XHXFZZNHDVTMLI-UHFFFAOYSA-N
InChi Code: InChI=1S/C22H26ClN7O2S.H2O/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);1H2
SMILES Code: O=C(C1=CN=C(NC2=NC(C)=NC(N3CCN(CCO)CC3)=C2)S1)NC4=C(C)C=CC=C4Cl.[H]O[H]
Appearance: white 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, not in 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
| Biological target: | Dasatinib (BMS-354825) monohydrate is an inhibitor that targets Abl, Src and c-Kit with IC50s of <1 nM, 0.8 nM and 79 nM, 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 intra-cardiac 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 |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 100.0 | 197.62 |
The following data is based on the product molecular weight 506.02 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. 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. |
1: Korashy HM, Rahman AF, Kassem MG. Dasatinib. Profiles Drug Subst Excip Relat Methodol. 2014;39:205-37. doi: 10.1016/B978-0-12-800173-8.00004-0. Review. PubMed PMID: 24794907.
2: Lindauer M, Hochhaus A. Dasatinib. Recent Results Cancer Res. 2014;201:27-65. doi: 10.1007/978-3-642-54490-3_2. Review. PubMed PMID: 24756784.
3: Qiu ZY, Xu W, Li JY. Large granular lymphocytosis during dasatinib therapy. Cancer Biol Ther. 2014 Mar 1;15(3):247-55. doi: 10.4161/cbt.27310. Epub 2013 Dec 18. Review. PubMed PMID: 24352048; PubMed Central PMCID: PMC3974824.
4: Nagao T, Takahashi N, Kameoka Y, Noguchi S, Shinohara Y, Ohyagi H, Kume M, Sawada K. Dasatinib-responsive chronic lymphocytic leukemia in a patient treated for coexisting chronic myeloid leukemia. Intern Med. 2013;52(22):2567-71. Review. PubMed PMID: 24240798.
5: Paydas S. Dasatinib, large granular lymphocytosis, and pleural effusion: useful or adverse effect? Crit Rev Oncol Hematol. 2014 Feb;89(2):242-7. doi: 10.1016/j.critrevonc.2013.10.005. Epub 2013 Oct 12. Review. PubMed PMID: 24210599.
6: Signorovitch J, Ayyagari R, Reichmann WM, Wu EQ, Chen L. Major molecular response during the first year of dasatinib, imatinib or nilotinib treatment for newly diagnosed chronic myeloid leukemia: a network meta-analysis. Cancer Treat Rev. 2014 Mar;40(2):285-92. doi: 10.1016/j.ctrv.2013.09.004. Epub 2013 Sep 17. Review. PubMed PMID: 24112812.
7: Eadie LN, Hughes TP, White DL. Interaction of the efflux transporters ABCB1 and ABCG2 with imatinib, nilotinib, and dasatinib. Clin Pharmacol Ther. 2014 Mar;95(3):294-306. doi: 10.1038/clpt.2013.208. Epub 2013 Oct 9. Review. PubMed PMID: 24107928.
8: Hochhaus A, Kantarjian H. The development of dasatinib as a treatment for chronic myeloid leukemia (CML): from initial studies to application in newly diagnosed patients. J Cancer Res Clin Oncol. 2013 Dec;139(12):1971-84. doi: 10.1007/s00432-013-1488-z. Epub 2013 Aug 13. Review. PubMed PMID: 23942795; PubMed Central PMCID: PMC3825579.
9: Brazzelli V, Grasso V, Borroni G. Imatinib, dasatinib and nilotinib: a review of adverse cutaneous reactions with emphasis on our clinical experience. J Eur Acad Dermatol Venereol. 2013 Dec;27(12):1471-80. doi: 10.1111/jdv.12172. Epub 2013 Apr 24. Review. PubMed PMID: 23611501.
10: Keating GM, Lyseng-Williamson KA, McCormack PL, Keam SJ. Dasatinib: a guide to its use in chronic myeloid leukemia in the EU. BioDrugs. 2013 Jun;27(3):275-9. doi: 10.1007/s40259-013-0024-7. Review. PubMed PMID: 23549840.
Related CAS#
863127-77-9 (Dasatinib monohydrate);
302962-49-8 (Dasatinib).
