MBC-11

Chemical Information
Etidronate-Cytarabine Conjugate MBC-11 is a synthetic conjugate composed of the bisphosphonate etidronate linked to the cytostatic agent and antimetabolite cytarabine, with potential antineoplastic and antiresorptive activities. Upon intravenous administration of the etidronate-cytarabine conjugate MBC-11, the etidronate moiety targets bone and the two moieties are released upon hydrolysis. Etidronate binds to hydroxyapatite crystals in bone tissues and prevents its resorption. This prevents bone destruction and induces bone cell mineralization. In addition, the bone-targeting nature of this agent allows for the accumulation of cytarabine in bone tissue, where it is able to exert its antitumor effect locally by competing with cytidine for incorporation into DNA, thereby inhibiting DNA synthesis, while reducing systemic exposure. This leads to a destruction of bone-associated tumor cells, an inhibition of tumor cell proliferation and bone metastasis, and prevents tumor-mediated bone destruction.
| CAS Number | 332863-86-2 |
| PubChem CID | 44463769 |
| IUPAC Name | [1-[[[(2R,3S,4S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]-1-hydroxyethyl]phosphonic acid |
| Molecular Formula | C11H20N3O14P3 |
| Molecular Weight | 511.21 |
| XLogP | -6.1 |
| Topological Polar Surface Area | 279 |
| Hydrogen Bond Donor Count | 8 |
| Hydrogen Bond Acceptor Count | 14 |
| Rotatable Bond Count | 8 |
| Heavy Atom Count | 31 |
| Formal Charge | 0 |
| Complexity | 934 |
| Property | Value |
|---|---|
| Molecular Weight | 511.21 |
| XLogP3 | -6.1 |
| Hydrogen Bond Donor Count | 8 |
| Hydrogen Bond Acceptor Count | 14 |
| Rotatable Bond Count | 8 |
| Exact Mass | 511.01581331 |
| Monoisotopic Mass | 511.01581331 |
| Topological Polar Surface Area | 279 Ų |
| Heavy Atom Count | 31 |
| Formal Charge | 0 |
| Complexity | 934 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 4 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
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