Stereochemistry | ABSOLUTE |
Molecular Formula | C9H11BrN2O5 |
Molecular Weight | 307.098 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC[C@H]1O[C@H](C[C@@H]1O)N2C=C(Br)C(=O)NC2=O
InChI
InChIKey=WOVKYSAHUYNSMH-RRKCRQDMSA-N
InChI=1S/C9H11BrN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1
Molecular Formula | C9H11BrN2O5 |
Molecular Weight | 307.098 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Broxuridine (5-Bromo-2-deoxyuridine, BrdU) is a thymidine analogue that is incorporated into replicating DNA. BrdU taken up by cells is phosphorylated and incorporated into DNA in place of dT. Although originally designed as a chemotherapeutic agent, sublethal concentrations of BrdU have long been known to alter the growth and phenotype of a wide range of cell types. The most popular use of BrdU is as a tracer of DNA synthesis. The other well-known use of BrdU is as a DNA photosensitizer. BrdU substitution of dT in DNA sensitizes it to near-UV light, and cells with BrdU-substituted DNA cannot survive after exposure to near-UV light. BUdR has side effects on cell functions. Cell growth can be inhibited, normal development of differentiating systems be perturbed, activities of specific enzymes be reduced. Mutagenic effects of BUdR are interpreted as reflections of a mispairing of BUdR in its rare enol form. Effects of BUdR which can be reversed by addition of thymidine are not likely to be mutagenic. As another mechanism of action of BUdR has been suggested that incorporation of BUdR into DNA alters the pattern of transcription.
CNS Activity
Originator
Approval Year
PubMed
Patents
Sample Use Guides
Broxuridine (BrdUrd) was infused via the arterial catheter for 7 days at a dose rate of 25 mg/kg/day
Route of Administration:
Intra-arterial
Tritiated Broxuridine (BrdUrd) was used to estab lish the extent of variation between 3 glioblastoma cell lines (U-251, U-118, and D-54). Imax is the maximum amount of BrdUrd incorporation after one cell doubling and C50 is the BrdUrd concentration required to achieve half Imax after one population doubling (Imax/2). The C50 value for BrdUrd is 1.8±0.11 uM in the U-251 cell line.