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Details

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
Structure of BROXURIDINE

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

HIDE SMILES / InChI

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

Description

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

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown
Primary
Unknown
Diagnostic
Unknown
Primary
Unknown
Diagnostic
Unknown
Secondary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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.
Substance Class Chemical
Record UNII
G34N38R2N1
Record Status Validated (UNII)
Record Version