5-溴-2'-脱氧尿苷

Description

5-Bromo-2'-Deoxyuridine · CAS 59-14-3 · C9H11BrN2O5. UNII G34N38R2N1. Melting Point: 365 to 369 °F (NTP, 1992); Melting Point: 187-189 °C; Solubility: 10 to 50 mg/mL at 72 °F (NTP, 1992).

Identification

CAS Registry Number	59-14-3
PubChem CID	6035
Molecular formula	C9H11BrN2O5
IUPAC name	5-bromo-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
UNII (FDA)	G34N38R2N1

Computed Descriptors

Molecular Weight	307.10
XLogP3	-0.3
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	2
Exact Mass	305.98513
Monoisotopic Mass	305.98513
Topological Polar Surface Area	99.1
Heavy Atom Count	17
Formal Charge	0

Physical & Chemical Properties

Melting Point	365 to 369 °F (NTP, 1992)
Melting Point	187-189 °C
Solubility	10 to 50 mg/mL at 72 °F (NTP, 1992)
Solubility	Water 10 - 20 (mg/mL)
Solubility	1 N NaOH > 400 (mg/mL)
Solubility	Acetone ~ 4 (mg/mL)
LogP	log Kow = -0.29
LogP	-0.29

Physical description & handling notes

• 5-bromo-2'-deoxyuridine is a white crystalline powder. (NTP, 1992)
• Crystals from absolute ethanol
• Dimethylacetamide ~ 200 (mg/mL)
• Dimethylsulfoxide ~ 160 (mg/mL)
• Bulk: The bulk drug should be stored in tightly closed containers at controlled room temperature. Solution: BUdR solutions (0.5 and 25 mg/mL) are stable for at least seven days at room temperature.
• (c = 1, 0.1 N NaOH) [a]20 D = +31 ± 1°

GHS Hazard Classification

Reported hazard statements	H340 (83.3%), H341 (13%), H361 (79.6%)

Documented Uses

• A drug that makes cancer cells more sensitive to radiation and is also used as a diagnostic agent to determine how fast cancer cells grow.
• A nucleoside that substitutes for thymidine in DNA and thus acts as an antimetabolite. It causes breaks in chromosomes and has been proposed as an antiviral and antineoplastic agent. It has been given orphan drug status for use in the treatment of primary brain tumors.
• A thymidine analog that incorporates /into/ DNA of dividing cells during the S-phase of the cell cycle. ... However, BrdU is not a marker of the S-phase of the cell cycle. As a thymidine analog, it is a marker of DNA synthesis. BrdU immunohistochemistry has been instrumental for the study of the development of the nervous system, and to confirm that neurogenesis occurs in the adult mammalian brain, including in human. ... BrdU labeling is currently the most used technique for studying adult neurogenesis in situ.
• The standard method for assessment of cell proliferation in paraffin-embedded tissue sections is 5-bromodeoxyuridine (BrdU) immunohistochemistry (IHC). BrdU can be administered to laboratory animals via IP injections, is readily incorporated into nuclei during the DNA synthetic phase of the cell cycle, and is detected with an anti-BrdU antibody. ...
• Laboratory chemical used as a mutagen in mutagenesis experiments. It is more commonly used in the detection of proliferating cells in living tissues.
• Treatment of an aqueous solution of /deoxyuridine/ with saturated bromine water at 0 °C followed by removal of excess /bromine/ by suction, concentration at 30 °C, refluxing with /ethanol/, concentration at <35 °C, and crystallization from absolute /ethanol/ gave 60% /5-bromodeoxyuridine/ (purity 99%).

Synonyms

5-BROMO-2'-DEOXYURIDINE; 59-14-3; Broxuridine; Bromodeoxyuridine; 5-Bromodeoxyuridine; BRDU; BUDR; 5-Bromo-2-deoxyuridine; Radibud; Broxuridina; 5-Bdu; 5-Bromouracil deoxyriboside; Bromouracil deoxyriboside; 5-Bromodesoxyuridine; Broxuridinum; 5-Bromouracil-2-deoxyriboside

Frequently Asked Questions

What are the CAS number and molecular formula of 5-Bromo-2'-Deoxyuridine?

CAS 59-14-3; molecular formula C9H11BrN2O5; molecular weight — g/mol.

What other names is 5-Bromo-2'-Deoxyuridine known by?

5-BROMO-2'-DEOXYURIDINE, 59-14-3, Broxuridine, Bromodeoxyuridine, 5-Bromodeoxyuridine, BRDU.

Is 5-Bromo-2'-Deoxyuridine classified as hazardous?

Hazard statements reported: H340, H341, H361.

What are the key physical properties of 5-Bromo-2'-Deoxyuridine?

Melting Point: 365 to 369 °F (NTP, 1992); Melting Point: 187-189 °C; Solubility: 10 to 50 mg/mL at 72 °F (NTP, 1992); Solubility: Water 10 - 20 (mg/mL).

Facts on this page are taken from PubChem (US National Library of Medicine) and Wikidata. Grade-specific data — assay, moisture, particle size, packaging, shelf life — is issued per batch on the COA and is not published here.