CAS 69304-47-8 MFCD00058585-(E)-5-(2-Bromovinyl)-2’-Deoxyuridine 5-((E)-2-溴乙烯基)-1-((2R,4S,5R)-4-羟基-5-(羟甲基)四氢呋喃-2-基)嘧啶-2,4(1H,3H)-二酮 TAO{mole}

(E)-5-(2-Bromovinyl)-2’-Deoxyuridine 5-((E)-2-溴乙烯基)-1-((2R,4S,5R)-4-羟基-5-(羟甲基)四氢呋喃-2-基)嘧啶-2,4(1H,3H)-二酮

CAS 69304-47-8 MFCD00058585

化学结构图

SMILES: O=c1[nH]c(=O)n([C@H]2C[C@H](O)[C@@H](CO)O2)cc1/C=C/Br

化学属性

Mol. Formula	C11H13BrN2O5
Mol. Weight	333
Melting Point	ca 165° dec.
TSCA	No
Density	1.422
Appearance	Solid powder
Solubility	Soluble in DMSO, not in water

别名和识别编码

Chemical Name	(E)-5-(2-Bromovinyl)-2’-Deoxyuridine
MDL Number	MFCD00058585
Synonym	BVDU BVdU Bridic Brivox Brivudin Helpin Zerpex Zonavir and Zostex. Abbreviation: BVDU; Code name: RP101. Chemical structure name: (E)5(2bromovinyl)2deoxyuridine Brivudine
CAS Number	69304-47-8
PubChem Substance ID	87561214
Reaxys-RN	758153
Merck Number	1378
EC Number	250-023-7
Beilstein Registry Number	758153
Chemical Name Translation	5-((E)-2-溴乙烯基)-1-((2R,4S,5R)-4-羟基-5-(羟甲基)四氢呋喃-2-基)嘧啶-2,4(1H,3H)-二酮
Wiswesser Line Notation	T6NVMVJ E1U1E A- ET5OTJ B1Q CQ
Formula	C11H13BrN2O5
IUPAC Name	5-[(E)-2-bromoethenyl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
InChIKey	ODZBBRURCPAEIQ-PIXDULNESA-N
InChI	InChI=1S/C11H13BrN2O5/c12-2-1-6-4-14(11(18)13-10(6)17)9-3-7(16)8(5-15)19-9/h1-2,4,7-9,15-16H,3,5H2,(H,13,17,18)/b2-1+/t7-,8+,9+/m0/s1
Canonical SMILES	O=C1NC(C(/C=C/Br)=CN1[C@@H]2O[C@H](CO)[C@@H](O)C2)=O

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产品应用

Brivudine, also known as bromovinyl-deoxyuridine, is a uridine derivative and nucleoside analog with pro-apoptotic and chemosensitizing properties. In vitro, bromovinyl-deoxyuridine (BVDU) has been shown to downregulate the multifunctional DNA repair enzyme APEX nuclease 1, resulting in the inhibition of DNA repair and the induction of apoptosis. In addition, this agent may inhibit the expression of STAT3 (signal transducer and activator of transcription 3), which may result in the downregulation of vascular endothelial growth factor (VEGF). BVDU has also been found to inhibit the upregulation of chemoresistance genes (Mdr1 and DHFR) during chemotherapy. Overall, the gene expression changes associated with BVDU treatment result in the decrease or prevention of chemoresistance. In addition, this agent has been shown to enhance the cytolytic activity of NK-92 natural killer cells towards a pancreatic cancer cell line in vitro.

安全信息

RTECSYU7355000

WGK Germany3

Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Storage condition 0-10 0-10°C Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Signal word Warning

GHS Symbol

Safety Statements

S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触；

Risk Statements

R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性

Precautionary statements

P262 Do not get in eyes, on skin, or on clothing. 不要接触眼睛，皮肤或衣服。

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1420 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   CHATDV Chemioterapia Antimicrobica.  (Florence, Italy)  V.1-5, 1978-81(?).
   Volume(issue)/page/year: 4,70,1981

TYPE OF TEST            : Mutation in mammalian somatic cells
TEST SYSTEM             : Human HeLa cell
DOSE/DURATION           : 4 mg/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 267,125,1992

TYPE OF TEST            : Sister chromatid exchange
TEST SYSTEM             : Human Lymphocyte
DOSE/DURATION           : 50 mg/L
REFERENCE :
   BMJOAE British Medical Journal.  (British Medical Assoc., BMA House,
   Tavistock Sq., London WC1H 9JR, UK)  V.1-    1857- Volume(issue)/page/year:
   283,817,1981

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Human Fibroblast
DOSE/DURATION           : 24 mg/L
REFERENCE :
   AMACCQ Antimicrobial Agents and Chemotherapy.  (American Soc. for
   Microbiology, 1913 I St., NW, Washington, DC 20006)  V.1-    1972-
   Volume(issue)/page/year: 24,803,1983

TYPE OF TEST            : Sister chromatid exchange
TEST SYSTEM             : Human Fibroblast
DOSE/DURATION           : 50 mg/L
REFERENCE :
   BMJOAE British Medical Journal.  (British Medical Assoc., BMA House,
   Tavistock Sq., London WC1H 9JR, UK)  V.1-    1857- Volume(issue)/page/year:
   283,817,1981