Fludarabine (Standard)

CAT: 0804-HY-B0069R-01Size: 5 mgDry Ice: NoHazardous: No

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CAT#:0804-HY-B0069R-01Size:5 mg

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Description

Fludarabine (Standard) is the analytical standard of Fludarabine. This product is intended for research and analytical applications. Fludarabine (NSC 118218) is a DNA synthesis inhibitor and a fluorinated purine analogue with antineoplastic activity in lymphoproliferative malignancies. Fludarabine inhibits the cytokine-induced activation of STAT1 and STAT1-dependent gene transcription in normal resting or activated lymphocytes[1][2][3][4].

CAS Number

21679-14-1

Product Name Alternative

F-ara-A (Standard) ; NSC 118218 (Standard)

UNSPSC

12352005

Hazard Statement

H225-H301-H311-H331-H341-H361-H370-H371

Target

Apoptosis; DNA/RNA Synthesis; Nucleoside Antimetabolite/Analog; Reference Standards; STAT

Type

Reference Standards

Related Pathways

Apoptosis; Cell Cycle/DNA Damage; JAK/STAT Signaling; Others; Stem Cell/Wnt

Field of Research

Cancer

Assay Protocol

https://www.medchemexpress.com/fludarabine-standard.html

Smiles

O[C@H]1[C@H](O)[C@H](N2C(N=C(F)N=C3N)=C3N=C2)O[C@@H]1CO

Molecular Formula

C10H12FN5O4

Molecular Weight

285.23

Precautions

P280-P405-P501

References & Citations

[1]Tournilhac O, et al. Impact of frontline fludarabine and cyclophosphamide combined treatment on peripheral blood stem cell mobilization in B-cell chronic lymphocytic leukemia. Blood. 2004 Jan 1;103 (1) :363-5. Epub 2003 Sep 11.|[2]Liang YB, et al. Downregulated SOCS1 expression activates the JAK1/STAT1 pathway and promotes polarization of macrophages into M1 type. Mol Med Rep. 2017 Nov;16 (5) :6405-6411.|[3]Sanhes L, et al. Fludarabine-induced apoptosis of B chronic lymphocytic leukemia cells includes early cleavage of p27kip1 by caspases. Leukemia. 2003 Jun;17 (6) :1104-11.|[4]Weiss L, et al. Fludarabine in combination with cyclophosphamide decreases incidence of GVHD and maintainseffective graft-versus-leukemia effect after allogeneic stem cell transplantation in murinelymphocytic leukemia. Bone Marrow Transplant. 2003 Jan;31 (1) :11-5.|[5]Frank DA, et al. Fludarabine-induced immunosuppression is associated with inhibition of STAT1 signaling. Nat Med. 1999 Apr;5 (4) :444-7.|[6]Frank DA, et al. Fludarabine-induced immunosuppression is associated with inhibition of STAT1 signaling. Nat Med. 1999;5 (4) :444-447.

Shipping Conditions

Room temperature

Scientific Category

Reference Standards

Clinical Information

Launched

Chemical Information

Fludarabine

(2R,3S,4S,5R)-2-(6-amino-2-fluoro-9-purinyl)-5-(hydroxymethyl)oxolane-3,4-diol is a purine nucleoside.

CAS Number	21679-14-1
PubChem CID	657237
IUPAC Name	(2R,3S,4S,5R)-2-(6-amino-2-fluoropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Molecular Formula	C10H12FN5O4
Molecular Weight	285.23
XLogP	-0.6
Topological Polar Surface Area	140
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	2
Heavy Atom Count	20
Formal Charge	0
Complexity	367

SMILES

C1=NC2=C(N=C(N=C2N1[C@H]3[C@H]([C@@H]([C@H](O3)CO)O)O)F)N

InChI

InChI=1S/C10H12FN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5-,6+,9-/m1/s1

InChIKey

HBUBKKRHXORPQB-FJFJXFQQSA-N

Chemical Structure

2D Structure

CAS: 21679-14-1

CID: 657237

Formula: C10H12FN5O4

MW: 285.23

Interactive 3D Structure

Loading 3D structure...

View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	285.23
XLogP3	-0.6
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	2
Exact Mass	285.08733204
Monoisotopic Mass	285.08733204
Topological Polar Surface Area	140 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	367
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

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