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Plevitrexed

CAT: 0804-HY-13728-02Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-13728-02Size:5 mg
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Description
Plevitrexed (ZD 9331; BGC 9331) is an orally active and potent thymidylate synthase (TS) inhibitor with a Ki of 0.44 nM. Plevitrexed is taken up via the α-folate receptor as well as the reduced folate carrier. Plevitrexed is used for gastric cancer in clinical[1][2][3]. Plevitrexed is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
CAS Number
153537-73-6
Product Name Alternative
ZD 9331; BGC9331
UNSPSC
12352005
Target
Thymidylate Synthase
Type
Reference compound
Related Pathways
Apoptosis
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/plevitrexed.html
Purity
99.35
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
O=C(NC(C)=N1)C2=C1C=C(C)C(CN(C3=CC=C(C(N[C@H](C(O)=O)CCC4=NNN=N4)=O)C(F)=C3)CC#C)=C2
Molecular Formula
C26H25FN8O4
Molecular Weight
532.53
References & Citations
[1]Tochowicz A, et al. Development and binding mode assessment of N-[4-[2-propyn-1-yl[ (6S) -4,6,7,8-tetrahydro-2- (hydroxymethyl) -4-oxo-3H-cyclopenta[g]quinazolin-6-yl]amino]benzoyl]-l-γ-glutamyl-D-glutamic acid (BGC 945), a novel thymidylate synthase inhibitor that targets tumor cells. J Med Chem. 2013 Jul 11;56 (13) :5446-55.|[2]A. Thomas, et al. A phase I/II study of plevitrexed with nutritional vitamin supplementation in gastric cancer.|[3]Marsham PR, et al. Design and synthesis of potent non-polyglutamatable quinazoline antifolate thymidylate synthase inhibitors. J Med Chem. 1999 Sep 23;42 (19) :3809-20.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C, 3 years (Powder)
Scientific Category
Reference compound1
Clinical Information
Phase 2

Chemical Information

Plevitrexed

Plevitrexed is an orally bioavailable, small molecule, non-polyglutamatable, antifolate quinazoline derivative thymidine synthetase inhibitor with potential antineoplastic activity. Plevitrexed is transported into the cell via the physiological reduced folate carrier (RFC) system. Intracellularly, this agent selectively binds to the folate binding site of thymidylate synthase and inhibits thymidine synthesis, which may result in DNA synthesis inhibition and apoptosis.

CAS Number153537-73-6
PubChem CID135430970
IUPAC Name(2S)-2-[[4-[(2,7-dimethyl-4-oxo-3H-quinazolin-6-yl)methyl-prop-2-ynylamino]-2-fluorobenzoyl]amino]-4-(2H-tetrazol-5-yl)butanoic acid
Molecular FormulaC26H25FN8O4
Molecular Weight532.5
XLogP1.7
Topological Polar Surface Area166
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count10
Rotatable Bond Count10
Heavy Atom Count39
Formal Charge0
Complexity1000
SMILES
CC1=CC2=C(C=C1CN(CC#C)C3=CC(=C(C=C3)C(=O)N[C@@H](CCC4=NNN=N4)C(=O)O)F)C(=O)NC(=N2)C
InChI
InChI=1S/C26H25FN8O4/c1-4-9-35(13-16-11-19-22(10-14(16)2)28-15(3)29-25(19)37)17-5-6-18(20(27)12-17)24(36)30-21(26(38)39)7-8-23-31-33-34-32-23/h1,5-6,10-12,21H,7-9,13H2,2-3H3,(H,30,36)(H,38,39)(H,28,29,37)(H,31,32,33,34)/t21-/m0/s1
InChIKey
IEJSCSAMMLUINT-NRFANRHFSA-N
Chemical Structure
2D Structure
2D structure of Plevitrexed
CAS: 153537-73-6
CID: 135430970
Formula: C26H25FN8O4
MW: 532.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight532.5
XLogP31.7
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count10
Rotatable Bond Count10
Exact Mass532.19827947
Monoisotopic Mass532.19827947
Topological Polar Surface Area166 Ų
Heavy Atom Count39
Formal Charge0
Complexity1000
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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