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.

Product information

CAS Number: 153537-73-6

Molecular Weight: 532.53

Formula: C26H25FN8O4

Synonym:

ZD 9331

BGC9331

Chemical Name: (2S)-2-[(4-{[(2, 7-dimethyl-4-oxo-3, 4-dihydroquinazolin-6-yl)methyl](prop-2-yn-1-yl)amino}-2-fluorophenyl)formamido]-4-(2H-1, 2, 3, 4-tetrazol-5-yl)butanoic acid

Smiles: CC1NC(=O)C2=CC(CN(CC#C)C3=CC(F)=C(C=C3)C(=O)N[C@@H](CCC3N=NNN=3)C(O)=O)=C(C)C=C2N=1

InChiKey: IEJSCSAMMLUINT-NRFANRHFSA-N

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

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

ZD9331 inhibits the transport of [3H]-methotrexate into L1210 and W1L2 cells with a Ki of∼1 µM.

References:

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.

Products are for research use only. Not for human use.