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MedKoo Cat#: 202270 | Name: Plevitrexed

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Plevitrexed
Plevitrexed
CAS#153537-73-6

Theoretical Analysis

MedKoo Cat#: 202270

Name: Plevitrexed

CAS#: 153537-73-6

Chemical Formula: C26H25FN8O4

Exact Mass: 532.1983

Molecular Weight: 532.53

Elemental Analysis: C, 58.64; H, 4.73; F, 3.57; N, 21.04; O, 12.02

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
BGC-9331; BGC 9331; BGC9331. ZD-9331; ZD-9331; ZD-9331; NSC-696259； NSC696259； NSC 696259；Plevitrexed; Vamidex.
IUPAC/Chemical Name
(S)-2-(4-(((2,7-dimethyl-4-oxo-3,4-dihydroquinazolin-6-yl)methyl)(prop-2-yn-1-yl)amino)-2-fluorobenzamido)-4-(1H-tetrazol-5-yl)butanoic acid
InChi Key
IEJSCSAMMLUINT-NRFANRHFSA-N
InChi Code
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
SMILES Code
O=C(O)[C@@H](NC(C1=CC=C(N(CC2=CC3=C(N=C(C)NC3=O)C=C2C)CC#C)C=C1F)=O)CCC4=NN=NN4
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in water.
Shelf Life
>5 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
       

Preparing Stock Solutions

The following data is based on the product molecular weight 532.53 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
 1: Lovelace LL, Gibson LM, Lebioda L. Cooperative inhibition of human thymidylate synthase by mixtures of active site binding and allosteric inhibitors. Biochemistry. 2007 Mar 13;46(10):2823-30. Epub 2007 Feb 13. PubMed PMID: 17297914; PubMed Central PMCID: PMC2516748. 2: Peña MM, Xing YY, Koli S, Berger FG. Role of N-terminal residues in the ubiquitin-independent degradation of human thymidylate synthase. Biochem J. 2006 Feb 15;394(Pt 1):355-63. PubMed PMID: 16259621; PubMed Central PMCID: PMC1386034. 3: Coudray AM, Louvet C, Kornprobst M, Raymond E, André T, Tournigand C, Faivre S, De Gramont A, Larsen AK, Gespach C. Increased anticancer activity of the thymidylate synthase inhibitor BGC9331 combined with the topoisomerase I inhibitor SN-38 in human colorectal and breast cancer cells: induction of apoptosis and ROCK cleavage through caspase-3-dependent and -independent mechanisms. Int J Oncol. 2005 Aug;27(2):553-61. PubMed PMID: 16010439. 4: Louvet C, André T, Gamelin E, Garcia ML, Saavedra A, Lenaers G, de Gramont A, Méry-Mignard D, Kalla S. A phase I-II, dose-escalating trial of ZD9331 in combination with irinotecan (CPT11) in previously pretreated metastatic colorectal cancer patients. Bull Cancer. 2004 Dec;91(12):279-84. PubMed PMID: 15634630. 5: Benepal TS, Judson I. ZD9331: discovery to clinical development. Anticancer Drugs. 2005 Jan;16(1):1-9. Review. PubMed PMID: 15613898. 6: Damaraju VL, Hamilton KF, Seth-Smith ML, Cass CE, Sawyer MB. Characterization of binding of folates and antifolates to brush-border membrane vesicles isolated from human kidney. Mol Pharmacol. 2005 Feb;67(2):453-9. Epub 2004 Oct 27. PubMed PMID: 15509714. 7: Wang Y, Zhao R, Goldman ID. Characterization of a folate transporter in HeLa cells with a low pH optimum and high affinity for pemetrexed distinct from the reduced folate carrier. Clin Cancer Res. 2004 Sep 15;10(18 Pt 1):6256-64. PubMed PMID: 15448015. 8: Geller JI, Szekely-Szucs K, Petak I, Doyle B, Houghton JA. P21Cip1 is a critical mediator of the cytotoxic action of thymidylate synthase inhibitors in colorectal carcinoma cells. Cancer Res. 2004 Sep 1;64(17):6296-303. PubMed PMID: 15342418. 9: Ackland SP, Beale P, Peters GJ. Thymidylate synthase inhibitors. Cancer Chemother Biol Response Modif. 2003;21:1-28. Review. PubMed PMID: 15338738. 10: Schwartz GH, Jones CB, Garrison M, Patnaik A, Takimoto C, McCreery H, Skinner M, Tolcher AW, Rowinsky EK. A phase I and pharmacokinetic study of the nonpolyglutamatable thymidylate synthase inhibitor ZD9331 plus docetaxel in patients with advanced solid malignancies. Invest New Drugs. 2004 Nov;22(4):437-48. PubMed PMID: 15292714. 11: Schulz J, Keller A, Canfield V, Parker G, Douglass E. ZD9331 as second- or third-line therapy in patients with advanced colorectal cancer: a phase II multicenter trial. Am J Clin Oncol. 2004 Aug;27(4):337-42. PubMed PMID: 15289725. 12: Jackman AL, Theti DS, Gibbs DD. Antifolates targeted specifically to the folate receptor. Adv Drug Deliv Rev. 2004 Apr 29;56(8):1111-25. Review. PubMed PMID: 15094210. 13: Forsthoefel AM, Peña MM, Xing YY, Rafique Z, Berger FG. Structural determinants for the intracellular degradation of human thymidylate synthase. Biochemistry. 2004 Feb 24;43(7):1972-9. PubMed PMID: 14967037. 14: Theti DS, Jackman AL. The role of alpha-folate receptor-mediated transport in the antitumor activity of antifolate drugs. Clin Cancer Res. 2004 Feb 1;10(3):1080-9. PubMed PMID: 14871988. 15: Bilenker JH, Stevenson JP, Flaherty KT, Algazy K, McLaughlin K, Haller DG, Giantonio BJ, Koehler M, Garcia-Vargas JE, O'Dwyer PJ. Phase I trial of the antifolate ZD9331 in combination with cisplatin in patients with refractory solid malignancies. Cancer Chemother Pharmacol. 2004 Apr;53(4):357-60. Epub 2004 Jan 13. PubMed PMID: 14722734. 16: Geller J, Petak I, Szucs KS, Nagy K, Tillman DM, Houghton JA. Interferon-gamma-induced sensitization of colon carcinomas to ZD9331 targets caspases, downstream of Fas, independent of mitochondrial signaling and the inhibitor of apoptosis survivin. Clin Cancer Res. 2003 Dec 15;9(17):6504-15. PubMed PMID: 14695155. 17: Rader JS, Clarke-Pearson D, Moore M, Carson L, Holloway R, Kao MS, Wiznitzer I, Douglass EC. A phase II study to determine the efficacy and tolerability of intravenous ZD9331 in heavily pretreated patients with ovarian cancer. Gynecol Oncol. 2003 Nov;91(2):318-25. PubMed PMID: 14599861. 18: Benson A 3rd, Poplin E, Vergote I. ZD9331 in combination with topotecan: phase I and II experience. Anticancer Drugs. 2003 May;14 Suppl 1:S21-7. Review. PubMed PMID: 14567437. 19: Hainsworth J, Vergote I, Janssens J. A review of phase II studies of ZD9331 treatment for relapsed or refractory solid tumours. Anticancer Drugs. 2003 May;14 Suppl 1:S13-9. PubMed PMID: 14567436.