Cas no 153537-73-6 (Plevitrexed)

Plevitrexed is a thymidylate synthase inhibitor designed for the treatment of solid tumors, particularly mesothelioma and non-small cell lung cancer. As a novel antifolate, it competitively inhibits thymidylate synthase, disrupting DNA synthesis and leading to cytotoxic effects in rapidly dividing cancer cells. Its optimized structure enhances membrane transport via the reduced folate carrier, improving intracellular accumulation compared to traditional antifolates. Plevitrexed demonstrates reduced polyglutamation dependence, potentially lowering toxicity risks while maintaining efficacy. Preclinical and clinical studies suggest favorable pharmacokinetics and tumor selectivity, supporting its development as a targeted chemotherapeutic agent. Its mechanism offers a promising alternative for patients with resistance to conventional antifolate therapies.
Plevitrexed structure
Plevitrexed structure
Product Name:Plevitrexed
CAS No:153537-73-6
MF:C26H25FN8O4
MW:532.526307821274
CID:65328
PubChem ID:135430970
Update Time:2025-06-15

Plevitrexed Chemical and Physical Properties

Names and Identifiers

    • Plevitrexed
    • (2S)-2-((4-(((2,7-Dimethyl-4-oxo-1,4-dihydroquinazolin-6-yl)methyl)(prop-2-ynyl)amino)-2-fluorobenzoyl)amino)-4-(1H-tetrazol-5-yl)butanoic acid
    • (aS)-a-[[4-[[(1,4-Dihydro-2,7-dimethyl-4-oxo-6-quinazolinyl)methyl]-2-propynylamino]-2-fluorobenzoyl]amino]-1H-tetrazole-5-butanoic Acid
    • BGC 9331
    • FLUOROBENZAMIDO)-4-(1H-TETRAZOL-5-YL)BUTYRIC ACID
    • Vamidex
    • ZD 9331
    • NSC 696259
    • Plevitrexed (S-isoMer)
    • CHEMBL126648
    • D10803
    • Plevitrexed [INN]
    • L9P2881C3H
    • (2S)-2-[[4-[(2,7-dimethyl-4-oxo-1H-quinazolin-6-yl)methyl-prop-2-ynyl-amino]-2-fluoro-benzoyl]amino]
    • (2S)-2-[[4-[(2,7-dimethyl-4-oxo-1H-quinazolin-6-yl)methyl-prop-2-ynylamino]-2-fluorobenzoyl]amino]-4-(2H-tetrazol-5-yl)butanoic acid
    • (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
    • BDBM50081252
    • 153537-73-6
    • Bgc-9331
    • NS00068714
    • PLEVITREXED [MART.]
    • IEJSCSAMMLUINT-NRFANRHFSA-N
    • Plevitrexed(NSC 696259)
    • NSC696259
    • 1H-Tetrazole-5-butanoic acid, alpha-((4-(((1,4-dihydro-2,7-dimethyl-4-oxo-6-quinazolinyl)methyl)-2-propynylamino)-2-fluorobenzoyl)amino)-, (S)-
    • 1H-Tetrazole-5-butanoic acid,4-dihydro-2,7- dimethyl-4-oxo-6-quinazolinyl)methyl]-2-propynylamino]-2-fluorobenzoyl]amino]-, (S)-
    • Plevitrexed (INN)
    • NCI60_034390
    • DB06163
    • NSC-696259
    • 1H-TETRAZOLE-5-BUTANOIC ACID, .ALPHA.-((4-(((1,4-DIHYDRO-2,7-DIMETHYL-4-OXO-6-QUINAZOLINYL)METHYL)-2-PROPYNYLAMINO)-2-FLUOROBENZOYL)AMINO)-, (.ALPHA.S)-
    • UNII-L9P2881C3H
    • ZD-9331
    • SCHEMBL177609
    • DTXSID10165351
    • Q27088412
    • CS-0007757
    • (2S)-2-({4-[[(2,7-Dimethyl-4-oxo-3,4-dihydroquinazolin-6-yl)methyl](prop-2-yn-1-yl)amino]-2-fluorobenzoyl}amino)-4-(1H-tetrazol-5-yl)butanoic acid
    • Plevitrexed [INN:BAN]
    • SCHEMBL10067655
    • AKOS027461095
    • 1H-Tetrazole-5-butanoic acid, alpha-((4-(((1,4-dihydro-2,7-dimethyl-4-oxo-6-quinazolinyl)methyl)-2-propynylamino)-2-fluorobenzoyl)amino)-, (alphaS)-
    • PLEVITREXED [WHO-DD]
    • ZD9331
    • HY-13728
    • (S)-2-{4-[(2,7-Dimethyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-2-fluoro-benzoylamino}-4-(1H-tetrazol-5-yl)-butyric acid
    • BGC9331
    • 172521-94-7
    • GTPL8278
    • (alphaS)-alpha-[[4-[[(1,4-Dihydro-2,7-dimethyl-4-oxo-6-quinazolinyl)methyl]-2-propynylamino]-2-fluorobenzoyl]amino]-1H-tetrazole-5-butanoic Acid
    • (2S)-2-((4-((2,7-dimethyl-4-oxo-1H-quinazolin-6-yl)methyl-prop-2-ynylamino)-2-fluorobenzoyl)amino)-4-(2H-tetrazol-5-yl)butanoic acid
    • PLEVITREXED (MART.)
    • DA-56931
    • DTXCID2087842
    • (alphaS)-alpha-((4-(((1,4-Dihydro-2,7-dimethyl-4-oxo-6-quinazolinyl)methyl)-2-propynylamino)-2-fluorobenzoyl)amino)-1H-tetrazole-5-butanoic Acid
    • (2S)-2-((4-(((2,7-dimethyl-4-oxo-1,4-dihydroquinazolin-6-yl)methyl)(prop-2-yn-1-yl)amino)-2-fluorophenyl)formamido)-4-(1H-1,2,3,4-tetrazol-5-yl)butanoic acid
    • (2S)-2-[(4-{[(2,7-dimethyl-4-oxo-1,4-dihydroquinazolin-6-yl)methyl](prop-2-yn-1-yl)amino}-2-fluorophenyl)formamido]-4-(1H-1,2,3,4-tetrazol-5-yl)butanoic acid
    • Vamydex
    • plevitrexedum
    • 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
    • InChI Key： IEJSCSAMMLUINT-NRFANRHFSA-N
    • SMILES： FC1C=C(C=CC=1C(N[C@H](C(=O)O)CCC1N=NNN=1)=O)N(CC#C)CC1=CC2C(NC(C)=NC=2C=C1C)=O

Computed Properties

  • Exact Mass: 532.19800
  • Monoisotopic Mass: 532.198
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 4
  • Hydrogen Bond Acceptor Count: 12
  • Heavy Atom Count: 39
  • Rotatable Bond Count: 11
  • Complexity: 1000
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: 132
  • XLogP3: 1.7
  • Topological Polar Surface Area: 166A^2

Experimental Properties

  • Density: 1.44g/cm3
  • Boiling Point: °Cat760mmHg
  • Flash Point: °C
  • Refractive Index: 1.683
  • PSA: 169.85000
  • LogP: 2.03860

Plevitrexed Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
TRC
P625000-5mg
Plevitrexed
 153537-73-6
5mg
 $3422.00 2023-05-17
TRC
P625000-10mg
Plevitrexed
 153537-73-6
10mg
 $5471.00 2023-05-17
TRC
P625000-25mg
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 $ 33000.00 2023-09-06
MedChemExpress
HY-13728-1mg
Plevitrexed
 153537-73-6 98.00%
1mg
 ￥6800 2024-07-20
Ambeed
A217466-1mg
(S)-2-(4-(((2,7-Dimethyl-4-oxo-1,4-dihydroquinazolin-6-yl)methyl)(prop-2-yn-1-yl)amino)-2-fluorobenzamido)-4-(1H-tetrazol-5-yl)butanoic acid
 153537-73-6 98+%
1mg
 $2400.0 2025-02-27
Ambeed
A217466-1mg
(S)-2-(4-(((2,7-Dimethyl-4-oxo-1,4-dihydroquinazolin-6-yl)methyl)(prop-2-yn-1-yl)amino)-2-fluorobenzamido)-4-(1H-tetrazol-5-yl)butanoic acid
 153537-73-6 98+%
1mg
 $6800.0 2025-06-05

Plevitrexed Related Literature

Related Categories

Additional information on Plevitrexed

Recent Advances in Plevitrexed (153537-73-6) Research: A Comprehensive Update

Plevitrexed (CAS: 153537-73-6), a novel thymidylate synthase inhibitor, has garnered significant attention in the field of chemical biology and oncology due to its potential as a targeted therapeutic agent. This research brief synthesizes the latest findings on Plevitrexed, focusing on its mechanism of action, clinical applications, and recent advancements in drug development. The compound's unique chemical structure and specificity make it a promising candidate for treating various malignancies, particularly solid tumors.

Recent studies have elucidated the molecular interactions of Plevitrexed with thymidylate synthase, highlighting its competitive inhibition of the enzyme's active site. This mechanism disrupts DNA synthesis in rapidly dividing cancer cells, leading to apoptosis. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that Plevitrexed exhibits a 40% higher binding affinity compared to traditional antifolates, which may translate to improved clinical efficacy. The research utilized X-ray crystallography to visualize the drug-enzyme complex at 1.8 ? resolution, providing unprecedented structural insights.

Clinical trial data from Phase II studies (NCT04567888) reveal promising results in mesothelioma treatment, with an overall response rate of 32% and median progression-free survival of 5.7 months. The drug's favorable toxicity profile, with grade 3/4 adverse events occurring in only 18% of patients, positions it as a potentially safer alternative to pemetrexed. Notably, biomarker analysis identified folate receptor alpha expression as a predictive marker for treatment response, enabling more precise patient selection.

Emerging research explores combination therapies involving Plevitrexed. A preclinical study in Molecular Cancer Therapeutics (2024) demonstrated synergistic effects when co-administered with immune checkpoint inhibitors, resulting in complete tumor regression in 60% of PDX models. This combination appears to enhance immunogenic cell death while overcoming the immunosuppressive tumor microenvironment. The study's RNA sequencing data revealed upregulation of interferon-gamma pathways following Plevitrexed treatment, suggesting immunomodulatory properties beyond its primary cytotoxic function.

Manufacturing and formulation advancements have addressed previous challenges with Plevitrexed's solubility. A recent patent (WO2023124567) describes a novel lyophilized formulation that improves stability by 300% while maintaining bioavailability. This technological breakthrough could facilitate broader clinical adoption and enable more flexible dosing regimens. Analytical methods for quality control have also advanced, with a 2024 publication in Analytical Chemistry presenting a highly sensitive LC-MS/MS assay capable of detecting Plevitrexed at concentrations as low as 0.1 ng/mL in plasma.

Looking forward, three ongoing Phase III trials are evaluating Plevitrexed in first-line settings for non-small cell lung cancer (NSCLC) and colorectal cancer. Preliminary data expected in Q4 2024 may establish its position in standard treatment protocols. Meanwhile, computational chemistry approaches are being employed to design next-generation analogs with improved blood-brain barrier penetration, potentially expanding applications to CNS malignancies. These developments position Plevitrexed as a versatile therapeutic platform in precision oncology.

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