A dihydrofolate reductase inhibitor
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Pralatrexate

Item No. 23689

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[4-[1-[(2,4-diamino-6-pteridinyl)methyl]-3-butyn-1-yl]benzoyl]-L-glutamic acid
CAS Number
146464-95-1
Synonyms
  • NSC 754230
  • PDX
  • 10-Propargyl-10-deazaaminopterin
Molecular Formula
C23H23N7O5
Formula Weight
477.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 14 mg/mlDMSO: 3 mg/mlPBS (pH 7.2): 1 mg/ml
λmax
241, 340 nm
SMILES
NC1=NC(N)=NC2=C1N=C(CC(CC#C)C3=CC=C(C(N[C@H](C(O)=O)CCC(O)=O)=O)C=C3)C=N2
InChi Code
InChI=1S/C23H23N7O5/c1-2-3-14(10-15-11-26-20-18(27-15)19(24)29-23(25)30-20)12-4-6-13(7-5-12)21(33)28-16(22(34)35)8-9-17(31)32/h1,4-7,11,14,16H,3,8-10H2,(H,28,33)(H,31,32)(H,34,35)(H4,24,25,26,29,30)/t14?,16-/m0/s1
InChi Key
OGSBUKJUDHAQEA-WMCAAGNKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

    $401

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    50 mg

    $501

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    100 mg

    $601

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    Cayman Chemical
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    Product Description

    Pralatrexate is a dihydrofolate reductase (DHFR) inhibitor (Ki = 13.4 pM) and antifolate.1 It inhibits growth of CCRF-CEM acute lymphocytic leukemia cells (IC50 = 0.04 μM), MDA-468, SK-BR-3, and ZR-75-1 breast cancer cells (IC50s = 0.11, 0.28, and 0.26 μM, respectively), and SK-LC8 and SK-LC16 non-small cell lung cancer cells (NSCLC; IC50s = 0.42 and 0.11 μM, respectively). In vivo, pralatrexate increases median survival from 21 to 40 days when administered in 4 doses of 15 mg/kg over 11 days in an H9 T cell lymphoma mouse xenograft model.2 Pralatrexate is transported into cells via the reduced folate carrier (RFC) and undergoes polyglutamation by folylpolyglutamate synthetase (FPGS) to a greater extent than methotrexate (Item No. 13960) or pemetrexed (Item No. 14269).3,4 Formulations containing pralatrexate have been used in the treatment of relapsed or refractory peripheral T cell lymphoma.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sirotnak, F.M., DeGraw, J.I., Colwell, W.T., et al. A new analogue of 10-deazaaminopterin with markedly enhanced curative effects against human tumor xenografts in mice. Cancer Chemother. Pharmacol. 42(4), 313-318 (1998).

    2. Jain, S., Jirau-Serrano, X., Zullo, K.M., et al. Preclinical pharmacologic evaluation of pralatrexate and romidepsin confirms potent synergy of the combination in a murine model of human T-cell lymphoma. Clin. Cancer Res. 21(9), 2096-2106 (2015).

    3. Visentin, M., Unal, E.S., Zhao, R., et al. The membrane transport and polyglutamation of pralatrexate, a new-generation dihydrofolate reductase inhibitor. Cancer Chemother. Pharmacol. 72(3), 597-606 (2013).

    4. Izbicka, E., Diaz, A., Streeper, R., et al. Distinct mechanistic activity profile of pralatrexate in comparison to other antifolates in in vitro and in vivo models of human cancers. Cancer Chemother. Pharmacol. 64(5), 993-999 (2009).

    Product Citations

    Wu, Z., Xiao, H., Rao, D., et al. Analytical strategy for oxylipin annotation by combining chemical derivatization-based retention index algorithm and feature tandem mass spectrometric fragmentation as a biomarker discovery tool. Anal. Chem. 95(43), 15933-15942 (2023).

    Archambault, A.-S., Brassard, J., Bernatchez, É., et al. Human and mouse eosinophils differ in their ability to biosynthesize eicosanoids, docosanoids, the endocannabinoid 2-arachidonoyl-glycerol and its congeners. Cells 11(1), 141 (2022).