A dihydrofolate reductase inhibitor
Technical Support & Resources

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Product Categories

Product Type

Small Molecule Modulators
Small Molecule Inhibitors

Research Area

Cancer

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
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
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    10 mg

    $401

    Add

    50 mg

    $501

    Add

    100 mg

    $601

    Add
    Cayman Chemical
    Visit Our Cancer Resource Center
    Find Tools & Resources to Study the Hallmarks of Cancer
    • Cancer cell signaling & regulation
    • Cancer metabolism
    • Tumor microenvironment
    EXPLORE NOW
    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).