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MedKoo Cat#: 597202 | Name: Pralatrexate, (S)-

Description:

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

Pralatrexate, (S)- is a folate analogue inhibitor of dihydrofolate reductase (DHFR) exhibiting high affinity for reduced folate carrier-1 (RFC-1) with antineoplastic and immunosuppressive activities. Pralatrexate selectively enters cells expressing RFC-1; intracellularly, this agent is highly polyglutamylated and competes for the folate binding site of DHFR, blocking tetrahydrofolate synthesis, which may result in depletion of nucleotide precursors; inhibition of DNA, RNA and protein synthesis; and apoptotic tumor cell death.

Chemical Structure

Pralatrexate, (S)-
Pralatrexate, (S)-
CAS#1320211-69-5

Theoretical Analysis

MedKoo Cat#: 597202

Name: Pralatrexate, (S)-

CAS#: 1320211-69-5

Chemical Formula: C23H23N7O5

Exact Mass: 477.1761

Molecular Weight: 477.48

Elemental Analysis: C, 57.86; H, 4.86; N, 20.53; O, 16.75

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 #
1320211-69-5 (S-isomer) 1320211-70-8 (R-isomer) 146464-95-1 (racemic)
Synonym
Pralatrexate, (S)-;
IUPAC/Chemical Name
(4-((S)-1-(2,4-diaminopteridin-6-yl)pent-4-yn-2-yl)benzoyl)-L-glutamic acid
InChi Key
OGSBUKJUDHAQEA-HOCLYGCPSA-N
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
SMILES Code
O=C(O)CC[C@@H](C(O)=O)NC(C1=CC=C([C@H](CC2=NC3=C(N)N=C(N)N=C3N=C2)CC#C)C=C1)=O
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 DMSO
Shelf Life
>3 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 477.48 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: O'Connor OA, Amengual J, Colbourn D, Deng C, Sawas A. Pralatrexate: a comprehensive update on pharmacology, clinical activity and strategies to optimize use. Leuk Lymphoma. 2017 Nov;58(11):2548-2557. doi: 10.1080/10428194.2017.1306642. Review. PubMed PMID: 28738754. 2: Makita S, Tobinai K. Mogamulizumab for the treatment of T-cell lymphoma. Expert Opin Biol Ther. 2017 Sep;17(9):1145-1153. doi: 10.1080/14712598.2017.1347634. Epub 2017 Jul 3. Review. Erratum in: Expert Opin Biol Ther. 2017 Sep;17 (9):1183. PubMed PMID: 28649848. 3: Chihara D, Fanale MA, Miranda RN, Noorani M, Westin JR, Nastoupil LJ, Hagemeister FB, Fayad LE, Romaguera JE, Samaniego F, Turturro F, Lee HJ, Neelapu SS, Rodriguez MA, Wang M, Fowler NH, Davis RE, Medeiros LJ, Hosing C, Nieto YL, Oki Y. The survival outcome of patients with relapsed/refractory peripheral T-cell lymphoma-not otherwise specified and angioimmunoblastic T-cell lymphoma. Br J Haematol. 2017 Mar;176(5):750-758. doi: 10.1111/bjh.14477. Epub 2016 Dec 16. PubMed PMID: 27983760; PubMed Central PMCID: PMC5836501. 4: Zinzani PL, Bonthapally V, Huebner D, Lutes R, Chi A, Pileri S. Panoptic clinical review of the current and future treatment of relapsed/refractory T-cell lymphomas: Peripheral T-cell lymphomas. Crit Rev Oncol Hematol. 2016 Mar;99:214-27. doi: 10.1016/j.critrevonc.2015.12.016. Epub 2016 Jan 3. Review. PubMed PMID: 26811013. 5: McPherson JP, Vrontikis A, Sedillo C, Halwani AS, Gilreath JA. Pralatrexate Monitoring Using a Commercially Available Methotrexate Assay to Avoid Potential Drug Interactions. Pharmacotherapy. 2016 Feb;36(2):e8-e11. doi: 10.1002/phar.1699. Epub 2016 Jan 26. PubMed PMID: 26809959. 6: Advani RH, Ansell SM, Lechowicz MJ, Beaven AW, Loberiza F, Carson KR, Evens AM, Foss F, Horwitz S, Pro B, Pinter-Brown LC, Smith SM, Shustov AR, Savage KJ, Vose JM. A phase II study of cyclophosphamide, etoposide, vincristine and prednisone (CEOP) Alternating with Pralatrexate (P) as front line therapy for patients with peripheral T-cell lymphoma (PTCL): final results from the T- cell consortium trial. Br J Haematol. 2016 Feb;172(4):535-44. doi: 10.1111/bjh.13855. Epub 2015 Dec 2. PubMed PMID: 26627450; PubMed Central PMCID: PMC5642048. 7: Wood GS, Wu J. Methotrexate and Pralatrexate. Dermatol Clin. 2015 Oct;33(4):747-55. doi: 10.1016/j.det.2015.05.009. Epub 2015 Aug 1. Review. PubMed PMID: 26433846; PubMed Central PMCID: PMC5549926. 8: Lunning MA. Treatment of Peripheral T-Cell Lymphoma: Many Shades of Gray. Oncology (Williston Park). 2015 Aug;29(8):545-50. Review. PubMed PMID: 26281838. 9: Grem JL, Kos ME, Evande RE, Meza JL, Schwarz JK. A phase 1 clinical trial of sequential pralatrexate followed by a 48-hour infusion of 5-fluorouracil given every other week in adult patients with solid tumors. Cancer. 2015 Nov 1;121(21):3862-8. doi: 10.1002/cncr.29504. Epub 2015 Aug 4. PubMed PMID: 26242208. 10: Tedeschi PM, Kathari YK, Johnson-Farley N, Bertino JR. Methylthioadenosine phosphorylase (MTAP)-deficient T-cell ALL xenografts are sensitive to pralatrexate and 6-thioguanine alone and in combination. Cancer Chemother Pharmacol. 2015 Jun;75(6):1247-52. doi: 10.1007/s00280-015-2747-2. Epub 2015 Apr 28. PubMed PMID: 25917288; PubMed Central PMCID: PMC4441744. 11: Zullo KM, Guo Y, Cooke L, Jirau-Serrano X, Mangone M, Scotto L, Amengual JE, Mao Y, Nandakumar R, Cremers S, Duong J, Mahadevan D, O'Connor OA. Aurora A Kinase Inhibition Selectively Synergizes with Histone Deacetylase Inhibitor through Cytokinesis Failure in T-cell Lymphoma. Clin Cancer Res. 2015 Sep 15;21(18):4097-109. doi: 10.1158/1078-0432.CCR-15-0033. Epub 2015 Apr 15. PubMed PMID: 25878331; PubMed Central PMCID: PMC4581881. 12: Jain S, Jirau-Serrano X, Zullo KM, Scotto L, Palermo CF, Sastra SA, Olive KP, Cremers S, Thomas T, Wei Y, Zhang Y, Bhagat G, Amengual JE, Deng C, Karan C, Realubit R, Bates SE, O'Connor OA. 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. 2015 May 1;21(9):2096-106. doi: 10.1158/1078-0432.CCR-14-2249. Epub 2015 Feb 12. PubMed PMID: 25677697. 13: Tedeschi PM, Kathari YK, Farooqi IN, Bertino JR. Leucovorin rescue allows effective high-dose pralatrexate treatment and an increase in therapeutic index in mesothelioma xenografts. Cancer Chemother Pharmacol. 2014 Nov;74(5):1029-32. doi: 10.1007/s00280-014-2580-z. Epub 2014 Sep 9. PubMed PMID: 25205429; PubMed Central PMCID: PMC4209237. 14: Coiffier B, Federico M, Caballero D, Dearden C, Morschhauser F, Jäger U, Trümper L, Zucca E, Gomes da Silva M, Pettengell R, Weidmann E, d'Amore F, Tilly H, Zinzani PL. Therapeutic options in relapsed or refractory peripheral T-cell lymphoma. Cancer Treat Rev. 2014 Oct;40(9):1080-8. doi: 10.1016/j.ctrv.2014.08.001. Epub 2014 Aug 24. Review. PubMed PMID: 25199959. 15: Visentin M, Unal ES, Goldman ID. The impact of 5-formyltetrahydrofolate on the anti-tumor activity of pralatrexate, as compared to methotrexate, in HeLa cells in vitro. Cancer Chemother Pharmacol. 2014 May;73(5):1055-62. doi: 10.1007/s00280-014-2441-9. Epub 2014 Mar 29. PubMed PMID: 24682532; PubMed Central PMCID: PMC4018754. 16: Ho AL, Lipson BL, Sherman EJ, Xiao H, Fury MG, Apollo A, Seetharamu N, Sima CS, Haque S, Lyo JK, Sales R, Cox L, Pfister DG. A phase II study of pralatrexate with vitamin B12 and folic acid supplementation for previously treated recurrent and/or metastatic head and neck squamous cell cancer. Invest New Drugs. 2014 Jun;32(3):549-54. doi: 10.1007/s10637-014-0073-x. Epub 2014 Feb 25. PubMed PMID: 24566705. 17: Guenova E, Hoetzenecker W, Rozati S, Levesque MP, Dummer R, Cozzio A. Novel therapies for cutaneous T-cell lymphoma: what does the future hold? Expert Opin Investig Drugs. 2014 Apr;23(4):457-67. doi: 10.1517/13543784.2014.876407. Epub 2014 Jan 8. Review. PubMed PMID: 24397291. 18: Eyre TA, Collins GP. Current treatment and future prospects for peripheral T-cell lymphoma. Drugs Today (Barc). 2013 Oct;49(10):631-46. doi: 10.1358/dot.2013.49.10.2025391. Review. PubMed PMID: 24191256. 19: Marchi E, Mangone M, Zullo K, O'Connor OA. Pralatrexate pharmacology and clinical development. Clin Cancer Res. 2013 Dec 15;19(24):6657-61. doi: 10.1158/1078-0432.CCR-12-2251. Epub 2013 Aug 21. PubMed PMID: 23965902. 20: Visentin M, Unal ES, Zhao R, Goldman ID. The membrane transport and polyglutamation of pralatrexate: a new-generation dihydrofolate reductase inhibitor. Cancer Chemother Pharmacol. 2013 Sep;72(3):597-606. doi: 10.1007/s00280-013-2231-9. Epub 2013 Jul 24. PubMed PMID: 23881211; PubMed Central PMCID: PMC3784351.

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