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

MedKoo CAT#: 206221

CAS#: 146464-95-1

Description: Pralatrexate 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.


Price and Availability

Size
Price

25mg
USD 90
200mg
USD 450
2g
USD 1950
Size
Price

50mg
USD 150
500mg
USD 750
5g
USD 3650
Size
Price

100mg
USD 250
1g
USD 1250
10g
USD 5850

Pralatrexate, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 206221
Name: Pralatrexate
CAS#: 146464-95-1
Chemical Formula: C23H23N7O5
Exact Mass: 477.17607
Molecular Weight: 477.47
Elemental Analysis: C, 57.86; H, 4.86; N, 20.53; O, 16.75


Related CAS #: 1320211-69-5 (S-isomer)   1320211-70-8 (R-isomer)   146464-95-1    

Synonym: Pralatrexate; 10-Propargyl-10-deazaaminopterin; brand name: Folotyn.

IUPAC/Chemical Name: N -(4-{1-[(2,4-diaminopteridin-6-yl)methyl]but-3-yn-1-yl}benzoyl)-L-glutamic acid

InChi Key: OGSBUKJUDHAQEA-WMCAAGNKSA-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(CC2=NC3=C(N)N=C(N)N=C3N=C2)CC#C)C=C1)=O


Technical Data

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, not in water

Shelf Life:
>2 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).

Harmonized System Code:
293490


Additional Information


References

1: Kelly KR, Gabrail N, Weitman S, Sarantopoulos J, Olszanski AJ, Edenfield W, Venitz J, Reddy G, Yang A, Hasal SJ, Lockhart AC. Phase 1 study evaluating the safety and pharmacokinetics of pralatrexate in relapsed/refractory advanced solid tumors and lymphoma patients with mild, moderate, and severe renal impairment. Cancer Chemother Pharmacol. 2016 Nov;78(5):929-939. PubMed PMID: 27638045.

2: Del Carmen MG, Supko JG, Horick NK, Rauh-Hain JA, Clark RM, Campos SM, Krasner CN, Atkinson T, Birrer MJ. Phase 1 and 2 study of carboplatin and pralatrexate in patients with recurrent, platinum-sensitive ovarian, fallopian tube, or primary peritoneal cancer. Cancer. 2016 Nov 15;122(21):3297-3306. doi: 10.1002/cncr.30196. PubMed PMID: 27421044.

3: Sastry RV, Venkatesan CS, Sastry BS, Mahesh K. Identification and characterization of forced degradation products of pralatrexate injection by LC-PDA and LC-MS. J Pharm Biomed Anal. 2016 Nov 30;131:400-409. doi: 10.1016/j.jpba.2016.08.023. PubMed PMID: 27643862.

4: Lee SS, Jung SH, Ahn JS, Kim YK, Cho MS, Jung SY, Lee JJ, Kim HJ, Yang DH. Pralatrexate in Combination with Bortezomib for Relapsed or Refractory Peripheral T Cell Lymphoma in 5 Elderly Patients. J Korean Med Sci. 2016 Jul;31(7):1160-3. doi: 10.3346/jkms.2016.31.7.1160. PubMed PMID: 27366017; PubMed Central PMCID: PMC4901011.

5: Dunn TJ, Dinner S, Price E, Coutré SE, Gotlib J, Hao Y, Berube C, Medeiros BC, Liedtke M. A phase 1, open-label, dose-escalation study of pralatrexate in combination with bortezomib in patients with relapsed/refractory multiple myeloma. Br J Haematol. 2016 Apr;173(2):253-9. doi: 10.1111/bjh.13946. PubMed PMID: 27040320.

6: 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. PubMed PMID: 26809959.

7: 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. PubMed PMID: 26627450.

8: Wood GS, Wu J. Methotrexate and Pralatrexate. Dermatol Clin. 2015 Oct;33(4):747-55. doi: 10.1016/j.det.2015.05.009. Review. PubMed PMID: 26433846.

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. PubMed PMID: 26242208.

10: Petullo B, Wei L, Yereb M, Neal A, Rose J, Bekaii-Saab T, Wu C. A phase II study of biweekly pralatrexate and docetaxel in patients with advanced esophageal and gastroesophageal carcinoma that have failed first-line platinum-based therapy. J Gastrointest Oncol. 2015 Jun;6(3):336-40. doi: 10.3978/j.issn.2078-6891.2015.011. PubMed PMID: 26029462; PubMed Central PMCID: PMC4397239.

11: 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. PubMed PMID: 25917288; PubMed Central PMCID: PMC4441744.

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. 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. PubMed PMID: 25205429; PubMed Central PMCID: PMC4209237.

14: 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): preliminary results from the T-Cell Consortium trial. Clin Adv Hematol Oncol. 2014 Feb;12(2 Suppl 5):6-7. PubMed PMID: 24852788.

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. PubMed PMID: 24682532; PubMed Central PMCID: PMC4018754.

16: Dondi A, Bari A, Pozzi S, Ferri P, Sacchi S. The potential of pralatrexate as a treatment of peripheral T-cell lymphoma. Expert Opin Investig Drugs. 2014 May;23(5):711-8. doi: 10.1517/13543784.2014.902050. Review. PubMed PMID: 24661228.

17: Talpur R, Thompson A, Gangar P, Duvic M. Pralatrexate alone or in combination with bexarotene: long-term tolerability in relapsed/refractory mycosis fungoides. Clin Lymphoma Myeloma Leuk. 2014 Aug;14(4):297-304. doi: 10.1016/j.clml.2014.01.010. PubMed PMID: 24589156.

18: 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. PubMed PMID: 24566705.

19: Kerdel FA, Styperek AR, Maini A. Clinical remission of primary aggressive CD8+ cutaneous T-cell lymphoma after pralatrexate infusion. JAMA Dermatol. 2014 Mar;150(3):320-2. doi: 10.1001/jamadermatol.2013.8647. PubMed PMID: 24452280.

20: 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. PubMed PMID: 23965902.