Pralatrexate, (R)- | CAS#1320211-70-8 | dihydrofolate reductase inhibitor

MedKoo Cat#: 597203 | Name: Pralatrexate, (R)-

Description:

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

Pralatrexate, (R)- 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, (R)-

CAS#1320211-70-8 (R-isomer)

Theoretical Analysis

MedKoo Cat#: 597203

Name: Pralatrexate, (R)-

CAS#: 1320211-70-8 (R-isomer)

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.

Bulk Inquiry

Related CAS #

1320211-69-5 (S-isomer) 1320211-70-8 (R-isomer) 146464-95-1 (racemic)

Synonym

Pralatrexate, (R)-;

IUPAC/Chemical Name

(4-((R)-1-(2,4-diaminopteridin-6-yl)pent-4-yn-2-yl)benzoyl)-L-glutamic acid

InChi Key

OGSBUKJUDHAQEA-ZBFHGGJFSA-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+/m1/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

Instruction

View handling instruction

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.

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: 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. 2: 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. 3: Zhao R, Diop-Bove N, Goldman ID. Enhanced receptor-mediated endocytosis and cytotoxicity of a folic acid-desacetylvinblastine monohydrazide conjugate in a pemetrexed-resistant cell line lacking folate-specific facilitative carriers but with increased folate receptor expression. Mol Pharmacol. 2014 Feb;85(2):310-21. doi: 10.1124/mol.113.089110. Epub 2013 Nov 18. PubMed PMID: 24249723; PubMed Central PMCID: PMC3913358. 4: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2006 Nov;28(9):657-78. PubMed PMID: 17200730.