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Merck
CN

SML2494

Sigma-Aldrich

Pralatrexate

≥98% (HPLC), DHFR inhibitor, powder

Synonym(s):

(2S)-2-[[4-[(1RS)-1-[(2,4-diaminopteridin-6-yl)methyl]but-3-ynyl]benzoyl]amino]pentanedioic acid, 10-propargyl-10-deazaaminopterin, N-(4-{1-[(2,4-diaminopteridin-6-yl)methyl]but-3-yn-1-yl}benzoyl)-L-glutamic acid, PDX

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About This Item

Empirical Formula (Hill Notation):
C23H23N7O5
CAS Number:
146464-95-1
Molecular Weight:
477.47
MDL number:
MFCD00920897
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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Product Name

Pralatrexate, ≥98% (HPLC)

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL

storage temp.

−20°C

SMILES string

O=C([C@@H](NC(C1=CC=C(C(CC(N=C23)=CN=C3N=C(N=C2N)N)CC#C)C=C1)=O)CCC(O)=O)O

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

Related Categories

Biochem/physiol Actions

Potent DHFR inhibitor; antifolate; antineoplastic;
Pralatrexate is an antifolate that selectively enters cancer cells expressing reduced folate carrier type 1 (RFC-1). Pralatrexate potently inhibits DHFR (dihydrofolate reductase).

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H361fd

Hazard Classifications

Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000419845
0000419845
0000358663
0000358663
0000211712

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Enrica Marchi et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 19(24), 6657-6661 (2013-08-24)
Folates are well known to be essential for many cellular processes, including cellular proliferation. As a consequence, antifolates, the fraudulent mimics of folic acid, have been shown to be potent therapeutic agents in many cancers. Over the past several decades
Jennifer E Amengual et al.
Blood, 131(4), 397-407 (2017-11-17)
Peripheral T-cell lymphomas (PTCL) are a group of rare malignancies characterized by chemotherapy resistance and poor prognosis. Romidepsin and pralatrexate were approved by the US Food and Drug Administration for patients with relapsed/refractory PTCL, exhibiting response rates of 25% and
Owen A O'Connor et al.
Leukemia & lymphoma, 58(11), 2548-2557 (2017-07-26)
It has been nearly 8 years since pralatrexate became the first drug approved by the U.S. Food and Drug Administration for the treatment of relapsed or refractory peripheral T-cell lymphoma (PTCL). Like most drugs approved for a particular clinical indication

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