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Pralatrexate (Standard)

CAT: 0804-HY-10446R-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-10446R-01Size:1 mg
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Description
Pralatrexate (Standard) is the analytical standard of Pralatrexate. This product is intended for research and analytical applications. Pralatrexate is an antifolate and is a potent dihydrofolate reductasean (DHFR) inhibitor with a Ki of 13.4 pM. Pralatrexate is a substrate for folylpolyglutamate synthetase with improved cellular uptake and retention. Pralatrexate has antitumor activities and has the potential for relapsed/refractory T-cell lymphoma treatment[1][2][3][4]. Pralatrexate is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
CAS Number
146464-95-1
UNSPSC
12352005
Target
Antifolate; Apoptosis; Reference Standards
Related Pathways
Apoptosis; Cell Cycle/DNA Damage; Others
Field of Research
Cancer
Smiles
O=C(CC[C@H](NC(C1=CC=C(C=C1)C(CC#C)CC2=NC3=C(N=C(N=C3N=C2)N)N)=O)C(O)=O)O
Molecular Formula
C23H23N7O5
Molecular Weight
477.47
References & Citations
[1]Enrica Marchi, et al. Pralatrexate Is Synergistic With the Proteasome Inhibitor Bortezomib in in Vitro and in Vivo Models of T-cell Lymphoid Malignancies. Clin Cancer Res. 2010 Jul 15;16 (14) :3648-58.|[2]Francine Foss, et al. Pralatrexate Is an Effective Treatment for Relapsed or Refractory Transformed Mycosis Fungoides: A Subgroup Efficacy Analysis From the PROPEL Study. Clin Lymphoma Myeloma Leuk. 2012 Aug;12 (4) :238-43.|[3]Karen Kelly, et al. Randomized Phase 2b Study of Pralatrexate Versus Erlotinib in Patients With Stage IIIB/IV Non-Small-Cell Lung Cancer (NSCLC) After Failure of Prior Platinum-Based Therapy. J Thorac Oncol. 2012 Jun;7 (6) :1041-8.|[4]F M Sirotnak, et al. A New Analogue of 10-deazaaminopterin With Markedly Enhanced Curative Effects Against Human Tumor Xenografts in Mice. Cancer Chemother Pharmacol. 1998;42 (4) :313-8.
Shipping Conditions
Room temperature
Scientific Category
Reference Standards

Chemical Information

Pralatrexate

Pralatrexate is a pteridine that is the N-4-[1-(2,4-diaminopteridin-6-yl)pent-4-yn-2-yl]benzoyl derivative of L-glutamic acid. Used for treatment of Peripheral T-Cell Lymphoma, an aggressive form of non-Hodgkins lymphoma. It has a role as an antimetabolite, an antineoplastic agent and an EC 1.5.1.3 (dihydrofolate reductase) inhibitor. It is a N-acyl-L-glutamic acid, a member of pteridines and a terminal acetylenic compound.

CAS Number146464-95-1
PubChem CID148121
IUPAC Name(2S)-2-[[4-[1-(2,4-diaminopteridin-6-yl)pent-4-yn-2-yl]benzoyl]amino]pentanedioic acid
Molecular FormulaC23H23N7O5
Molecular Weight477.5
XLogP-0.9
Topological Polar Surface Area207
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count11
Rotatable Bond Count10
Heavy Atom Count35
Formal Charge0
Complexity809
SMILES
C#CCC(CC1=CN=C2C(=N1)C(=NC(=N2)N)N)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)O)C(=O)O
InChI
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
InChIKey
OGSBUKJUDHAQEA-WMCAAGNKSA-N
Chemical Structure
2D Structure
2D structure of Pralatrexate
CAS: 146464-95-1
CID: 148121
Formula: C23H23N7O5
MW: 477.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight477.5
XLogP3-0.9
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count11
Rotatable Bond Count10
Exact Mass477.17606686
Monoisotopic Mass477.17606686
Topological Polar Surface Area207 Ų
Heavy Atom Count35
Formal Charge0
Complexity809
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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