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10-Propargyl-10-deazaaminopterin

CAS No.
146464-95-1
Chemical Name:
10-Propargyl-10-deazaaminopterin
Synonyms
Pralatrexate;Pdx;Folotyn;CS-2172;Pralatrexat;Prelatrexate;Unii-A8Q8I19Q20;Pralatrexate, >=98%;FOLOTYN PRALATREXATE;Pralatrexate(Folotyn)
CBNumber:
CB31856065
Molecular Formula:
C23H23N7O5
Molecular Weight:
477.47
MDL Number:
MFCD00920897
MOL File:
146464-95-1.mol
MSDS File:
SDS
Last updated:2024-11-19 15:53:33

10-Propargyl-10-deazaaminopterin Properties

Melting point 215 °C(dec.)
Density 1.471±0.06 g/cm3(Predicted)
storage temp. 2-8°C
Water Solubility Insoluble in water
solubility ≥23.85 mg/mL in DMSO; insoluble in H2O; insoluble in EtOH
form powder to crystal
pka 3.53±0.10(Predicted)
color White to Light yellow
NCI Dictionary of Cancer Terms 10-propargyl-10-deazaaminopterin; Folotyn; PDX; pralatrexate
FDA UNII A8Q8I19Q20
NCI Drug Dictionary Folotyn
ATC code L01BA05

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS08
Signal word  Warning
Hazard statements  H302-H361
Precautionary statements  P201-P202-P264-P270-P280-P301+P310+P330-P308+P313-P405-P501
HS Code  2933.59.5300
Hazardous Substances Data 146464-95-1(Hazardous Substances Data)
NFPA 704
0
2 0

10-Propargyl-10-deazaaminopterin price More Price(29)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
TCI Chemical P2645 Pralatrexate 146464-95-1 100MG $550 2024-03-01 Buy
TCI Chemical P2645 Pralatrexate 146464-95-1 25MG $160 2021-12-16 Buy
Cayman Chemical 23689 Pralatrexate ≥98% 146464-95-1 10mg $364 2024-03-01 Buy
Cayman Chemical 23689 Pralatrexate ≥98% 146464-95-1 50mg $455 2024-03-01 Buy
Cayman Chemical 23689 Pralatrexate ≥98% 146464-95-1 100mg $546 2024-03-01 Buy
Product number Packaging Price Buy
P2645 100MG $550 Buy
P2645 25MG $160 Buy
23689 10mg $364 Buy
23689 50mg $455 Buy
23689 100mg $546 Buy

10-Propargyl-10-deazaaminopterin Chemical Properties,Uses,Production

Description

Pralatrexate, an injectable DHFR inhibitor, was launched for the treatment of patients with relapsed or refractory PTCL. PTCL is an aggressive form of non-Hodgkin’s lymphoma (NHL) characterized by the proliferation of abnormal T-lymphocytes that circulate in the peripheral bloodstream. The inhibition of the folate enzymes DHFR and thymidylate synthase is a well-validated method of cancer treatment. In vitro, pralatrexate is slightly less potent than MTX in inhibiting DHFR derived from murine leukemia L1210 cells (Ki = 18.2 pM vs. 5.75 pM) and human leukemia CCRF-CEM cells (Ki = 13.4 pM vs. 5.4 pM). However, it is transported into both types of cells with 10-fold higher efficiency than MTX, thereby providing a more potent inhibition of cell growth as compared with MTX. In vivo, intraperitonally administered pralatrexate at 60 mg/ kg twice weekly for three or four doses caused complete lymphoma regressions in 89, 56, and 30% of HT, RL, and SKI-DLBCL-1 xenografted mice, respectively, whereas a similar dosing of MTX at 40 mg/kg twice weekly did not produce complete regression. The posttreatment tumor diameter was also smaller in pralatrexate-treated animals.

Description

Pralatrexate is a dihydrofolate reductase (DHFR) inhibitor (Ki = 13.4 pM) and antifolate. It inhibits growth of CCRF-CEM acute lymphocytic leukemia cells (IC50 = 0.04 μM), MDA-468, SK-BR-3, and ZR-75-1 breast cancer cells (IC50s = 0.11, 0.28, and 0.26 μM, respectively), and SK-LC8 and SK-LC16 non-small cell lung cancer cells (NSCLC; IC50s = 0.42 and 0.11 μM, respectively). In vivo, pralatrexate increases median survival from 21 to 40 days when administered in 4 doses of 15 mg/kg over 11 days in an H9 T cell lymphoma mouse xenograft model. Pralatrexate is transported into cells via the reduced folate carrier (RFC) and undergoes polyglutamation by folylpolyglutamate synthetase (FPGS) to a greater extent than methotrexate or pemetrexed . Formulations containing pralatrexate have been used in the treatment of relapsed or refractory peripheral T cell lymphoma.

Originator

SRI International/ Southern Research Institute/Sloan-Kettering (US)

Uses

An antifolate with high affinity for the reduced folate carrier-type 1, produces marked complete and durable remissions in a diversity of chemotherapy refractory cases of T-cell lymphoma.

Definition

ChEBI: 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.

brand name

Folotyn

Clinical Use

Pralatrexate, an injectable dihydrofolate reductase (DHFR) inhibitor, has a superior potency and toxicity profile compared to other DHFR inhibitors. In 2009, the compound was launched by Allos and approved in the U.S. for the treatment of patients with relapsed or refractory peripheral T-cell lymphoma (PTCL) as a single agent. It is the first drug approved for this indication.70 In 2010, orphan drug designation was received in the E.U. for the treatment of cutaneous T-cell lymphoma (CTCL).

Side effects

The most common adverse reactions associated with pralatrexate are mucositis, thrombocytopenia, nausea, and fatigue. Folic acid and vitamin B12 supplements are administered as adjunct therapies to potentially reduce pralatrexate-related hematological toxicity and mucositis.

Synthesis

The chemical synthesis of pralatrexate starts with the alkylation of the anion of dimethyl homoterephthalate with propargyl bromide, promoted by potassium hydride in dimethylformamide, to afford the corresponding a-propargyl diester. Further alkylation of the potassium salt of a-propargyl diester with 2,4-diamino-6-(bromomethyl)pteridine followed by saponification with sodium hydroxide yields a diacid intermediate (2,4diamino- 4-deoxy-10-propargyl-10-deazapteroic acid). Mono-decarboxylation of the diacid intermediate by heating in dimethylsulfoxide at 120 C, followed by coupling with diethyl L-glutamate, and subsequent ester hydrolysis with sodium hydroxide yields pralatrexate.

References

[1]. izbicka e, diaz a, streeper r, et al. distinct mechanistic activity profile of pralatrexate in comparison to other antifolates in in vitro and in vivo models of human cancers. cancer chemother pharmacol, 2009, 64(5): 993-999.
[2]. serova m, bieche i, sablin mp, et al. single agent and combination studies of pralatrexate and molecular correlates of sensitivity. br j cancer, 2011, 104(2): 272-280.

10-Propargyl-10-deazaaminopterin Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 174)Suppliers
Supplier Tel Email Country ProdList Advantage
BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
+86-18600796368 +86-18600796368 sales@sjar-tech.com China 456 58
Shanghai Daken Advanced Materials Co.,Ltd
+86-371-66670886 info@dakenam.com China 18751 58
Henan Tianfu Chemical Co.,Ltd.
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Hangzhou FandaChem Co.,Ltd.
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career henan chemical co
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18871490254 linda@hubeijusheng.com CHINA 28172 58
BOC Sciences
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Chongqing Chemdad Co., Ltd
+86-023-6139-8061 +86-86-13650506873 sales@chemdad.com China 39894 58
CONIER CHEM AND PHARMA LIMITED
+8618523575427 sales@conier.com China 49374 58

View Lastest Price from 10-Propargyl-10-deazaaminopterin manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Pralatrexate pictures 2024-12-23 Pralatrexate
146464-95-1
US $0.00 / g 1g More Than 99% 100kg/Month BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
Pralatrexate pictures 2024-11-19 Pralatrexate
146464-95-1
US $30.00-68.00 / mg 99.59% 10g TargetMol Chemicals Inc.
10-Propargyl-10-deazaaminopterin pictures 2019-07-06 10-Propargyl-10-deazaaminopterin
146464-95-1
US $2.00 / kg 1kg 99% ask Career Henan Chemical Co
  • Pralatrexate pictures
  • Pralatrexate
    146464-95-1
  • US $0.00 / g
  • More Than 99%
  • BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
  • Pralatrexate pictures
  • Pralatrexate
    146464-95-1
  • US $30.00-68.00 / mg
  • 99.59%
  • TargetMol Chemicals Inc.

10-Propargyl-10-deazaaminopterin Spectrum

N-(4-(1-((2,4-Diamino-6-pteridinyl)methyl)-3-butynyl)benzoyl)-L-glutamic acid 10-Propargyl-10-deazaaminopterin L-Glutamic acid, N-(4-(1-((2,4-diamino-6-pteridinyl)methyl)-3-butynyl)benzoyl)- Unii-A8Q8I19Q20 FOLOTYN PRALATREXATE N-(4-{1-[(2,4-diaMinopteridin-6-yl)Methyl]but-3-yn-1-yl}benzoyl)-L-glutaMic acid N-[4-[1-[(2,4-DiaMino-6-pteridinyl)Methyl]-3-butyn-1-yl]benzoyl]-L-glutaMic Acid (2S)-2-(4-(1-(2,4-diaMinopteridin-6-yl)pent-4-yn-2-yl)benzaMido)pentanedioic acid Prelatrexate 10-Propargyl-10-deazaaMinopteri Pralatrexate(Folotyn) 10-Propargyl-10-deazaaminopterin N-(4-(1-((2,4-Diamino-6-pteridinyl)methyl)-3-butynyl)benzoyl)-L-glutamic acid N-(4-(1-((2,4-Diamino-6-pteridinyl)methyl)-3-butynyl)benzoyl)-L-glutamic acid Pralatrexate Pralatrexate, >=98% Pralatrexat CS-2172 Pralatrexate Impurity L-Glutamic acid, N-[4-[1-[(2,4-diamino-6-pteridinyl)methyl]-3-butyn-1-yl]benzoyl]- 10-Propargyl-10-deazaaminopterin USP/EP/BP Pralatrexate (racemic) Pralatrexate Pdx Folotyn 146464-95-1 10-Propargyl-10-deazaaminopterin Pralatrexate (NSC 754230) 146464-95-1 Amino Acids & Derivatives Aromatics Heterocycles Inhibitors Intermediates & Fine Chemicals Pharmaceuticals