10-Propargyl-10-deazaaminopterin

ChemicalBook > CAS DataBase List > 10-Propargyl-10-deazaaminopterin

10-Propargyl-10-deazaaminopterin

Product Name: 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
Formula Weight: 477.47
MOL File: 146464-95-1.mol

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10-Propargyl-10-deazaaminopterin Property

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
pka: 3.53±0.10(Predicted)
form: powder to crystal
color: White to Light yellow

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Safety

HS Code: 2933.59.5300
Hazardous Substances Data: 146464-95-1(Hazardous Substances Data)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H361Suspected of damaging fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

TCI Chemical

Product number: P2645
Product name: Pralatrexate
Packaging: 100MG
Price: $550
Updated: 2024/03/01

TCI Chemical

Product number: P2645
Product name: Pralatrexate
Packaging: 25MG
Price: $160
Updated: 2021/12/16

Cayman Chemical

Product number: 23689
Product name: Pralatrexate
Purity: ≥98%
Packaging: 10mg
Price: $364
Updated: 2024/03/01

Cayman Chemical

Product number: 23689
Product name: Pralatrexate
Purity: ≥98%
Packaging: 50mg
Price: $455
Updated: 2024/03/01

Cayman Chemical

Product number: 23689
Product name: Pralatrexate
Purity: ≥98%
Packaging: 100mg
Price: $546
Updated: 2024/03/01

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10-Propargyl-10-deazaaminopterin Chemical Properties,Usage,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 (K_i = 18.2 pM vs. 5.75 pM) and human leukemia CCRF-CEM cells (K_i = 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 (K_i = 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

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

BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.

Product: Pralatrexate 146464-95-1
Price: US $0.00/g
Min. Order: 1g
Purity: More Than 99%
Supply Ability: 100kg/Month
Release date: 2024-09-25

Career Henan Chemical Co

Product: 10-Propargyl-10-deazaaminopterin 146464-95-1
Price: US $2.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: ask
Release date: 2018-12-23

146464-95-1, 10-Propargyl-10-deazaaminopterinRelated Search:

Tris(hydroxymethyl)aminomethane BENZOYL ISOCYANATE Triamterene DIMETHYLAMINOPYRIDINE, POLYMER-BOUND Dimethylcarbamoyl chloride N,N-Dimethyl-1,4-phenylenediamine 3-Bromopropyne Thiophanate-methyl Lithium diisopropylamide Aminopterin L-Glutamic acid Benzoyl chloride Methyl salicylate Amino tris(methylene phosphonic acid) Benzoyl peroxide Methyl Glutamic acid Methyl bromide

Pralatrexate

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)-

Pdx

Unii-A8Q8I19Q20

FOLOTYN PRALATREXATE

N-(4-{1-[(2,4-diaMinopteridin-6-yl)Methyl]but-3-yn-1-yl}benzoyl)-L-glutaMic acid

Folotyn

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)

146464-95-1 10-Propargyl-10-deazaaminopterin

Pralatrexate (NSC 754230)

146464-95-1

Amino Acids & Derivatives

Aromatics

Heterocycles

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