137281-23-3 | Pemetrexed

Packsize	Purity	Availability	Price	Discounted Price
1g	95%	in stock	$55.00	$39.00
5g	98% +(contains <4%EtOH)(Loss on drying≤6%)	in stock	$115.00	$81.00

Description

• Catalog Number: AA50407
• Chemical Name: Pemetrexed
• CAS Number: 137281-23-3
• Molecular Formula: C20H21N5O6
• Molecular Weight: 427.4106
• MDL Number: MFCD00902635
• SMILES: OC(=O)CC[C@@H](C(=O)O)NC(=O)c1ccc(cc1)CCc1c[nH]c2c1c(=O)[nH]c(n2)N
• NSC Number: 698037

Computed Properties

• Complexity: 748
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 1
• Heavy Atom Count: 31
• Hydrogen Bond Acceptor Count: 7
• Hydrogen Bond Donor Count: 6
• Rotatable Bond Count: 9
• XLogP3: 0.2

Literature

• Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.

  Chemical research in toxicology 20150518

• Proteomic identification of differentially expressed proteins associated with the multiple drug resistance in methotrexate-resistant human breast cancer cells.

  International journal of oncology 20140701

• KRAS mutation status is associated with enhanced dependency on folate metabolism pathways in non-small cell lung cancer cells.

  Molecular cancer therapeutics 20140601

• Pemetrexed downregulates ERCC1 expression and enhances cytotoxicity effected by resveratrol in human nonsmall cell lung cancer cells.

  Naunyn-Schmiedeberg's archives of pharmacology 20131201

• Targeted agents in the third-/fourth-line treatment of patients with advanced (stage III/IV) non-small cell lung cancer (NSCLC).

  Cancer treatment reviews 20130501

• Pemetrexed-based chemotherapy in patients with advanced, ALK-positive non-small cell lung cancer.

  Annals of oncology : official journal of the European Society for Medical Oncology 20130101

• Pemetrexed alters folate phenotype and inflammatory profile in EA.hy 926 cells grown under low-folate conditions.

  European journal of pharmacology 20121205

• Treatment paradigms for patients with metastatic non-small-cell lung cancer: first-, second-, and third-line.

  Current oncology (Toronto, Ont.) 20120601

• Death receptor 5 and cellular FLICE-inhibitory protein regulate pemetrexed-induced apoptosis in human lung cancer cells.

  European journal of cancer (Oxford, England : 1990) 20111101

• Establishment of pemetrexed-resistant non-small cell lung cancer cell lines.

  Cancer letters 20111028

• Synthesis, biological, and antitumor activity of a highly potent 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitor with proton-coupled folate transporter and folate receptor selectivity over the reduced folate carrier that inhibits β-glycinamide ribonucleotide formyltransferase.

  Journal of medicinal chemistry 20111027

• Medical treatment of mesothelioma: anything new?

  Current oncology reports 20110801

• Treatment of advanced non-small-cell lung cancer: Italian Association of Thoracic Oncology (AIOT) clinical practice guidelines.

  Lung cancer (Amsterdam, Netherlands) 20110701

• Phase II study of pemetrexed and cisplatin, with chest radiotherapy followed by docetaxel in patients with stage III non-small cell lung cancer.

  Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20110501

• Anaplastic lymphoma kinase gene rearrangements in non-small cell lung cancer are associated with prolonged progression-free survival on pemetrexed.

  Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20110401

• Targeted therapies and other agents as first-line maintenance and beyond: particular benefit in pulmonary adenocarcinoma patients.

  Current medicinal chemistry 20110101

• ABCC11/MRP8 confers pemetrexed resistance in lung cancer.

  Cancer science 20101101

• Pemetrexed in advanced non-small-cell lung cancer.

  Expert opinion on pharmacotherapy 20100601

• Cancer chemotherapy: targeting folic acid synthesis.

  Cancer management and research 20100101

• Phase III study of pemetrexed plus carboplatin compared with etoposide plus carboplatin in chemotherapy-naive patients with extensive-stage small-cell lung cancer.

  Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20091001

• Phase II study of pemetrexed and carboplatin plus bevacizumab with maintenance pemetrexed and bevacizumab as first-line therapy for nonsquamous non-small-cell lung cancer.

  Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20090710

• Valproate, in combination with pemetrexed and cisplatin, provides additional efficacy to the treatment of malignant mesothelioma.

  Clinical cancer research : an official journal of the American Association for Cancer Research 20090415

• A randomized, double-blind, phase II study of two doses of pemetrexed as first-line chemotherapy for advanced breast cancer.

  Clinical cancer research : an official journal of the American Association for Cancer Research 20070615

• Changes in the status of p53 affect drug sensitivity to thymidylate synthase (TS) inhibitors by altering TS levels.

  British journal of cancer 20070312

• Sequence-dependent administration of raloxifene and 5-fluorouracil/pemetrexed protects against pemetrexed cytotoxicity in human bone marrow.

  Anticancer research 20070101

• [Pemetrexed: from preclinic to clinic].

  Bulletin du cancer 20070101

• A semimechanistic-physiologic population pharmacokinetic/pharmacodynamic model for neutropenia following pemetrexed therapy.

  Cancer chemotherapy and pharmacology 20060401

• Pemetrexed-associated urticarial vasculitis.

  Lung cancer (Amsterdam, Netherlands) 20060201

• The inverse relationship between reduced folate carrier function and pemetrexed activity in a human colon cancer cell line.

  Molecular cancer therapeutics 20060201

• Pemetrexed: a multitargeted antifolate.

  Clinical therapeutics 20050901

• Human splicing factor SPF45 (RBM17) confers broad multidrug resistance to anticancer drugs when overexpressed--a phenotype partially reversed by selective estrogen receptor modulators.

  Cancer research 20050801

• Cytotoxic effects of pemetrexed in gastric cancer cells.

  Cancer science 20050601

• The multidrug resistance protein 5 (ABCC5) confers resistance to 5-fluorouracil and transports its monophosphorylated metabolites.

  Molecular cancer therapeutics 20050501

• The roles of thymidylate synthase and p53 in regulating Fas-mediated apoptosis in response to antimetabolites.

  Clinical cancer research : an official journal of the American Association for Cancer Research 20040515

• Accumulation of 5-phosphoribosyl-1-pyrophosphate in human CCRF-CEM leukaemia cells treated with antifolates.

  The international journal of biochemistry & cell biology 20040301

• Thymidine rescue: an antidote for pemetrexed-related toxicity in the setting of acute renal failure.

  Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20031101

• Pemetrexed (Alimta): a novel multitargeted antifolate agent.

  Expert review of anticancer therapy 20030401

• Design, synthesis, and biological activities of classical N-[4-[2-(2-amino-4-ethylpyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-l-glutamic acid and its 6-methyl derivative as potential dual inhibitors of thymidylate synthase and dihydrofolate reductase and as potential antitumor agents.

  Journal of medicinal chemistry 20030213

• Pemetrexed combination therapy in the treatment of non-small cell lung cancer.

  Seminars in oncology 20020401

• A new route to 7-substituted derivatives of n-[4-(2-[2-amino-3,4-dihydro-4-oxo-7H-pyrrolo(2,3-d)pyrimidin-5-yl]ethyl)benzoyl]-L-glutamic acid [ALIMTA (LY231514, MTA)].

  The Journal of organic chemistry 20010601