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Raltitrexed

CAS No.:
112887-68-0
Catalog Number:
AG0038YQ
Molecular Formula:
C21H22N4O6S
Molecular Weight:
458.4876
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
98%(HPLC)
In Stock USA
United States
$73
- +
10mg
95%
In Stock USA
United States
$88
- +
25mg
95%
In Stock USA
United States
$157
- +
50mg
95%
In Stock USA
United States
$282
- +
100mg
95%
In Stock USA
United States
$438
- +
Product Description
Catalog Number:
AG0038YQ
Chemical Name:
Raltitrexed
CAS Number:
112887-68-0
Molecular Formula:
C21H22N4O6S
Molecular Weight:
458.4876
MDL Number:
MFCD12828867
IUPAC Name:
(2S)-2-[[5-[methyl-[(2-methyl-4-oxo-3H-quinazolin-6-yl)methyl]amino]thiophene-2-carbonyl]amino]pentanedioic acid
InChI:
InChI=1S/C21H22N4O6S/c1-11-22-14-4-3-12(9-13(14)19(28)23-11)10-25(2)17-7-6-16(32-17)20(29)24-15(21(30)31)5-8-18(26)27/h3-4,6-7,9,15H,5,8,10H2,1-2H3,(H,24,29)(H,26,27)(H,30,31)(H,22,23,28)/t15-/m0/s1
InChI Key:
IVTVGDXNLFLDRM-HNNXBMFYSA-N
SMILES:
OC(=O)CC[C@@H](C(=O)O)NC(=O)c1ccc(s1)N(CC1C=CC2=NC(=NC(=O)C2=C1)C)C
UNII:
FCB9EGG971
NSC Number:
639186
Properties
Complexity:
790  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Defined Bond Stereocenter Count:
0
Exact Mass:
458.126g/mol
Formal Charge:
0
Heavy Atom Count:
32  
Hydrogen Bond Acceptor Count:
9  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
458.489g/mol
Monoisotopic Mass:
458.126g/mol
Rotatable Bond Count:
9  
Topological Polar Surface Area:
177A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.4  
Literature
Title Journal
Diffuse malignant peritoneal mesothelioma--an update on treatment. Cancer treatment reviews 20121001
Thymidylate synthase mRNA levels in plasma and tumor as potential predictive biomarkers for raltitrexed sensitivity in gastric cancer. International journal of cancer 20120915
A randomized phase II study to compare oxaliplatin plus 5-fluorouracil and leucovorin (FOLFOX4) versus oxaliplatin plus raltitrexed (TOMOX) as first-line chemotherapy for advanced colorectal cancer. Clinical & translational oncology : official publication of the Federation of Spanish Oncology Societies and of the National Cancer Institute of Mexico 20120801
Novel tricyclic indeno[2,1-d]pyrimidines with dual antiangiogenic and cytotoxic activities as potent antitumor agents. Bioorganic & medicinal chemistry 20120715
Influence of resistance to 5-fluorouracil and tomudex on [18F]‑FDG incorporation, glucose transport and hexokinase activity. International journal of oncology 20120701
Preclinical studies identify novel targeted pharmacological strategies for treatment of human malignant pleural mesothelioma. British journal of pharmacology 20120501
Systemic treatment of malignant pleural mesothelioma. Future oncology (London, England) 20120301
Raltitrexed plus cisplatin is cost-effective compared with pemetrexed plus cisplatin in patients with malignant pleural mesothelioma. Lung cancer (Amsterdam, Netherlands) 20120201
Substrate- and pH-specific antifolate transport mediated by organic anion-transporting polypeptide 2B1 (OATP2B1-SLCO2B1). Molecular pharmacology 20120201
Folic acid supplementation increases survival and modulates high risk HPV-induced phenotypes in oral squamous cell carcinoma cells and correlates with p53 mRNA transcriptional down-regulation. Cancer cell international 20120101
Constitutive and treatment-induced CXCL8-signalling selectively modulates the efficacy of anti-metabolite therapeutics in metastatic prostate cancer. PloS one 20120101
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PEA3/ETV4-related transcription factors coupled with active ERK signalling are associated with poor prognosis in gastric adenocarcinoma. British journal of cancer 20110628
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Tumor response is predicted by patient genetic profile in rectal cancer patients treated with neo-adjuvant chemo-radiotherapy. The pharmacogenomics journal 20110601
Thymidylate synthase as a determinant of pemetrexed sensitivity in non-small cell lung cancer. British journal of cancer 20110510
MicroRNA dysregulation in colorectal cancer: a clinical perspective. British journal of cancer 20110315
Oxaliplatin plus dual inhibition of thymidilate synthase during preoperative pelvic radiotherapy for locally advanced rectal carcinoma: long-term outcome. International journal of radiation oncology, biology, physics 20110301
Value of ADC measurements for nodal staging after chemoradiation in locally advanced rectal cancer-a per lesion validation study. European radiology 20110201
Adjuvant chemotherapy for localised colon cancer. Fluorouracil + folinic acid for node-positive, non-metastatic disease. Prescrire international 20110201
Single agent and combination studies of pralatrexate and molecular correlates of sensitivity. British journal of cancer 20110118
Human thymidylate synthase with loop 181-197 stabilized in an inactive conformation: ligand interactions, phosphorylation, and inhibition profiles. Protein science : a publication of the Protein Society 20110101
Assessing methods for dealing with treatment switching in randomised controlled trials: a simulation study. BMC medical research methodology 20110101
GTI: a novel algorithm for identifying outlier gene expression profiles from integrated microarray datasets. PloS one 20110101
Cytoreductive surgery plus hyperthermic intraperitoneal chemotherapy improves survival of gastric cancer with peritoneal carcinomatosis: evidence from an experimental study. Journal of translational medicine 20110101
Heath-related quality of life in thyroid cancer patients following radioiodine ablation. Health and quality of life outcomes 20110101
An unusual presentation of multiple cavitated lung metastases from colon carcinoma. BMC medical imaging 20110101
Expression of RFC/SLC19A1 is associated with tumor type in bladder cancer patients. PloS one 20110101
A 26-year-old male with mesothelioma due to asbestos exposure. Case reports in medicine 20110101
Critical appraisal of pralatrexate in the management of difficult-to-treat peripheral T cell lymphoma. Therapeutics and clinical risk management 20110101
Clinical characteristics and treatment outcomes in 132 patients with malignant mesothelioma. Lung India : official organ of Indian Chest Society 20110101
The state of research into children with cancer across Europe: new policies for a new decade. Ecancermedicalscience 20110101
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Phenotypic enhancement of thymidylate synthetase pathway inhibitors following ablation of Neil1 DNA glycosylase/lyase. Cell cycle (Georgetown, Tex.) 20101215
Antifolate inhibitors of thymidylate synthase as anticancer drugs. Mini reviews in medicinal chemistry 20101101
Combination 5-fluorouracil, folinic acid and cisplatin (LV5FU2-CDDP) followed by gemcitabine or the reverse sequence in metastatic pancreatic cancer: final results of a randomised strategic phase III trial (FFCD 0301). Gut 20101101
Vorinostat synergises with capecitabine through upregulation of thymidine phosphorylase. British journal of cancer 20101101
Substrate-specific binding and conformational changes involving Ser313 and transmembrane domain 8 of the human reduced folate carrier, as determined by site-directed mutagenesis and protein cross-linking. The Biochemical journal 20100901
Identification of thymidylate synthase as a potential therapeutic target for lung cancer. British journal of cancer 20100727
Understanding chemotherapy treatment pathways of advanced colorectal cancer patients to inform an economic evaluation in the United Kingdom. British journal of cancer 20100727
Raltitrexed and oxaliplatin hepatic arterial infusion for advanced colorectal cancer: a retrospective study. Anti-cancer drugs 20100701
Characterisation of the bifunctional dihydrofolate synthase-folylpolyglutamate synthase from Plasmodium falciparum; a potential novel target for antimalarial antifolate inhibition. Molecular and biochemical parasitology 20100701
Pyridinium 5-nitro-thio-phene-2-carboxyl-ate. Acta crystallographica. Section E, Structure reports online 20100601
The role of folate receptor alpha (FRalpha) in the response of malignant pleural mesothelioma to pemetrexed-containing chemotherapy. British journal of cancer 20100202
[Prerequisites to the administration and prevention of adverse effects of chemotherapy in colorectal cancer]. Bulletin du cancer 20100201
Defining patient outcomes in stage IV colorectal cancer: a prospective study with baseline stratification according to disease resectability status. British journal of cancer 20100119
Colorectal cancer: response to sunitinib in a heavily pretreated colorectal cancer patient. Anti-cancer drugs 20100101
Synthesis and biological activity of raltitrexed-carrier conjugates. Acta biochimica Polonica 20100101
Molecular mechanism of chemoresistance by miR-215 in osteosarcoma and colon cancer cells. Molecular cancer 20100101
Interaction between thymidylate synthase and its cognate mRNA in zebrafish embryos. PloS one 20100101
Analysis of the thymidylate synthase gene structure in colorectal cancer patients and its possible relation with the 5-Fluorouracil drug response. Journal of nucleic acids 20100101
Molecular docking studies on quinazoline antifolate derivatives as human thymidylate synthase inhibitors. Bioinformation 20100101
The ERK MAP kinase-PEA3/ETV4-MMP-1 axis is operative in oesophageal adenocarcinoma. Molecular cancer 20100101
CoFactor: Folate Requirement for Optimization of 5-Fluouracil Activity in Anticancer Chemotherapy. Journal of oncology 20100101
Cancer chemotherapy: targeting folic acid synthesis. Cancer management and research 20100101
Raltitrexed: optimism and reality. Expert opinion on drug metabolism & toxicology 20091101
Distinct mechanistic activity profile of pralatrexate in comparison to other antifolates in in vitro and in vivo models of human cancers. Cancer chemotherapy and pharmacology 20091001
Malignant pleural mesothelioma: an update on biomarkers and treatment. Chest 20090901
Adjuvant chemotherapy for stages II, III and IV of colon cancer. Clinical & translational oncology : official publication of the Federation of Spanish Oncology Societies and of the National Cancer Institute of Mexico 20090801
Cost-effectiveness analysis of XELOX for metastatic colorectal cancer based on the NO16966 and NO16967 trials. British journal of cancer 20090707
C677T and A1298C MTHFR polymorphisms, a challenge for antifolate and fluoropyrimidine-based therapy personalisation. European journal of cancer (Oxford, England : 1990) 20090501
Modulation of thymidilate synthase and p53 expression by HDAC inhibitor vorinostat resulted in synergistic antitumor effect in combination with 5FU or raltitrexed. Cancer biology & therapy 20090501
Future developments in the management of malignant pleural mesothelioma. Expert review of anticancer therapy 20090401
Trimodality therapy with induction chemotherapy followed by extrapleural pneumonectomy and adjuvant high-dose hemithoracic radiation for malignant pleural mesothelioma. Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20090320
Chiral separation of raltitrexed by cyclodextrin-modified micellar electrokinetic chromatography. Analytical and bioanalytical chemistry 20090101
Late cutaneous metastases to the face from malignant pleural mesothelioma: a case report and review of the literature. World journal of surgical oncology 20090101
Acute coronary syndrome associated with continuous 5-Fluorouracil infusion in a patient with metastatic colorectal cancer-a case report with a discussion on this clinical dilemma. Journal of gastrointestinal cancer 20090101
An open label randomized multicentre phase IIIb trial comparing parenteral substitution versus best supportive nutritional care in subjects with pancreatic adenocarcinoma receiving 5-FU plus oxaliplatin as 2nd or higher line chemotherapy regarding clinical benefit - PANUSCO. BMC cancer 20090101
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Outcome for esophageal cancer following treatment with chemotherapy and radiotherapy but not esophagectomy: Nonsurgical treatment of esophageal cancer. Clinical and experimental gastroenterology 20090101
Dynamics of antifolate transport via the reduced folate carrier and the membrane folate receptor in murine leukaemia cells in vitro and in vivo. Cancer chemotherapy and pharmacology 20081101
DNA damage and homologous recombination signaling induced by thymidylate deprivation. Biochemical pharmacology 20081015
Induction of intrachromosomal homologous recombination in human cells by raltitrexed, an inhibitor of thymidylate synthase. DNA repair 20081001
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[18F]2-fluoro-2-deoxy-D-glucose incorporation by AGS gastric adenocarcinoma cells in vitro during response to epirubicin, cisplatin and 5-fluorouracil. British journal of cancer 20071008
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Recent advances in classical and non-classical antifolates as antitumor and antiopportunistic infection agents: part I. Anti-cancer agents in medicinal chemistry 20070901
Human mass balance study of the novel anticancer agent ixabepilone using accelerator mass spectrometry. Investigational new drugs 20070801
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A preclinical evaluation of pemetrexed and irinotecan combination as second-line chemotherapy in pancreatic cancer. British journal of cancer 20070507
Mechanisms of acquired chemoresistance to 5-fluorouracil and tomudex: thymidylate synthase dependent and independent networks. Cancer chemotherapy and pharmacology 20070501
Chemotherapy in advanced biliary tract carcinoma: a pooled analysis of clinical trials. British journal of cancer 20070326
Failure to complete adjuvant chemotherapy is associated with adverse survival in stage III colon cancer patients. British journal of cancer 20070312
Changes in the status of p53 affect drug sensitivity to thymidylate synthase (TS) inhibitors by altering TS levels. British journal of cancer 20070312
An evaluation of thymidine phosphorylase as a means of preventing thymidine rescue from the thymidylate synthase inhibitor raltitrexed. Cancer chemotherapy and pharmacology 20070201
Polymorphisms in the thymidylate synthase and dihydropyrimidine dehydrogenase genes predict response and toxicity to capecitabine-raltitrexed in colorectal cancer. Oncology reports 20070201
Cost-effectiveness analysis of cetuximab/irinotecan vs active/best supportive care for the treatment of metastatic colorectal cancer patients who have failed previous chemotherapy treatment. British journal of cancer 20070129
Antisense targeting of thymidylate synthase (TS) mRNA increases TS gene transcription and TS protein: effects on human tumor cell sensitivity to TS enzyme-inhibiting drugs. Gene expression 20070101
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Identification of gene polymorphisms of human DNA topoisomerase I in the National Cancer Institute panel of human tumour cell lines. British journal of cancer 20061009
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A phase I study of pemetrexed (LY231514) supplemented with folate and vitamin B12 in Japanese patients with solid tumours. British journal of cancer 20060918
A multicenter phase III trial comparing irinotecan-gemcitabine (IG) with gemcitabine (G) monotherapy as first-line treatment in patients with locally advanced or metastatic pancreatic cancer. British journal of cancer 20060904
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Systemic chemotherapy in the management of malignant peritoneal mesothelioma. European journal of surgical oncology : the journal of the European Society of Surgical Oncology and the British Association of Surgical Oncology 20060801
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18F-FDG PET is an early predictor of pathologic tumor response to preoperative radiochemotherapy in locally advanced rectal cancer. Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20060801
The combination of raltitrexed (Tomudex) and mitomycin-C in the treatment of advanced colorectal cancer--a phase II study. Clinical oncology (Royal College of Radiologists (Great Britain)) 20060801
Severe enteropathy associated with raltitrexed and oxaliplatin chemotherapy: report of two patients experiencing this rare, potentially lethal gastrointestinal adverse event. Anti-cancer drugs 20060801
The clinical and economic benefits of capecitabine and tegafur with uracil in metastatic colorectal cancer. British journal of cancer 20060703
The use of chemotherapy in patients with advanced malignant pleural mesothelioma: a systematic review and practice guideline. Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20060701
Computer modelling of antifolate inhibition of folate metabolism using hybrid functional petri nets. Journal of theoretical biology 20060621
Biweekly oxaliplatin, raltitrexed, 5-fluorouracil and folinic acid combination chemotherapy during preoperative radiation therapy for locally advanced rectal cancer: a phase I-II study. British journal of cancer 20060619
Raltitrexed plus levofolinic acid and bolus/continuous infusion 5-fluorouracil on a biweekly schedule for elderly patients with advanced colorectal carcinomas. Annals of oncology : official journal of the European Society for Medical Oncology 20060601
Adding raltitrexed to cisplatin improves overall survival in people with malignant pleural mesothelioma. Cancer treatment reviews 20060501
XELOX (capecitabine plus oxaliplatin) as first-line treatment for elderly patients over 70 years of age with advanced colorectal cancer. British journal of cancer 20060410
Irinotecan, oxaliplatin and raltitrexed for the treatment of advanced colorectal cancer. Expert opinion on pharmacotherapy 20060401
Raltitrexed-eloxatin salvage chemotherapy in gemcitabine-resistant metastatic pancreatic cancer. British journal of cancer 20060327
Short-term treatment-related symptoms and quality of life: results from an international randomized phase III study of cisplatin with or without raltitrexed in patients with malignant pleural mesothelioma: an EORTC Lung-Cancer Group and National Cancer Institute, Canada, Intergroup Study. Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20060320
Preoperative hyperfractionated chemoradiation for locally recurrent rectal cancer in patients previously irradiated to the pelvis: A multicentric phase II study. International journal of radiation oncology, biology, physics 20060315
Quantitative structure-pharmacokinetic relationships for drug clearance by using statistical learning methods. Journal of molecular graphics & modelling 20060301
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Role of N-terminal residues in the ubiquitin-independent degradation of human thymidylate synthase. The Biochemical journal 20060215
The inverse relationship between reduced folate carrier function and pemetrexed activity in a human colon cancer cell line. Molecular cancer therapeutics 20060201
Antimetabolites and cancer: emerging data with a focus on antifolates. Expert opinion on therapeutic patents 20060201
Low folate conditions may enhance the interaction of trifluorothymidine with antifolates in colon cancer cells. Cancer chemotherapy and pharmacology 20060101
Study on brain targeting of raltitrexed following intranasal administration in rats. Cancer chemotherapy and pharmacology 20060101
A National Cancer Institute of Canada Clinical Trials Group Study--IND.135: Phase I/II study of irinotecan (camptosar), oxaliplatin and raltitrexed (tomudex) (COT) in patients with advanced colorectal cancer. European journal of cancer (Oxford, England : 1990) 20060101
Raltitrexed plus oxaliplatin in the second-line treatment of metastatic colorectal cancer. Neoplasma 20060101
Analysis of folylpoly-gamma-glutamate synthetase gene expression in human B-precursor ALL and T-lineage ALL cells. BMC cancer 20060101
Randomised trial comparing three different schedules of infusional 5FU and raltitrexed alone as first-line therapy in metastatic colorectal cancer. Final results of the Fédération Francophone de Cancérologie Digestive (FFCD) 9601 trial. Oncology 20060101
Pre-operative radiochemotherapy with raltitrexed for resectable locally-advanced rectal cancer: a phase II study. Anticancer research 20060101
The role of multidrug resistance efflux transporters in antifolate resistance and folate homeostasis. Drug resistance updates : reviews and commentaries in antimicrobial and anticancer chemotherapy 20060101
Metachronic malignant transformation of small bowel and rectal endometriosis in the same patient. World journal of surgical oncology 20060101
Financial considerations in the conduct of multi-centre randomised controlled trials: evidence from a qualitative study. Trials 20060101
Oxaliplatin with raltitrexed and preoperative radiotherapy in T3-T4 extraperitoneal rectal cancer. A dose finding study. Tumori 20060101
[A review of chemotherapy for metastatic colon cancer]. Farmacia hospitalaria : organo oficial de expresion cientifica de la Sociedad Espanola de Farmacia Hospitalaria 20060101
Cost-effectiveness analysis of first-line chemotherapies in metastatic colorectal cancer. Results of the Fédération Francophone de Cancérologie Digestive (FFCD) 9601 randomized trial. Oncology 20060101
[Mesothelioma: advances in chemotherapy]. Revue des maladies respiratoires 20051201
Pemetrexed: new drug. Pleural mesothelioma: a first encouraging trial. Prescrire international 20051201
Chemotherapy of metastatic colorectal cancer: fluorouracil plus folinic acid and irinotecan or oxaliplatin. Prescrire international 20051201
Phase II randomised trial of raltitrexed-oxaliplatin vs raltitrexed-irinotecan as first-line treatment in advanced colorectal cancer. British journal of cancer 20051128
Determination of apoptosis, uracil incorporation, DNA strand breaks, and sister chromatid exchanges under conditions of thymidylate deprivation in a model of BER deficiency. Biochemical pharmacology 20051115
A phase I/II study of oxaliplatin when added to 5-fluorouracil and leucovorin and pelvic radiation in locally advanced rectal cancer: a Colorectal Clinical Oncology Group (CCOG) study. British journal of cancer 20051031
A phase I pharmacokinetic and pharmacodynamic study of BGC9331 and carboplatin in relapsed gynaecological malignancies. British journal of cancer 20051017
Randomized phase III study of cisplatin with or without raltitrexed in patients with malignant pleural mesothelioma: an intergroup study of the European Organisation for Research and Treatment of Cancer Lung Cancer Group and the National Cancer Institute of Canada. Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20051001
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