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598-41-4,MFCD01859715
Catalog No.:AA00E91J

598-41-4 | Glycinamide

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1g
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$70.00   $49.00
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5g
95%
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$201.00   $141.00
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10g
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$334.00   $234.00
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00E91J
Chemical Name:
Glycinamide
CAS Number:
598-41-4
Molecular Formula:
C2H6N2O
Molecular Weight:
74.0818
MDL Number:
MFCD01859715
SMILES:
NCC(=O)N
Properties
Properties
 
BP:
281.3°C at 760 mmHg  
Form:
Solid  
MP:
65-67°C  
Storage:
Inert atmosphere;-20 ℃;  

Computed Properties
 
Complexity:
42.9  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
5  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
1  
XLogP3:
-1.8  

Literature

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Journal: European journal of pharmacology 20121205

Title: Association between expression of thymidylate synthase, dihydrofolate reductase, and glycinamide ribonucleotide formyltransferase and efficacy of pemetrexed in advanced non-small cell lung cancer.

Journal: Anticancer research 20121001

Title: Preventing cleavage of Mer promotes efferocytosis and suppresses acute lung injury in bleomycin treated mice.

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Title: Biomarker analysis in a phase III study of pemetrexed-carboplatin versus etoposide-carboplatin in chemonaive patients with extensive-stage small-cell lung cancer.

Journal: Annals of oncology : official journal of the European Society for Medical Oncology 20120701

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Title: Design and pharmacological activity of glycinamide and N-methoxy amide derivatives of analogs and constitutional isomers of valproic acid.

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Title: N-Heteroaryl glycinamides and glycinamines as potent NPY5 antagonists.

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Title: Quantitative shotgun proteomics using a uniform ¹⁵N-labeled standard to monitor proteome dynamics in time course experiments reveals new insights into the heat stress response of Chlamydomonas reinhardtii.

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Title: N-Acryloyl glycinamide.

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Title: Targeting the proton-coupled folate transporter for selective delivery of 6-substituted pyrrolo[2,3-d]pyrimidine antifolate inhibitors of de novo purine biosynthesis in the chemotherapy of solid tumors.

Journal: Molecular pharmacology 20101001

Title: Crystal structures of glycinamide ribonucleotide synthetase, PurD, from thermophilic eubacteria.

Journal: Journal of biochemistry 20101001

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Title: Cellular and molecular mechanisms for the synergistic cytotoxicity elicited by oxaliplatin and pemetrexed in colon cancer cell lines.

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Title: Well-defined synthetic polymers with a protein-like gelation behavior in water.

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Title: Glycine amides as PPARalpha agonists.

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Title: gamma-Lactams as glycinamide replacements in cyclohexane-based CC chemokine receptor 2 (CCR2) antagonists.

Journal: Bioorganic & medicinal chemistry letters 20100415

Title: Synthesis and antitumor activity of a novel series of 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitors of purine biosynthesis with selectivity for high affinity folate receptors and the proton-coupled folate transporter over the reduced folate carrier for cellular entry.

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Title: Pemetrexed plus cisplatin/carboplatin in previously treated locally advanced or metastatic non-small cell lung cancer patients.

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Title: Antibiotic optimization in the difficult-to-treat patient with complicated intra-abdominal or complicated skin and skin structure infections: focus on tigecycline.

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Title: Inhibition of de novo purine synthesis in human prostate cells results in ATP depletion, AMPK activation and induces senescence.

Journal: The Prostate 20090801

Title: A mapping of drug space from the viewpoint of small molecule metabolism.

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Title: Protein preparation, crystallization and preliminary crystallographic studies of Bacillus subtilis glycinamide ribonucleotide transformylase.

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Title: Structures of glycinamide ribonucleotide transformylase (PurN) from Mycobacterium tuberculosis reveal a novel dimer with relevance to drug discovery.

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Title: Computational study of urea and its homologue glycinamide: conformations, rotational barriers, and relative interactions with sodium chloride.

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Title: Discovery of 3,5-bis(trifluoromethyl)benzyl L-arylglycinamide based potent CCR2 antagonists.

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Journal: The Journal of biological chemistry 20060616

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Journal: Life sciences 20060522

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Journal: Bioorganic & medicinal chemistry 20060515

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Journal: Seminars in oncology 20060201

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Title: A quantum chemical study on the mechanism of glycinamide ribonucleotide transformylase inhibitor: 10-Formyl-5,8,10-trideazafolic acid.

Journal: Biophysical chemistry 20051201

Title: Adenosine kinase inhibitors. 6. Synthesis, water solubility, and antinociceptive activity of 5-phenyl-7-(5-deoxy-beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidines substituted at C4 with glycinamides and related compounds.

Journal: Journal of medicinal chemistry 20051201

Title: Application of Fourier transform infrared spectroscopy for monitoring hydrolysis and synthesis reactions catalyzed by a recombinant amidase.

Journal: Analytical biochemistry 20051101

Title: Synthesis of some derivatives of C-(1-deoxy-1-N-substituted-D-glucopyranosyl)formic acid (D-gluco-hept-2-ulopyranosonic acid) as potential inhibitors of glycogen phosphorylase.

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Journal: Biochemistry 20050802

Title: The apo and ternary complex structures of a chemotherapeutic target: human glycinamide ribonucleotide transformylase.

Journal: Biochemistry 20050726

Title: Kinetic and mechanistic investigation of the selective acidolysis of the C-terminal amide bond of N-acyl-N,alpha,alpha-trialkyl glycine amides.

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Title: Cellular and pharmacogenetics foundation of synergistic interaction of pemetrexed and gemcitabine in human non-small-cell lung cancer cells.

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Title: Design, synthesis, and biological evaluation of 10-methanesulfonyl-DDACTHF, 10-methanesulfonyl-5-DACTHF, and 10-methylthio-DDACTHF as potent inhibitors of GAR Tfase and the de novo purine biosynthetic pathway.

Journal: Bioorganic & medicinal chemistry 20050516

Title: Synthesis and biological evaluation of N-[4-[5-(2,4-diamino-6-oxo-1,6-dihydropyrimidin-5-yl)-2-(2,2,2-trifluoroacetyl)pentyl]benzoyl]-L-glutamic acid as a potential inhibitor of GAR Tfase and the de novo purine biosynthetic pathway.

Journal: Bioorganic & medicinal chemistry 20050516

Title: Application of intramolecular 1,3-dipolar cyclic addition of azide and olefin; construction of (pyrrolidine-2-ylidene)glycinate and glycinamides.

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Title: Double proton transfer and one-electron oxidation behavior in double H-bonded glycinamide-glycine complex in the gas phase.

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Journal: Biochemistry 20050412

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Journal: Molecular biology and evolution 20050401

Title: Three emerging new drugs for NSCLC: pemetrexed, bortezomib, and cetuximab.

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Title: Theoretical study of the effect of water in the process of proton transfer of glycinamide.

Journal: The journal of physical chemistry. B 20050331

Title: Molecular characterization and chromosomal assignment of the bovine glycinamide ribonucleotide formyltransferase (GART) gene on cattle chromosome 1q12.1-q12.2.

Journal: Gene 20050328

Title: Loss of reduced folate carrier function and folate depletion result in enhanced pemetrexed inhibition of purine synthesis.

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Title: Chiral ion-exchange capillary electrochromatography of arylglycine amides with dextran sulfate as a pseudostationary phase.

Journal: Electrophoresis 20050201

Title: Specific inhibition and stabilization of aspergilloglutamic peptidase by the propeptide. Identification of critical sequences and residues in the propeptide.

Journal: The Journal of biological chemistry 20050114

Title: Glycine-amide is an active metabolite of the antiretroviral tripeptide glycyl-prolyl-glycine-amide.

Journal: Antimicrobial agents and chemotherapy 20050101

Title: Genome-wide screening for genes whose deletions confer sensitivity to mutagenic purine base analogs in yeast.

Journal: BMC genetics 20050101

Title: Folate system correlations in DNA microarray data.

Journal: BMC cancer 20050101

Title: Inhibition of glycinamide ribonucleotide formyltransferase results in selective inhibition of macrophage cytokine secretion in vitro and in vivo efficacy in rat adjuvant arthritis.

Journal: Clinical and experimental rheumatology 20050101

Title: CamTHP*OH: a camphor-derived delta-lactol auxiliary for the effective desymmetrization of attached glycinamide residues. Asymmetric synthesis of alpha-amino carbonyl compounds.

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Title: Highly stereoselective Michael addition reactions of CamTHP*-desymmetrized glycinamide for the synthesis of functionally dense amino acid derivatives.

Journal: Organic letters 20041125

Title: Double proton transfer behavior and one-electron oxidation effect in double H-bonded glycinamide-formic acid complex.

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Title: Phase II clinical trial of capecitabine and gemcitabine chemotherapy in patients with metastatic renal carcinoma.

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Title: Tumor necrosis factor-alpha-converting enzyme (ADAM17) mediates GPIbalpha shedding from platelets in vitro and in vivo.

Journal: Circulation research 20041001

Title: Tumor necrosis factor alpha stimulates MUC1 synthesis and ectodomain release in a human uterine epithelial cell line.

Journal: Endocrinology 20040901

Title: Construction, characterization, and use of small-insert gene banks of DNA isolated from soil and enrichment cultures for the recovery of novel amidases.

Journal: Environmental microbiology 20040901

Title: A quantum chemical study of the water-assisted mechanism in one-carbon unit transfer reaction catalyzed by glycinamide ribonucleotide transformylase.

Journal: Biophysical chemistry 20040801

Title: BMS-201620: a selective beta 3 agonist.

Journal: Bioorganic & medicinal chemistry letters 20040705

Title: A second-generation system for unbiased reading frame selection.

Journal: Protein engineering, design & selection : PEDS 20040701

Title: Pemetrexed (ALIMTA), a novel multitargeted antineoplastic agent.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20040615

Title: Analysis of antigen-specific T-cell responses with synthetic peptides--what kind of peptide for which purpose?

Journal: Human immunology 20040501

Title: The crystal structure of the hydrolase domain of 10-formyltetrahydrofolate dehydrogenase: mechanism of hydrolysis and its interplay with the dehydrogenase domain.

Journal: The Journal of biological chemistry 20040402

Title: Pharmacology and mechanism of action of pemetrexed.

Journal: Clinical lung cancer 20040401

Title: CHF 3381.

Journal: Drugs in R&D 20040101

Title: Basal jawed vertebrate phylogeny inferred from multiple nuclear DNA-coded genes.

Journal: BMC biology 20040101

Title: FDA drug approval summaries: pemetrexed (Alimta).

Journal: The oncologist 20040101

Title: One-step synthesis of hypoxanthine from glycinamide and diformylurea.

Journal: Chemistry & biodiversity 20040101

Title: Membrane topology of guinea pig cytochrome P450 17 alpha revealed by a combination of chemical modifications and mass spectrometry.

Journal: Biochemistry 20031216

Title: A defect in the p53 response pathway induced by de novo purine synthesis inhibition.

Journal: The Journal of biological chemistry 20031205

Title: Using a residue clash map to functionally characterize protein recombination hybrids.

Journal: Protein engineering 20031201

Title: Design, synthesis, and biological evaluation of simplified alpha-keto heterocycle, trifluoromethyl ketone, and formyl substituted folate analogues as potential inhibitors of GAR transformylase and AICAR transformylase.

Journal: Bioorganic & medicinal chemistry 20031001

Title: 10-(2-benzoxazolcarbonyl)-5,10-dideaza-acyclic-5,6,7,8-tetrahydrofolic acid: a potential inhibitor of GAR transformylase and AICAR transformylase.

Journal: Bioorganic & medicinal chemistry 20031001

Title: Design, synthesis and biological evaluation of 10-CF3CO-DDACTHF analogues and derivatives as inhibitors of GAR Tfase and the de novo purine biosynthetic pathway.

Journal: Bioorganic & medicinal chemistry 20031001

Title: On the structural and functional modularity of glycinamide ribonucleotide formyltransferases.

Journal: Protein science : a publication of the Protein Society 20031001

Title: Tomoregulin ectodomain shedding by proinflammatory cytokines.

Journal: Life sciences 20030815

Title: Thymidine and hypoxanthine protection patterns of the folic acid-enhanced synergies for combinations of trimetrexate plus a polyglutamylatable inhibitor of purine or thymidylate synthesis against human ileocecal HCT-8 cells.

Journal: International journal of oncology 20030801

Title: The role of Pemetrexed (Alimta , LY231514) in lung cancer therapy.

Journal: Clinical lung cancer 20030701

Title: Pemetrexed and its emerging role in the treatment of thoracic malignancies.

Journal: Expert opinion on investigational drugs 20030501

Title: Decreased expression of the reduced folate carrier and folypolyglutamate synthetase is the basis for acquired resistance to the pemetrexed antifolate (LY231514) in an L1210 murine leukemia cell line.

Journal: Biochemical pharmacology 20030401

Title: Pemetrexed (Alimta): a promising new agent for the treatment of breast cancer.

Journal: Seminars in oncology 20030401

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

Journal: Expert review of anticancer therapy 20030401

Title: Metal-catalyzed hydroxylaminolysis of unactivated amide and peptide bonds.

Journal: Organic & biomolecular chemistry 20030307

Title: Novel antifolate drugs.

Journal: Current oncology reports 20030301

Title: Loss of folylpoly-gamma-glutamate synthetase activity is a dominant mechanism of resistance to polyglutamylation-dependent novel antifolates in multiple human leukemia sublines.

Journal: International journal of cancer 20030220

Title: Antineoplastic agents. 487. Synthesis and biological evaluation of the antineoplastic agent 3,4-methylenedioxy-5,4'-dimethoxy-3'-amino-Z-stilbene and derived amino acid amides.

Journal: Journal of medicinal chemistry 20030213

Title: Fragmentation reactions of protonated peptides containing glutamine or glutamic acid.

Journal: Journal of mass spectrometry : JMS 20030201

Title: Deaza analogs of folic acid as antitumor agents.

Journal: Current pharmaceutical design 20030101

Title: Practical asymmetric synthesis of vicinal diamines through the catalytic highly enantioselective alkylation of glycine amide derivatives.

Journal: Angewandte Chemie (International ed. in English) 20030101

Title: Current data with pemetrexed (Alimta) in non-small-cell lung cancer.

Journal: Clinical lung cancer 20030101

Title: LY309887, antifolate via the folate receptor suppresses murine type II collagen-induced arthritis.

Journal: Clinical and experimental rheumatology 20030101

Title: Biochemical and structural characterization of the cross-linked complex of nitrogenase: comparison to the ADP-AlF4(-)-stabilized structure.

Journal: Biochemistry 20021231

Title: Crystal structures of human GAR Tfase at low and high pH and with substrate beta-GAR.

Journal: Biochemistry 20021203

Title: Molecular, biochemical, and cellular pharmacology of pemetrexed.

Journal: Seminars in oncology 20021201

Title: Pemetrexed safety and dosing strategy.

Journal: Seminars in oncology 20021201

Title: Preclinical and clinical studies with combinations of pemetrexed and gemcitabine.

Journal: Seminars in oncology 20021201

Title: Pemetrexed in pancreatic cancer.

Journal: Seminars in oncology 20021201

Title: Pemetrexed: an active new agent for breast cancer.

Journal: Seminars in oncology 20021201

Title: A universal, vector-based system for nucleic acid reading-frame selection.

Journal: Protein engineering 20021201

Title: Alimta (pemetrexed disodium): a multitargeted antifolate for the treatment of mesothelioma.

Journal: Lung cancer (Amsterdam, Netherlands) 20021101

Title: New 2H-tetrahydro-1, 3, 5-thiadiazine-2-thiones incorporating glycine and glycinamide as potential antifungal agents.

Journal: Archiv der Pharmazie 20021101

Title: Chemotactic agents induce IL-6Ralpha shedding from polymorphonuclear cells: involvement of a metalloproteinase of the TNF-alpha-converting enzyme (TACE) type.

Journal: European journal of immunology 20021001

Title: Endotoxin induces rapid metalloproteinase-mediated shedding followed by up-regulation of the monocyte hemoglobin scavenger receptor CD163.

Journal: Journal of leukocyte biology 20021001

Title: Chemically modified 'polar patch' mutants of subtilisin in peptide synthesis with remarkably broad substrate acceptance: designing combinatorial biocatalysts.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20020916

Title: Antifolates targeting purine synthesis allow entry of tumor cells into S phase regardless of p53 function.

Journal: Cancer research 20020915

Title: The pemetrexed/gemcitabine combination in pancreatic cancer.

Journal: Cancer 20020815

Title: 10-Formyl-5,10-dideaza-acyclic-5,6,7,8-tetrahydrofolic acid (10-formyl-DDACTHF): a potent cytotoxic agent acting by selective inhibition of human GAR Tfase and the de novo purine biosynthetic pathway.

Journal: Bioorganic & medicinal chemistry 20020801

Title: Pemetrexed disodium combined with oxaliplatin, SN38, or 5-fluorouracil, based on the quantitation of drug interactions in human HT29 colon cancer cells.

Journal: International journal of oncology 20020801

Title: Effect of short-term N(2) deficiency on expression of the ureide pathway in cowpea root nodules.

Journal: Plant physiology 20020701

Title: [Differentially expressed genes in vascular endothelial cell line ECV 304 induced by high density lipoprotein].

Journal: Zhonghua yi xue za zhi 20020701

Title: PurT-encoded glycinamide ribonucleotide transformylase. Accommodation of adenosine nucleotide analogs within the active site.

Journal: The Journal of biological chemistry 20020628

Title: New N(3)S donor ligand small peptide analogues of the N-mercaptoacetyl-glycylglycylglycine ligand in the clinically used Tc-99m renal imaging agent: evidence for unusual amide oxygen coordination by two new ligands.

Journal: Inorganic chemistry 20020603

Title: Incorporation of pemetrexed (Alimta) into the treatment of non-small cell lung cancer (thoracic tumors).

Journal: Seminars in oncology 20020601

Title: Pemetrexed: translational research in breast cancer.

Journal: Seminars in oncology 20020601

Title: Pemetrexed: a promising new treatment for breast cancer.

Journal: Seminars in oncology 20020401

Title: Pemetrexed in the treatment of selected solid tumors.

Journal: Seminars in oncology 20020401

Title: Nonpeptide alpha(v)beta(3) antagonists. Part 2: constrained glycyl amides derived from the RGD tripeptide.

Journal: Bioorganic & medicinal chemistry letters 20020107

Title: Synthesis of a new antischistosomally active and toxicologically tolerant C-12 monothione surrogate of the universal antihelmintic praziquantel.

Journal: Acta poloniae pharmaceutica 20020101

Title: Gemcitabine and pemetrexed disodium combinations in vitro and in vivo.

Journal: Lung cancer (Amsterdam, Netherlands) 20011201

Title: Unexpected formation of an epoxide-derived multisubstrate adduct inhibitor on the active site of GAR transformylase.

Journal: Biochemistry 20011113

Title: Proton transfer dynamics of GART: the pH-dependent catalytic mechanism examined by electrostatic calculations.

Journal: Protein science : a publication of the Protein Society 20011101

Title: Pemetrexed disodium (Eli Lilly).

Journal: Current opinion in investigational drugs (London, England : 2000) 20011101

Title: Pemetrexed disodium in recurrent locally advanced or metastatic squamous cell carcinoma of the head and neck.

Journal: British journal of cancer 20010901

Title: Site-directed mutagenesis of ATP binding residues of biotin carboxylase. Insight into the mechanism of catalysis.

Journal: The Journal of biological chemistry 20010706

Title: Synthesis and biological activity of 7-oxo substituted analogues of 5-deaza-5,6,7,8-tetrahydrofolic acid (5-DATHF) and 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF).

Journal: Journal of medicinal chemistry 20010705

Title: Involvement of a transformylase enzyme in siderophore synthesis in Pseudomonas aeruginosa.

Journal: Microbiology (Reading, England) 20010601

Title: A permissive role for tumor necrosis factor in vascular endothelial growth factor-induced vascular permeability.

Journal: Blood 20010301

Title: Increased shedding of angiotensin-converting enzyme by a mutation identified in the stalk region.

Journal: The Journal of biological chemistry 20010223

Title: Gemcitabine and Pemetrexed disodium in treating breast cancer.

Journal: Oncology (Williston Park, N.Y.) 20010201

Title: Synthetic Cu(II) and Ni(II) peptidases.

Journal: Metal ions in biological systems 20010101

Title: Pemetrexed disodium: a novel antifolate clinically active against multiple solid tumors.

Journal: The oncologist 20010101

Title: Preparation of Fab' from murine IgG2a for thiol reactive conjugation.

Journal: Journal of drug targeting 20010101

Title: Sequence dependence of Alimta (LY231514, MTA) combined with doxorubicin in ZR-75-1 human breast carcinoma cells.

Journal: Anticancer research 20010101

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Tags:598-41-4 Molecular Formula|598-41-4 MDL|598-41-4 SMILES|598-41-4 Glycinamide