Home Amines 200933-27-3
200933-27-3,MFCD00924747
Catalog No.:AA00BHQL

200933-27-3 | Hydrazinecarbothioamide, 2-[(3-amino-2-pyridinyl)methylene]-, (E)-

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5mg
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$300.00   $210.00
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10mg
98%
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25mg
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$899.00   $629.00
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50mg
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100mg
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  • Technical Information
  • Properties
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Technical Information
Catalog Number:
AA00BHQL
Chemical Name:
Hydrazinecarbothioamide, 2-[(3-amino-2-pyridinyl)methylene]-, (E)-
CAS Number:
200933-27-3
Molecular Formula:
C7H9N5S
Molecular Weight:
195.2449
MDL Number:
MFCD00924747
SMILES:
NC(=S)NN=Cc1ncccc1N
NSC Number:
663249
Properties
Computed Properties
 
Complexity:
205  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
13  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
2  
XLogP3:
-0.2  

Literature

Title: Distinct mechanisms of cell-kill by triapine and its terminally dimethylated derivative Dp44mT due to a loss or gain of activity of their copper(II) complexes.

Journal: Biochemical pharmacology 20141001

Title: Mechanistic studies of semicarbazone triapine targeting human ribonucleotide reductase in vitro and in mammalian cells: tyrosyl radical quenching not involving reactive oxygen species.

Journal: The Journal of biological chemistry 20121012

Title: The anticancer thiosemicarbazones Dp44mT and triapine lack inhibitory effects as catalytic inhibitors or poisons of DNA topoisomerase IIα.

Journal: Biochemical pharmacology 20120701

Title: Methemoglobin formation by triapine, di-2-pyridylketone-4,4-dimethyl-3-thiosemicarbazone (Dp44mT), and other anticancer thiosemicarbazones: identification of novel thiosemicarbazones and therapeutics that prevent this effect.

Journal: Molecular pharmacology 20120701

Title: A phase I and pharmacokinetic study of oral 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP, NSC #663249) in the treatment of advanced-stage solid cancers: a California Cancer Consortium Study.

Journal: Cancer chemotherapy and pharmacology 20120301

Title: Management of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone-induced methemoglobinemia.

Journal: Future oncology (London, England) 20120201

Title: Ribonucleotide reductase inhibition restores platinum-sensitivity in platinum-resistant ovarian cancer: a Gynecologic Oncology Group Study.

Journal: Journal of translational medicine 20120101

Title: Ribonucleotide reductase inhibition by metal complexes of Triapine (3-aminopyridine-2-carboxaldehyde thiosemicarbazone): a combined experimental and theoretical study.

Journal: Journal of inorganic biochemistry 20111101

Title: Deoxynucleoside salvage facilitates DNA repair during ribonucleotide reductase blockade in human cervical cancers.

Journal: Radiation research 20111001

Title: Phase II trial of the ribonucleotide reductase inhibitor 3-aminopyridine-2-carboxaldehydethiosemicarbazone plus gemcitabine in patients with advanced biliary tract cancer.

Journal: Cancer chemotherapy and pharmacology 20110801

Title: Radiosensitization of human cervical cancer cells by inhibiting ribonucleotide reductase: enhanced radiation response at low-dose rates.

Journal: International journal of radiation oncology, biology, physics 20110715

Title: Interaction of Triapine and related thiosemicarbazones with iron(III)/(II) and gallium(III): a comparative solution equilibrium study.

Journal: Dalton transactions (Cambridge, England : 2003) 20110614

Title: The iron-chelating drug triapine causes pronounced mitochondrial thiol redox stress.

Journal: Toxicology letters 20110305

Title: Population pharmacokinetics of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (Triapine®) in cancer patients.

Journal: Cancer chemotherapy and pharmacology 20110201

Title: Ribonucleotide reductase inhibition enhances chemoradiosensitivity of human cervical cancers.

Journal: Radiation research 20101101

Title: The maximum tolerated dose and biologic effects of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP) in combination with irinotecan for patients with refractory solid tumors.

Journal: Cancer chemotherapy and pharmacology 20101001

Title: Phase I trial of pelvic radiation, weekly cisplatin, and 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP, NSC #663249) for locally advanced cervical cancer.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20100215

Title: A phase II trial of triapine (NSC# 663249) and gemcitabine as second line treatment of advanced non-small cell lung cancer: Eastern Cooperative Oncology Group Study 1503.

Journal: Investigational new drugs 20100201

Title: Fluorescence properties and cellular distribution of the investigational anticancer drug triapine (3-aminopyridine-2-carboxaldehyde thiosemicarbazone) and its zinc(II) complex.

Journal: Dalton transactions (Cambridge, England : 2003) 20100121

Title: Modulating radiation resistance by inhibiting ribonucleotide reductase in cancers with virally or mutationally silenced p53 protein.

Journal: Radiation research 20091201

Title: Impact of metal coordination on cytotoxicity of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (triapine) and novel insights into terminal dimethylation.

Journal: Journal of medicinal chemistry 20090827

Title: Synthesis, activity, and pharmacophore development for isatin-beta-thiosemicarbazones with selective activity toward multidrug-resistant cells.

Journal: Journal of medicinal chemistry 20090528

Title: PAN-811 inhibits oxidative stress-induced cell death of human Alzheimer's disease-derived and age-matched olfactory neuroepithelial cells via suppression of intracellular reactive oxygen species.

Journal: Journal of Alzheimer's disease : JAD 20090101

Title: Synthesis and ribonucleotide reductase inhibitory activity of thiosemicarbazones.

Journal: Bioorganic & medicinal chemistry letters 20081201

Title: A phase 2 consortium (P2C) trial of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP) for advanced adenocarcinoma of the pancreas.

Journal: Investigational new drugs 20080801

Title: Phase I study of the ribonucleotide reductase inhibitor 3-aminopyridine-2-carboxaldehyde-thiosemicarbazone (3-AP) in combination with high dose cytarabine in patients with advanced myeloid leukemia.

Journal: Investigational new drugs 20080601

Title: A multicenter phase II trial of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP, Triapine) and gemcitabine in advanced non-small-cell lung cancer with pharmacokinetic evaluation using peripheral blood mononuclear cells.

Journal: Investigational new drugs 20080401

Title: Structure-activity relationships of novel iron chelators for the treatment of iron overload disease: the methyl pyrazinylketone isonicotinoyl hydrazone series.

Journal: Journal of medicinal chemistry 20080124

Title: A phase I study of the novel ribonucleotide reductase inhibitor 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP, Triapine) in combination with the nucleoside analog fludarabine for patients with refractory acute leukemias and aggressive myeloproliferative disorders.

Journal: Leukemia research 20080101

Title: A Phase II study of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP) and gemcitabine in advanced pancreatic carcinoma. A trial of the Princess Margaret hospital Phase II consortium.

Journal: Investigational new drugs 20071201

Title: Design, synthesis, and characterization of new iron chelators with anti-proliferative activity: structure-activity relationships of novel thiohydrazone analogues.

Journal: Journal of medicinal chemistry 20071129

Title: Design, synthesis, and characterization of novel iron chelators: structure-activity relationships of the 2-benzoylpyridine thiosemicarbazone series and their 3-nitrobenzoyl analogues as potent antitumor agents.

Journal: Journal of medicinal chemistry 20070726

Title: PAN-811 provides neuroprotection against glutamate toxicity by suppressing activation of JNK and p38 MAPK.

Journal: Neuroscience letters 20070705

Title: The synergistic interaction of gemcitabine and cytosine arabinoside with the ribonucleotide reductase inhibitor triapine is schedule dependent.

Journal: Biochemical pharmacology 20070515

Title: Future of toxicology--iron chelators and differing modes of action and toxicity: the changing face of iron chelation therapy.

Journal: Chemical research in toxicology 20070501

Title: Investigating biological activity spectrum for novel quinoline analogues.

Journal: Bioorganic & medicinal chemistry 20070201

Title: Rediscovery of the susceptibility of G6PD deficient persons to methemoglobinemia from oxidant drugs, and to hemolysis from methylene blue.

Journal: American journal of hematology 20070101

Title: Chelators at the cancer coalface: desferrioxamine to Triapine and beyond.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20061201

Title: Triapine and cytarabine is an active combination in patients with acute leukemia or myelodysplastic syndrome.

Journal: Leukemia research 20060701

Title: Developmental clinical trials: building one step at a time.

Journal: Leukemia research 20060701

Title: Therapeutic potential of iron chelators in diseases associated with iron mismanagement.

Journal: The Journal of pharmacy and pharmacology 20060501

Title: Recognition and management of methemoglobinemia and hemolysis in a G6PD-deficient patient on experimental anticancer drug Triapine.

Journal: American journal of hematology 20060301

Title: A Ferrous-Triapine complex mediates formation of reactive oxygen species that inactivate human ribonucleotide reductase.

Journal: Molecular cancer therapeutics 20060301

Title: Neuroprotective activity of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (PAN-811), a cancer therapeutic agent.

Journal: CNS drug reviews 20060101

Title: Drug-induced haemolysis and methaemoglobinaemia in glucose 6-phosphate dehydrogenase deficiency.

Journal: British journal of haematology 20050501

Title: PAN-811 (3-aminopyridine-2-carboxaldehyde thiosemicarbazone), a novel neuroprotectant, elicits its function in primary neuronal cultures by up-regulating Bcl-2 expression.

Journal: Neuroscience 20050101

Title: A phase I trial of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone in combination with gemcitabine for patients with advanced cancer.

Journal: Cancer chemotherapy and pharmacology 20041001

Title: Stable suppression of the R2 subunit of ribonucleotide reductase by R2-targeted short interference RNA sensitizes p53(-/-) HCT-116 colon cancer cells to DNA-damaging agents and ribonucleotide reductase inhibitors.

Journal: The Journal of biological chemistry 20040625

Title: Phase I and pharmacokinetic study of the ribonucleotide reductase inhibitor, 3-aminopyridine-2-carboxaldehyde thiosemicarbazone, administered by 96-hour intravenous continuous infusion.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20040501

Title: Phase I and pharmacodynamic study of Triapine, a novel ribonucleotide reductase inhibitor, in patients with advanced leukemia.

Journal: Leukemia research 20031201

Title: Phase I and pharmacokinetic study of triapine, a potent ribonucleotide reductase inhibitor, administered daily for five days in patients with advanced solid tumors.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20030915

Title: Examination of the antiproliferative activity of iron chelators: multiple cellular targets and the different mechanism of action of triapine compared with desferrioxamine and the potent pyridoxal isonicotinoyl hydrazone analogue 311.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20030101

Title: The role of iron in cell cycle progression and the proliferation of neoplastic cells.

Journal: Biochimica et biophysica acta 20021002

Title: Phase I and pharmacokinetic study of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP) using a single intravenous dose schedule.

Journal: Cancer chemotherapy and pharmacology 20020901

Title: Syntheses and antitumor activities of potent inhibitors of ribonucleotide reductase: 3-amino-4-methylpyridine-2-carboxaldehyde-thiosemicarba-zone (3-AMP), 3-amino-pyridine-2-carboxaldehyde-thiosemicarbazone (3-AP) and its water-soluble prodrugs.

Journal: Current medicinal chemistry 20010201

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Tags:200933-27-3 Molecular Formula|200933-27-3 MDL|200933-27-3 SMILES|200933-27-3 Hydrazinecarbothioamide, 2-[(3-amino-2-pyridinyl)methylene]-, (E)-