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55661-38-6 | Nimustine hydrochloride
CAS No: 55661-38-6 Catalog No: AG003T3V MDL No:MFCD01676942
Product Description
Catalog Number:
AG003T3V
Chemical Name:
Nimustine hydrochloride
CAS Number:
55661-38-6
Molecular Formula:
C9H14Cl2N6O2
Molecular Weight:
309.1525
MDL Number:
MFCD01676942
IUPAC Name:
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-1-(2-chloroethyl)-1-nitrosourea;hydrochloride
InChI:
InChI=1S/C9H13ClN6O2.ClH/c1-6-12-4-7(8(11)14-6)5-13-9(17)16(15-18)3-2-10;/h4H,2-3,5H2,1H3,(H,13,17)(H2,11,12,14);1H
InChI Key:
KPMKNHGAPDCYLP-UHFFFAOYSA-N
SMILES:
ClCCN(C(=O)NCc1cnc(nc1N)C)N=O.Cl
UNII:
DFR965WKBU
NSC Number:
245382
Properties
Complexity:
292
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
2
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
308.056g/mol
Formal Charge:
0
Heavy Atom Count:
19
Hydrogen Bond Acceptor Count:
6
Hydrogen Bond Donor Count:
3
Isotope Atom Count:
0
Molecular Weight:
309.151g/mol
Monoisotopic Mass:
308.056g/mol
Rotatable Bond Count:
4
Topological Polar Surface Area:
114A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
Literature
| Title | Journal |
|---|---|
| Apoptosis induced by temozolomide and nimustine in glioblastoma cells is supported by JNK/c-Jun-mediated induction of the BH3-only protein BIM. | Oncotarget 20151020 |
| F2A sequence linking MGMT(P140K) and MDR1 in a bicistronic lentiviral vector enables efficient chemoprotection of haematopoietic stem cells. | Cancer gene therapy 20121101 |
| p53R2 is a prognostic factor of melanoma and regulates proliferation and chemosensitivity of melanoma cells. | Journal of dermatological science 20121001 |
| Chloroethylnitrosourea-induced cell death and genotoxicity: cell cycle dependence and the role of DNA double-strand breaks, HR and NHEJ. | Cell cycle (Georgetown, Tex.) 20120715 |
| Effects of chemotherapeutics on organotypic corticostriatal slice cultures identified by a panel of fluorescent and immunohistochemical markers. | Neurotoxicity research 20120701 |
| The chloroethylating anticancer drug ACNU induces FRA1 that is involved in drug resistance of glioma cells. | Biochimica et biophysica acta 20120701 |
| Safety and feasibility of convection-enhanced delivery of nimustine hydrochloride co-infused with free gadolinium for real-time monitoring in the primate brain. | Neurological research 20120701 |
| [Selected arterial infusion chemotherapy combined with target drugs for non-small cell lung cancer with multiple brain metastase]. | Zhongguo fei ai za zhi = Chinese journal of lung cancer 20120520 |
| Nimustine hydrochloride: the first crystal structure determination of a 2-chloroethyl-N-nitrosourea hydrochloride derivative by X-ray powder diffraction and solid-state NMR. | Acta crystallographica. Section C, Crystal structure communications 20120301 |
| Phase II trial of radiotherapy after hyperbaric oxygenation with multiagent chemotherapy (procarbazine, nimustine, and vincristine) for high-grade gliomas: long-term results. | International journal of radiation oncology, biology, physics 20120201 |
| Anaplastic oligodendroglial tumors harboring 1p/19q deletion can be successfully treated without radiotherapy. | Anticancer research 20111201 |
| Local convection-enhanced delivery of chemotherapeutic agent transiently opens blood-brain barrier and improves efficacy of systemic chemotherapy in intracranial xenograft tumor model. | Cancer letters 20111101 |
| An anti-transferrin receptor antibody enhanced the growth inhibitory effects of chemotherapeutic drugs on human glioma cells. | International immunopharmacology 20111101 |
| Regression of recurrent glioblastoma infiltrating the brainstem after convection-enhanced delivery of nimustine hydrochloride. | Journal of neurosurgery. Pediatrics 20110501 |
| [Nimotuzumab in combination with chemotherapy for patients with malignant gliomas]. | Zhonghua zhong liu za zhi [Chinese journal of oncology] 20110301 |
| Primary malignant melanoma of the esophagus: a study of clinical features, pathology, management and prognosis. | Diseases of the esophagus : official journal of the International Society for Diseases of the Esophagus 20110201 |
| Therapy-related myelodysplastic syndrome developed by dacarbazine, nimustine hydrochloride and vincristine sulfate (DAV) therapy for patient with malignant melanoma. | The Journal of dermatology 20110201 |
| Effectiveness of interferon-beta therapy for recurrent glioblastoma: a case report. | Tumori 20110101 |
| FANCD1/BRCA2 plays predominant role in the repair of DNA damage induced by ACNU or TMZ. | PloS one 20110101 |
| [A case report of anorectal malignant melanoma showing a complete response after DTIC/ACNU/VCR therapy]. | Gan to kagaku ryoho. Cancer & chemotherapy 20101001 |
| Malignant melanoma of the breast: N-isopropyl-p-(123) I-iodoamphetamine single photon emission computed tomography ((123) I-IMP SPECT) is useful for the detection of metastasis. | The Journal of dermatology 20100901 |
| Effect of inhibition of the ROCK isoform on RT2 malignant glioma cells. | Anticancer research 20100901 |
| [Case of primary amelanotic malignant melanoma of the female urethra]. | Nihon Hinyokika Gakkai zasshi. The japanese journal of urology 20100901 |
| DNA ligase IV is a potential molecular target in ACNU sensitivity. | Cancer science 20100801 |
| Complete remission of metastatic malignant melanoma after surgery in association with development of systemic vitiligo. | The Journal of dermatology 20100801 |
| Phase I/II trial of hyperfractionated concomitant boost proton radiotherapy for supratentorial glioblastoma multiforme. | International journal of radiation oncology, biology, physics 20100501 |
| Changes of the O6-methylguanine-DNA methyltransferase promoter methylation and MGMT protein expression after adjuvant treatment in glioblastoma. | Oncology reports 20100501 |
| Radiation-induced glioblastoma occurring 35 years after radiation therapy for medulloblastoma: case report. | Brain tumor pathology 20100401 |
| Prognostic factors for patients with gliomatosis cerebri: retrospective analysis of 17 consecutive cases. | Neurosurgical review 20100401 |
| Chemoprotection of human hematopoietic stem cells by simultaneous lentiviral overexpression of multidrug resistance 1 and O(6)-methylguanine-DNA methyltransferase(P140K). | Gene therapy 20100301 |
| Decreasing expression of the interleukin-13 receptor IL-13Ralpha2 in treated recurrent malignant gliomas. | Neurologia medico-chirurgica 20100101 |
| Phase II study of nimustine hydrochloride (ACNU) plus paclitaxel for refractory small cell lung cancer. | Lung cancer (Amsterdam, Netherlands) 20091201 |
| Long-term survivors of glioblastoma: clinical features and molecular analysis. | Acta neurochirurgica 20091101 |
| [Metastatic malignant melanoma of the urinary bladder: a case report]. | Nihon Hinyokika Gakkai zasshi. The japanese journal of urology 20091101 |
| Methylation status of the MGMT gene promoter fails to predict the clinical outcome of glioblastoma patients treated with ACNU plus cisplatin. | Neuropathology : official journal of the Japanese Society of Neuropathology 20090801 |
| Coincidence of central neurocytoma and multiple glioblastomas: a rare case report. | Journal of neuro-oncology 20090701 |
| FEN1 is overexpressed in testis, lung and brain tumors. | Anticancer research 20090701 |
| [Detection of O6-methylguanine-DNA methyltransferase promoter methylation in chemotherapy for glioma]. | Ai zheng = Aizheng = Chinese journal of cancer 20090601 |
| Melanocytoma in the orbital apex. | Journal of neuro-oncology 20090301 |
| ACNU-based chemotherapy for recurrent glioma in the temozolomide era. | Journal of neuro-oncology 20090301 |
| Nimustine (ACNU) plus teniposide (VM26) in recurrent glioblastoma. | Oncology 20090101 |
| Preradiation chemotherapy with ACNU-CDDP in patients with newly diagnosed glioblastoma: a retrospective analysis. | Chemotherapy 20090101 |
| Successful treatment of neoadjuvant therapy for papillary tumor of the pineal region. | Brain tumor pathology 20090101 |
| Cervical intramedullary glioblastoma: report of a long-term survival case and a review of the literature. | Journal of UOEH 20081201 |
| Enhanced antitumor effect of combined-modality treatment using convection-enhanced delivery of hydrophilic nitrosourea with irradiation or systemic administration of temozolomide in intracranial brain tumor xenografts. | Neurological research 20081101 |
| [Combined treatment with dacarbazine, nimustine, cisplatin, and tamoxifen plus interferon-beta in a patient with advanced anorectal malignant melanoma]. | Nihon Shokakibyo Gakkai zasshi = The Japanese journal of gastro-enterology 20081101 |
| Different initial steps of apoptosis induced by two types of antineoplastic drugs. | Biochemical pharmacology 20080801 |
| Carmustine-resistant cancer cells are sensitized to temozolomide as a result of enhanced mismatch repair during the development of carmustine resistance. | Molecular pharmacology 20080701 |
| Treatment and prognosis of malignant melanoma of the oral cavity: preoperative surgical procedure increases risk of distant metastasis. | Oral surgery, oral medicine, oral pathology, oral radiology, and endodontics 20080701 |
| Survival following CyberKnife radiosurgery and hypofractionated radiotherapy for newly diagnosed glioblastoma multiforme. | Technology in cancer research & treatment 20080601 |
| Intrathecal chemotherapy for refractory disseminated medulloblastoma. | Child's nervous system : ChNS : official journal of the International Society for Pediatric Neurosurgery 20080501 |
| Nitrosourea efficacy in high-grade glioma: a survival gain analysis summarizing 504 cohorts with 24193 patients. | Journal of neuro-oncology 20080501 |
| Chemotherapeutic choice of ranimustine or nimustine on the basis of regional polyamine levels in rat brain. | Methods and findings in experimental and clinical pharmacology 20080301 |
| Response to chemotherapy and tandem autologous transplantation of multiple myeloma patients and GSTP1 and TYMS polymorphisms. | Leukemia research 20080101 |
| Prospective single-arm study of 72 Gy hyperfractionated radiation therapy and combination chemotherapy for anaplastic astrocytomas. | BMC cancer 20080101 |
| Intra-axial brainstem malignant melanoma mimicking cavernous angioma--case report. | Neurologia medico-chirurgica 20080101 |
| Modes of actions of two types of anti-neoplastic drugs, dacarbazine and ACNU, to induce apoptosis. | Carcinogenesis 20071201 |
| Primary CNS lymphoma treated with combined intra-arterial ACNU and radiotherapy. | Acta neurochirurgica 20071101 |
| Phase I/II clinical trial of carbon ion radiotherapy for malignant gliomas: combined X-ray radiotherapy, chemotherapy, and carbon ion radiotherapy. | International journal of radiation oncology, biology, physics 20071001 |
| Long-term follow-up of busulfan, etoposide, and nimustine hydrochloride (ACNU) or melphalan as conditioning regimens for childhood acute leukemia and lymphoma. | International journal of hematology 20071001 |
| Specific mTOR inhibitor rapamycin enhances cytotoxicity induced by alkylating agent 1-(4-amino-2-methyl-5-pyrimidinyl)methyl-3-(2-chloroethyl)-3-nitrosourea (ACNU) in human U251 malignant glioma cells. | Journal of neuro-oncology 20070901 |
| The combined effects of multiple chemotherapeutic agents for malignant glioma cells. | Journal of neuro-oncology 20070801 |
| Local injection of interferon beta in malignant melanoma of the esophagus as adjuvant of systemic pre- and postoperative DAV chemotherapy: case report with 7 years of long-term survival. | Gastrointestinal endoscopy 20070801 |
| Collagen gel matrix assay as an in vitro chemosensitivity test for malignant astrocytic tumors. | International journal of clinical oncology 20070401 |
| Safety and efficacy of convection-enhanced delivery of ACNU, a hydrophilic nitrosourea, in intracranial brain tumor models. | Journal of neuro-oncology 20070301 |
| Chromosome arm 1q gain associated with good response to chemotherapy in a malignant glioma. Case report. | Journal of neurosurgery 20070301 |
| Feasibility and response to 1-(4-amino-2-methyl-5-pyrimidynyl) methyl-3-(2-chloroethyl)-3-nitrosourea hydrochloride chemotherapy with pre-treated procarbazine for elderly patients with newly diagnosed glioblastoma. | Journal of neuro-oncology 20070201 |
| Analysis of long-term survivors of glioblastoma multiforme in a single institution with aggressive local retreatment protocol. | Anticancer research 20070101 |
| Pegfilgrastim compared with filgrastim after high-dose melphalan and autologous hematopoietic peripheral blood stem cell transplantation in multiple myeloma patients. | European journal of haematology 20061101 |
| Phase II trial of radiotherapy after hyperbaric oxygenation with chemotherapy for high-grade gliomas. | British journal of cancer 20061009 |
| Gene expression profiles of 1-(4-amino-2-methyl-5-pyrimidinyl)-methyl-3-(2-chloroethyl)-3-nitrosourea (ACNU)-resistant C6 rat glioma cells. | Journal of neuro-oncology 20060901 |
| Phase II study of nimustine, carboplatin, vincristine, and interferon-beta with radiotherapy for glioblastoma multiforme: experience of the Kyoto Neuro-Oncology Group. | Journal of neurosurgery 20060901 |
| [Glioma]. | Nihon rinsho. Japanese journal of clinical medicine 20060701 |
| Microsphere-based protease assays and screening application for lethal factor and factor Xa. | Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501 |
| Acute myocardial infarction induced by cisplatin-based combination chemotherapy for malignant melanoma: a case report. | Journal of cardiology 20060401 |
| High-dose idarubicin, busulphan and melphalan for autologous stem cell transplantation in multiple myeloma responsive to DAV chemotherapy: comparison with a historical control. | Acta haematologica 20060101 |
| Acquisition of resistance to antitumor alkylating agent ACNU: a possible target of positron emission tomography monitoring. | Nuclear medicine and biology 20060101 |
| A randomized phase III study: comparison between intravenous and intraarterial ACNU administration in newly diagnosed primary glioblastomas. | Anticancer research 20060101 |
| Hyperfractionated radiotherapy and multi-agent chemotherapy (procarbazine, ACNU and vincristine) for high-grade gliomas: a prospective study. | Anticancer research 20060101 |
| Glioblastoma multiforme with oligodendroglial component (GBMO): favorable outcome after post-operative radiotherapy and chemotherapy with nimustine (ACNU) and teniposide (VM26). | BMC cancer 20060101 |
| Combination hepatic arterial infusion therapy is effective for ocular melanoma metastasis to the liver. | Oncology reports 20051201 |
| [Treatment for malignant glioma]. | No to shinkei = Brain and nerve 20051201 |
| ACNU-cisplatin continuous infusion chemotherapy as salvage therapy for recurrent glioblastomas: phase II study. | Journal of neuro-oncology 20051101 |
| Down-regulation of O6-methylguanine-DNA methyltransferase gene expression in gliomas by platinum compounds. | Oncology reports 20051101 |
| [Standards and new developments in the chemotherapy of glioblastomas]. | Deutsche medizinische Wochenschrift (1946) 20051007 |
| [Chemotherapy for brain tumor]. | Nihon rinsho. Japanese journal of clinical medicine 20050901 |
| Amelanotic malignant melanoma of the esophagus: report of a patient with recurrence successfully treated with chemoendocrine therapy. | International journal of clinical oncology 20050601 |
| Cisplatin represses transcriptional activity from the minimal promoter of the O6-methylguanine methyltransferase gene and increases sensitivity of human gallbladder cancer cells to 1-(4-amino-2-methyl-5-pyrimidinyl) methyl-3-2-chloroethyl)-3-nitrosourea. | Oncology reports 20050501 |
| Local drug delivery in recurrent malignant gliomas. | Neurological sciences : official journal of the Italian Neurological Society and of the Italian Society of Clinical Neurophysiology 20050501 |
| [Resent advances in chemotherapy for malignant brain tumors]. | Gan to kagaku ryoho. Cancer & chemotherapy 20050401 |
| Human interferon beta, nimustine hydrochloride, and radiation therapy in the treatment of newly diagnosed malignant astrocytomas. | Journal of neuro-oncology 20050301 |
| O6-methylguanine-DNA methyltransferase methylation and TP53 mutation in malignant astrocytomas and their relationships with clinical course. | International journal of cancer 20050210 |
| [Medulloblastoma with mandibular metastasis after complete remission of the central nervous system lesions]. | No to shinkei = Brain and nerve 20050101 |
| Hypofractionated stereotactic re-irradiation: treatment option in recurrent malignant glioma. | BMC cancer 20050101 |
| The effect of o6-methylguanine-DNA methyltransferase (MGMT) and mismatch repair gene (hMLH1) status on the sensitivity to alkylating agent 1-(4-amino-2-methyl-5-pyrimidinyl)methyl-3-(2-chloroethyl)-3-nitrosourea(ACNU) in gallbladder carcinoma cells. | Anticancer research 20050101 |
| Treatment of low-grade oligodendroglial tumors without radiotherapy. | Neurology 20041228 |
| Immunohistochemical study for O6-methylguanine-DNA methyltransferase in the non-neoplastic and neoplastic components of gliomas. | Journal of neuro-oncology 20041201 |
| [Glioblastoma multiforme of the optic nerve]. | RoFo : Fortschritte auf dem Gebiete der Rontgenstrahlen und der Nuklearmedizin 20041101 |
| Induction of the DNA repair gene O6-methylguanine-DNA methyltransferase by dexamethasone in glioblastomas. | Journal of neurosurgery 20041001 |
| [Study on MGMT assay and tumor individual predictable chemotherapy]. | Ai zheng = Aizheng = Chinese journal of cancer 20040601 |
| Randomized controlled trial on malignant brain tumors--activities of the Japan Clinical Oncology Group-Brain Tumor Study Group. | Neurologia medico-chirurgica 20040401 |
| Correlation between promoter hypermethylation of the O6-methylguanine-deoxyribonucleic acid methyltransferase gene and prognosis in patients with high-grade astrocytic tumors treated with surgery, radiotherapy, and 1-(4-amino-2-methyl-5-pyrimidinyl)methyl-3-(2-chloroethyl)-3-nitrosourea-based chemotherapy. | Neurosurgery 20040201 |
| [Role of thallium SPECT for evaluating the effect of maintenance chemotherapy against malignant gliomas]. | No shinkei geka. Neurological surgery 20031201 |
| Primary malignant melanoma of the oral mucosa. | Journal of oral and maxillofacial surgery : official journal of the American Association of Oral and Maxillofacial Surgeons 20031001 |
| Neuro-Oncology Working Group 01 trial of nimustine plus teniposide versus nimustine plus cytarabine chemotherapy in addition to involved-field radiotherapy in the first-line treatment of malignant glioma. | Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20030901 |
| In vitro growth suppression of human glioma cells by a 16-mer oligopeptide: a potential new treatment modality for malignant glioma. | Journal of neuro-oncology 20030601 |
| [Malignant melanoma of the alimentary tract]. | Gan to kagaku ryoho. Cancer & chemotherapy 20030501 |
| Relationship between expression of O6-methylguanine-DNA methyltransferase, glutathione-S-transferase pi in glioblastoma and the survival of the patients treated with nimustine hydrochloride: an immunohistochemical analysis. | Neurological research 20030401 |
| Prospective trial of radiotherapy after hyperbaric oxygenation with chemotherapy for high-grade gliomas. | Radiotherapy and oncology : journal of the European Society for Therapeutic Radiology and Oncology 20030401 |
| Regression of refractory rhabdomyosarcoma after allogeneic stem-cell transplantation. | Pediatric hematology and oncology 20030301 |
| O6-methylguanine-DNA methyltranspherase gene expression in gliomas by means of real-time quantitative RT-PCR and clinical response to nitrosoureas. | International journal of cancer 20030101 |
| Complete remission of metastatic clear cell sarcoma with DAV chemotherapy. | Clinical and experimental dermatology 20030101 |
| A phase II study of radiotherapy after hyperbaric oxygenation combined with interferon-beta and nimustine hydrochloride to treat supratentorial malignant gliomas. | Journal of neuro-oncology 20030101 |
| Anti-vascular endothelial growth factor antibody and nimustine as combined therapy: effects on tumour growth and angiogenesis in human glioblastoma xenografts. | Neuro-oncology 20030101 |
| Intra-arterial ACNU and carboplatin versus intravenous chemotherapy with cisplatin and BCNU in newly diagnosed patients with glioblastoma. | Neurological sciences : official journal of the Italian Neurological Society and of the Italian Society of Clinical Neurophysiology 20021201 |
| Phase II study of chemotherapy with ACNU plus cisplatin followed by cranial irradiation in patients with newly diagnosed glioblastoma multiforme. | Journal of neuro-oncology 20021101 |
| Suppression of Cdc2 dephosphorylation at the tyrosine 15 residue during nitrosourea-induced G2M phase arrest in glioblastoma cell lines. | Journal of neuro-oncology 20020801 |
| Effects of combination chemotherapy with biscoclaurine-derived alkaloid (Cepharanthine) and nimustine hydrochloride on malignant glioma cell lines. | Journal of neuro-oncology 20020101 |
| Comparative cytotoxicity of carmustine (BCNU), nimustine (ACNU) and elmustine (HeCNU) after depletion of O6-alkylguanine-DNA alkyltransferase (O6-AGT). | Anticancer research 20020101 |
| Protection of hematopoietic cells from O(6)-alkylation damage by O(6)-methylguanine DNA methyltransferase gene transfer: studies with different O(6)-alkylating agents and retroviral backbones. | European journal of haematology 20010701 |
| Radiotherapy combined with nimustine hydrochloride and etoposide for malignant gliomas: results of a pilot study. | Japanese journal of clinical oncology 20010601 |
| Pharmacokinetics of nimustine, cytosine arabinoside, and methotrexate in cerebrospinal fluid during cerebrospinal fluid perfusion chemotherapy. | Biological & pharmaceutical bulletin 20010401 |
| Efficacy of single-bolus vs. frequent low-dose treatment with nitrosourea in experimental gliomas. | Anticancer research 20010101 |
| Intratumoral microinfusion of nimustine (ACNU) for recurrent glioma. | Brain tumor pathology 20010101 |
| Primary malignant melanoma of the esophagus treated by esophagectomy and systemic chemotherapy. | Diseases of the esophagus : official journal of the International Society for Diseases of the Esophagus 20010101 |
| Increased susceptibility to chemotherapeutic alkylating agents of mice deficient in DNA repair methyltransferase. | Carcinogenesis 20001001 |
| Actinomycin D and staurosporine, potent apoptosis inducers in vitro, are potentially effective chemotherapeutic agents against glioblastoma multiforme. | Cancer chemotherapy and pharmacology 20000101 |
| Transient induction of the MRP/GS-X pump and gamma-glutamylcysteine synthetase by 1-(4-amino-2-methyl-5-pyrimidinyl)methyl-3-(2-chloroethyl)-3- nitrosourea in human glioma cells. | Cancer research 19971201 |
| Transgenerational effects of maternal exposure to chemicals on the functional development of the brain in the offspring. | Cancer causes & control : CCC 19970501 |
| Determinants of drug response in a cisplatin-resistant human lung cancer cell line. | Japanese journal of cancer research : Gann 19900501 |
| [The combination chemotherapy of vincristine, methotrexate, ACNU, and adriamycin for anaplastic carcinoma of the lung]. | Gan to kagaku ryoho. Cancer & chemotherapy 19820701 |
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