NIMUSTINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H13ClN6O2
Molecular Weight	272.692
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=NC(N)=C(CNC(=O)N(CCCl)N=O)C=N1

InChI

InChIKey=VFEDRRNHLBGPNN-UHFFFAOYSA-N

InChI=1S/C9H13ClN6O2/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)

HIDE SMILES / InChI

Molecular Formula	C9H13ClN6O2
Molecular Weight	272.692
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.cancer.gov/publications/dictionaries/cancer-drug?cdrid=38853
Curator's Comment: description was created based on several sources, including: http://www.kegg.jp/medicus-bin/japic_med_product?id=00043575-002 | http://www.rlsnet.ru/tn_index_id_2291.htm

Nimustine is one of nitrosoureas used in the treatment of cancer. Nimustine alkylates and crosslinks DNA, thereby causing DNA fragmentation, inhibition of protein synthesis, and cell death. It is used in the treatment of brain tumor (in particular, high-grade gliomas), gastrointestinal cancers (stomach cancer, liver cancer, colorectal cancer), lung cancer, malignant lymphoma, chronic leukemia. Nimustine side effects are: leukopenia, thrombocytopenia, hypoproteinemia, anemia, Increased bleeding, proteinuria, interstitial pneumonia, anorexia, stomatitis, nausea, vomiting, general weakness, fever, headache, dizziness, seizures, alopecia, allergic reactions (rash).

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 278 Target ID: CHEMBL2311221 Sources: https://www.cancer.gov/publications/dictionaries/cancer-drug?cdrid=38853 \| DOI: 10.7763/IJBBB.2013.V3.208	Crosslinking Agent 81

Conditions

Condition	Modality	Highest Phase	Product
Brain cancer 10 Sources: http://www.kegg.jp/medicus-bin/japic_med_product?id=00043575-001#00043575-001	Primary	Approved 8429	NIDRAN Approved Use Drug is indicated for the treatment of brain tumor, gastrointestinal cancer, lung cancer, malignant lymphoma, chronic leukemia.
Gastrointestinal cancer 3 Sources: http://www.kegg.jp/medicus-bin/japic_med_product?id=00043575-001#00043575-001	Primary	Approved 8429	NIDRAN Approved Use Drug is indicated for the treatment of brain tumor, gastrointestinal cancer, lung cancer, malignant lymphoma, chronic leukemia.
Lung cancer 69 Sources: http://www.kegg.jp/medicus-bin/japic_med_product?id=00043575-001#00043575-001	Primary	Approved 8429	NIDRAN Approved Use Drug is indicated for the treatment of brain tumor, gastrointestinal cancer, lung cancer, malignant lymphoma, chronic leukemia.
Malignant lymphoma 10 Sources: http://www.kegg.jp/medicus-bin/japic_med_product?id=00043575-001#00043575-001	Primary	Approved 8429	NIDRAN Approved Use Drug is indicated for the treatment of brain tumor, gastrointestinal cancer, lung cancer, malignant lymphoma, chronic leukemia.
Chronic leukemia 2 Sources: http://www.kegg.jp/medicus-bin/japic_med_product?id=00043575-001#00043575-001	Primary	Approved 8429	NIDRAN Approved Use Drug is indicated for the treatment of brain tumor, gastrointestinal cancer, lung cancer, malignant lymphoma, chronic leukemia.

PubMed

Title	Date	PubMed
In vitro growth suppression of human glioma cells by a 16-mer oligopeptide: a potential new treatment modality for malignant glioma.	2003 Jun	12825820
Primary malignant melanoma of the oral mucosa.	2003 Oct	14586846
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.	2003 Sep 1	12947063
Randomized controlled trial on malignant brain tumors--activities of the Japan Clinical Oncology Group-Brain Tumor Study Group.	2004 Apr	15185766
Immunohistochemical study for O6-methylguanine-DNA methyltransferase in the non-neoplastic and neoplastic components of gliomas.	2004 Dec	15662974
Treatment of low-grade oligodendroglial tumors without radiotherapy.	2004 Dec 28	15623706
[Study on MGMT assay and tumor individual predictable chemotherapy].	2004 Jun	15191682
Dependence of chemotherapy response on p53 mutation status in a panel of human cancer lines maintained in nude mice.	2004 Jun	15182437
Induction of the DNA repair gene O6-methylguanine-DNA methyltransferase by dexamethasone in glioblastomas.	2004 Oct	15481722
Total reconstruction of the upper lip after resection of a malignant melanoma.	2005	15848964
[Resent advances in chemotherapy for malignant brain tumors].	2005 Apr	15853207
Proteome-based identification of molecular markers predicting chemosensitivity to each category of anticancer agents in human gliomas.	2005 Apr	15753994
[Treatment for malignant glioma].	2005 Dec	16375187
O6-methylguanine-DNA methyltransferase methylation and TP53 mutation in malignant astrocytomas and their relationships with clinical course.	2005 Feb 10	15455376
[Medulloblastoma with mandibular metastasis after complete remission of the central nervous system lesions].	2005 Jan	15782598
Amelanotic malignant melanoma of the esophagus: report of a patient with recurrence successfully treated with chemoendocrine therapy.	2005 Jun	15990972
Long-term follow-up high-dose chemotherapy (drug-only program) followed by autologous stem cell transplantation for aggressive non-Hodgkin's lymphomas.	2005 Jun	15989704
Human interferon beta, nimustine hydrochloride, and radiation therapy in the treatment of newly diagnosed malignant astrocytomas.	2005 Mar	15803376
Glioblastoma multiforme metastasis to the axis. Case report.	2005 Mar	15796392
Local drug delivery in recurrent malignant gliomas.	2005 May	15883691
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.	2005 May	15809756
Hypofractionated stereotactic re-irradiation: treatment option in recurrent malignant glioma.	2005 May 30	15924621
Brain metastases in breast cancer--an in vitro study to evaluate new systemic chemotherapeutic options.	2005 May-Jun	16033055
ACNU-cisplatin continuous infusion chemotherapy as salvage therapy for recurrent glioblastomas: phase II study.	2005 Nov	16132508
[Standards and new developments in the chemotherapy of glioblastomas].	2005 Oct 7	16208603
A case of Werner syndrome with three primary lesions of malignant melanoma.	2005 Sep	16361718
[Chemotherapy for brain tumor].	2005 Sep	16201563
High-dose idarubicin, busulphan and melphalan for autologous stem cell transplantation in multiple myeloma responsive to DAV chemotherapy: comparison with a historical control.	2006	16424643
Acute myocardial infarction induced by cisplatin-based combination chemotherapy for malignant melanoma: a case report.	2006 Apr	16637253
Hyperfractionated radiotherapy and multi-agent chemotherapy (procarbazine, ACNU and vincristine) for high-grade gliomas: a prospective study.	2006 May-Jun	16821632
Pegfilgrastim compared with filgrastim after high-dose melphalan and autologous hematopoietic peripheral blood stem cell transplantation in multiple myeloma patients.	2006 Nov	16930141
Phase II study of nimustine, carboplatin, vincristine, and interferon-beta with radiotherapy for glioblastoma multiforme: experience of the Kyoto Neuro-Oncology Group.	2006 Sep	16961130
Collagen gel matrix assay as an in vitro chemosensitivity test for malignant astrocytic tumors.	2007 Apr	17443280
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.	2007 Aug	17643724
Effectiveness of interferon-beta and temozolomide combination therapy against temozolomide-refractory recurrent anaplastic astrocytoma.	2007 Aug 4	17683572
Primary malignant melanoma of the female urethra.	2007 Dec	18158055
Modes of actions of two types of anti-neoplastic drugs, dacarbazine and ACNU, to induce apoptosis.	2007 Dec	17881774
Induction of peptide-specific immune response in patients with primary malignant melanoma of the esophagus after immunotherapy using dendritic cells pulsed with MAGE peptides.	2007 Feb	17255158
Analysis of long-term survivors of glioblastoma multiforme in a single institution with aggressive local retreatment protocol.	2007 Jul-Aug	17695484
Extraneural metastasis of high grade glioma without simultaneous central nervous system recurrence: case report.	2007 Jun	17587781
Gene expressions associated with chemosensitivity in human hepatoma cells.	2007 Mar	17523305
Chromosome arm 1q gain associated with good response to chemotherapy in a malignant glioma. Case report.	2007 Mar	17367075
Primary CNS lymphoma treated with combined intra-arterial ACNU and radiotherapy.	2007 Nov	17712511
Case of rectal malignant melanoma showing immunohistochemical variability in a tumor.	2007 Oct	17965534
Phase I/II clinical trial of carbon ion radiotherapy for malignant gliomas: combined X-ray radiotherapy, chemotherapy, and carbon ion radiotherapy.	2007 Oct 1	17459607
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.	2007 Sep	17390104
Treatment outcomes and dose-volume histogram analysis of simultaneous integrated boost method for malignant gliomas using intensity-modulated radiotherapy.	2008 Feb	18307019
Response to chemotherapy and tandem autologous transplantation of multiple myeloma patients and GSTP1 and TYMS polymorphisms.	2008 Jan	17512053
Prospective single-arm study of 72 Gy hyperfractionated radiation therapy and combination chemotherapy for anaplastic astrocytomas.	2008 Jan 16	18199339
Nitrosourea efficacy in high-grade glioma: a survival gain analysis summarizing 504 cohorts with 24193 patients.	2008 May	18253699

Patents

Sample Use Guides

In Vivo Use Guide

2-3 mg/kg or 90-100 mg/m2 as a single dose at intervals of 6 wk according to haematological response.

Route of Administration: Other

In Vitro Use Guide

After 24h treated of drug, ACNU induced cytotoxicity in NIH/3T3 cells with the IC50 about 600 ug/ml. At lower ACNU concentrations (<100 ug/ml), less growth inhibition was observed, but it can produce markedly increased cytotoxicity between the concentration of 100~900 ug/ml.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 05:31:55 GMT 2023` Edited by `admin` on `Sat Dec 16 05:31:55 GMT 2023`
Record UNII	0S726V972K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NIMUSTINE

Official Name

English

NSC-758675

Code

English

nimustine [INN]

Common Name

English

NIMUSTINE [MI]

Common Name

English

3-((4-AMINO-2-METHYL-5-PYRIMIDINYL)METHYL)-1-(2-CHLOROETHYL)-1-NITROSOUREA

Systematic Name

English

Nimustine [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QL01AD06