NIMUSTINE

Possibly Marketed Outside US

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 282 Target ID: CHEMBL2311221 Sources: https://www.cancer.gov/publications/dictionaries/cancer-drug?cdrid=38853 \| DOI: 10.7763/IJBBB.2013.V3.208	Crosslinking Agent 83

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 8583	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 8583	NIDRAN Approved Use Drug is indicated for the treatment of brain tumor, gastrointestinal cancer, lung cancer, malignant lymphoma, chronic leukemia.
Lung cancer 70 Sources: http://www.kegg.jp/medicus-bin/japic_med_product?id=00043575-001#00043575-001	Primary	Approved 8583	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 8583	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 8583	NIDRAN Approved Use Drug is indicated for the treatment of brain tumor, gastrointestinal cancer, lung cancer, malignant lymphoma, chronic leukemia.

C_max

Value	Dose	Co-administered	Analyte	Population
0.59 μg/mL EXPERIMENT https://www.info.pmda.go.jp/go/interview/2/430574_4219400D1029_2_ND7_1F.pdf#page=30	100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered:		NIMUSTINE cerebrospinal fluid	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
3.86 μg/mL EXPERIMENT https://www.info.pmda.go.jp/go/interview/2/430574_4219400D1029_2_ND7_1F.pdf#page=31	100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered:		NIMUSTINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
1.08 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11305611/	5 mg single, intraventricular dose: 5 mg route of administration: Intraventricular experiment type: SINGLE co-administered: CYTARABINE	CYTARABINE	NIMUSTINE cerebrospinal fluid	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
2.21 μg × h/mL EXPERIMENT https://www.info.pmda.go.jp/go/interview/2/430574_4219400D1029_2_ND7_1F.pdf#page=31	100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered:		NIMUSTINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
1.08 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11305611/	5 mg single, intraventricular dose: 5 mg route of administration: Intraventricular experiment type: SINGLE co-administered: CYTARABINE	CYTARABINE	NIMUSTINE cerebrospinal fluid	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.49 h EXPERIMENT https://www.info.pmda.go.jp/go/interview/2/430574_4219400D1029_2_ND7_1F.pdf#page=30	100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered:		NIMUSTINE cerebrospinal fluid	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
0.58 h EXPERIMENT https://www.info.pmda.go.jp/go/interview/2/430574_4219400D1029_2_ND7_1F.pdf#page=31	100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered:		NIMUSTINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
35.1% EXPERIMENT https://www.info.pmda.go.jp/go/interview/2/430574_4219400D1029_2_ND7_1F.pdf#page=33 \| https://pubmed.ncbi.nlm.nih.gov/2245489/			NIMUSTINE serum	Homo sapiens

Doses

Dose	Population	Adverse events
90 mg/m2 1 times / 5 weeks multiple, intraarterial Highest studied dose Dose: 90 mg/m2, 1 times / 5 weeks Route: intraarterial Route: multiple Dose: 90 mg/m2, 1 times / 5 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/16739319/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/16739319/	Sources: https://pubmed.ncbi.nlm.nih.gov/16739319/
90 mg/m2 1 times / 5 weeks multiple, intravenous Highest studied dose Dose: 90 mg/m2, 1 times / 5 weeks Route: intravenous Route: multiple Dose: 90 mg/m2, 1 times / 5 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/16739319/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/16739319/	Sources: https://pubmed.ncbi.nlm.nih.gov/16739319/
40 mg/m2 1 times / 4 weeks multiple, intravenous MTD Dose: 40 mg/m2, 1 times / 4 weeks Route: intravenous Route: multiple Dose: 40 mg/m2, 1 times / 4 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/27725524/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/27725524/	DLT: Neutropenia... Dose limiting toxicities: Neutropenia (grade 3, 16.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/27725524/
45 mg/m2 1 times / 4 weeks multiple, intravenous Studied dose Dose: 45 mg/m2, 1 times / 4 weeks Route: intravenous Route: multiple Dose: 45 mg/m2, 1 times / 4 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/27725524/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/27725524/	DLT: Thrombocytopenia, Neutropenia... Dose limiting toxicities: Thrombocytopenia (grade 3, 33.3%) Neutropenia (grade 3, 66.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/27725524/
75 mg/m2 1 times / 6 weeks multiple, intravenous Studied dose Dose: 75 mg/m2, 1 times / 6 weeks Route: intravenous Route: multiple Dose: 75 mg/m2, 1 times / 6 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/1312909/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1312909/	Disc. AE: Myelosuppression... AEs leading to discontinuation/dose reduction: Myelosuppression (4.2%) Sources: https://pubmed.ncbi.nlm.nih.gov/1312909/

AEs

AE	Significance	Dose	Population
Neutropenia	grade 3, 16.7% DLT	40 mg/m2 1 times / 4 weeks multiple, intravenous MTD Dose: 40 mg/m2, 1 times / 4 weeks Route: intravenous Route: multiple Dose: 40 mg/m2, 1 times / 4 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/27725524/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/27725524/
Thrombocytopenia	grade 3, 33.3% DLT	45 mg/m2 1 times / 4 weeks multiple, intravenous Studied dose Dose: 45 mg/m2, 1 times / 4 weeks Route: intravenous Route: multiple Dose: 45 mg/m2, 1 times / 4 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/27725524/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/27725524/
Neutropenia	grade 3, 66.7% DLT	45 mg/m2 1 times / 4 weeks multiple, intravenous Studied dose Dose: 45 mg/m2, 1 times / 4 weeks Route: intravenous Route: multiple Dose: 45 mg/m2, 1 times / 4 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/27725524/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/27725524/
Myelosuppression	4.2% Disc. AE	75 mg/m2 1 times / 6 weeks multiple, intravenous Studied dose Dose: 75 mg/m2, 1 times / 6 weeks Route: intravenous Route: multiple Dose: 75 mg/m2, 1 times / 6 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/1312909/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1312909/

PubMed

Title	Date	PubMed
Nitrosourea efficacy in high-grade glioma: a survival gain analysis summarizing 504 cohorts with 24193 patients.	2008-05	18253699
Intrathecal chemotherapy for refractory disseminated medulloblastoma.	2008-05	18057943
Treatment outcomes and dose-volume histogram analysis of simultaneous integrated boost method for malignant gliomas using intensity-modulated radiotherapy.	2008-02	18307019
Prospective single-arm study of 72 Gy hyperfractionated radiation therapy and combination chemotherapy for anaplastic astrocytomas.	2008-01-16	18199339
Response to chemotherapy and tandem autologous transplantation of multiple myeloma patients and GSTP1 and TYMS polymorphisms.	2008-01	17512053
Differential sensitivity of malignant glioma cells to methylating and chloroethylating anticancer drugs: p53 determines the switch by regulating xpc, ddb2, and DNA double-strand breaks.	2007-12-15	18089819
Primary malignant melanoma of the female urethra.	2007-12	18158055
Modes of actions of two types of anti-neoplastic drugs, dacarbazine and ACNU, to induce apoptosis.	2007-12	17881774
Primary CNS lymphoma treated with combined intra-arterial ACNU and radiotherapy.	2007-11	17712511
Phase I/II clinical trial of carbon ion radiotherapy for malignant gliomas: combined X-ray radiotherapy, chemotherapy, and carbon ion radiotherapy.	2007-10-01	17459607
Long-term follow-up of busulfan, etoposide, and nimustine hydrochloride (ACNU) or melphalan as conditioning regimens for childhood acute leukemia and lymphoma.	2007-10	17988993
Case of rectal malignant melanoma showing immunohistochemical variability in a tumor.	2007-10	17965534
Anaplastic ganglioglioma in a middle-aged woman: a case report with a review of the literature.	2007-09	17923741
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.	2007-09	17390104
Analysis of long-term survivors of glioblastoma multiforme in a single institution with aggressive local retreatment protocol.	2007-08-19	17695484
Effectiveness of interferon-beta and temozolomide combination therapy against temozolomide-refractory recurrent anaplastic astrocytoma.	2007-08-04	17683572
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.	2007-08	17643724
The combined effects of multiple chemotherapeutic agents for malignant glioma cells.	2007-08	17361333
Extraneural metastasis of high grade glioma without simultaneous central nervous system recurrence: case report.	2007-06	17587781
Collagen gel matrix assay as an in vitro chemosensitivity test for malignant astrocytic tumors.	2007-04	17443280
Gene expressions associated with chemosensitivity in human hepatoma cells.	2007-03	17523305
Chromosome arm 1q gain associated with good response to chemotherapy in a malignant glioma. Case report.	2007-03	17367075
Safety and efficacy of convection-enhanced delivery of ACNU, a hydrophilic nitrosourea, in intracranial brain tumor models.	2007-03	17031554
Induction of peptide-specific immune response in patients with primary malignant melanoma of the esophagus after immunotherapy using dendritic cells pulsed with MAGE peptides.	2007-02	17255158
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.	2007-02	16937011
Case of metastatic melanoma in an epitrochlear lymph node arising in a pregnant woman.	2007-01	17204101
Pegfilgrastim compared with filgrastim after high-dose melphalan and autologous hematopoietic peripheral blood stem cell transplantation in multiple myeloma patients.	2006-11	16930141
Glioblastoma multiforme with oligodendroglial component (GBMO): favorable outcome after post-operative radiotherapy and chemotherapy with nimustine (ACNU) and teniposide (VM26).	2006-10-18	17049083
Phase II trial of radiotherapy after hyperbaric oxygenation with chemotherapy for high-grade gliomas.	2006-10-09	16953239
Phase II study of nimustine, carboplatin, vincristine, and interferon-beta with radiotherapy for glioblastoma multiforme: experience of the Kyoto Neuro-Oncology Group.	2006-09	16961130
Gene expression profiles of 1-(4-amino-2-methyl-5-pyrimidinyl)-methyl-3-(2-chloroethyl)-3-nitrosourea (ACNU)-resistant C6 rat glioma cells.	2006-09	16645721
Hyperfractionated radiotherapy and multi-agent chemotherapy (procarbazine, ACNU and vincristine) for high-grade gliomas: a prospective study.	2006-07-11	16821632
[Glioma].	2006-07	16838652
[A case of malignant melanoma from the esophagus responding to weekly paclitaxel therapy].	2006-07	16835489
A randomized phase III study: comparison between intravenous and intraarterial ACNU administration in newly diagnosed primary glioblastomas.	2006-06-03	16739319
Treatment of primary glioblastoma multiforme with cetuximab, radiotherapy and temozolomide (GERT)--phase I/II trial: study protocol.	2006-05-18	16709245
Acute myocardial infarction induced by cisplatin-based combination chemotherapy for malignant melanoma: a case report.	2006-04	16637253
Acquisition of resistance to antitumor alkylating agent ACNU: a possible target of positron emission tomography monitoring.	2006-01	16459256
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
[Treatment for malignant glioma].	2005-12	16375187
Combination hepatic arterial infusion therapy is effective for ocular melanoma metastasis to the liver.	2005-12	16273253
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.	2005-11-29	16309194
Down-regulation of O6-methylguanine-DNA methyltransferase gene expression in gliomas by platinum compounds.	2005-11	16211296
ACNU-cisplatin continuous infusion chemotherapy as salvage therapy for recurrent glioblastomas: phase II study.	2005-11	16132508
[Standards and new developments in the chemotherapy of glioblastomas].	2005-10-07	16208603
A case of epidermotropic metastatic malignant melanoma with multiple nodular lesions of the scalp.	2005-10	16361735
A case of Werner syndrome with three primary lesions of malignant melanoma.	2005-09	16361718
[Chemotherapy for brain tumor].	2005-09	16201563
Brain metastases in breast cancer--an in vitro study to evaluate new systemic chemotherapeutic options.	2005-07-22	16033055
Amelanotic malignant melanoma of the esophagus: report of a patient with recurrence successfully treated with chemoendocrine therapy.	2005-06	15990972

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 `Mon Mar 31 21:30:13 GMT 2025` Edited by `admin` on `Mon Mar 31 21:30:13 GMT 2025`
Record UNII	0S726V972K
Record Status	`Validated (UNII)`
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Name

Type

Language

NSC-758675

Preferred Name

English

NIMUSTINE

Official Name

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