U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C9H16ClN3O2
Molecular Weight 233.695
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LOMUSTINE

SMILES

ClCCN(N=O)C(=O)NC1CCCCC1

InChI

InChIKey=GQYIWUVLTXOXAJ-UHFFFAOYSA-N
InChI=1S/C9H16ClN3O2/c10-6-7-13(12-15)9(14)11-8-4-2-1-3-5-8/h8H,1-7H2,(H,11,14)

HIDE SMILES / InChI

Description

Lomustine is used in the treatment of certain neoplastic diseases. Although it is generally agreed that lomustine alkylates DNA and RNA, it is not cross resistant with other alkylators. As with other nitrosoureas, it may also inhibit several key enzymatic processes by carbamoylation of amino acids in proteins. Common adverse reactions include delayed myelosupression, nausea, vomiting, stomatitis, and alopecia.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Efficacy and toxicity of a CCNU-containing high-dose chemotherapy regimen followed by autologous hematopoietic cell transplantation in relapsed or refractory Hodgkin's disease.
2001
[Post-operative neoadjuvant chemotherapy before radiotherapy as compared to immediate radiotherapy followed by maintenance chemotherapy in the treatment of medulloblastoma in childhood: results of German prospective randomised trial HIT'91].
2001 Apr
Multidisciplinary management of adult anaplastic oligodendrogliomas and anaplastic mixed oligo-astrocytomas.
2001 Apr
Chemotherapy for the treatment of oligodendroglial tumors.
2001 Aug
Melanoma-associated retinopathy: does autoimmunity prolong survival?
2001 Aug
Recurrent intracranial ependymoma in children: salvage therapy with oral etoposide.
2001 Feb
Adult medulloblastoma: multiagent chemotherapy.
2001 Jan
Randomized trial of procarbazine, lomustine, and vincristine in the adjuvant treatment of high-grade astrocytoma: a Medical Research Council trial.
2001 Jan 15
Spin labelled nitrosoureas and triazenes and their non-labelled clinically used analogues--a comparative study on their physicochemical properties and antimelanomic effects.
2001 Jan 16
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.
2001 Jul
PCV chemotherapy for recurrent glioblastoma multiforme.
2001 Jun 26
[Therapeutic effect on glioblastoma of chemotherapy on the basis of brain irradiation].
2001 Mar
Death receptor-independent cytochrome c release and caspase activation mediate thymidine kinase plus ganciclovir-mediated cytotoxicity in LN-18 and LN-229 human malignant glioma cells.
2001 Mar
Safety and efficacy of temozolomide in patients with recurrent anaplastic oligodendrogliomas after standard radiotherapy and chemotherapy.
2001 May 1
Lipid association improves the therapeutic index of lomustine [1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea] to suppress 36B-10 tumor growth in rats.
2001 May 1
The effectiveness of the O(6)-alkylguanine-DNA alkyltransferase encoded by the ogt(ST) gene from S. typhimurium in protection against alkylating drugs, resistance to O(6)-benzylguanine and sensitisation to dibromoalkane genotoxicity.
2001 Oct 18
Nitric oxide and free stable nitroxyl radicals in the mechanism of biological action of the spin-labeled compounds.
2001 Sep
11q23 balanced chromosome aberrations in treatment-related myelodysplastic syndromes and acute leukemia: report from an international workshop.
2002 Apr
Treatment of advanced neuroendocrine tumours using combination chemotherapy with lomustine and 5-fluorouracil.
2002 Aug
Coeliac disease following high-dose chemotherapy.
2002 Dec
Recurrent malignant glioma in adults.
2002 Dec
Pulmonary complications in survivors of childhood and adolescent cancer. A report from the Childhood Cancer Survivor Study.
2002 Dec 1
An elevated serum beta-2-microglobulin level is an adverse prognostic factor for overall survival in patients with early-stage Hodgkin disease.
2002 Dec 15
High expression levels of collagenase-1 and stromelysin-1 correlate with shorter disease-free survival in human metastatic melanoma.
2002 Feb 1
Long-term follow-up in managing anaplastic astrocytoma by multimodality approach with surgery followed by postoperative radiotherapy and PCV-chemotherapy: phase II trial.
2002 Jun
Study of three hepatobiliary agents in experimental animals.
2002 Mar-Apr
NO-mediated chemoresistance in C6 glioma cells.
2002 May
[Chemo-radiotherapy for malignant brain tumors].
2002 May
Phase II study of accelerated fractionation radiation therapy with carboplatin followed by PCV chemotherapy for the treatment of anaplastic gliomas.
2002 May 1
Radiotherapy alone for lymphocyte-predominant Hodgkin's disease.
2002 Sep-Oct
Low-dose continuous chemotherapy for metastatic melanoma: a phase II trial.
2003 Apr
Recent developments in the molecular characterization and treatment of oligodendroglial tumors.
2003 Apr
Partially successful treatment of a patient with chronic lymphocytic leukemia and Hodgkin's disease: case report and literature review.
2003 Apr
Second-line chemotherapy with temozolomide in recurrent oligodendroglioma after PCV (procarbazine, lomustine and vincristine) chemotherapy: EORTC Brain Tumor Group phase II study 26972.
2003 Apr
Chemotherapy alone as initial treatment for primary CNS lymphoma in patients older than 60 years: a multicenter phase II study (26952) of the European Organization for Research and Treatment of Cancer Brain Tumor Group.
2003 Jul 15
Phase I study of temozolamide (TMZ) combined with procarbazine (PCB) in patients with gliomas.
2003 Jul 21
Myeloid clonogenic assays for comparison of the in vitro toxicity of alkylating agents.
2003 Jun
Survival improvement in patients with glioblastoma multiforme during the last 20 years in a single tertiary-care center.
2003 Jun 24
Phase III randomized study of postradiotherapy chemotherapy with combination alpha-difluoromethylornithine-PCV versus PCV for anaplastic gliomas.
2003 Mar
Interobserver variability in the radiological assessment of response to chemotherapy in glioma.
2003 Mar 11
Conformal irradiation for pure and mixed oligodendroglioma: the experience of Centre Leon Berard Lyon.
2003 May 1
Patents

Sample Use Guides

In Vivo Use Guide
Recommended dose in adult and pediatric patients is 130 mg/m2 orally every 6 weeks.
Route of Administration: Oral
In Vitro Use Guide
Alkylation of the nuclear matrix by Lomustine was 1.27 pmoles drug/micrograms protein, whereas carbamoylation by Lomustine was 32.5 pmoles/micrograms.
Name Type Language
LOMUSTINE
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
1-(2-CHLOROETHYL)-3-CYCLOHEXYL-1-NITROSOUREA [IARC]
Common Name English
1-(2-CHLOROETHYL)-3-CYCLOHEXYL-1-NITROSOUREA
Systematic Name English
LOMUSTINE [HSDB]
Common Name English
LOMUSTINE [WHO-DD]
Common Name English
CEENU
Brand Name English
CCN-U
Code English
LOMUSTINE [MART.]
Common Name English
CCNU
Code English
LOMUSTINE [VANDF]
Common Name English
UREA, N-(2-CHLOROETHYL)-N'-CYCLOHEXYL-N-NITROSO-
Systematic Name English
LOMUSTINE [EP]
Common Name English
LOMUSTINE [USP-RS]
Common Name English
LOMUSTINE [ORANGE BOOK]
Common Name English
NSC-79037
Code English
LOMUSTINE [USAN]
Common Name English
LOMUSTINE [MI]
Common Name English
LOMUSTINE [INN]
Common Name English
Classification Tree Code System Code
LIVERTOX 566
Created by admin on Tue Oct 22 00:33:23 UTC 2019 , Edited by admin on Tue Oct 22 00:33:23 UTC 2019
NCI_THESAURUS C699
Created by admin on Tue Oct 22 00:33:23 UTC 2019 , Edited by admin on Tue Oct 22 00:33:23 UTC 2019
NDF-RT N0000000236
Created by admin on Tue Oct 22 00:33:23 UTC 2019 , Edited by admin on Tue Oct 22 00:33:23 UTC 2019
WHO-VATC QL01AD02
Created by admin on Tue Oct 22 00:33:23 UTC 2019 , Edited by admin on Tue Oct 22 00:33:23 UTC 2019
WHO-ATC L01AD02
Created by admin on Tue Oct 22 00:33:23 UTC 2019 , Edited by admin on Tue Oct 22 00:33:23 UTC 2019
NDF-RT N0000175558
Created by admin on Tue Oct 22 00:33:23 UTC 2019 , Edited by admin on Tue Oct 22 00:33:23 UTC 2019
Code System Code Type Description
EVMPD
SUB08567MIG
Created by admin on Tue Oct 22 00:33:23 UTC 2019 , Edited by admin on Tue Oct 22 00:33:23 UTC 2019
PRIMARY
CAS
13010-47-4
Created by admin on Tue Oct 22 00:33:23 UTC 2019 , Edited by admin on Tue Oct 22 00:33:23 UTC 2019
PRIMARY
MERCK INDEX
M6891
Created by admin on Tue Oct 22 00:33:23 UTC 2019 , Edited by admin on Tue Oct 22 00:33:23 UTC 2019
PRIMARY Merck Index
PUBCHEM
3950
Created by admin on Tue Oct 22 00:33:23 UTC 2019 , Edited by admin on Tue Oct 22 00:33:23 UTC 2019
PRIMARY
EPA CompTox
13010-47-4
Created by admin on Tue Oct 22 00:33:23 UTC 2019 , Edited by admin on Tue Oct 22 00:33:23 UTC 2019
PRIMARY
RXCUI
6466
Created by admin on Tue Oct 22 00:33:23 UTC 2019 , Edited by admin on Tue Oct 22 00:33:23 UTC 2019
PRIMARY RxNorm
HSDB
13010-47-4
Created by admin on Tue Oct 22 00:33:23 UTC 2019 , Edited by admin on Tue Oct 22 00:33:23 UTC 2019
PRIMARY
WIKIPEDIA
LOMUSTINE
Created by admin on Tue Oct 22 00:33:23 UTC 2019 , Edited by admin on Tue Oct 22 00:33:23 UTC 2019
PRIMARY
MESH
D008130
Created by admin on Tue Oct 22 00:33:23 UTC 2019 , Edited by admin on Tue Oct 22 00:33:23 UTC 2019
PRIMARY
IUPHAR
7214
Created by admin on Tue Oct 22 00:33:23 UTC 2019 , Edited by admin on Tue Oct 22 00:33:23 UTC 2019
PRIMARY
NCI_THESAURUS
C617
Created by admin on Tue Oct 22 00:33:23 UTC 2019 , Edited by admin on Tue Oct 22 00:33:23 UTC 2019
PRIMARY
DRUG BANK
DB01206
Created by admin on Tue Oct 22 00:33:23 UTC 2019 , Edited by admin on Tue Oct 22 00:33:23 UTC 2019
PRIMARY
ECHA (EC/EINECS)
235-859-2
Created by admin on Tue Oct 22 00:33:23 UTC 2019 , Edited by admin on Tue Oct 22 00:33:23 UTC 2019
PRIMARY
INN
3184
Created by admin on Tue Oct 22 00:33:23 UTC 2019 , Edited by admin on Tue Oct 22 00:33:23 UTC 2019
PRIMARY
ChEMBL
CHEMBL514
Created by admin on Tue Oct 22 00:33:23 UTC 2019 , Edited by admin on Tue Oct 22 00:33:23 UTC 2019
PRIMARY