LOMUSTINE

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 Search

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

Targets

Primary Target	Pharmacology	Condition	Potency
RNA 16	Binding Agent 965	Hodgkin Disease
DNA 250	Crosslinking Agent 73	Hodgkin Disease

Conditions

Condition	Modality	Targets	Highest Phase	Product
Brain Neoplasms 5	Primary	DNA RNA	Approved 7883	GLEOSTINE
Hodgkin Disease 28	Primary	DNA RNA	Approved 7883	GLEOSTINE
[Breast cancer, Colon cancer, Lung cancer, Melanoma, Multiple myeloma, non-Hodgkin lymphoma, Renal carcinoma] 1			Approved (off-label) 8

PubMed

Title	Date	PubMed
Spin-labeled 1-alkyl-1-nitrosourea synergists of antitumor antibiotics.	2001 Aug-Oct	12049483
Adults with newly diagnosed high-grade gliomas.	2001 Dec	12057096
A possible correlation between unscheduled DNA repair and cholesterolemia in Wistar rat, modulated by vitamin E.	2001 Oct-Dec	12561677
Intensified PCV-chemotherapy with optional stem cell support in recurrent malignant oligodendroglioma.	2002 Aug	12195453
Treatment of advanced neuroendocrine tumours using combination chemotherapy with lomustine and 5-fluorouracil.	2002 Aug	12153595
Coeliac disease following high-dose chemotherapy.	2002 Dec	12512973
Recurrent malignant glioma in adults.	2002 Dec	12392640
Pulmonary complications in survivors of childhood and adolescent cancer. A report from the Childhood Cancer Survivor Study.	2002 Dec 1	12436452
Chemoimmunotherapy with bleomycin, vincristine, lomustine, dacarbazine (BOLD), and human leukocyte interferon for metastatic uveal melanoma.	2002 Dec 1	12436444
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	12467067
Hematological toxicity and therapeutic efficacy of lomustine in 20 tumor-bearing cats: critical assessment of a practical dosing regimen.	2002 Jul-Aug	12118689
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	12040293
Evaluation of naphthal-NU, a 2-chloroethylnitrosourea derivative of naphthalimide, as a mixed-function anticancer agent.	2002 Mar	12071535
Study of three hepatobiliary agents in experimental animals.	2002 Mar-Apr	11990340
Concurrent modified PCV chemotherapy and radiotherapy in newly diagnosed grade IV astrocytoma.	2002 May	12125984
NO-mediated chemoresistance in C6 glioma cells.	2002 May	12076959
[Chemo-radiotherapy for malignant brain tumors].	2002 May	12040669
Phase II study of accelerated fractionation radiation therapy with carboplatin followed by PCV chemotherapy for the treatment of anaplastic gliomas.	2002 May 1	12007942
Acute diarrhea during adjuvant therapy for rectal cancer: a detailed analysis from a randomized intergroup trial.	2002 Oct 1	12243815
Complete response of a recurrent, multicentric malignant glioma in a patient treated with phenylbutyrate.	2002 Sep	12241121
Modulation of growth and radiochemosensitivity of human malignant glioma cells by acidosis.	2002 Sep 1	12209698
Phase I study of fotemustine in pediatric patients with refractory brain tumors.	2002 Sep 15	12216098
Radiotherapy alone for lymphocyte-predominant Hodgkin's disease.	2002 Sep-Oct	12416895
Low-dose continuous chemotherapy for metastatic melanoma: a phase II trial.	2003 Apr	12690305
Survival and prognostic factors of patients with unresectable glioblastoma multiforme.	2003 Apr	12679735
Recent developments in the molecular characterization and treatment of oligodendroglial tumors.	2003 Apr	12672285
Partially successful treatment of a patient with chronic lymphocytic leukemia and Hodgkin's disease: case report and literature review.	2003 Apr	12666139
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	12649108
Feasibility and toxicity of CCNU therapy in elderly patients with glioblastoma multiforme.	2003 Feb	12569300
Survival with dacarbazine and fotemustine in newly diagnosed glioblastoma multiforme.	2003 Feb 24	12592361
Primary intraspinal primitive neuroectodermal tumor: report of two cases and review of the literature.	2003 Jan	12622449
Dramatic response to chemotherapy in oligodendroglial gliomatosis cerebri.	2003 Jan 14	12525747
Phase II trial of procarbazine, lomustine, and vincristine as initial therapy for patients with low-grade oligodendroglioma or oligoastrocytoma: efficacy and associations with chromosomal abnormalities.	2003 Jan 15	12525516
Phase II study of first-line chemotherapy with temozolomide in recurrent oligodendroglial tumors: the European Organization for Research and Treatment of Cancer Brain Tumor Group Study 26971.	2003 Jul 1	12829671
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	12860951
Phase I study of temozolamide (TMZ) combined with procarbazine (PCB) in patients with gliomas.	2003 Jul 21	12865911
Myeloid clonogenic assays for comparison of the in vitro toxicity of alkylating agents.	2003 Jun	12781205
High-dose therapy and autologous stem-cell transplantation versus conventional therapy for patients with advanced Hodgkin's lymphoma responding to front-line therapy.	2003 Jun 15	12805333
Survival improvement in patients with glioblastoma multiforme during the last 20 years in a single tertiary-care center.	2003 Jun 24	12879737
Genetic alterations of human brain tumors as molecular prognostic factors.	2003 Mar	12722932
Phase III randomized study of postradiotherapy chemotherapy with combination alpha-difluoromethylornithine-PCV versus PCV for anaplastic gliomas.	2003 Mar	12631596
Chromosomal anomalies in oligodendroglial tumors are correlated with clinical features.	2003 Mar 1	12599236
Glioma treatment, radionecrosis, and growth factors. In regard to Levin et al., IJROBP 2002;53:58-66.	2003 Mar 1	12573773
Interobserver variability in the radiological assessment of response to chemotherapy in glioma.	2003 Mar 11	12629241
New chemotherapy agents in veterinary medicine.	2003 May	12852240
Combined modality therapy for poorly differentiated gliomas of the posterior fossa in children: a Children's Cancer Group report.	2003 May	12814254
Bleomycin, vincristine, lomustine and dacarbazine (BOLD) in combination with recombinant interferon alpha-2b for metastatic uveal melanoma.	2003 May	12736111
Irinotecan in the treatment of glioma patients: current and future studies of the North Central Cancer Treatment Group.	2003 May 1	12712456
Conformal irradiation for pure and mixed oligodendroglioma: the experience of Centre Leon Berard Lyon.	2003 May 1	12694851
Role of mismatch repair in the induction of chromosomal aberrations and sister chromatid exchanges in cells treated with different chemotherapeutic agents.	2003 Sep	12827294

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

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