LOMUSTINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H16ClN3O2
Molecular Weight	233.695
Optical Activity	NONE
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

Molecular Formula	C9H16ClN3O2
Molecular Weight	233.695
Charge	0
Count

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

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017588s043lbl.pdf
Curator's Comment: description was created based on several sources, including: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=7f77526b-4c40-409c-82ea-d0f934d89cc2

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
DNA 282 Target ID: CHEMBL2311221 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017588s043lbl.pdf	Crosslinking Agent 83
RNA 19 Target ID: CHEMBL2311222 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017588s043lbl.pdf	Binding Agent 1076

Conditions

Condition	Modality	Targets	Highest Phase	Product
Brain cancer 10 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017588s043lbl.pdf	Primary		Approved 8583	GLEOSTINE Approved Use CeeNU has been shown to be useful as a single agent in addition to other treatment modalities, or in established combination therapy with other approved chemotherapeutic agents in the following: Brain tumors—both primary and metastatic, in patients who have already received appropriate surgical and/or radiotherapeutic procedures. Hodgkin’s disease—secondary therapy in combination with other approved drugs in patients who relapse while being treated with primary therapy, or who fail to respond to primary therapy. Launch Date 1976
Hodgkin's lymphoma 33 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017588s043lbl.pdf	Primary		Approved 8583	GLEOSTINE Approved Use CeeNU has been shown to be useful as a single agent in addition to other treatment modalities, or in established combination therapy with other approved chemotherapeutic agents in the following: Brain tumors—both primary and metastatic, in patients who have already received appropriate surgical and/or radiotherapeutic procedures. Hodgkin’s disease—secondary therapy in combination with other approved drugs in patients who relapse while being treated with primary therapy, or who fail to respond to primary therapy. Launch Date 1976

C_max

Value	Dose	Co-administered	Analyte	Population
0.85 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3971475/	130 mg/m² single, oral dose: 130 mg/m² route of administration: Oral experiment type: SINGLE co-administered:		4-OH-CCNU plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
2 ng/mL OTHER GOV https://www.medicines.org.uk/emc/product/1401/smpc	100 mg/m² single, oral dose: 100 mg/m² route of administration: Oral experiment type: SINGLE co-administered:		LOMUSTINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
3.76 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3971475/	130 mg/m² single, oral dose: 130 mg/m² route of administration: Oral experiment type: SINGLE co-administered:		4-OH-CCNU plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3971475/	130 mg/m² single, oral dose: 130 mg/m² route of administration: Oral experiment type: SINGLE co-administered:		4-OH-CCNU plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
50% REVIEW http://www.bccancer.bc.ca/drug-database-site/Drug%20Index/Lomustine_monograph.pdf	unknown		LOMUSTINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
400 mg/m2 single, oral Highest studied dose Dose: 400 mg/m2 Route: oral Route: single Dose: 400 mg/m2 Sources: https://www.tctjournal.org/action/showPdf?pii=S1083-8791%2813%2900730-1 https://pubmed.ncbi.nlm.nih.gov/24887380	unhealthy, 36 Health Status: unhealthy Age Group: 36 Sources: https://www.tctjournal.org/action/showPdf?pii=S1083-8791%2813%2900730-1 https://pubmed.ncbi.nlm.nih.gov/24887380	DLT: Gastrointestinal toxicity, Sinusoidal obstruction syndrome... Dose limiting toxicities: Gastrointestinal toxicity (grade 4, 50%) Sinusoidal obstruction syndrome (grade 4, 50%) Sources: https://www.tctjournal.org/action/showPdf?pii=S1083-8791%2813%2900730-1 https://pubmed.ncbi.nlm.nih.gov/24887380
300 mg/m2 single, oral MTD Dose: 300 mg/m2 Route: oral Route: single Dose: 300 mg/m2 Sources: https://www.tctjournal.org/action/showPdf?pii=S1083-8791%2813%2900730-1 https://pubmed.ncbi.nlm.nih.gov/24887380	unhealthy, 36 Health Status: unhealthy Age Group: 36 Sources: https://www.tctjournal.org/action/showPdf?pii=S1083-8791%2813%2900730-1 https://pubmed.ncbi.nlm.nih.gov/24887380	DLT: Neurotoxicity... Dose limiting toxicities: Neurotoxicity (grade 4, 33.3%) Sources: https://www.tctjournal.org/action/showPdf?pii=S1083-8791%2813%2900730-1 https://pubmed.ncbi.nlm.nih.gov/24887380
130 mg/m2 1 times / 6 weeks multiple, oral Recommended Dose: 130 mg/m2, 1 times / 6 weeks Route: oral Route: multiple Dose: 130 mg/m2, 1 times / 6 weeks Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017588s042lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017588s042lbl.pdf	Disc. AE: Myelosuppression, Pulmonary toxicity... AEs leading to discontinuation/dose reduction: Myelosuppression (grade 5) Pulmonary toxicity Pulmonary fibrosis Acute leukemia Myelodysplasia Hepatotoxicity Nephrotoxicity Fetal damage Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017588s042lbl.pdf

AEs

AE	Significance	Dose	Population
Gastrointestinal toxicity	grade 4, 50% DLT	400 mg/m2 single, oral Highest studied dose Dose: 400 mg/m2 Route: oral Route: single Dose: 400 mg/m2 Sources: https://www.tctjournal.org/action/showPdf?pii=S1083-8791%2813%2900730-1 https://pubmed.ncbi.nlm.nih.gov/24887380	unhealthy, 36 Health Status: unhealthy Age Group: 36 Sources: https://www.tctjournal.org/action/showPdf?pii=S1083-8791%2813%2900730-1 https://pubmed.ncbi.nlm.nih.gov/24887380
Sinusoidal obstruction syndrome	grade 4, 50% DLT	400 mg/m2 single, oral Highest studied dose Dose: 400 mg/m2 Route: oral Route: single Dose: 400 mg/m2 Sources: https://www.tctjournal.org/action/showPdf?pii=S1083-8791%2813%2900730-1 https://pubmed.ncbi.nlm.nih.gov/24887380	unhealthy, 36 Health Status: unhealthy Age Group: 36 Sources: https://www.tctjournal.org/action/showPdf?pii=S1083-8791%2813%2900730-1 https://pubmed.ncbi.nlm.nih.gov/24887380
Neurotoxicity	grade 4, 33.3% DLT	300 mg/m2 single, oral MTD Dose: 300 mg/m2 Route: oral Route: single Dose: 300 mg/m2 Sources: https://www.tctjournal.org/action/showPdf?pii=S1083-8791%2813%2900730-1 https://pubmed.ncbi.nlm.nih.gov/24887380	unhealthy, 36 Health Status: unhealthy Age Group: 36 Sources: https://www.tctjournal.org/action/showPdf?pii=S1083-8791%2813%2900730-1 https://pubmed.ncbi.nlm.nih.gov/24887380
Acute leukemia	Disc. AE	130 mg/m2 1 times / 6 weeks multiple, oral Recommended Dose: 130 mg/m2, 1 times / 6 weeks Route: oral Route: multiple Dose: 130 mg/m2, 1 times / 6 weeks Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017588s042lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017588s042lbl.pdf
Fetal damage	Disc. AE	130 mg/m2 1 times / 6 weeks multiple, oral Recommended Dose: 130 mg/m2, 1 times / 6 weeks Route: oral Route: multiple Dose: 130 mg/m2, 1 times / 6 weeks Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017588s042lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017588s042lbl.pdf
Hepatotoxicity	Disc. AE	130 mg/m2 1 times / 6 weeks multiple, oral Recommended Dose: 130 mg/m2, 1 times / 6 weeks Route: oral Route: multiple Dose: 130 mg/m2, 1 times / 6 weeks Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017588s042lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017588s042lbl.pdf
Myelodysplasia	Disc. AE	130 mg/m2 1 times / 6 weeks multiple, oral Recommended Dose: 130 mg/m2, 1 times / 6 weeks Route: oral Route: multiple Dose: 130 mg/m2, 1 times / 6 weeks Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017588s042lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017588s042lbl.pdf
Nephrotoxicity	Disc. AE	130 mg/m2 1 times / 6 weeks multiple, oral Recommended Dose: 130 mg/m2, 1 times / 6 weeks Route: oral Route: multiple Dose: 130 mg/m2, 1 times / 6 weeks Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017588s042lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017588s042lbl.pdf
Pulmonary fibrosis	Disc. AE	130 mg/m2 1 times / 6 weeks multiple, oral Recommended Dose: 130 mg/m2, 1 times / 6 weeks Route: oral Route: multiple Dose: 130 mg/m2, 1 times / 6 weeks Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017588s042lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017588s042lbl.pdf
Pulmonary toxicity	Disc. AE	130 mg/m2 1 times / 6 weeks multiple, oral Recommended Dose: 130 mg/m2, 1 times / 6 weeks Route: oral Route: multiple Dose: 130 mg/m2, 1 times / 6 weeks Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017588s042lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017588s042lbl.pdf
Myelosuppression	grade 5 Disc. AE	130 mg/m2 1 times / 6 weeks multiple, oral Recommended Dose: 130 mg/m2, 1 times / 6 weeks Route: oral Route: multiple Dose: 130 mg/m2, 1 times / 6 weeks Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017588s042lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017588s042lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252		inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 2633	inhibitor 4027 Sources: https://cancerres.aacrjournals.org/content/canres/53/21/5121.full.pdf	likely
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/8258200/	yes [Ki 7.7 uM]

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:6520	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6520
ChemicalBook	CB5123021	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5123021
eMolecules	734270	https://www.emolecules.com/cgi-bin/more?vid=734270
MolPort	MolPort-001-768-818	https://www.molport.com/shop/molecule-link/MolPort-001-768-818
Selleck Chemicals	Lomustine(CeeNU)	http://www.selleckchem.com/products/Lomustine(CeeNU).html
ZINC	ZINC000003831006	http://zinc15.docking.org/substances/ZINC000003831006

PubMed

Title	Date	PubMed
Role of mismatch repair in the induction of chromosomal aberrations and sister chromatid exchanges in cells treated with different chemotherapeutic agents.	2003-09	12827294
Phase I study of temozolamide (TMZ) combined with procarbazine (PCB) in patients with gliomas.	2003-07-21	12865911
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.	2003-07-15	12860951
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.	2003-07-01	12829671
Survival improvement in patients with glioblastoma multiforme during the last 20 years in a single tertiary-care center.	2003-06-24	12879737
High-dose therapy and autologous stem-cell transplantation versus conventional therapy for patients with advanced Hodgkin's lymphoma responding to front-line therapy.	2003-06-15	12805333
Myeloid clonogenic assays for comparison of the in vitro toxicity of alkylating agents.	2003-06	12781205
Irinotecan in the treatment of glioma patients: current and future studies of the North Central Cancer Treatment Group.	2003-05-01	12712456
Conformal irradiation for pure and mixed oligodendroglioma: the experience of Centre Leon Berard Lyon.	2003-05-01	12694851
New chemotherapy agents in veterinary medicine.	2003-05	12852240
Combined modality therapy for poorly differentiated gliomas of the posterior fossa in children: a Children's Cancer Group report.	2003-05	12814254
Bleomycin, vincristine, lomustine and dacarbazine (BOLD) in combination with recombinant interferon alpha-2b for metastatic uveal melanoma.	2003-05	12736111
Low-dose continuous chemotherapy for metastatic melanoma: a phase II trial.	2003-04	12690305
Survival and prognostic factors of patients with unresectable glioblastoma multiforme.	2003-04	12679735
Recent developments in the molecular characterization and treatment of oligodendroglial tumors.	2003-04	12672285
Partially successful treatment of a patient with chronic lymphocytic leukemia and Hodgkin's disease: case report and literature review.	2003-04	12666139
Second-line chemotherapy with temozolomide in recurrent oligodendroglioma after PCV (procarbazine, lomustine and vincristine) chemotherapy: EORTC Brain Tumor Group phase II study 26972.	2003-04	12649108
Interobserver variability in the radiological assessment of response to chemotherapy in glioma.	2003-03-11	12629241
Chromosomal anomalies in oligodendroglial tumors are correlated with clinical features.	2003-03-01	12599236
Glioma treatment, radionecrosis, and growth factors. In regard to Levin et al., IJROBP 2002;53:58-66.	2003-03-01	12573773
Genetic alterations of human brain tumors as molecular prognostic factors.	2003-03	12722932
Phase III randomized study of postradiotherapy chemotherapy with combination alpha-difluoromethylornithine-PCV versus PCV for anaplastic gliomas.	2003-03	12631596
Long-term sequelae in children treated for brain tumors: impairments, disability, and handicap.	2003-03	12554520
Survival with dacarbazine and fotemustine in newly diagnosed glioblastoma multiforme.	2003-02-24	12592361
A possible correlation between unscheduled DNA repair and cholesterolemia in Wistar rat, modulated by vitamin E.	2003-02-04	12561677
A prospective study on glioblastoma in the elderly.	2003-02-01	12548608
Feasibility and toxicity of CCNU therapy in elderly patients with glioblastoma multiforme.	2003-02	12569300
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.	2003-01-15	12525516
Dramatic response to chemotherapy in oligodendroglial gliomatosis cerebri.	2003-01-14	12525747
Primary intraspinal primitive neuroectodermal tumor: report of two cases and review of the literature.	2003-01	12622449
An elevated serum beta-2-microglobulin level is an adverse prognostic factor for overall survival in patients with early-stage Hodgkin disease.	2002-12-15	12467067
Pulmonary complications in survivors of childhood and adolescent cancer. A report from the Childhood Cancer Survivor Study.	2002-12-01	12436452
Chemoimmunotherapy with bleomycin, vincristine, lomustine, dacarbazine (BOLD), and human leukocyte interferon for metastatic uveal melanoma.	2002-12-01	12436444
Coeliac disease following high-dose chemotherapy.	2002-12	12512973
Recurrent malignant glioma in adults.	2002-12	12392640
Radiotherapy alone for lymphocyte-predominant Hodgkin's disease.	2002-11-06	12416895
Acute diarrhea during adjuvant therapy for rectal cancer: a detailed analysis from a randomized intergroup trial.	2002-10-01	12243815
Phase I study of fotemustine in pediatric patients with refractory brain tumors.	2002-09-15	12216098
Modulation of growth and radiochemosensitivity of human malignant glioma cells by acidosis.	2002-09-01	12209698
Complete response of a recurrent, multicentric malignant glioma in a patient treated with phenylbutyrate.	2002-09	12241121
Neuroprotection by hypoxic preconditioning requires sequential activation of vascular endothelial growth factor receptor and Akt.	2002-08-01	12151519
Intensified PCV-chemotherapy with optional stem cell support in recurrent malignant oligodendroglioma.	2002-08	12195453
Treatment of advanced neuroendocrine tumours using combination chemotherapy with lomustine and 5-fluorouracil.	2002-08	12153595
Hematological toxicity and therapeutic efficacy of lomustine in 20 tumor-bearing cats: critical assessment of a practical dosing regimen.	2002-07-18	12118689
Treatment of intracranial metastatic esthesioneuroblastoma.	2002-07-15	12124822
Concurrent modified PCV chemotherapy and radiotherapy in newly diagnosed grade IV astrocytoma.	2002-05	12125984
NO-mediated chemoresistance in C6 glioma cells.	2002-05	12076959
Evaluation of naphthal-NU, a 2-chloroethylnitrosourea derivative of naphthalimide, as a mixed-function anticancer agent.	2002-03	12071535
[Role of adjuvant chemotherapy in the treatment of medulloblastoma in children].	2002	12455354
Adults with newly diagnosed high-grade gliomas.	2001-12	12057096

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:23:27 GMT 2025` Edited by `admin` on `Mon Mar 31 18:23:27 GMT 2025`
Record UNII	7BRF0Z81KG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CEENU

Preferred Name

English

LOMUSTINE

Official Name

English

LOMUSTINE [USP MONOGRAPH]

Common 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 [EP MONOGRAPH]

Common 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 [USP-RS]

Common Name

English

LOMUSTINE [ORANGE BOOK]

Common Name

English

Lomustine [WHO-DD]

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

NBK548631