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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

1976
89
Targets

Targets

Primary TargetPharmacologyConditionPotency
Binding Agent
907
Brain Neoplasms
Crosslinking Agent
64
Brain Neoplasms
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
RNA
DNA
Approved
7817
GLEOSTINE
Primary
RNA
DNA
Approved
7817
GLEOSTINE
Approved (off-label)
8
PubMed

PubMed

TitleDatePubMed
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
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
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
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
Survival improvement in patients with glioblastoma multiforme during the last 20 years in a single tertiary-care center.
2003 Jun 24
New chemotherapy agents in veterinary medicine.
2003 May
Combined modality therapy for poorly differentiated gliomas of the posterior fossa in children: a Children's Cancer Group report.
2003 May
Bleomycin, vincristine, lomustine and dacarbazine (BOLD) in combination with recombinant interferon alpha-2b for metastatic uveal melanoma.
2003 May
Role of mismatch repair in the induction of chromosomal aberrations and sister chromatid exchanges in cells treated with different chemotherapeutic agents.
2003 Sep
Patents

Patents

JP2003529540A
44
JP2005519871A
24
JP2006528196A
37
JP2008519861A
29
JP2009513567A
58
JP2010506837A
73
JP2011519819A
8
JP2011522802A
27
JP2011524416A
125
JP4787165B2
91

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
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 Mar 06 12:28:48 UTC 2018 , Edited by admin on Tue Mar 06 12:28:48 UTC 2018
NDF-RT N0000000236
Created by admin on Tue Mar 06 12:28:48 UTC 2018 , Edited by admin on Tue Mar 06 12:28:48 UTC 2018
WHO-VATC QL01AD02
Created by admin on Tue Mar 06 12:28:48 UTC 2018 , Edited by admin on Tue Mar 06 12:28:48 UTC 2018
WHO-ATC L01AD02
Created by admin on Tue Mar 06 12:28:48 UTC 2018 , Edited by admin on Tue Mar 06 12:28:48 UTC 2018
NDF-RT N0000175558
Created by admin on Tue Mar 06 12:28:48 UTC 2018 , Edited by admin on Tue Mar 06 12:28:48 UTC 2018
Code System Code Type Description
EVMPD
SUB08567MIG
Created by admin on Tue Mar 06 12:28:48 UTC 2018 , Edited by admin on Tue Mar 06 12:28:48 UTC 2018
PRIMARY
CAS
13010-47-4
Created by admin on Tue Mar 06 12:28:48 UTC 2018 , Edited by admin on Tue Mar 06 12:28:48 UTC 2018
PRIMARY
MERCK INDEX
M6891
Created by admin on Tue Mar 06 12:28:48 UTC 2018 , Edited by admin on Tue Mar 06 12:28:48 UTC 2018
PRIMARY Merck Index
PUBCHEM
3950
Created by admin on Tue Mar 06 12:28:48 UTC 2018 , Edited by admin on Tue Mar 06 12:28:48 UTC 2018
PRIMARY SWITZERF
EPA CompTox
13010-47-4
Created by admin on Tue Mar 06 12:28:48 UTC 2018 , Edited by admin on Tue Mar 06 12:28:48 UTC 2018
PRIMARY
RXCUI
6466
Created by admin on Tue Mar 06 12:28:48 UTC 2018 , Edited by admin on Tue Mar 06 12:28:48 UTC 2018
PRIMARY RxNorm
HSDB
13010-47-4
Created by admin on Tue Mar 06 12:28:48 UTC 2018 , Edited by admin on Tue Mar 06 12:28:48 UTC 2018
PRIMARY
WIKIPEDIA
LOMUSTINE
Created by admin on Tue Mar 06 12:28:48 UTC 2018 , Edited by admin on Tue Mar 06 12:28:48 UTC 2018
PRIMARY
MESH
D008130
Created by admin on Tue Mar 06 12:28:48 UTC 2018 , Edited by admin on Tue Mar 06 12:28:48 UTC 2018
PRIMARY
IUPHAR
7214
Created by admin on Tue Mar 06 12:28:48 UTC 2018 , Edited by admin on Tue Mar 06 12:28:48 UTC 2018
PRIMARY
NCI_THESAURUS
C617
Created by admin on Tue Mar 06 12:28:48 UTC 2018 , Edited by admin on Tue Mar 06 12:28:48 UTC 2018
PRIMARY
DRUG BANK
DB01206
Created by admin on Tue Mar 06 12:28:48 UTC 2018 , Edited by admin on Tue Mar 06 12:28:48 UTC 2018
PRIMARY
ECHA (EC/EINECS)
235-859-2
Created by admin on Tue Mar 06 12:28:48 UTC 2018 , Edited by admin on Tue Mar 06 12:28:48 UTC 2018
PRIMARY
INN
3184
Created by admin on Tue Mar 06 12:28:48 UTC 2018 , Edited by admin on Tue Mar 06 12:28:48 UTC 2018
PRIMARY
ChEMBL
CHEMBL514
Created by admin on Tue Mar 06 12:28:48 UTC 2018 , Edited by admin on Tue Mar 06 12:28:48 UTC 2018
PRIMARY
ACTIVE MOIETY
Structure of LOMUSTINE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
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