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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

Molecular Formula C9H16ClN3O2
Molecular Weight 233.695
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Spin-labeled 1-alkyl-1-nitrosourea synergists of antitumor antibiotics.
2001 Aug-Oct
Adults with newly diagnosed high-grade gliomas.
2001 Dec
A possible correlation between unscheduled DNA repair and cholesterolemia in Wistar rat, modulated by vitamin E.
2001 Oct-Dec
[Role of adjuvant chemotherapy in the treatment of medulloblastoma in children].
2002
Structure-based design of nitrosoureas containing tyrosine derivatives as potential antimelanoma agents.
2002 Apr
11q23 balanced chromosome aberrations in treatment-related myelodysplastic syndromes and acute leukemia: report from an international workshop.
2002 Apr
Intensified PCV-chemotherapy with optional stem cell support in recurrent malignant oligodendroglioma.
2002 Aug
Treatment of advanced neuroendocrine tumours using combination chemotherapy with lomustine and 5-fluorouracil.
2002 Aug
Neuroprotection by hypoxic preconditioning requires sequential activation of vascular endothelial growth factor receptor and Akt.
2002 Aug 1
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
Chemoimmunotherapy with bleomycin, vincristine, lomustine, dacarbazine (BOLD), and human leukocyte interferon for metastatic uveal melanoma.
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
Role of radiotherapy in the treatment of supratentorial primitive neuroectodermal tumors in childhood: results of the prospective German brain tumor trials HIT 88/89 and 91.
2002 Feb 1
Preradiation chemotherapy for pediatric patients with high-grade glioma.
2002 Jan 1
Treatment of intracranial metastatic esthesioneuroblastoma.
2002 Jul 15
Hematological toxicity and therapeutic efficacy of lomustine in 20 tumor-bearing cats: critical assessment of a practical dosing regimen.
2002 Jul-Aug
Evaluation of naphthal-NU, a 2-chloroethylnitrosourea derivative of naphthalimide, as a mixed-function anticancer agent.
2002 Mar
Prevention of irradiation-induced glioma cell invasion by temozolomide involves caspase 3 activity and cleavage of focal adhesion kinase.
2002 Mar 15
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
Identification of CD70-mediated apoptosis of immune effector cells as a novel immune escape pathway of human glioblastoma.
2002 May 1
Acute diarrhea during adjuvant therapy for rectal cancer: a detailed analysis from a randomized intergroup trial.
2002 Oct 1
Complete response of a recurrent, multicentric malignant glioma in a patient treated with phenylbutyrate.
2002 Sep
Modulation of growth and radiochemosensitivity of human malignant glioma cells by acidosis.
2002 Sep 1
Phase I study of fotemustine in pediatric patients with refractory brain tumors.
2002 Sep 15
Radiotherapy alone for lymphocyte-predominant Hodgkin's disease.
2002 Sep-Oct
Low-dose continuous chemotherapy for metastatic melanoma: a phase II trial.
2003 Apr
Survival and prognostic factors of patients with unresectable glioblastoma multiforme.
2003 Apr
Partially successful treatment of a patient with chronic lymphocytic leukemia and Hodgkin's disease: case report and literature review.
2003 Apr
Feasibility and toxicity of CCNU therapy in elderly patients with glioblastoma multiforme.
2003 Feb
Survival with dacarbazine and fotemustine in newly diagnosed glioblastoma multiforme.
2003 Feb 24
Primary intraspinal primitive neuroectodermal tumor: report of two cases and review of the literature.
2003 Jan
Dramatic response to chemotherapy in oligodendroglial gliomatosis cerebri.
2003 Jan 14
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
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
Genetic alterations of human brain tumors as molecular prognostic factors.
2003 Mar
Chromosomal anomalies in oligodendroglial tumors are correlated with clinical features.
2003 Mar 1
Glioma treatment, radionecrosis, and growth factors. In regard to Levin et al., IJROBP 2002;53:58-66.
2003 Mar 1
New chemotherapy agents in veterinary medicine.
2003 May
Bleomycin, vincristine, lomustine and dacarbazine (BOLD) in combination with recombinant interferon alpha-2b for metastatic uveal melanoma.
2003 May
Irinotecan in the treatment of glioma patients: current and future studies of the North Central Cancer Treatment Group.
2003 May 1
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.
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:33:23 UTC 2019
Edited
by admin
on Tue Oct 22 00:33:23 UTC 2019
Record UNII
7BRF0Z81KG
Record Status Validated (UNII)
Record Version
  • Download
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
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