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
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)
DescriptionCurator's Comment: description was created based on several sources, including:
https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=7f77526b-4c40-409c-82ea-d0f934d89cc2
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 |
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Target ID: CHEMBL2311221 |
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Target ID: CHEMBL2311222 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | GLEOSTINE Approved UseCeeNU 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 Date2.07964799E11 |
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Primary | GLEOSTINE Approved UseCeeNU 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 Date2.07964799E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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8.6 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3966974 |
20 mg/kg single, oral dose: 20 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
LOMUSTINE plasma | Mus musculus population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
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2 ng/mL |
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 |
---|---|---|---|---|
705 μg × min/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3966974 |
20 mg/kg single, oral dose: 20 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
LOMUSTINE plasma | Mus musculus population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
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50% |
LOMUSTINE plasma | Homo sapiens |
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 Co-administed with:: etoposide, i.v(1 g/m2) Sources: ara-C, i.v(4g/m2) melphalan(140 mg/m2) |
unhealthy, 36 n = 2 Health Status: unhealthy Condition: Lymphoma Age Group: 36 Population Size: 2 Sources: |
DLT: Gastrointestinal toxicity, Sinusoidal obstruction syndrome... Dose limiting toxicities: Gastrointestinal toxicity (grade 4, 50%) Sources: Sinusoidal obstruction syndrome (grade 4, 50%) |
300 mg/m2 single, oral MTD Dose: 300 mg/m2 Route: oral Route: single Dose: 300 mg/m2 Co-administed with:: etoposide, i.v(1 g/m2) Sources: ara-C, i.v(4g/m2) melphalan(140 mg/m2) |
unhealthy, 36 n = 6 Health Status: unhealthy Condition: Lymphoma Age Group: 36 Population Size: 6 Sources: |
DLT: Neurotoxicity... Dose limiting toxicities: Neurotoxicity (grade 4, 33.3%) Sources: |
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Brain tumors|Hodgkin’s lymphoma Sources: Page: p.1 |
Disc. AE: Myelosuppression, Pulmonary toxicity... AEs leading to discontinuation/dose reduction: Myelosuppression (grade 5) Sources: Page: p.1Pulmonary toxicity Pulmonary fibrosis Acute leukemia Myelodysplasia Hepatotoxicity Nephrotoxicity Fetal damage |
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 Co-administed with:: etoposide, i.v(1 g/m2) Sources: ara-C, i.v(4g/m2) melphalan(140 mg/m2) |
unhealthy, 36 n = 2 Health Status: unhealthy Condition: Lymphoma Age Group: 36 Population Size: 2 Sources: |
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 Co-administed with:: etoposide, i.v(1 g/m2) Sources: ara-C, i.v(4g/m2) melphalan(140 mg/m2) |
unhealthy, 36 n = 2 Health Status: unhealthy Condition: Lymphoma Age Group: 36 Population Size: 2 Sources: |
Neurotoxicity | grade 4, 33.3% DLT |
300 mg/m2 single, oral MTD Dose: 300 mg/m2 Route: oral Route: single Dose: 300 mg/m2 Co-administed with:: etoposide, i.v(1 g/m2) Sources: ara-C, i.v(4g/m2) melphalan(140 mg/m2) |
unhealthy, 36 n = 6 Health Status: unhealthy Condition: Lymphoma Age Group: 36 Population Size: 6 Sources: |
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Brain tumors|Hodgkin’s lymphoma Sources: Page: p.1 |
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Brain tumors|Hodgkin’s lymphoma Sources: Page: p.1 |
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Brain tumors|Hodgkin’s lymphoma Sources: Page: p.1 |
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Brain tumors|Hodgkin’s lymphoma Sources: Page: p.1 |
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Brain tumors|Hodgkin’s lymphoma Sources: Page: p.1 |
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Brain tumors|Hodgkin’s lymphoma Sources: Page: p.1 |
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Brain tumors|Hodgkin’s lymphoma Sources: Page: p.1 |
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Brain tumors|Hodgkin’s lymphoma Sources: Page: p.1 |
PubMed
Title | Date | PubMed |
---|---|---|
[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 |
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Adenovirus-mediated expression of HSV1-TK or Fas ligand induces cell death in primary human glioma-derived cell cultures that are resistant to the chemotherapeutic agent CCNU. | 2001 Aug |
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Melanoma-associated retinopathy: does autoimmunity prolong survival? | 2001 Aug |
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Adults with newly diagnosed high-grade gliomas. | 2001 Dec |
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Incidence, cost, and outcomes of bleeding and chemotherapy dose modification among solid tumor patients with chemotherapy-induced thrombocytopenia. | 2001 Feb 15 |
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Bleomycin, lomustine, cyclophosphamide, vincristine, procarbazine and prednisone (BLEO-CCVPP) in patients with Hodgkin's disease who relapsed after radiotherapy alone: a long-term follow-up study of the Eastern Cooperative Oncology Group (E3481). | 2001 Jan |
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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 |
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Retrolective cohort study of an additive therapy with an oral enzyme preparation in patients with multiple myeloma. | 2001 Jul |
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Bleomycin, methotrexate, and CCNU in locally advanced or recurrent, inoperable, squamous-cell carcinoma of the vulva: an EORTC Gynaecological Cancer Cooperative Group Study. European Organization for Research and Treatment of Cancer. | 2001 Jun |
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PCV chemotherapy for recurrent glioblastoma multiforme. | 2001 Jun 26 |
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[Therapeutic effect on glioblastoma of chemotherapy on the basis of brain irradiation]. | 2001 Mar |
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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 |
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Medical Research Council adjuvant trial in high-grade gliomas. | 2001 Oct 1 |
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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 |
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Neuroprotection by hypoxic preconditioning requires sequential activation of vascular endothelial growth factor receptor and Akt. | 2002 Aug 1 |
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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 |
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High expression levels of collagenase-1 and stromelysin-1 correlate with shorter disease-free survival in human metastatic melanoma. | 2002 Feb 1 |
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Treatment of intracranial metastatic esthesioneuroblastoma. | 2002 Jan 1 |
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Treatment of intracranial metastatic esthesioneuroblastoma. | 2002 Jul 15 |
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Evaluation of naphthal-NU, a 2-chloroethylnitrosourea derivative of naphthalimide, as a mixed-function anticancer agent. | 2002 Mar |
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Concurrent modified PCV chemotherapy and radiotherapy in newly diagnosed grade IV astrocytoma. | 2002 May |
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NO-mediated chemoresistance in C6 glioma cells. | 2002 May |
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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 |
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Dramatic response to chemotherapy in oligodendroglial gliomatosis cerebri. | 2003 Jan 14 |
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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 |
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Irinotecan in the treatment of glioma patients: current and future studies of the North Central Cancer Treatment Group. | 2003 May 1 |
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Role of mismatch repair in the induction of chromosomal aberrations and sister chromatid exchanges in cells treated with different chemotherapeutic agents. | 2003 Sep |
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Lomustine is available in 5 mg, 10 mg, 40 mg, and 100 mg capsules.
In individuals with compromised bone marrow function, the dose should be reduced to 100 mg/m2 every 6 weeks.
Recommended dose in adult and pediatric patients is 130 mg/m2 orally every 6 weeks.
Route of Administration:
Oral
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/6228232
Curator's Comment: A single dose of Lomustine (40 mg/kg) caused a significant reduction in hepatic mixed-function oxidase activities within 3 days after administration
http://www.ncbi.nlm.nih.gov/pubmed/6722931
Alkylation of the nuclear matrix by Lomustine was 1.27 pmoles drug/micrograms protein, whereas carbamoylation by Lomustine was 32.5 pmoles/micrograms.
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LIVERTOX |
NBK548631
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NCI_THESAURUS |
C699
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N0000000236
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QL01AD02
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L01AD02
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N0000175558
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6519
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LOMUSTINE
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DB01206
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ACTIVE MOIETY