Identification

Name
Lomustine
Accession Number
DB01206  (APRD00292)
Type
Small Molecule
Groups
Approved
Description

An alkylating agent of value against both hematologic malignancies and solid tumors. [PubChem]

Structure
Thumb
Synonyms
  • 1-(2-Chloroethyl)-3-cyclohexyl-1-nitrosourea
  • 1-(2-Chloroethyl)-3-cyclohexylnitrosourea
  • Belustine
  • Cecenu
  • Chloroethylcyclohexylnitrosourea
  • CINU
  • Cyclohexyl chloroethyl nitrosourea
  • Lomustina
  • Lomustinum
  • N-(2-Chloroethyl)-n'-cyclohexyl-N-nitrosourea
External IDs
NSC-79037
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CeenuCapsule, gelatin coated10 mg/1OralE.R. Squibb & Sons, L.L.C.2008-12-152016-04-15Us
CeenuCapsule40 mgOralBristol Myers Squibb1976-12-31Not applicableCanada
CeenuCapsule, gelatin coated40 mg/1OralE.R. Squibb & Sons, L.L.C.2008-12-152016-04-15Us
CeenuCapsule10 mgOralBristol Myers Squibb1976-12-31Not applicableCanada
CeenuCapsule100 mgOralBristol Myers Squibb1976-12-31Not applicableCanada
GleostineCapsule, gelatin coated10 mg/1OralNext Source Biotechnology, Llc2014-08-18Not applicableUs
GleostineCapsule, gelatin coated5 mg/1OralNext Source Biotechnology, Llc2015-11-05Not applicableUs
GleostineCapsule, gelatin coated40 mg/1OralNext Source Biotechnology, Llc2014-08-18Not applicableUs
GleostineCapsule, gelatin coated100 mg/1OralNext Source Biotechnology, Llc2014-08-18Not applicableUs
LomustineCapsule, gelatin coated40 mg/1OralNext Source Biotechnology, Llc2014-07-292016-01-16Us
International/Other Brands
Belustine / CCNU / Cecenu / CeeNU
Categories
UNII
7BRF0Z81KG
CAS number
13010-47-4
Weight
Average: 233.695
Monoisotopic: 233.093104478
Chemical Formula
C9H16ClN3O2
InChI Key
GQYIWUVLTXOXAJ-UHFFFAOYSA-N
InChI
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)
IUPAC Name
3-(2-chloroethyl)-1-cyclohexyl-3-nitrosourea
SMILES
ClCCN(N=O)C(=O)NC1CCCCC1

Pharmacology

Indication

For the treatment of primary and metastatic brain tumors as a component of combination chemotherapy in addition to appropriate surgical and/or radiotherapeutic procedures. Also used in combination with other agents as secondary therapy for the treatment of refractory or relapsed Hodgkin's disease.

Structured Indications
Pharmacodynamics

Lomustine is an alkylating agent of the nitrosourea type. Lomustine and its metabolites interferes with the function of DNA and RNA. It is cell cycle–phase nonspecific. Cancers form when some cells within the body multiply uncontrollably and abnormally. These cells then spread and destroy nearby tissues. Lomustine acts by slowing this process down. It kills cancer cells by damaging the DNA (the genetic material inside the cells) and stops them from dividing.

Mechanism of action

Lomustine is a highly lipophilic nitrosourea compound which undergoes hydrolysis in vivo to form reactive metabolites. These metabolites cause alkylation and cross-linking of DNA (at the O6 position of guanine-containing bases) and RNA, thus inducing cytotoxicity. Other biologic effects include inhibition of DNA synthesis and some cell cycle phase specificity. Nitrosureas generally lack cross-resistance with other alkylating agents. As lomustine is a nitrosurea, it may also inhibit several key processes such as carbamoylation and modification of cellular proteins.

TargetActionsOrganism
ADNA
cross-linking/alkylation
Human
UStathmin-4
antagonist
Human
Absorption

Well and rapidly absorbed from the gastrointestinal tract.

Volume of distribution
Not Available
Protein binding

50%

Metabolism

Hepatic. Rapid and complete, with active metabolites.

Route of elimination

Following oral administration of radioactive CeeNU at doses ranging from 30 mg/m2 to 100 mg/m2, about half of the radioactivity given was excreted in the urine in the form of degradation products within 24 hours.

Half life

Approximately 94 minutes, however the metabolites have a serum half-life of 16 to 48 hours.

Clearance
Not Available
Toxicity

Oral, rat: LD50 = 70 mg/kg. Pulmonary toxicity has been reported at cumulative doses usually greater than 1,100 mg/m2. There is one report of pulmonary toxicity at a cumulative dose of only 600 mg. The onset of toxicity has varied from 6 months after initiation of therapy, to as late as 15 years after.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Lomustine can be increased when it is combined with Abiraterone.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Lomustine.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Lomustine.Experimental
AmiodaroneThe metabolism of Lomustine can be decreased when combined with Amiodarone.Approved, Investigational
ArtemetherThe metabolism of Lomustine can be decreased when combined with Artemether.Approved
AtomoxetineThe metabolism of Lomustine can be decreased when combined with Atomoxetine.Approved
AtorvastatinThe risk or severity of adverse effects can be increased when Lomustine is combined with Atorvastatin.Approved
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Lomustine.Investigational
BetaxololThe metabolism of Lomustine can be decreased when combined with Betaxolol.Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Lomustine.Approved, Investigational
BromocriptineThe risk or severity of adverse effects can be increased when Bromocriptine is combined with Lomustine.Approved, Investigational
BupropionThe metabolism of Lomustine can be decreased when combined with Bupropion.Approved
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Lomustine.Approved
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Lomustine.Approved
CelecoxibThe metabolism of Lomustine can be decreased when combined with Celecoxib.Approved, Investigational
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Lomustine.Withdrawn
ChloroquineThe metabolism of Lomustine can be decreased when combined with Chloroquine.Approved, Vet Approved
ChlorpromazineThe metabolism of Lomustine can be decreased when combined with Chlorpromazine.Approved, Vet Approved
CholecalciferolThe metabolism of Lomustine can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CimetidineThe metabolism of Lomustine can be decreased when combined with Cimetidine.Approved
CinacalcetThe metabolism of Lomustine can be decreased when combined with Cinacalcet.Approved
CitalopramThe metabolism of Lomustine can be decreased when combined with Citalopram.Approved
ClemastineThe metabolism of Lomustine can be decreased when combined with Clemastine.Approved
ClobazamThe metabolism of Lomustine can be decreased when combined with Clobazam.Approved, Illicit
ClomipramineThe metabolism of Lomustine can be decreased when combined with Clomipramine.Approved, Vet Approved
Clostridium tetani toxoid antigen (formaldehyde inactivated)The therapeutic efficacy of Clostridium tetani toxoid antigen (formaldehyde inactivated) can be decreased when used in combination with Lomustine.Approved
ClotrimazoleThe metabolism of Lomustine can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe risk or severity of adverse effects can be increased when Lomustine is combined with Clozapine.Approved
CobicistatThe serum concentration of Lomustine can be increased when it is combined with Cobicistat.Approved
CocaineThe metabolism of Lomustine can be decreased when combined with Cocaine.Approved, Illicit
Corynebacterium diphtheriae toxoid antigen (formaldehyde inactivated)The therapeutic efficacy of Corynebacterium diphtheriae toxoid antigen (formaldehyde inactivated) can be decreased when used in combination with Lomustine.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Lomustine.Approved, Investigational
CymarinCymarin may decrease the cardiotoxic activities of Lomustine.Experimental
DarifenacinThe metabolism of Lomustine can be decreased when combined with Darifenacin.Approved, Investigational
DarunavirThe serum concentration of Lomustine can be increased when it is combined with Darunavir.Approved
DelavirdineThe metabolism of Lomustine can be decreased when combined with Delavirdine.Approved
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Lomustine.Approved
DesipramineThe metabolism of Lomustine can be decreased when combined with Desipramine.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Lomustine.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Lomustine.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Lomustine.Approved
Digoxin Immune Fab (Ovine)Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Lomustine.Approved
DihydroergocornineThe risk or severity of adverse effects can be increased when Dihydroergocornine is combined with Lomustine.Approved
DihydroergocristineThe risk or severity of adverse effects can be increased when Dihydroergocristine is combined with Lomustine.Experimental
DihydroergocryptineThe risk or severity of adverse effects can be increased when Dihydroergocryptine is combined with Lomustine.Experimental
DihydroergotamineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Lomustine.Approved
DiphenhydramineThe metabolism of Lomustine can be decreased when combined with Diphenhydramine.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Lomustine.Approved, Investigational
DosulepinThe metabolism of Lomustine can be decreased when combined with Dosulepin.Approved
DronedaroneThe metabolism of Lomustine can be decreased when combined with Dronedarone.Approved
DuloxetineThe metabolism of Lomustine can be decreased when combined with Duloxetine.Approved
EliglustatThe metabolism of Lomustine can be decreased when combined with Eliglustat.Approved
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Lomustine.Approved
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Lomustine.Approved
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Lomustine.Approved
FingolimodLomustine may increase the immunosuppressive activities of Fingolimod.Approved, Investigational
FluoxetineThe metabolism of Lomustine can be decreased when combined with Fluoxetine.Approved, Vet Approved
FluvastatinThe serum concentration of Fluvastatin can be increased when it is combined with Lomustine.Approved
FluvoxamineThe metabolism of Lomustine can be decreased when combined with Fluvoxamine.Approved, Investigational
G17DTThe therapeutic efficacy of G17DT can be decreased when used in combination with Lomustine.Investigational
GI-5005The therapeutic efficacy of GI-5005 can be decreased when used in combination with Lomustine.Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of Lomustine.Experimental
HaloperidolThe metabolism of Lomustine can be decreased when combined with Haloperidol.Approved
Hepatitis A VaccineThe therapeutic efficacy of Hepatitis A Vaccine can be decreased when used in combination with Lomustine.Approved
Hepatitis B Vaccine (Recombinant)The therapeutic efficacy of Hepatitis B Vaccine (Recombinant) can be decreased when used in combination with Lomustine.Approved, Withdrawn
ImipramineThe metabolism of Lomustine can be decreased when combined with Imipramine.Approved
IndinavirThe metabolism of Lomustine can be decreased when combined with Indinavir.Approved
INGN 201The therapeutic efficacy of INGN 201 can be decreased when used in combination with Lomustine.Investigational
INGN 225The therapeutic efficacy of INGN 225 can be decreased when used in combination with Lomustine.Investigational
IsoniazidThe metabolism of Lomustine can be decreased when combined with Isoniazid.Approved
KetoconazoleThe metabolism of Lomustine can be decreased when combined with Ketoconazole.Approved, Investigational
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Lomustine.Experimental
LeflunomideThe risk or severity of adverse effects can be increased when Lomustine is combined with Leflunomide.Approved, Investigational
LisurideThe risk or severity of adverse effects can be increased when Lisuride is combined with Lomustine.Approved, Investigational
LopinavirThe metabolism of Lomustine can be decreased when combined with Lopinavir.Approved
LorcaserinThe metabolism of Lomustine can be decreased when combined with Lorcaserin.Approved
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Lomustine.Approved, Investigational
LumefantrineThe metabolism of Lomustine can be decreased when combined with Lumefantrine.Approved
Lysergic Acid DiethylamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Lomustine.Illicit, Investigational, Withdrawn
ManidipineThe metabolism of Lomustine can be decreased when combined with Manidipine.Approved, Investigational
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Lomustine.Investigational, Withdrawn
MetergolineThe risk or severity of adverse effects can be increased when Metergoline is combined with Lomustine.Experimental
MethadoneThe metabolism of Lomustine can be decreased when combined with Methadone.Approved
MethotrimeprazineThe metabolism of Lomustine can be decreased when combined with Methotrimeprazine.Approved
MethylergometrineThe risk or severity of adverse effects can be increased when Methylergometrine is combined with Lomustine.Approved
MethysergideThe risk or severity of adverse effects can be increased when Methysergide is combined with Lomustine.Approved
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Lomustine.Experimental
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Lomustine.Approved, Investigational
MevastatinThe serum concentration of Mevastatin can be increased when it is combined with Lomustine.Experimental
MidostaurinThe metabolism of Lomustine can be decreased when combined with Midostaurin.Approved
MirabegronThe metabolism of Lomustine can be decreased when combined with Mirabegron.Approved
NatalizumabThe risk or severity of adverse effects can be increased when Lomustine is combined with Natalizumab.Approved, Investigational
NevirapineThe metabolism of Lomustine can be decreased when combined with Nevirapine.Approved
NicardipineThe metabolism of Lomustine can be decreased when combined with Nicardipine.Approved
NicergolineThe risk or severity of adverse effects can be increased when Nicergoline is combined with Lomustine.Approved, Investigational
NilotinibThe metabolism of Lomustine can be decreased when combined with Nilotinib.Approved, Investigational
OleandrinOleandrin may decrease the cardiotoxic activities of Lomustine.Experimental, Investigational
OuabainOuabain may decrease the cardiotoxic activities of Lomustine.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Lomustine.Approved, Vet Approved
PanobinostatThe serum concentration of Lomustine can be increased when it is combined with Panobinostat.Approved, Investigational
ParoxetineThe metabolism of Lomustine can be decreased when combined with Paroxetine.Approved, Investigational
Peginterferon alfa-2bThe serum concentration of Lomustine can be decreased when it is combined with Peginterferon alfa-2b.Approved
PergolideThe risk or severity of adverse effects can be increased when Pergolide is combined with Lomustine.Approved, Investigational, Vet Approved, Withdrawn
PeruvosidePeruvoside may decrease the cardiotoxic activities of Lomustine.Experimental
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Lomustine.Approved, Investigational
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Lomustine.Approved
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Lomustine.Approved
PromazineThe metabolism of Lomustine can be decreased when combined with Promazine.Approved, Vet Approved
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Lomustine.Experimental
QuinidineThe metabolism of Lomustine can be decreased when combined with Quinidine.Approved
QuinineThe metabolism of Lomustine can be decreased when combined with Quinine.Approved
Rabies virus inactivated antigen, AThe risk or severity of adverse effects can be increased when Lomustine is combined with Rabies virus inactivated antigen, A.Approved
Rabies virus inactivated antigen, AThe therapeutic efficacy of Rabies virus inactivated antigen, A can be decreased when used in combination with Lomustine.Approved
RanolazineThe metabolism of Lomustine can be decreased when combined with Ranolazine.Approved, Investigational
RindopepimutThe therapeutic efficacy of Rindopepimut can be decreased when used in combination with Lomustine.Investigational
RitonavirThe metabolism of Lomustine can be decreased when combined with Ritonavir.Approved, Investigational
RoflumilastRoflumilast may increase the immunosuppressive activities of Lomustine.Approved
RolapitantThe metabolism of Lomustine can be decreased when combined with Rolapitant.Approved
RopiniroleThe metabolism of Lomustine can be decreased when combined with Ropinirole.Approved, Investigational
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Lomustine.Approved
Rotavirus VaccineThe therapeutic efficacy of Rotavirus Vaccine can be decreased when used in combination with Lomustine.Approved
Rubella virus vaccineThe therapeutic efficacy of Rubella virus vaccine can be decreased when used in combination with Lomustine.Approved
Salmonella typhi ty21a live antigenThe therapeutic efficacy of Salmonella typhi ty21a live antigen can be decreased when used in combination with Lomustine.Approved
SertralineThe metabolism of Lomustine can be decreased when combined with Sertraline.Approved
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Lomustine.Approved
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Lomustine.Approved
SRP 299The therapeutic efficacy of SRP 299 can be decreased when used in combination with Lomustine.Investigational
StiripentolThe metabolism of Lomustine can be decreased when combined with Stiripentol.Approved
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Lomustine.Approved, Investigational
TecemotideThe therapeutic efficacy of Tecemotide can be decreased when used in combination with Lomustine.Investigational
TerbinafineThe metabolism of Lomustine can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
TergurideThe risk or severity of adverse effects can be increased when Terguride is combined with Lomustine.Experimental
TG4010The therapeutic efficacy of TG4010 can be decreased when used in combination with Lomustine.Investigational
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Lomustine.Approved, Withdrawn
TiclopidineThe metabolism of Lomustine can be decreased when combined with Ticlopidine.Approved
TipranavirThe metabolism of Lomustine can be decreased when combined with Tipranavir.Approved, Investigational
TofacitinibLomustine may increase the immunosuppressive activities of Tofacitinib.Approved, Investigational
TranylcypromineThe metabolism of Lomustine can be decreased when combined with Tranylcypromine.Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Lomustine.Approved, Investigational
UbidecarenoneThe serum concentration of Ubidecarenone can be increased when it is combined with Lomustine.Approved, Experimental
VenlafaxineThe metabolism of Lomustine can be decreased when combined with Venlafaxine.Approved
Yellow fever vaccineThe therapeutic efficacy of Yellow fever vaccine can be decreased when used in combination with Lomustine.Approved
ZiprasidoneThe metabolism of Lomustine can be decreased when combined with Ziprasidone.Approved
Zoster vaccineThe therapeutic efficacy of Zoster vaccine can be decreased when used in combination with Lomustine.Approved
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB15337
KEGG Drug
D00363
KEGG Compound
C07079
PubChem Compound
3950
PubChem Substance
46506562
ChemSpider
3813
ChEBI
6520
ChEMBL
CHEMBL514
Therapeutic Targets Database
DAP000991
PharmGKB
PA164749407
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Lomustine
ATC Codes
L01AD02 — Lomustine
AHFS Codes
  • 10:00.00 — Antineoplastic Agents
MSDS
Download (56.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentGliomas1
1CompletedTreatmentBone Marrow Suppression / Brain and Central Nervous System Tumors / Drug/Agent Toxicity by Tissue/Organ1
1CompletedTreatmentMelanoma / Neoplasms, Brain1
1CompletedTreatmentNeoplasms, Brain / Recurrent Glioblastoma1
1CompletedTreatmentNeoplasms, Brain / Tumors, Central Nervous System1
1TerminatedTreatmentLeptomeningeal Metastasis From Malignant Melanoma1
1TerminatedTreatmentMalignant Glioma (WHO Grade III or IV)1
1, 2Active Not RecruitingTreatmentMedulloblastomas1
1, 2Active Not RecruitingTreatmentRelapsed/Recurrent GBM (Phase 2) / Solid Tumors (Phase 1)1
1, 2CompletedTreatmentRecurrent Glioblastoma Multiforme (rGBM)1
1, 2TerminatedTreatmentGlioblastomas1
2Active Not RecruitingTreatmentGlioblastoma Multiforme2
2Active Not RecruitingTreatmentGlioblastomas1
2Active Not RecruitingTreatmentNeoplasms, Brain / Tumors, Central Nervous System1
2CompletedTreatmentAnaplastic Astrocytoma (AA) / Glioblastomas1
2CompletedTreatmentAnaplastic Glioma of Brain / Brain Cancer / Glioblastoma Multiforme1
2CompletedTreatmentBrain Cancer / Glioblastomas1
2CompletedTreatmentBrain and Central Nervous System Tumors2
2CompletedTreatmentGlioblastomas1
2CompletedTreatmentIntraocular Melanoma / Melanoma (Skin)1
2CompletedTreatmentLung Cancers1
2CompletedTreatmentMalignant Lymphomas3
2Not Yet RecruitingTreatmentUntreated Childhood Medulloblastoma1
2RecruitingTreatmentAIDS-Related Diffuse Large Cell Lymphoma / AIDS-Related Diffuse Mixed Cell Lymphoma / AIDS-Related Diffuse Small Cleaved Cell Lymphoma / AIDS-related Immunoblastic Large Cell Lymphoma / AIDS-Related Lymphoblastic Lymphoma / AIDS-related Peripheral/Systemic Lymphoma / AIDS-related Small Noncleaved Cell Lymphoma / Stage III AIDS-related Lymphoma / Stage IV AIDS-related Lymphoma1
2RecruitingTreatmentAnaplastic Astrocytoma (AA) / Glioblastomas / Malignant Neoplasms of Eye Brain and Other Parts of Central Nervous System1
2RecruitingTreatmentGlioblastoma Multiforme1
2RecruitingTreatmentMalignant Gliomas1
2TerminatedTreatmentMalignant Lymphomas1
2TerminatedTreatmentMedulloblastomas / Neoplasms, Brain / Primitive Neuroectodermal Tumor / Tumors, Central Nervous System1
2Unknown StatusTreatmentBrain and Central Nervous System Tumors2
2Unknown StatusTreatmentPrimary Non Hodgkin Lymphoma of the Central Nervous System1
2Unknown StatusTreatmentRecurrent Glioblastoma Multiforme1
2WithdrawnTreatmentMalignant Lymphomas1
2WithdrawnTreatmentMelanoma / Neoplasms, Brain1
2, 3Active Not RecruitingTreatmentBrain and Central Nervous System Tumors1
2, 3Not Yet RecruitingTreatmentGBM / Glioblastoma Multiforme / Glioblastoma, Adult / Glioblastomas / Recurrent Brain Tumors1
2, 3RecruitingTreatmentAnaplastic Astrocytoma (AA) / Glioblastoma Multiforme1
2, 3RecruitingTreatmentNeoplasms, Brain1
3Active Not RecruitingTreatmentBrain and Central Nervous System Tumors1
3Active Not RecruitingTreatmentCognition Disorders / Disability Evaluation / Glioblastoma Multiforme1
3CompletedTreatmentBrain and Central Nervous System Tumors3
3CompletedTreatmentGlioblastomas3
3CompletedTreatmentLeukemia Acute Myeloid Leukemia (AML)1
3CompletedTreatmentNeoplasms, Brain / Tumors, Central Nervous System2
3CompletedTreatmentNeoplasms, Brain / Tumors, Central Nervous System / Untreated Childhood Medulloblastoma1
3RecruitingTreatmentAnaplastic Astrocytoma (AA) / Recurrent Anaplastic Astrocytoma1
3RecruitingTreatmentBrain and Central Nervous System Tumors1
3TerminatedTreatmentAnaplastic Astrocytoma (AA) / Glioblastomas1
3Unknown StatusTreatmentBrain and Central Nervous System Tumors3
3Unknown StatusTreatmentMultiple Myeloma and Plasma Cell Neoplasm1
Not AvailableActive Not RecruitingTreatmentBrain and Central Nervous System Tumors1
Not AvailableActive Not RecruitingTreatmentMalignant Lymphomas1
Not AvailableCompletedTreatmentBrain and Central Nervous System Tumors1
Not AvailableNot Yet RecruitingTreatmentRecurrent High-grade Glioma1
Not AvailableRecruitingDiagnosticRecurrent Glioblastoma1
Not AvailableRecruitingTreatmentMedulloblastomas1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
CapsuleOral10 mg
CapsuleOral100 mg
CapsuleOral40 mg
Capsule, gelatin coatedOral10 mg/1
Capsule, gelatin coatedOral40 mg/1
Capsule, gelatin coatedOral5 mg/1
Capsule, gelatin coatedOral100 mg/1
Prices
Unit descriptionCostUnit
Ceenu 100 mg capsule60.61USD capsule
Ceenu 40 mg capsule31.88USD capsule
CeeNU 300 mg capsule31.69USD capsule
Ceenu dose pack30.47USD each
Ceenu 10 mg capsule10.77USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)88-90 °CPhysProp
water solubility111 mg/LNot Available
logP2.83HANSCH,C & LEO,AJ (1985)
Predicted Properties
PropertyValueSource
Water Solubility0.755 mg/mLALOGPS
logP2.62ALOGPS
logP2.16ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)13.3ChemAxon
pKa (Strongest Basic)-5.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area61.77 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity58.65 m3·mol-1ChemAxon
Polarizability23.61 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9962
Blood Brain Barrier+0.9383
Caco-2 permeable-0.5443
P-glycoprotein substrateNon-substrate0.6803
P-glycoprotein inhibitor INon-inhibitor0.837
P-glycoprotein inhibitor IINon-inhibitor0.8642
Renal organic cation transporterNon-inhibitor0.7664
CYP450 2C9 substrateNon-substrate0.763
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.651
CYP450 1A2 substrateNon-inhibitor0.8127
CYP450 2C9 inhibitorNon-inhibitor0.829
CYP450 2D6 inhibitorNon-inhibitor0.9159
CYP450 2C19 inhibitorNon-inhibitor0.7446
CYP450 3A4 inhibitorNon-inhibitor0.8499
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.789
Ames testAMES toxic0.9309
CarcinogenicityCarcinogens 0.5074
BiodegradationNot ready biodegradable0.7517
Rat acute toxicity3.5549 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.8183
hERG inhibition (predictor II)Non-inhibitor0.8735
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as nitrosoureas. These are compounds containing a nitro group and an urea group N-N linked together, with the general structure R1N(R2)C(=O)N(R3)N=O.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Organic carbonic acids and derivatives
Sub Class
Ureas
Direct Parent
Nitrosoureas
Alternative Parents
Semicarbazides / Nitrosamides / Organopnictogen compounds / Organochlorides / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds / Alkyl chlorides
Substituents
Nitrosourea / Semicarbazide / Nitrosamide / Organic n-nitroso compound / Organic nitroso compound / Organic oxygen compound / Organopnictogen compound / Organic oxide / Hydrocarbon derivative / Alkyl chloride
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
organochlorine compound, N-nitrosoureas (CHEBI:6520)

Targets

1. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
Yes
Actions
Cross-linking/alkylation
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Larkin JM, Hughes SA, Beirne DA, Patel PM, Gibbens IM, Bate SC, Thomas K, Eisen TG, Gore ME: A phase I/II study of lomustine and temozolomide in patients with cerebral metastases from malignant melanoma. Br J Cancer. 2007 Jan 15;96(1):44-8. Epub 2006 Dec 5. [PubMed:17146474]
  4. Spiro T, Liu L, Gerson S: New cytotoxic agents for the treatment of metastatic malignant melanoma: temozolomide and related alkylating agents in combination with guanine analogues to abrogate drug resistance. Forum (Genova). 2000 Jul-Sep;10(3):274-85. [PubMed:11007934]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Tubulin binding
Specific Function
Exhibits microtubule-destabilizing activity.
Gene Name
STMN4
Uniprot ID
Q9H169
Uniprot Name
Stathmin-4
Molecular Weight
22071.02 Da
References
  1. Liang XJ, Choi Y, Sackett DL, Park JK: Nitrosoureas inhibit the stathmin-mediated migration and invasion of malignant glioma cells. Cancer Res. 2008 Jul 1;68(13):5267-72. doi: 10.1158/0008-5472.CAN-07-6482. [PubMed:18593927]
  2. Wu WW, Wang G, Liang XJ, Park JK, Shen RF: Covalent modification of stathmin by CCNU determined by FTMS analysis of modified proteins and tryptic peptides. Biochem Biophys Res Commun. 2008 Feb 29;367(1):7-13. Epub 2007 Dec 26. [PubMed:18162179]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Drug created on June 13, 2005 07:24 / Updated on November 19, 2017 20:33