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Identification
NameAmsacrine
Accession NumberDB00276  (APRD00064)
TypeSmall Molecule
GroupsApproved
DescriptionAminoacridine derivative that is a potent intercalating antineoplastic agent. It is effective in the treatment of acute leukemias and malignant lymphomas, but has poor activity in the treatment of solid tumors. It is frequently used in combination with other antineoplastic agents in chemotherapy protocols. It produces consistent but acceptable myelosuppression and cardiotoxic effects. [PubChem]
Structure
Thumb
Synonyms
4'-(9-Acridinylamino)-3'-methoxymethanesulfonanilide
4'-(9-Acridinylamino)methanesulfon-m-anisidide
4'-(9-Acridinylamino)methanesulfon-meta-anisidide
4'-(9-Acridinylamino)methanesulphon-m-anisidide
Acridinyl anisidide
Amsacrine
m-AMSA
mAMSA
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Amsa Pd Inj 50mg/mlLiquid50 mgIntravenousErfa Canada 2012 Inc1983-12-31Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AmekrinNot Available
AMSA P-DNot Available
AmsidineNot Available
AmsidylNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII00DPD30SOY
CAS number51264-14-3
WeightAverage: 393.459
Monoisotopic: 393.114712179
Chemical FormulaC21H19N3O3S
InChI KeyXCPGHVQEEXUHNC-UHFFFAOYSA-N
InChI
InChI=1S/C21H19N3O3S/c1-27-20-13-14(24-28(2,25)26)11-12-19(20)23-21-15-7-3-5-9-17(15)22-18-10-6-4-8-16(18)21/h3-13,24H,1-2H3,(H,22,23)
IUPAC Name
N-{4-[(acridin-9-yl)amino]-3-methoxyphenyl}methanesulfonamide
SMILES
COC1=C(NC2=C3C=CC=CC3=NC3=CC=CC=C23)C=CC(NS(C)(=O)=O)=C1
Pharmacology
IndicationFor treatment of acute myeloid leukaemia.
Structured Indications
PharmacodynamicsAmsacrine is an aminoacridine derivative that is a potent intercalating antineoplastic agent. It is effective in the treatment of acute leukemias and malignant lymphomas, but has poor activity in the treatment of solid tumors. It is frequently used in combination with other antineoplastic agents in chemotherapy protocols. It produces consistent but acceptable myelosuppression and cardiotoxic effects.
Mechanism of actionAmsacrine binds to DNA through intercalation and external binding. It has a base specificity for A-T pairs. Rapidly dividing cells are two to four times more sensitive to amsacrine than are resting cells. Amsacrine appears to cleave DNA by inducing double stranded breaks. Amsacrine also targets and inhibits topoisomerase II. Cytotoxicity is greatest during the S phase of the cell cycle when topoisomerase levels are at a maximum.
TargetKindPharmacological actionActionsOrganismUniProt ID
DNANucleotideyes
intercalation
Humannot applicabledetails
DNA topoisomerase 2-alphaProteinyes
inhibitor
HumanP11388 details
Potassium voltage-gated channel subfamily H member 2Proteinunknown
inhibitor
HumanQ12809 details
Related Articles
AbsorptionPoorly absorbed
Volume of distributionNot Available
Protein binding96-98%
Metabolism

Extensive, primarily hepatic, converted to glutathione conjugate.

Route of eliminationNot Available
Half life8-9 hours
ClearanceNot Available
ToxicitySymptoms of overdose include nausea and vomiting, diarrhea, some cardiotoxicity (rarely).
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Amsacrine can be increased when it is combined with Abiraterone.Approved
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Amsacrine.Approved
AcetaminophenThe serum concentration of Acetaminophen can be increased when it is combined with Amsacrine.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Amsacrine.Approved
Acetylsalicylic acidThe serum concentration of Acetylsalicylic acid can be increased when it is combined with Amsacrine.Approved, Vet Approved
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Amsacrine.Approved
AldosteroneThe serum concentration of Aldosterone can be increased when it is combined with Amsacrine.Experimental
AlitretinoinThe serum concentration of Alitretinoin can be increased when it is combined with Amsacrine.Approved, Investigational
ALT-110The risk or severity of adverse effects can be increased when Amsacrine is combined with ALT-110.Investigational
AmbrisentanThe serum concentration of Ambrisentan can be increased when it is combined with Amsacrine.Approved, Investigational
AmiodaroneThe metabolism of Amsacrine can be decreased when combined with Amiodarone.Approved, Investigational
AmitriptylineThe serum concentration of Amitriptyline can be increased when it is combined with Amsacrine.Approved
AnvirzelAnvirzel may decrease the cardiotoxic activities of Amsacrine.Investigational
ApixabanThe serum concentration of Apixaban can be increased when it is combined with Amsacrine.Approved
Arsenic trioxideThe serum concentration of Arsenic trioxide can be increased when it is combined with Amsacrine.Approved, Investigational
ArtemetherThe metabolism of Amsacrine can be decreased when combined with Artemether.Approved
AtazanavirThe serum concentration of Atazanavir can be increased when it is combined with Amsacrine.Approved, Investigational
AtenololThe serum concentration of Atenolol can be increased when it is combined with Amsacrine.Approved
AtomoxetineThe metabolism of Amsacrine can be decreased when combined with Atomoxetine.Approved
AxitinibThe serum concentration of Axitinib can be increased when it is combined with Amsacrine.Approved, Investigational
BcgThe therapeutic efficacy of Bcg can be decreased when used in combination with Amsacrine.Investigational
BetamethasoneThe serum concentration of Betamethasone can be increased when it is combined with Amsacrine.Approved, Vet Approved
BetaxololThe metabolism of Amsacrine can be decreased when combined with Betaxolol.Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Amsacrine.Approved, Investigational
BoceprevirThe serum concentration of Boceprevir can be increased when it is combined with Amsacrine.Approved
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Amsacrine.Approved
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Amsacrine.Approved
BromocriptineThe serum concentration of Bromocriptine can be increased when it is combined with Amsacrine.Approved, Investigational
BupropionThe metabolism of Amsacrine can be decreased when combined with Bupropion.Approved
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Amsacrine.Approved
CaffeineThe serum concentration of Caffeine can be increased when it is combined with Amsacrine.Approved
CamptothecinThe serum concentration of Camptothecin can be increased when it is combined with Amsacrine.Experimental
CanagliflozinThe serum concentration of Canagliflozin can be increased when it is combined with Amsacrine.Approved
CarbamazepineThe serum concentration of Carbamazepine can be increased when it is combined with Amsacrine.Approved, Investigational
CarfilzomibThe serum concentration of Carfilzomib can be increased when it is combined with Amsacrine.Approved
CDX-110The risk or severity of adverse effects can be increased when Amsacrine is combined with CDX-110.Investigational
CelecoxibThe metabolism of Amsacrine can be decreased when combined with Celecoxib.Approved, Investigational
CeritinibThe serum concentration of Ceritinib can be increased when it is combined with Amsacrine.Approved
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Amsacrine.Withdrawn
ChloroquineThe metabolism of Amsacrine can be decreased when combined with Chloroquine.Approved, Vet Approved
ChlorpromazineThe serum concentration of Chlorpromazine can be increased when it is combined with Amsacrine.Approved, Vet Approved
CholecalciferolThe metabolism of Amsacrine can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CimetidineThe serum concentration of Cimetidine can be increased when it is combined with Amsacrine.Approved
CinacalcetThe metabolism of Amsacrine can be decreased when combined with Cinacalcet.Approved
CiprofloxacinThe serum concentration of Ciprofloxacin can be increased when it is combined with Amsacrine.Approved, Investigational
CisplatinThe serum concentration of Cisplatin can be increased when it is combined with Amsacrine.Approved
CitalopramThe serum concentration of Citalopram can be increased when it is combined with Amsacrine.Approved
ClarithromycinThe serum concentration of Clarithromycin can be increased when it is combined with Amsacrine.Approved
ClemastineThe metabolism of Amsacrine can be decreased when combined with Clemastine.Approved
ClobazamThe serum concentration of Clobazam can be increased when it is combined with Amsacrine.Approved, Illicit
ClomifeneThe serum concentration of Clomifene can be increased when it is combined with Amsacrine.Approved, Investigational
ClomipramineThe metabolism of Amsacrine can be decreased when combined with Clomipramine.Approved, Vet Approved
ClonidineThe serum concentration of Clonidine can be increased when it is combined with Amsacrine.Approved
ClopidogrelThe serum concentration of Clopidogrel can be increased when it is combined with Amsacrine.Approved, Nutraceutical
ClotrimazoleThe metabolism of Amsacrine can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe risk or severity of adverse effects can be increased when Amsacrine is combined with Clozapine.Approved
CobicistatThe serum concentration of Amsacrine can be increased when it is combined with Cobicistat.Approved
CobimetinibThe serum concentration of Cobimetinib can be increased when it is combined with Amsacrine.Approved
CocaineThe metabolism of Amsacrine can be decreased when combined with Cocaine.Approved, Illicit
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Amsacrine.Approved
Conjugated Equine EstrogensThe serum concentration of Conjugated Equine Estrogens can be increased when it is combined with Amsacrine.Approved
CrizotinibThe serum concentration of Crizotinib can be increased when it is combined with Amsacrine.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Amsacrine.Approved, Investigational
CyclosporineThe serum concentration of Cyclosporine can be increased when it is combined with Amsacrine.Approved, Investigational, Vet Approved
Dabigatran etexilateThe serum concentration of the active metabolites of Dabigatran etexilate can be increased when Dabigatran etexilate is used in combination with Amsacrine.Approved
DabrafenibThe serum concentration of Dabrafenib can be increased when it is combined with Amsacrine.Approved
DactinomycinThe serum concentration of Dactinomycin can be increased when it is combined with Amsacrine.Approved
DapagliflozinThe serum concentration of Dapagliflozin can be increased when it is combined with Amsacrine.Approved
DarifenacinThe metabolism of Amsacrine can be decreased when combined with Darifenacin.Approved, Investigational
DarunavirThe serum concentration of Amsacrine can be increased when it is combined with Darunavir.Approved
DasatinibThe serum concentration of Dasatinib can be increased when it is combined with Amsacrine.Approved, Investigational
DaunorubicinThe serum concentration of Daunorubicin can be increased when it is combined with Amsacrine.Approved
DebrisoquinThe serum concentration of Debrisoquin can be increased when it is combined with Amsacrine.Approved
DelavirdineThe metabolism of Amsacrine can be decreased when combined with Delavirdine.Approved
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Amsacrine.Approved
DesipramineThe metabolism of Amsacrine can be decreased when combined with Desipramine.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Amsacrine.Approved
DexamethasoneThe serum concentration of Dexamethasone can be increased when it is combined with Amsacrine.Approved, Investigational, Vet Approved
DiazepamThe serum concentration of Diazepam can be increased when it is combined with Amsacrine.Approved, Illicit, Vet Approved
DiethylstilbestrolThe serum concentration of Diethylstilbestrol can be increased when it is combined with Amsacrine.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Amsacrine.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Amsacrine.Approved
DihydrotestosteroneThe serum concentration of Dihydrotestosterone can be increased when it is combined with Amsacrine.Illicit
DiltiazemThe serum concentration of Diltiazem can be increased when it is combined with Amsacrine.Approved
DiphenhydramineThe metabolism of Amsacrine can be decreased when combined with Diphenhydramine.Approved
DipyridamoleThe serum concentration of Dipyridamole can be increased when it is combined with Amsacrine.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Amsacrine.Approved, Investigational
DomperidoneThe serum concentration of Domperidone can be increased when it is combined with Amsacrine.Approved, Investigational, Vet Approved
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Amsacrine.Approved, Investigational
DronedaroneThe metabolism of Amsacrine can be decreased when combined with Dronedarone.Approved
DuloxetineThe metabolism of Amsacrine can be decreased when combined with Duloxetine.Approved
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Amsacrine.Approved
EletriptanThe serum concentration of Eletriptan can be increased when it is combined with Amsacrine.Approved, Investigational
EliglustatThe metabolism of Amsacrine can be decreased when combined with Eliglustat.Approved
EpinastineThe serum concentration of Epinastine can be increased when it is combined with Amsacrine.Approved, Investigational
ErlotinibThe serum concentration of Erlotinib can be increased when it is combined with Amsacrine.Approved, Investigational
ErythromycinThe serum concentration of Erythromycin can be increased when it is combined with Amsacrine.Approved, Vet Approved
EstradiolThe serum concentration of Estradiol can be increased when it is combined with Amsacrine.Approved, Investigational, Vet Approved
EstriolThe serum concentration of Estriol can be increased when it is combined with Amsacrine.Approved, Vet Approved
EstroneThe serum concentration of Estrone can be increased when it is combined with Amsacrine.Approved
Ethinyl EstradiolThe serum concentration of Ethinyl Estradiol can be increased when it is combined with Amsacrine.Approved
EtoposideThe serum concentration of Etoposide can be increased when it is combined with Amsacrine.Approved
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Amsacrine.Approved
EzetimibeThe serum concentration of Ezetimibe can be increased when it is combined with Amsacrine.Approved
FesoterodineThe serum concentration of Fesoterodine can be increased when it is combined with Amsacrine.Approved
FexofenadineThe serum concentration of Fexofenadine can be increased when it is combined with Amsacrine.Approved
FidaxomicinThe serum concentration of Fidaxomicin can be increased when it is combined with Amsacrine.Approved
FingolimodAmsacrine may increase the immunosuppressive activities of Fingolimod.Approved, Investigational
FluoxetineThe metabolism of Amsacrine can be decreased when combined with Fluoxetine.Approved, Vet Approved
Fluticasone furoateThe serum concentration of Fluticasone furoate can be increased when it is combined with Amsacrine.Approved
FluvoxamineThe metabolism of Amsacrine can be decreased when combined with Fluvoxamine.Approved, Investigational
G17DTThe risk or severity of adverse effects can be increased when Amsacrine is combined with G17DT.Investigational
GefitinibThe serum concentration of Gefitinib can be increased when it is combined with Amsacrine.Approved, Investigational
GemcitabineThe serum concentration of Gemcitabine can be increased when it is combined with Amsacrine.Approved
GI-5005The risk or severity of adverse effects can be increased when Amsacrine is combined with GI-5005.Investigational
GrazoprevirThe serum concentration of Grazoprevir can be increased when it is combined with Amsacrine.Approved
GrepafloxacinThe serum concentration of Grepafloxacin can be increased when it is combined with Amsacrine.Withdrawn
HaloperidolThe serum concentration of Haloperidol can be increased when it is combined with Amsacrine.Approved
HydrocortisoneThe serum concentration of Hydrocortisone can be increased when it is combined with Amsacrine.Approved, Vet Approved
IbuprofenThe serum concentration of Ibuprofen can be increased when it is combined with Amsacrine.Approved
IdelalisibThe serum concentration of Idelalisib can be increased when it is combined with Amsacrine.Approved
ImatinibThe serum concentration of Imatinib can be increased when it is combined with Amsacrine.Approved
ImipramineThe serum concentration of Imipramine can be increased when it is combined with Amsacrine.Approved
IndacaterolThe serum concentration of Indacaterol can be increased when it is combined with Amsacrine.Approved
IndinavirThe serum concentration of Indinavir can be increased when it is combined with Amsacrine.Approved
IndomethacinThe serum concentration of Indomethacin can be increased when it is combined with Amsacrine.Approved, Investigational
INGN 201The risk or severity of adverse effects can be increased when Amsacrine is combined with INGN 201.Investigational
INGN 225The risk or severity of adverse effects can be increased when Amsacrine is combined with INGN 225.Investigational
IrinotecanThe serum concentration of Irinotecan can be increased when it is combined with Amsacrine.Approved, Investigational
IsoniazidThe metabolism of Amsacrine can be decreased when combined with Isoniazid.Approved
IvermectinThe serum concentration of Ivermectin can be increased when it is combined with Amsacrine.Approved, Vet Approved
KetazolamThe serum concentration of Ketazolam can be increased when it is combined with Amsacrine.Approved
KetoconazoleThe serum concentration of Ketoconazole can be increased when it is combined with Amsacrine.Approved, Investigational
LamivudineThe serum concentration of Lamivudine can be increased when it is combined with Amsacrine.Approved, Investigational
LamotrigineThe serum concentration of Lamotrigine can be increased when it is combined with Amsacrine.Approved, Investigational
LansoprazoleThe serum concentration of Lansoprazole can be increased when it is combined with Amsacrine.Approved, Investigational
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Amsacrine.Approved
LeflunomideThe risk or severity of adverse effects can be increased when Amsacrine is combined with Leflunomide.Approved, Investigational
LenalidomideThe serum concentration of Lenalidomide can be increased when it is combined with Amsacrine.Approved
LenvatinibThe serum concentration of Lenvatinib can be increased when it is combined with Amsacrine.Approved
LevetiracetamThe serum concentration of Levetiracetam can be increased when it is combined with Amsacrine.Approved, Investigational
LevofloxacinThe serum concentration of Levofloxacin can be increased when it is combined with Amsacrine.Approved, Investigational
LevomilnacipranThe serum concentration of Levomilnacipran can be increased when it is combined with Amsacrine.Approved
LinagliptinThe serum concentration of Linagliptin can be increased when it is combined with Amsacrine.Approved
LoperamideThe serum concentration of Loperamide can be increased when it is combined with Amsacrine.Approved
LopinavirThe metabolism of Amsacrine can be decreased when combined with Lopinavir.Approved
LorcaserinThe metabolism of Amsacrine can be decreased when combined with Lorcaserin.Approved
LosartanThe serum concentration of Losartan can be increased when it is combined with Amsacrine.Approved
LumefantrineThe metabolism of Amsacrine can be decreased when combined with Lumefantrine.Approved
MannitolThe serum concentration of Mannitol can be increased when it is combined with Amsacrine.Approved, Investigational
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Amsacrine.Withdrawn
MethadoneThe metabolism of Amsacrine can be decreased when combined with Methadone.Approved
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Amsacrine.Approved
MethotrimeprazineThe metabolism of Amsacrine can be decreased when combined with Methotrimeprazine.Approved
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Amsacrine.Approved, Vet Approved
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Amsacrine.Approved, Investigational
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Amsacrine.Approved, Illicit
MirabegronThe serum concentration of Mirabegron can be increased when it is combined with Amsacrine.Approved
MitoxantroneThe serum concentration of Mitoxantrone can be increased when it is combined with Amsacrine.Approved, Investigational
MorphineThe serum concentration of Morphine can be increased when it is combined with Amsacrine.Approved, Investigational
Mycophenolate mofetilThe serum concentration of Mycophenolate mofetil can be increased when it is combined with Amsacrine.Approved, Investigational
NadololThe serum concentration of Nadolol can be increased when it is combined with Amsacrine.Approved
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Amsacrine.Approved
NaloxoneThe serum concentration of Naloxone can be increased when it is combined with Amsacrine.Approved, Vet Approved
NatalizumabThe risk or severity of adverse effects can be increased when Amsacrine is combined with Natalizumab.Approved, Investigational
NelfinavirThe serum concentration of Nelfinavir can be increased when it is combined with Amsacrine.Approved
NevirapineThe metabolism of Amsacrine can be decreased when combined with Nevirapine.Approved
NicardipineThe serum concentration of Nicardipine can be increased when it is combined with Amsacrine.Approved
NifedipineThe serum concentration of Nifedipine can be increased when it is combined with Amsacrine.Approved
NilotinibThe serum concentration of Nilotinib can be increased when it is combined with Amsacrine.Approved, Investigational
NintedanibThe serum concentration of Nintedanib can be increased when it is combined with Amsacrine.Approved
NizatidineThe serum concentration of Nizatidine can be increased when it is combined with Amsacrine.Approved
OlanzapineThe serum concentration of Olanzapine can be increased when it is combined with Amsacrine.Approved, Investigational
OmbitasvirThe serum concentration of Ombitasvir can be increased when it is combined with Amsacrine.Approved
OsimertinibThe serum concentration of Osimertinib can be increased when it is combined with Amsacrine.Approved
OuabainOuabain may decrease the cardiotoxic activities of Amsacrine.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Amsacrine.Approved, Vet Approved
PanobinostatThe serum concentration of Amsacrine can be increased when it is combined with Panobinostat.Approved, Investigational
ParoxetineThe metabolism of Amsacrine can be decreased when combined with Paroxetine.Approved, Investigational
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Amsacrine.Approved
Peginterferon alfa-2bThe serum concentration of Amsacrine can be decreased when it is combined with Peginterferon alfa-2b.Approved
PhenobarbitalThe serum concentration of Phenobarbital can be increased when it is combined with Amsacrine.Approved
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Amsacrine.Approved, Vet Approved
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Amsacrine.Approved, Investigational
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Amsacrine.Approved
PomalidomideThe serum concentration of Pomalidomide can be increased when it is combined with Amsacrine.Approved
PonatinibThe serum concentration of Ponatinib can be increased when it is combined with Amsacrine.Approved
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Amsacrine.Approved
PrazosinThe serum concentration of Prazosin can be increased when it is combined with Amsacrine.Approved
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Amsacrine.Approved, Vet Approved
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Amsacrine.Approved, Vet Approved
ProgesteroneThe serum concentration of Progesterone can be increased when it is combined with Amsacrine.Approved, Vet Approved
PromazineThe metabolism of Amsacrine can be decreased when combined with Promazine.Approved, Vet Approved
PropranololThe serum concentration of Propranolol can be increased when it is combined with Amsacrine.Approved, Investigational
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Amsacrine.Approved
QuetiapineThe serum concentration of Quetiapine can be increased when it is combined with Amsacrine.Approved
QuinidineThe metabolism of Amsacrine can be decreased when combined with Quinidine.Approved
QuinineThe serum concentration of Quinine can be increased when it is combined with Amsacrine.Approved
Rabies vaccineThe risk or severity of adverse effects can be increased when Amsacrine is combined with Rabies vaccine.Approved
Rabies vaccineThe therapeutic efficacy of Rabies vaccine can be decreased when used in combination with Amsacrine.Approved
RanitidineThe serum concentration of Ranitidine can be increased when it is combined with Amsacrine.Approved
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Amsacrine.Approved, Investigational
ReserpineThe serum concentration of Reserpine can be increased when it is combined with Amsacrine.Approved
RifampicinThe serum concentration of Rifampicin can be increased when it is combined with Amsacrine.Approved
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Amsacrine.Approved, Investigational
RisperidoneThe serum concentration of Risperidone can be increased when it is combined with Amsacrine.Approved, Investigational
RitonavirThe metabolism of Amsacrine can be decreased when combined with Ritonavir.Approved, Investigational
RivaroxabanThe serum concentration of Rivaroxaban can be increased when it is combined with Amsacrine.Approved
RoflumilastRoflumilast may increase the immunosuppressive activities of Amsacrine.Approved
RolapitantThe metabolism of Amsacrine can be decreased when combined with Rolapitant.Approved
RomidepsinThe serum concentration of Romidepsin can be increased when it is combined with Amsacrine.Approved, Investigational
RopiniroleThe metabolism of Amsacrine can be decreased when combined with Ropinirole.Approved, Investigational
Salicylic acidThe serum concentration of Salicylic acid can be increased when it is combined with Amsacrine.Approved, Vet Approved
SaquinavirThe serum concentration of Saquinavir can be increased when it is combined with Amsacrine.Approved, Investigational
SelexipagThe serum concentration of Selexipag can be increased when it is combined with Amsacrine.Approved
SertralineThe metabolism of Amsacrine can be decreased when combined with Sertraline.Approved
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Amsacrine.Approved
SimeprevirThe serum concentration of Simeprevir can be increased when it is combined with Amsacrine.Approved
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Amsacrine.Approved
SitagliptinThe serum concentration of Sitagliptin can be increased when it is combined with Amsacrine.Approved, Investigational
SofosbuvirThe serum concentration of Sofosbuvir can be increased when it is combined with Amsacrine.Approved
SorafenibThe serum concentration of Sorafenib can be increased when it is combined with Amsacrine.Approved, Investigational
SparfloxacinThe serum concentration of Sparfloxacin can be increased when it is combined with Amsacrine.Approved
SphingosineThe serum concentration of Sphingosine can be increased when it is combined with Amsacrine.Experimental
SRP 299The risk or severity of adverse effects can be increased when Amsacrine is combined with SRP 299.Investigational
StiripentolThe metabolism of Amsacrine can be decreased when combined with Stiripentol.Approved
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Amsacrine.Approved, Investigational
TacrolimusThe serum concentration of Tacrolimus can be increased when it is combined with Amsacrine.Approved, Investigational
TamoxifenThe serum concentration of Tamoxifen can be increased when it is combined with Amsacrine.Approved
Taurocholic AcidThe serum concentration of Taurocholic Acid can be increased when it is combined with Amsacrine.Experimental
Technetium Tc-99m sestamibiThe serum concentration of Technetium Tc-99m sestamibi can be increased when it is combined with Amsacrine.Approved
TelaprevirThe serum concentration of Telaprevir can be increased when it is combined with Amsacrine.Approved
TemsirolimusThe serum concentration of Temsirolimus can be increased when it is combined with Amsacrine.Approved
TerbinafineThe metabolism of Amsacrine can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
TG4010The risk or severity of adverse effects can be increased when Amsacrine is combined with TG4010.Investigational
ThioridazineThe metabolism of Amsacrine can be decreased when combined with Thioridazine.Approved
TicagrelorThe serum concentration of Ticagrelor can be increased when it is combined with Amsacrine.Approved
TiclopidineThe metabolism of Amsacrine can be decreased when combined with Ticlopidine.Approved
TimololThe serum concentration of Timolol can be increased when it is combined with Amsacrine.Approved
TipranavirThe metabolism of Amsacrine can be decreased when combined with Tipranavir.Approved, Investigational
TofacitinibAmsacrine may increase the immunosuppressive activities of Tofacitinib.Approved, Investigational
TolvaptanThe serum concentration of Tolvaptan can be increased when it is combined with Amsacrine.Approved
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Amsacrine.Approved, Investigational
ToremifeneThe serum concentration of Toremifene can be increased when it is combined with Amsacrine.Approved, Investigational
TranylcypromineThe metabolism of Amsacrine can be decreased when combined with Tranylcypromine.Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Amsacrine.Approved, Investigational
Trastuzumab emtansineThe serum concentration of Trastuzumab emtansine can be increased when it is combined with Amsacrine.Approved
UlipristalThe serum concentration of Ulipristal can be increased when it is combined with Amsacrine.Approved
UmeclidiniumThe serum concentration of Umeclidinium can be increased when it is combined with Amsacrine.Approved
VecuroniumThe serum concentration of Vecuronium can be increased when it is combined with Amsacrine.Approved
VenetoclaxThe serum concentration of Venetoclax can be increased when it is combined with Amsacrine.Approved
VenlafaxineThe serum concentration of Venlafaxine can be increased when it is combined with Amsacrine.Approved
VerapamilThe serum concentration of Verapamil can be increased when it is combined with Amsacrine.Approved
VinblastineThe serum concentration of Vinblastine can be increased when it is combined with Amsacrine.Approved
VincristineThe serum concentration of Vincristine can be increased when it is combined with Amsacrine.Approved, Investigational
VismodegibThe serum concentration of Vismodegib can be increased when it is combined with Amsacrine.Approved
ZidovudineThe serum concentration of Zidovudine can be increased when it is combined with Amsacrine.Approved
ZiprasidoneThe metabolism of Amsacrine can be decreased when combined with Ziprasidone.Approved
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General References
  1. Link [Link]
External Links
ATC CodesL01XX01
AHFS Codes
  • 10:00.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (48.7 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.667
Caco-2 permeable+0.5
P-glycoprotein substrateNon-substrate0.766
P-glycoprotein inhibitor INon-inhibitor0.5625
P-glycoprotein inhibitor IINon-inhibitor0.7178
Renal organic cation transporterNon-inhibitor0.8983
CYP450 2C9 substrateNon-substrate0.7427
CYP450 2D6 substrateNon-substrate0.8266
CYP450 3A4 substrateNon-substrate0.5159
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9232
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9051
Ames testAMES toxic0.9107
CarcinogenicityNon-carcinogens0.8098
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.2509 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7711
hERG inhibition (predictor II)Inhibitor0.7355
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
LiquidIntravenous50 mg
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point235 °CPhysProp
water solubility<1 mg/mLNot Available
logP3.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00317 mg/mLALOGPS
logP4.66ALOGPS
logP3.16ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)10.82ChemAxon
pKa (Strongest Basic)8.44ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.32 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity107.69 m3·mol-1ChemAxon
Polarizability41.65 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as acridines. These are organic compounds containing the acridine moiety, a linear tricyclic heterocycle which consists of two benzene rings joined by a pyridine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassBenzoquinolines
Direct ParentAcridines
Alternative Parents
Substituents
  • Acridine
  • Aminoquinoline
  • Sulfanilide
  • Methoxyaniline
  • Methoxybenzene
  • Substituted aniline
  • Phenol ether
  • Anisole
  • Aniline
  • Aminopyridine
  • Alkyl aryl ether
  • Benzenoid
  • Pyridine
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Azacycle
  • Secondary amine
  • Ether
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Targets

1. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
yes
Actions
intercalation
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. Gabelica V, Rosu F, De Pauw E, Antoine R, Tabarin T, Broyer M, Dugourd P: Electron photodetachment dissociation of DNA anions with covalently or noncovalently bound chromophores. J Am Soc Mass Spectrom. 2007 Nov;18(11):1990-2000. Epub 2007 Aug 22. [PubMed:17900923 ]
  4. Capranico G, Guano F, Moro S, Zagotto G, Sissi C, Gatto B, Zunino F, Menta E, Palumbo M: Mapping drug interactions at the covalent topoisomerase II-DNA complex by bisantrene/amsacrine congeners. J Biol Chem. 1998 May 22;273(21):12732-9. [PubMed:9582297 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Ubiquitin binding
Specific Function:
Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks. Essential during mitosis and meiosis for proper segregation of daughter chromosomes. May play a role in regulating the period length of ARNTL/BMAL1 transcriptional oscillation (By similarity).
Gene Name:
TOP2A
Uniprot ID:
P11388
Molecular Weight:
174383.88 Da
References
  1. Finlay GJ, Atwell GJ, Baguley BC: Inhibition of the action of the topoisomerase II poison amsacrine by simple aniline derivatives: evidence for drug-protein interactions. Oncol Res. 1999;11(6):249-54. [PubMed:10691026 ]
  2. Ferlin MG, Marzano C, Chiarelotto G, Baccichetti F, Bordin F: Synthesis and antiproliferative activity of some variously substituted acridine and azacridine derivatives. Eur J Med Chem. 2000 Sep;35(9):827-37. [PubMed:11006484 ]
  3. Matsumoto Y, Takano H, Kunishio K, Nagao S, Fojo T: Hypophosphorylation of topoisomerase IIalpha in etoposide (VP-16)-resistant human carcinoma cell lines associated with carboxy-terminal truncation. Jpn J Cancer Res. 2001 Jul;92(7):799-805. [PubMed:11473732 ]
  4. Lee MS, Wang JC, Beran M: Two independent amsacrine-resistant human myeloid leukemia cell lines share an identical point mutation in the 170 kDa form of human topoisomerase II. J Mol Biol. 1992 Feb 20;223(4):837-43. [PubMed:1311390 ]
  5. Nitiss JL, Liu YX, Harbury P, Jannatipour M, Wasserman R, Wang JC: Amsacrine and etoposide hypersensitivity of yeast cells overexpressing DNA topoisomerase II. Cancer Res. 1992 Aug 15;52(16):4467-72. [PubMed:1322791 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  7. Arimondo P, Boukarim C, Bailly C, Dauzonne D, Monneret C: Design of two etoposide-amsacrine conjugates: topoisomerase II and tubuline polymerization inhibition and relation to cytotoxicity. Anticancer Drug Des. 2000 Dec;15(6):413-21. [PubMed:11716434 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization
Specific Function:
Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the delayed rectifying potassium current in heart (IKr). Isoforms USO have no channel activity by themself, but modulates channel characteristics by forming heterotetramers with other isoforms which are r...
Gene Name:
KCNH2
Uniprot ID:
Q12809
Molecular Weight:
126653.52 Da
References
  1. Thomas D, Hammerling BC, Wu K, Wimmer AB, Ficker EK, Kirsch GE, Kochan MC, Wible BA, Scholz EP, Zitron E, Kathofer S, Kreye VA, Katus HA, Schoels W, Karle CA, Kiehn J: Inhibition of cardiac HERG currents by the DNA topoisomerase II inhibitor amsacrine: mode of action. Br J Pharmacol. 2004 Jun;142(3):485-94. Epub 2004 May 17. [PubMed:15148258 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
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 antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
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 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
References
  1. Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [PubMed:14985103 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23