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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 KeyInChIKey=XCPGHVQEEXUHNC-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
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
Pharmacology
IndicationFor treatment of acute myeloid leukaemia.
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.
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
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
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)
Interactions
Drug Interactions
Drug
AbirateroneThe metabolism of Amsacrine can be decreased when combined with Abiraterone.
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Amsacrine.
AcetaminophenThe serum concentration of Acetaminophen can be increased when it is combined with Amsacrine.
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Amsacrine.
Acetylsalicylic acidThe serum concentration of Acetylsalicylic acid can be increased when it is combined with Amsacrine.
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Amsacrine.
AldosteroneThe serum concentration of Aldosterone can be increased when it is combined with Amsacrine.
AlitretinoinThe serum concentration of Alitretinoin can be increased when it is combined with Amsacrine.
AmbrisentanThe serum concentration of Ambrisentan can be increased when it is combined with Amsacrine.
AmiodaroneThe metabolism of Amsacrine can be decreased when combined with Amiodarone.
AmitriptylineThe serum concentration of Amitriptyline can be increased when it is combined with Amsacrine.
ApixabanThe serum concentration of Apixaban can be increased when it is combined with Amsacrine.
Arsenic trioxideThe serum concentration of Arsenic trioxide can be increased when it is combined with Amsacrine.
ArtemetherThe metabolism of Amsacrine can be decreased when combined with Artemether.
AtazanavirThe serum concentration of Atazanavir can be increased when it is combined with Amsacrine.
AtenololThe serum concentration of Atenolol can be increased when it is combined with Amsacrine.
AtomoxetineThe metabolism of Amsacrine can be decreased when combined with Atomoxetine.
AxitinibThe serum concentration of Axitinib can be increased when it is combined with Amsacrine.
BetamethasoneThe serum concentration of Betamethasone can be increased when it is combined with Amsacrine.
BetaxololThe metabolism of Amsacrine can be decreased when combined with Betaxolol.
BevacizumabBevacizumab may increase the cardiotoxic activities of Amsacrine.
BoceprevirThe serum concentration of Boceprevir can be increased when it is combined with Amsacrine.
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Amsacrine.
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Amsacrine.
BromocriptineThe serum concentration of Bromocriptine can be increased when it is combined with Amsacrine.
BupropionThe metabolism of Amsacrine can be decreased when combined with Bupropion.
CabazitaxelThe serum concentration of Cabazitaxel can be increased when it is combined with Amsacrine.
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Amsacrine.
CaffeineThe serum concentration of Caffeine can be increased when it is combined with Amsacrine.
CamptothecinThe serum concentration of Camptothecin can be increased when it is combined with Amsacrine.
CanagliflozinThe serum concentration of Canagliflozin can be increased when it is combined with Amsacrine.
CarbamazepineThe serum concentration of Carbamazepine can be increased when it is combined with Amsacrine.
CarfilzomibThe serum concentration of Carfilzomib can be increased when it is combined with Amsacrine.
CelecoxibThe metabolism of Amsacrine can be decreased when combined with Celecoxib.
CeritinibThe serum concentration of Ceritinib can be increased when it is combined with Amsacrine.
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Amsacrine.
ChloroquineThe metabolism of Amsacrine can be decreased when combined with Chloroquine.
ChlorpromazineThe serum concentration of Chlorpromazine can be increased when it is combined with Amsacrine.
ChlorpromazineThe metabolism of Amsacrine can be decreased when combined with Chlorpromazine.
CholecalciferolThe metabolism of Amsacrine can be decreased when combined with Cholecalciferol.
CimetidineThe serum concentration of Cimetidine can be increased when it is combined with Amsacrine.
CimetidineThe metabolism of Amsacrine can be decreased when combined with Cimetidine.
CinacalcetThe metabolism of Amsacrine can be decreased when combined with Cinacalcet.
CiprofloxacinThe serum concentration of Ciprofloxacin can be increased when it is combined with Amsacrine.
CisplatinThe serum concentration of Cisplatin can be increased when it is combined with Amsacrine.
CitalopramThe serum concentration of Citalopram can be increased when it is combined with Amsacrine.
CitalopramThe metabolism of Amsacrine can be decreased when combined with Citalopram.
ClarithromycinThe serum concentration of Clarithromycin can be increased when it is combined with Amsacrine.
ClemastineThe metabolism of Amsacrine can be decreased when combined with Clemastine.
ClobazamThe serum concentration of Clobazam can be increased when it is combined with Amsacrine.
ClobazamThe metabolism of Amsacrine can be decreased when combined with Clobazam.
ClomifeneThe serum concentration of Clomifene can be increased when it is combined with Amsacrine.
ClomipramineThe metabolism of Amsacrine can be decreased when combined with Clomipramine.
ClonidineThe serum concentration of Clonidine can be increased when it is combined with Amsacrine.
ClopidogrelThe serum concentration of Clopidogrel can be increased when it is combined with Amsacrine.
ClotrimazoleThe metabolism of Amsacrine can be decreased when combined with Clotrimazole.
ClozapineThe risk or severity of adverse effects can be increased when Amsacrine is combined with Clozapine.
ClozapineThe metabolism of Amsacrine can be decreased when combined with Clozapine.
CobicistatThe serum concentration of Amsacrine can be increased when it is combined with Cobicistat.
CobimetinibThe serum concentration of Cobimetinib can be increased when it is combined with Amsacrine.
CocaineThe metabolism of Amsacrine can be decreased when combined with Cocaine.
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Amsacrine.
Conjugated Equine EstrogensThe serum concentration of Conjugated Equine Estrogens can be increased when it is combined with Amsacrine.
CrizotinibThe serum concentration of Crizotinib can be increased when it is combined with Amsacrine.
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Amsacrine.
CyclosporineThe serum concentration of Cyclosporine can be increased when it is combined with Amsacrine.
Dabigatran etexilateThe serum concentration of Dabigatran etexilate can be increased when it is combined with Amsacrine.
DabrafenibThe serum concentration of Dabrafenib can be increased when it is combined with Amsacrine.
DactinomycinThe serum concentration of Dactinomycin can be increased when it is combined with Amsacrine.
DapagliflozinThe serum concentration of Dapagliflozin can be increased when it is combined with Amsacrine.
DarifenacinThe metabolism of Amsacrine can be decreased when combined with Darifenacin.
DarunavirThe serum concentration of Amsacrine can be increased when it is combined with Darunavir.
DasatinibThe serum concentration of Dasatinib can be increased when it is combined with Amsacrine.
DaunorubicinThe serum concentration of Daunorubicin can be increased when it is combined with Amsacrine.
DebrisoquinThe serum concentration of Debrisoquin can be increased when it is combined with Amsacrine.
DelavirdineThe metabolism of Amsacrine can be decreased when combined with Delavirdine.
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Amsacrine.
DesipramineThe metabolism of Amsacrine can be decreased when combined with Desipramine.
DeslanosideDeslanoside may decrease the cardiotoxic activities of Amsacrine.
DexamethasoneThe serum concentration of Dexamethasone can be increased when it is combined with Amsacrine.
DiazepamThe serum concentration of Diazepam can be increased when it is combined with Amsacrine.
DiethylstilbestrolThe serum concentration of Diethylstilbestrol can be increased when it is combined with Amsacrine.
DigitoxinDigitoxin may decrease the cardiotoxic activities of Amsacrine.
DigitoxinThe serum concentration of Digitoxin can be increased when it is combined with Amsacrine.
DigoxinDigoxin may decrease the cardiotoxic activities of Amsacrine.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Amsacrine.
DihydrotestosteroneThe serum concentration of Dihydrotestosterone can be increased when it is combined with Amsacrine.
DiltiazemThe serum concentration of Diltiazem can be increased when it is combined with Amsacrine.
DiphenhydramineThe metabolism of Amsacrine can be decreased when combined with Diphenhydramine.
DipyridamoleThe serum concentration of Dipyridamole can be increased when it is combined with Amsacrine.
DocetaxelThe serum concentration of Docetaxel can be increased when it is combined with Amsacrine.
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Amsacrine.
DomperidoneThe serum concentration of Domperidone can be increased when it is combined with Amsacrine.
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Amsacrine.
DronedaroneThe metabolism of Amsacrine can be decreased when combined with Dronedarone.
DuloxetineThe metabolism of Amsacrine can be decreased when combined with Duloxetine.
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Amsacrine.
EletriptanThe serum concentration of Eletriptan can be increased when it is combined with Amsacrine.
EliglustatThe metabolism of Amsacrine can be decreased when combined with Eliglustat.
EpinastineThe serum concentration of Epinastine can be increased when it is combined with Amsacrine.
ErlotinibThe serum concentration of Erlotinib can be increased when it is combined with Amsacrine.
ErythromycinThe serum concentration of Erythromycin can be increased when it is combined with Amsacrine.
EstradiolThe serum concentration of Estradiol can be increased when it is combined with Amsacrine.
EstriolThe serum concentration of Estriol can be increased when it is combined with Amsacrine.
EstroneThe serum concentration of Estrone can be increased when it is combined with Amsacrine.
Ethinyl EstradiolThe serum concentration of Ethinyl Estradiol can be increased when it is combined with Amsacrine.
EtoposideThe serum concentration of Etoposide can be increased when it is combined with Amsacrine.
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Amsacrine.
EzetimibeThe serum concentration of Ezetimibe can be increased when it is combined with Amsacrine.
FesoterodineThe serum concentration of Fesoterodine can be increased when it is combined with Amsacrine.
FexofenadineThe serum concentration of Fexofenadine can be increased when it is combined with Amsacrine.
FidaxomicinThe serum concentration of Fidaxomicin can be increased when it is combined with Amsacrine.
FingolimodAmsacrine may increase the immunosuppressive activities of Fingolimod.
FluoxetineThe metabolism of Amsacrine can be decreased when combined with Fluoxetine.
Fluticasone furoateThe serum concentration of Fluticasone furoate can be increased when it is combined with Amsacrine.
FluvoxamineThe metabolism of Amsacrine can be decreased when combined with Fluvoxamine.
GefitinibThe serum concentration of Gefitinib can be increased when it is combined with Amsacrine.
GemcitabineThe serum concentration of Gemcitabine can be increased when it is combined with Amsacrine.
GrazoprevirThe serum concentration of Grazoprevir can be increased when it is combined with Amsacrine.
GrepafloxacinThe serum concentration of Grepafloxacin can be increased when it is combined with Amsacrine.
HaloperidolThe serum concentration of Haloperidol can be increased when it is combined with Amsacrine.
HaloperidolThe metabolism of Amsacrine can be decreased when combined with Haloperidol.
HydrocortisoneThe serum concentration of Hydrocortisone can be increased when it is combined with Amsacrine.
IbuprofenThe serum concentration of Ibuprofen can be increased when it is combined with Amsacrine.
IdelalisibThe serum concentration of Idelalisib can be increased when it is combined with Amsacrine.
ImatinibThe serum concentration of Imatinib can be increased when it is combined with Amsacrine.
ImipramineThe serum concentration of Imipramine can be increased when it is combined with Amsacrine.
ImipramineThe metabolism of Amsacrine can be decreased when combined with Imipramine.
IndacaterolThe serum concentration of Indacaterol can be increased when it is combined with Amsacrine.
IndinavirThe serum concentration of Indinavir can be increased when it is combined with Amsacrine.
IndinavirThe metabolism of Amsacrine can be decreased when combined with Indinavir.
IndomethacinThe serum concentration of Indomethacin can be increased when it is combined with Amsacrine.
IrinotecanThe serum concentration of Irinotecan can be increased when it is combined with Amsacrine.
IsoniazidThe metabolism of Amsacrine can be decreased when combined with Isoniazid.
IvermectinThe serum concentration of Ivermectin can be increased when it is combined with Amsacrine.
KetazolamThe serum concentration of Ketazolam can be increased when it is combined with Amsacrine.
KetoconazoleThe serum concentration of Ketoconazole can be increased when it is combined with Amsacrine.
KetoconazoleThe metabolism of Amsacrine can be decreased when combined with Ketoconazole.
LamivudineThe serum concentration of Lamivudine can be increased when it is combined with Amsacrine.
LamotrigineThe serum concentration of Lamotrigine can be increased when it is combined with Amsacrine.
LansoprazoleThe serum concentration of Lansoprazole can be increased when it is combined with Amsacrine.
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Amsacrine.
LeflunomideThe risk or severity of adverse effects can be increased when Amsacrine is combined with Leflunomide.
LenalidomideThe serum concentration of Lenalidomide can be increased when it is combined with Amsacrine.
LenvatinibThe serum concentration of Lenvatinib can be increased when it is combined with Amsacrine.
LevetiracetamThe serum concentration of Levetiracetam can be increased when it is combined with Amsacrine.
LevofloxacinThe serum concentration of Levofloxacin can be increased when it is combined with Amsacrine.
LevomilnacipranThe serum concentration of Levomilnacipran can be increased when it is combined with Amsacrine.
LinagliptinThe serum concentration of Linagliptin can be increased when it is combined with Amsacrine.
LoperamideThe serum concentration of Loperamide can be increased when it is combined with Amsacrine.
LopinavirThe metabolism of Amsacrine can be decreased when combined with Lopinavir.
LorcaserinThe metabolism of Amsacrine can be decreased when combined with Lorcaserin.
LosartanThe serum concentration of Losartan can be increased when it is combined with Amsacrine.
LumefantrineThe metabolism of Amsacrine can be decreased when combined with Lumefantrine.
MannitolThe serum concentration of Mannitol can be increased when it is combined with Amsacrine.
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Amsacrine.
MethadoneThe metabolism of Amsacrine can be decreased when combined with Methadone.
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Amsacrine.
MethotrimeprazineThe metabolism of Amsacrine can be decreased when combined with Methotrimeprazine.
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Amsacrine.
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Amsacrine.
MetoprololThe metabolism of Amsacrine can be decreased when combined with Metoprolol.
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Amsacrine.
MirabegronThe serum concentration of Mirabegron can be increased when it is combined with Amsacrine.
MirabegronThe metabolism of Amsacrine can be decreased when combined with Mirabegron.
MitoxantroneThe serum concentration of Mitoxantrone can be increased when it is combined with Amsacrine.
MorphineThe serum concentration of Morphine can be increased when it is combined with Amsacrine.
Mycophenolate mofetilThe serum concentration of Mycophenolate mofetil can be increased when it is combined with Amsacrine.
NadololThe serum concentration of Nadolol can be increased when it is combined with Amsacrine.
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Amsacrine.
NaloxoneThe serum concentration of Naloxone can be increased when it is combined with Amsacrine.
NatalizumabThe risk or severity of adverse effects can be increased when Amsacrine is combined with Natalizumab.
NelfinavirThe serum concentration of Nelfinavir can be increased when it is combined with Amsacrine.
NevirapineThe metabolism of Amsacrine can be decreased when combined with Nevirapine.
NicardipineThe serum concentration of Nicardipine can be increased when it is combined with Amsacrine.
NicardipineThe metabolism of Amsacrine can be decreased when combined with Nicardipine.
NifedipineThe serum concentration of Nifedipine can be increased when it is combined with Amsacrine.
NilotinibThe serum concentration of Nilotinib can be increased when it is combined with Amsacrine.
NilotinibThe metabolism of Amsacrine can be decreased when combined with Nilotinib.
NintedanibThe serum concentration of Nintedanib can be increased when it is combined with Amsacrine.
NizatidineThe serum concentration of Nizatidine can be increased when it is combined with Amsacrine.
OlanzapineThe serum concentration of Olanzapine can be increased when it is combined with Amsacrine.
OmbitasvirThe serum concentration of Ombitasvir can be increased when it is combined with Amsacrine.
OsimertinibThe serum concentration of Osimertinib can be increased when it is combined with Amsacrine.
OuabainOuabain may decrease the cardiotoxic activities of Amsacrine.
PaclitaxelThe serum concentration of Paclitaxel can be increased when it is combined with Amsacrine.
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Amsacrine.
PanobinostatThe serum concentration of Panobinostat can be increased when it is combined with Amsacrine.
PanobinostatThe metabolism of Amsacrine can be decreased when combined with Panobinostat.
ParoxetineThe metabolism of Amsacrine can be decreased when combined with Paroxetine.
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Amsacrine.
Peginterferon alfa-2bThe serum concentration of Amsacrine can be decreased when it is combined with Peginterferon alfa-2b.
PhenobarbitalThe serum concentration of Phenobarbital can be increased when it is combined with Amsacrine.
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Amsacrine.
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Amsacrine.
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Amsacrine.
PomalidomideThe serum concentration of Pomalidomide can be increased when it is combined with Amsacrine.
PonatinibThe serum concentration of Ponatinib can be increased when it is combined with Amsacrine.
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Amsacrine.
PrazosinThe serum concentration of Prazosin can be increased when it is combined with Amsacrine.
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Amsacrine.
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Amsacrine.
ProgesteroneThe serum concentration of Progesterone can be increased when it is combined with Amsacrine.
PromazineThe metabolism of Amsacrine can be decreased when combined with Promazine.
PropranololThe serum concentration of Propranolol can be increased when it is combined with Amsacrine.
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Amsacrine.
QuetiapineThe serum concentration of Quetiapine can be increased when it is combined with Amsacrine.
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Amsacrine.
QuinidineThe metabolism of Amsacrine can be decreased when combined with Quinidine.
QuinineThe serum concentration of Quinine can be increased when it is combined with Amsacrine.
QuinineThe metabolism of Amsacrine can be decreased when combined with Quinine.
Rabies vaccineThe risk or severity of adverse effects can be increased when Amsacrine is combined with Rabies vaccine.
RanitidineThe serum concentration of Ranitidine can be increased when it is combined with Amsacrine.
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Amsacrine.
RanolazineThe metabolism of Amsacrine can be decreased when combined with Ranolazine.
ReserpineThe serum concentration of Reserpine can be increased when it is combined with Amsacrine.
RifampicinThe serum concentration of Rifampicin can be increased when it is combined with Amsacrine.
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Amsacrine.
RisperidoneThe serum concentration of Risperidone can be increased when it is combined with Amsacrine.
RitonavirThe serum concentration of Ritonavir can be increased when it is combined with Amsacrine.
RitonavirThe metabolism of Amsacrine can be decreased when combined with Ritonavir.
RivaroxabanThe serum concentration of Rivaroxaban can be increased when it is combined with Amsacrine.
RoflumilastRoflumilast may increase the immunosuppressive activities of Amsacrine.
RolapitantThe metabolism of Amsacrine can be decreased when combined with Rolapitant.
RomidepsinThe serum concentration of Romidepsin can be increased when it is combined with Amsacrine.
RopiniroleThe metabolism of Amsacrine can be decreased when combined with Ropinirole.
Salicylic acidThe serum concentration of Salicylic acid can be increased when it is combined with Amsacrine.
SaquinavirThe serum concentration of Saquinavir can be increased when it is combined with Amsacrine.
SelexipagThe serum concentration of Selexipag can be increased when it is combined with Amsacrine.
SertralineThe metabolism of Amsacrine can be decreased when combined with Sertraline.
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Amsacrine.
SimeprevirThe serum concentration of Simeprevir can be increased when it is combined with Amsacrine.
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Amsacrine.
SitagliptinThe serum concentration of Sitagliptin can be increased when it is combined with Amsacrine.
SofosbuvirThe serum concentration of Sofosbuvir can be increased when it is combined with Amsacrine.
SorafenibThe serum concentration of Sorafenib can be increased when it is combined with Amsacrine.
SparfloxacinThe serum concentration of Sparfloxacin can be increased when it is combined with Amsacrine.
SphingosineThe serum concentration of Sphingosine can be increased when it is combined with Amsacrine.
StiripentolThe metabolism of Amsacrine can be decreased when combined with Stiripentol.
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Amsacrine.
TacrolimusThe serum concentration of Tacrolimus can be increased when it is combined with Amsacrine.
TamoxifenThe serum concentration of Tamoxifen can be increased when it is combined with Amsacrine.
Taurocholic AcidThe serum concentration of Taurocholic Acid can be increased when it is combined with Amsacrine.
Technetium Tc-99m sestamibiThe serum concentration of Technetium Tc-99m sestamibi can be increased when it is combined with Amsacrine.
TelaprevirThe serum concentration of Telaprevir can be increased when it is combined with Amsacrine.
TemsirolimusThe serum concentration of Temsirolimus can be increased when it is combined with Amsacrine.
TerbinafineThe metabolism of Amsacrine can be decreased when combined with Terbinafine.
ThioridazineThe metabolism of Amsacrine can be decreased when combined with Thioridazine.
TicagrelorThe serum concentration of Ticagrelor can be increased when it is combined with Amsacrine.
TiclopidineThe metabolism of Amsacrine can be decreased when combined with Ticlopidine.
TimololThe serum concentration of Timolol can be increased when it is combined with Amsacrine.
TipranavirThe metabolism of Amsacrine can be decreased when combined with Tipranavir.
TofacitinibAmsacrine may increase the immunosuppressive activities of Tofacitinib.
TolvaptanThe serum concentration of Tolvaptan can be increased when it is combined with Amsacrine.
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Amsacrine.
ToremifeneThe serum concentration of Toremifene can be increased when it is combined with Amsacrine.
TranylcypromineThe metabolism of Amsacrine can be decreased when combined with Tranylcypromine.
TrastuzumabTrastuzumab may increase the neutropenic activities of Amsacrine.
Trastuzumab emtansineThe serum concentration of Trastuzumab emtansine can be increased when it is combined with Amsacrine.
UlipristalThe serum concentration of Ulipristal can be increased when it is combined with Amsacrine.
UmeclidiniumThe serum concentration of Umeclidinium can be increased when it is combined with Amsacrine.
VecuroniumThe serum concentration of Vecuronium can be increased when it is combined with Amsacrine.
VenlafaxineThe serum concentration of Venlafaxine can be increased when it is combined with Amsacrine.
VenlafaxineThe metabolism of Amsacrine can be decreased when combined with Venlafaxine.
VerapamilThe serum concentration of Verapamil can be increased when it is combined with Amsacrine.
VinblastineThe serum concentration of Vinblastine can be increased when it is combined with Amsacrine.
VincristineThe serum concentration of Vincristine can be increased when it is combined with Amsacrine.
VismodegibThe serum concentration of Vismodegib can be increased when it is combined with Amsacrine.
ZidovudineThe serum concentration of Zidovudine can be increased when it is combined with Amsacrine.
ZiprasidoneThe metabolism of Amsacrine can be decreased when combined with Ziprasidone.
Food InteractionsNot Available

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