You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameCamptothecin
Accession NumberDB04690
TypeSmall Molecule
GroupsExperimental
DescriptionAn alkaloid isolated from the stem wood of the Chinese tree, Camptotheca acuminata. This compound selectively inhibits the nuclear enzyme DNA topoisomerase, type I. Several semisynthetic analogs of camptothecin have demonstrated antitumor activity. [PubChem]
Structure
Thumb
Synonyms
(+)-camptothecin
(+)-camptothecine
(s)-(+)-camptothecin
(s)-camptothecin
20(S)-Camptothecin
21,22-Secocamptothecin-21-oic acid lactone
Camptothecine
D-camptothecin
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIXT3Z54Z28A
CAS number7689-03-4
WeightAverage: 348.352
Monoisotopic: 348.11100701
Chemical FormulaC20H16N2O4
InChI KeyVSJKWCGYPAHWDS-FQEVSTJZSA-N
InChI
InChI=1S/C20H16N2O4/c1-2-20(25)14-8-16-17-12(7-11-5-3-4-6-15(11)21-17)9-22(16)18(23)13(14)10-26-19(20)24/h3-8,25H,2,9-10H2,1H3/t20-/m0/s1
IUPAC Name
(19S)-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione
SMILES
CC[C@@]1(O)C(=O)OCC2=C1C=C1N(CC3=CC4=CC=CC=C4N=C13)C2=O
Pharmacology
IndicationInvestigated for the treatment of cancer.
Structured Indications Not Available
PharmacodynamicsCamptothecin demonstrated strong anticancer activity in preliminary clinical trials but also low solubility and adverse drug reaction. Camptothecin is believed to be a potent topoisomerase inhibitor that interferes with the essential function of topoisomerase in DNA replication.
Mechanism of actionCamptothecin binds to the topoisomerase I and DNA complex (the covalent complex) resulting in a ternary complex, and thereby stabilizing it. This prevents DNA relegation and therefore causes DNA damage which results in apoptosis.
TargetKindPharmacological actionActionsOrganismUniProt ID
DNA topoisomerase 1ProteinunknownNot AvailableHumanP11387 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityAcute oral toxicity (LD50) in mouse: 50.1 mg/kg
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcetaminophenThe serum concentration of Camptothecin can be increased when it is combined with Acetaminophen.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Camptothecin.Approved
AfatinibThe serum concentration of Camptothecin can be increased when it is combined with Afatinib.Approved
AlbendazoleThe serum concentration of Camptothecin can be increased when it is combined with Albendazole.Approved, Vet Approved
AldosteroneThe serum concentration of Camptothecin can be decreased when it is combined with Aldosterone.Experimental
AlectinibThe serum concentration of Camptothecin can be increased when it is combined with Alectinib.Approved
AlfentanilThe serum concentration of Camptothecin can be increased when it is combined with Alfentanil.Approved, Illicit
AmantadineThe serum concentration of Camptothecin can be increased when it is combined with Amantadine.Approved
Aminohippuric acidThe serum concentration of Camptothecin can be increased when it is combined with Aminohippuric acid.Approved
AmiodaroneThe serum concentration of Camptothecin can be decreased when it is combined with Amiodarone.Approved, Investigational
AmitriptylineThe serum concentration of Camptothecin can be increased when it is combined with Amitriptyline.Approved
AmlodipineThe serum concentration of Camptothecin can be increased when it is combined with Amlodipine.Approved
AmprenavirThe serum concentration of Camptothecin can be decreased when it is combined with Amprenavir.Approved
AmsacrineThe serum concentration of Camptothecin can be increased when it is combined with Amsacrine.Approved
AnvirzelAnvirzel may decrease the cardiotoxic activities of Camptothecin.Investigational
AstemizoleThe serum concentration of Camptothecin can be increased when it is combined with Astemizole.Approved, Withdrawn
AtazanavirThe serum concentration of Camptothecin can be increased when it is combined with Atazanavir.Approved, Investigational
AtenololThe serum concentration of Camptothecin can be increased when it is combined with Atenolol.Approved
AtorvastatinThe serum concentration of Camptothecin can be increased when it is combined with Atorvastatin.Approved
AzelastineThe serum concentration of Camptothecin can be increased when it is combined with Azelastine.Approved
AzithromycinThe serum concentration of Camptothecin can be increased when it is combined with Azithromycin.Approved
BenzocaineThe serum concentration of Camptothecin can be increased when it is combined with Benzocaine.Approved
BepridilThe serum concentration of Camptothecin can be increased when it is combined with Bepridil.Approved, Withdrawn
BevacizumabBevacizumab may increase the cardiotoxic activities of Camptothecin.Approved, Investigational
BiperidenThe serum concentration of Camptothecin can be increased when it is combined with Biperiden.Approved
BosutinibThe serum concentration of Camptothecin can be increased when it is combined with Bosutinib.Approved
BromocriptineThe serum concentration of Camptothecin can be increased when it is combined with Bromocriptine.Approved, Investigational
BuprenorphineThe serum concentration of Camptothecin can be increased when it is combined with Buprenorphine.Approved, Illicit, Investigational, Vet Approved
BuspironeThe serum concentration of Camptothecin can be increased when it is combined with Buspirone.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Camptothecin.Approved
CaffeineThe serum concentration of Camptothecin can be increased when it is combined with Caffeine.Approved
CanagliflozinThe serum concentration of Camptothecin can be increased when it is combined with Canagliflozin.Approved
CandesartanThe serum concentration of Camptothecin can be increased when it is combined with Candesartan.Approved
CaptoprilThe serum concentration of Camptothecin can be increased when it is combined with Captopril.Approved
CarbamazepineThe serum concentration of Camptothecin can be decreased when it is combined with Carbamazepine.Approved, Investigational
CarvedilolThe serum concentration of Camptothecin can be increased when it is combined with Carvedilol.Approved, Investigational
CaspofunginThe serum concentration of Camptothecin can be increased when it is combined with Caspofungin.Approved
ChloroquineThe serum concentration of Camptothecin can be increased when it is combined with Chloroquine.Approved, Vet Approved
ChlorpromazineThe serum concentration of Camptothecin can be increased when it is combined with Chlorpromazine.Approved, Vet Approved
ChlorpropamideThe serum concentration of Camptothecin can be increased when it is combined with Chlorpropamide.Approved
ChlorprothixeneThe serum concentration of Camptothecin can be increased when it is combined with Chlorprothixene.Approved, Withdrawn
CholesterolThe serum concentration of Camptothecin can be increased when it is combined with Cholesterol.Experimental
Cholic AcidThe serum concentration of Camptothecin can be decreased when it is combined with Cholic Acid.Approved
CilazaprilThe serum concentration of Camptothecin can be increased when it is combined with Cilazapril.Approved
CimetidineThe serum concentration of Camptothecin can be decreased when it is combined with Cimetidine.Approved
CiprofloxacinThe serum concentration of Camptothecin can be increased when it is combined with Ciprofloxacin.Approved, Investigational
CitalopramThe serum concentration of Camptothecin can be increased when it is combined with Citalopram.Approved
ClarithromycinThe serum concentration of Camptothecin can be increased when it is combined with Clarithromycin.Approved
ClofazimineThe serum concentration of Camptothecin can be increased when it is combined with Clofazimine.Approved, Investigational
ClomipramineThe serum concentration of Camptothecin can be increased when it is combined with Clomipramine.Approved, Vet Approved
ClotrimazoleThe serum concentration of Camptothecin can be decreased when it is combined with Clotrimazole.Approved, Vet Approved
CobicistatThe serum concentration of Camptothecin can be increased when it is combined with Cobicistat.Approved
ColchicineThe serum concentration of Camptothecin can be increased when it is combined with Colchicine.Approved
ColforsinThe serum concentration of Camptothecin can be increased when it is combined with Colforsin.Experimental
CrizotinibThe serum concentration of Camptothecin can be increased when it is combined with Crizotinib.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Camptothecin.Approved, Investigational
CyclosporineThe serum concentration of Camptothecin can be decreased when it is combined with Cyclosporine.Approved, Investigational, Vet Approved
DaclatasvirThe serum concentration of Camptothecin can be increased when it is combined with Daclatasvir.Approved
DactinomycinThe serum concentration of Camptothecin can be increased when it is combined with Dactinomycin.Approved
DasatinibThe serum concentration of Camptothecin can be increased when it is combined with Dasatinib.Approved, Investigational
DaunorubicinThe serum concentration of Camptothecin can be decreased when it is combined with Daunorubicin.Approved
DesipramineThe serum concentration of Camptothecin can be increased when it is combined with Desipramine.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Camptothecin.Approved
DesloratadineThe serum concentration of Camptothecin can be increased when it is combined with Desloratadine.Approved, Investigational
DexamethasoneThe serum concentration of Camptothecin can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DextromethorphanThe serum concentration of Camptothecin can be increased when it is combined with Dextromethorphan.Approved
DiclofenacThe serum concentration of Camptothecin can be increased when it is combined with Diclofenac.Approved, Vet Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Camptothecin.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Camptothecin.Approved
DihydroergotamineThe serum concentration of Camptothecin can be increased when it is combined with Dihydroergotamine.Approved
DiltiazemThe serum concentration of Camptothecin can be increased when it is combined with Diltiazem.Approved
DipyridamoleThe serum concentration of Camptothecin can be increased when it is combined with Dipyridamole.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Camptothecin.Approved, Investigational
DoxazosinThe serum concentration of Camptothecin can be increased when it is combined with Doxazosin.Approved
DoxepinThe serum concentration of Camptothecin can be increased when it is combined with Doxepin.Approved
DoxorubicinThe serum concentration of Camptothecin can be decreased when it is combined with Doxorubicin.Approved, Investigational
DronabinolThe serum concentration of Camptothecin can be increased when it is combined with Dronabinol.Approved, Illicit
DronedaroneThe serum concentration of Camptothecin can be increased when it is combined with Dronedarone.Approved
ElbasvirThe serum concentration of Camptothecin can be increased when it is combined with Elbasvir.Approved
EltrombopagThe serum concentration of Camptothecin can be increased when it is combined with Eltrombopag.Approved
EnalaprilThe serum concentration of Camptothecin can be increased when it is combined with Enalapril.Approved, Vet Approved
EnzalutamideThe serum concentration of Camptothecin can be increased when it is combined with Enzalutamide.Approved
ErgonovineThe serum concentration of Camptothecin can be increased when it is combined with Ergonovine.Approved
ErgotamineThe serum concentration of Camptothecin can be increased when it is combined with Ergotamine.Approved
ErythromycinThe serum concentration of Camptothecin can be decreased when it is combined with Erythromycin.Approved, Vet Approved
EstramustineThe serum concentration of Camptothecin can be increased when it is combined with Estramustine.Approved
EstriolThe serum concentration of Camptothecin can be decreased when it is combined with Estriol.Approved, Vet Approved
EstroneThe serum concentration of Camptothecin can be decreased when it is combined with Estrone.Approved
EtoposideThe serum concentration of Camptothecin can be increased when it is combined with Etoposide.Approved
EtravirineThe serum concentration of Camptothecin can be increased when it is combined with Etravirine.Approved
FelodipineThe serum concentration of Camptothecin can be increased when it is combined with Felodipine.Approved, Investigational
FentanylThe serum concentration of Camptothecin can be increased when it is combined with Fentanyl.Approved, Illicit, Investigational, Vet Approved
FexofenadineThe serum concentration of Camptothecin can be increased when it is combined with Fexofenadine.Approved
FidaxomicinThe serum concentration of Camptothecin can be increased when it is combined with Fidaxomicin.Approved
FluconazoleThe serum concentration of Camptothecin can be increased when it is combined with Fluconazole.Approved
FluoxetineThe serum concentration of Camptothecin can be increased when it is combined with Fluoxetine.Approved, Vet Approved
FlupentixolThe serum concentration of Camptothecin can be increased when it is combined with Flupentixol.Approved, Withdrawn
FluphenazineThe serum concentration of Camptothecin can be increased when it is combined with Fluphenazine.Approved
FlurazepamThe serum concentration of Camptothecin can be increased when it is combined with Flurazepam.Approved, Illicit
FluvoxamineThe serum concentration of Camptothecin can be increased when it is combined with Fluvoxamine.Approved, Investigational
GefitinibThe serum concentration of Camptothecin can be increased when it is combined with Gefitinib.Approved, Investigational
GenisteinThe serum concentration of Camptothecin can be increased when it is combined with Genistein.Investigational
GlyburideThe serum concentration of Camptothecin can be increased when it is combined with Glyburide.Approved
GlycerolThe serum concentration of Camptothecin can be increased when it is combined with Glycerol.Experimental
Gramicidin DThe serum concentration of Camptothecin can be increased when it is combined with Gramicidin D.Approved
GrepafloxacinThe serum concentration of Camptothecin can be increased when it is combined with Grepafloxacin.Withdrawn
HaloperidolThe serum concentration of Camptothecin can be increased when it is combined with Haloperidol.Approved
HydrocortisoneThe serum concentration of Camptothecin can be increased when it is combined with Hydrocortisone.Approved, Vet Approved
IdelalisibThe serum concentration of Camptothecin can be increased when it is combined with Idelalisib.Approved
ImatinibThe serum concentration of Camptothecin can be increased when it is combined with Imatinib.Approved
ImipramineThe serum concentration of Camptothecin can be increased when it is combined with Imipramine.Approved
IndinavirThe serum concentration of Camptothecin can be decreased when it is combined with Indinavir.Approved
IndomethacinThe serum concentration of Camptothecin can be increased when it is combined with Indomethacin.Approved, Investigational
IsavuconazoniumThe serum concentration of Camptothecin can be increased when it is combined with Isavuconazonium.Approved, Investigational
ItraconazoleThe serum concentration of Camptothecin can be increased when it is combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Camptothecin can be increased when it is combined with Ivacaftor.Approved
IvermectinThe serum concentration of Camptothecin can be increased when it is combined with Ivermectin.Approved, Vet Approved
KetamineThe serum concentration of Camptothecin can be increased when it is combined with Ketamine.Approved, Vet Approved
KetoconazoleThe serum concentration of Camptothecin can be increased when it is combined with Ketoconazole.Approved, Investigational
LansoprazoleThe serum concentration of Camptothecin can be increased when it is combined with Lansoprazole.Approved, Investigational
LapatinibThe serum concentration of Camptothecin can be increased when it is combined with Lapatinib.Approved, Investigational
LevofloxacinThe serum concentration of Camptothecin can be increased when it is combined with Levofloxacin.Approved, Investigational
LevothyroxineThe serum concentration of Camptothecin can be decreased when it is combined with Levothyroxine.Approved
LidocaineThe serum concentration of Camptothecin can be increased when it is combined with Lidocaine.Approved, Vet Approved
LiothyronineThe serum concentration of Camptothecin can be decreased when it is combined with Liothyronine.Approved, Vet Approved
LiotrixThe serum concentration of Camptothecin can be decreased when it is combined with Liotrix.Approved
LisinoprilThe serum concentration of Camptothecin can be increased when it is combined with Lisinopril.Approved, Investigational
LomitapideThe serum concentration of Camptothecin can be increased when it is combined with Lomitapide.Approved
LoperamideThe serum concentration of Camptothecin can be increased when it is combined with Loperamide.Approved
LopinavirThe serum concentration of Camptothecin can be increased when it is combined with Lopinavir.Approved
LoratadineThe serum concentration of Camptothecin can be increased when it is combined with Loratadine.Approved
LosartanThe serum concentration of Camptothecin can be increased when it is combined with Losartan.Approved
LovastatinThe serum concentration of Camptothecin can be increased when it is combined with Lovastatin.Approved, Investigational
LumacaftorThe serum concentration of Camptothecin can be decreased when it is combined with Lumacaftor.Approved
MaprotilineThe serum concentration of Camptothecin can be increased when it is combined with Maprotiline.Approved
MebendazoleThe serum concentration of Camptothecin can be increased when it is combined with Mebendazole.Approved, Vet Approved
MefloquineThe serum concentration of Camptothecin can be increased when it is combined with Mefloquine.Approved
Megestrol acetateThe serum concentration of Camptothecin can be increased when it is combined with Megestrol acetate.Approved, Vet Approved
MeprobamateThe serum concentration of Camptothecin can be increased when it is combined with Meprobamate.Approved, Illicit
MethadoneThe serum concentration of Camptothecin can be increased when it is combined with Methadone.Approved
MetoprololThe serum concentration of Camptothecin can be increased when it is combined with Metoprolol.Approved, Investigational
MibefradilThe serum concentration of Camptothecin can be increased when it is combined with Mibefradil.Withdrawn
MiconazoleThe serum concentration of Camptothecin can be increased when it is combined with Miconazole.Approved, Investigational, Vet Approved
MidazolamThe serum concentration of Camptothecin can be decreased when it is combined with Midazolam.Approved, Illicit
MifepristoneThe serum concentration of Camptothecin can be decreased when it is combined with Mifepristone.Approved, Investigational
MitomycinThe serum concentration of Camptothecin can be increased when it is combined with Mitomycin.Approved
MitoxantroneThe serum concentration of Camptothecin can be decreased when it is combined with Mitoxantrone.Approved, Investigational
MorphineThe serum concentration of Camptothecin can be increased when it is combined with Morphine.Approved, Investigational
NaltrexoneThe serum concentration of Camptothecin can be increased when it is combined with Naltrexone.Approved, Investigational, Vet Approved
NaringeninThe serum concentration of Camptothecin can be increased when it is combined with Naringenin.Experimental
NefazodoneThe serum concentration of Camptothecin can be decreased when it is combined with Nefazodone.Approved, Withdrawn
NelfinavirThe serum concentration of Camptothecin can be decreased when it is combined with Nelfinavir.Approved
NeostigmineThe serum concentration of Camptothecin can be increased when it is combined with Neostigmine.Approved, Vet Approved
NicardipineThe serum concentration of Camptothecin can be increased when it is combined with Nicardipine.Approved
NifedipineThe serum concentration of Camptothecin can be decreased when it is combined with Nifedipine.Approved
NilotinibThe serum concentration of Camptothecin can be increased when it is combined with Nilotinib.Approved, Investigational
NisoldipineThe serum concentration of Camptothecin can be increased when it is combined with Nisoldipine.Approved
NitrazepamThe serum concentration of Camptothecin can be increased when it is combined with Nitrazepam.Approved
NitrendipineThe serum concentration of Camptothecin can be increased when it is combined with Nitrendipine.Approved
NorethisteroneThe serum concentration of Camptothecin can be decreased when it is combined with Norethisterone.Approved
OmeprazoleThe serum concentration of Camptothecin can be increased when it is combined with Omeprazole.Approved, Investigational, Vet Approved
OuabainOuabain may decrease the cardiotoxic activities of Camptothecin.Approved
P-NitrophenolThe serum concentration of Camptothecin can be increased when it is combined with P-Nitrophenol.Experimental
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Camptothecin.Approved, Vet Approved
Palmitic AcidThe serum concentration of Camptothecin can be increased when it is combined with Palmitic Acid.Experimental
PantoprazoleThe serum concentration of Camptothecin can be increased when it is combined with Pantoprazole.Approved
ParoxetineThe serum concentration of Camptothecin can be increased when it is combined with Paroxetine.Approved, Investigational
PerindoprilThe serum concentration of Camptothecin can be increased when it is combined with Perindopril.Approved
PhenobarbitalThe serum concentration of Camptothecin can be decreased when it is combined with Phenobarbital.Approved
PimozideThe serum concentration of Camptothecin can be increased when it is combined with Pimozide.Approved
Platelet Activating FactorThe serum concentration of Camptothecin can be decreased when it is combined with Platelet Activating Factor.Experimental
PonatinibThe serum concentration of Camptothecin can be increased when it is combined with Ponatinib.Approved
PosaconazoleThe serum concentration of Camptothecin can be increased when it is combined with Posaconazole.Approved, Investigational, Vet Approved
PravastatinThe serum concentration of Camptothecin can be increased when it is combined with Pravastatin.Approved
PrazosinThe serum concentration of Camptothecin can be increased when it is combined with Prazosin.Approved
PrednisoneThe serum concentration of Camptothecin can be increased when it is combined with Prednisone.Approved, Vet Approved
ProbenecidThe serum concentration of Camptothecin can be increased when it is combined with Probenecid.Approved
ProgesteroneThe serum concentration of Camptothecin can be decreased when it is combined with Progesterone.Approved, Vet Approved
PromethazineThe serum concentration of Camptothecin can be increased when it is combined with Promethazine.Approved
PropafenoneThe serum concentration of Camptothecin can be increased when it is combined with Propafenone.Approved
PropranololThe serum concentration of Camptothecin can be increased when it is combined with Propranolol.Approved, Investigational
ProtriptylineThe serum concentration of Camptothecin can be increased when it is combined with Protriptyline.Approved
QuercetinThe serum concentration of Camptothecin can be increased when it is combined with Quercetin.Experimental
QuinacrineThe serum concentration of Camptothecin can be increased when it is combined with Quinacrine.Approved
QuinidineThe serum concentration of Camptothecin can be increased when it is combined with Quinidine.Approved
QuinineThe serum concentration of Camptothecin can be increased when it is combined with Quinine.Approved
RanitidineThe serum concentration of Camptothecin can be increased when it is combined with Ranitidine.Approved
RanolazineThe serum concentration of Camptothecin can be increased when it is combined with Ranolazine.Approved, Investigational
ReboxetineThe serum concentration of Camptothecin can be increased when it is combined with Reboxetine.Approved, Investigational
RegorafenibThe serum concentration of Camptothecin can be increased when it is combined with Regorafenib.Approved
ReserpineThe serum concentration of Camptothecin can be decreased when it is combined with Reserpine.Approved
RifampicinThe serum concentration of Camptothecin can be decreased when it is combined with Rifampicin.Approved
RilpivirineThe serum concentration of Camptothecin can be increased when it is combined with Rilpivirine.Approved
RitonavirThe serum concentration of Camptothecin can be decreased when it is combined with Ritonavir.Approved, Investigational
RolapitantThe serum concentration of Camptothecin can be increased when it is combined with Rolapitant.Approved
SaquinavirThe serum concentration of Camptothecin can be decreased when it is combined with Saquinavir.Approved, Investigational
ScopolamineThe serum concentration of Camptothecin can be increased when it is combined with Scopolamine.Approved
SelegilineThe serum concentration of Camptothecin can be increased when it is combined with Selegiline.Approved, Investigational, Vet Approved
SertralineThe serum concentration of Camptothecin can be increased when it is combined with Sertraline.Approved
SimeprevirThe serum concentration of Camptothecin can be increased when it is combined with Simeprevir.Approved
SimvastatinThe serum concentration of Camptothecin can be increased when it is combined with Simvastatin.Approved
SirolimusThe serum concentration of Camptothecin can be decreased when it is combined with Sirolimus.Approved, Investigational
SorafenibThe serum concentration of Camptothecin can be increased when it is combined with Sorafenib.Approved, Investigational
SpironolactoneThe serum concentration of Camptothecin can be increased when it is combined with Spironolactone.Approved
St. John's WortThe serum concentration of Camptothecin can be decreased when it is combined with St. John's Wort.Nutraceutical
StaurosporineThe serum concentration of Camptothecin can be increased when it is combined with Staurosporine.Experimental
StreptozocinThe serum concentration of Camptothecin can be decreased when it is combined with Streptozocin.Approved
SulfinpyrazoneThe serum concentration of Camptothecin can be increased when it is combined with Sulfinpyrazone.Approved
SumatriptanThe serum concentration of Camptothecin can be increased when it is combined with Sumatriptan.Approved, Investigational
SunitinibThe serum concentration of Camptothecin can be increased when it is combined with Sunitinib.Approved, Investigational
TacrineThe serum concentration of Camptothecin can be increased when it is combined with Tacrine.Withdrawn
TacrolimusThe serum concentration of Camptothecin can be decreased when it is combined with Tacrolimus.Approved, Investigational
TamoxifenThe serum concentration of Camptothecin can be decreased when it is combined with Tamoxifen.Approved
Taurocholic AcidThe serum concentration of Camptothecin can be increased when it is combined with Taurocholic Acid.Experimental
TelmisartanThe serum concentration of Camptothecin can be increased when it is combined with Telmisartan.Approved, Investigational
TemsirolimusThe serum concentration of Camptothecin can be increased when it is combined with Temsirolimus.Approved
TerazosinThe serum concentration of Camptothecin can be increased when it is combined with Terazosin.Approved
TerfenadineThe serum concentration of Camptothecin can be increased when it is combined with Terfenadine.Withdrawn
TeriflunomideThe serum concentration of Camptothecin can be increased when it is combined with Teriflunomide.Approved
TesmilifeneThe serum concentration of Camptothecin can be decreased when it is combined with Tesmilifene.Investigational
TestosteroneThe serum concentration of Camptothecin can be increased when it is combined with Testosterone.Approved, Investigational
TicagrelorThe serum concentration of Camptothecin can be increased when it is combined with Ticagrelor.Approved
TolvaptanThe serum concentration of Camptothecin can be increased when it is combined with Tolvaptan.Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Camptothecin.Approved, Investigational
TrazodoneThe serum concentration of Camptothecin can be decreased when it is combined with Trazodone.Approved, Investigational
TrifluoperazineThe serum concentration of Camptothecin can be increased when it is combined with Trifluoperazine.Approved
TriflupromazineThe serum concentration of Camptothecin can be increased when it is combined with Triflupromazine.Approved, Vet Approved
TrimethoprimThe serum concentration of Camptothecin can be decreased when it is combined with Trimethoprim.Approved, Vet Approved
TrimipramineThe serum concentration of Camptothecin can be increased when it is combined with Trimipramine.Approved
TroleandomycinThe serum concentration of Camptothecin can be increased when it is combined with Troleandomycin.Approved
VenlafaxineThe serum concentration of Camptothecin can be increased when it is combined with Venlafaxine.Approved
VerapamilThe serum concentration of Camptothecin can be decreased when it is combined with Verapamil.Approved
VinblastineThe serum concentration of Camptothecin can be decreased when it is combined with Vinblastine.Approved
VincristineThe serum concentration of Camptothecin can be decreased when it is combined with Vincristine.Approved, Investigational
VinorelbineThe serum concentration of Camptothecin can be increased when it is combined with Vinorelbine.Approved, Investigational
ZimelidineThe serum concentration of Camptothecin can be increased when it is combined with Zimelidine.Withdrawn
Food InteractionsNot Available
References
Synthesis Reference

Tadashi Miyasaka, Seigo Sawada, Kenichiro Nokata, Masahiko Mutai, “Photochemical process for preparing camptothecin derivatives.” U.S. Patent US4545880, issued March, 1976.

US4545880
General References
  1. Wall ME, Wani MC: Camptothecin and taxol: from discovery to clinic. J Ethnopharmacol. 1996 Apr;51(1-3):239-53; discussion 253-4. [PubMed:9213622 ]
  2. Kepler JA, Wani MC, McNaull JN, Wall ME, Levine SG: Plant antitumor agents. IV. An approach toward the synthesis of camptothecin. J Org Chem. 1969 Dec;34(12):3853-8. [PubMed:5357525 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (73.9 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.841
Blood Brain Barrier-0.6345
Caco-2 permeable-0.5555
P-glycoprotein substrateSubstrate0.6039
P-glycoprotein inhibitor INon-inhibitor0.7852
P-glycoprotein inhibitor IINon-inhibitor0.9762
Renal organic cation transporterNon-inhibitor0.8376
CYP450 2C9 substrateNon-substrate0.8311
CYP450 2D6 substrateNon-substrate0.8454
CYP450 3A4 substrateSubstrate0.546
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9232
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorInhibitor0.7959
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5591
Ames testNon AMES toxic0.5393
CarcinogenicityNon-carcinogens0.8187
BiodegradationNot ready biodegradable1.0
Rat acute toxicity3.3261 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9939
hERG inhibition (predictor II)Non-inhibitor0.902
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point275-277 °CVolkmann
logP1.74HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.511 mg/mLALOGPS
logP1.91ALOGPS
logP1.22ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)11.71ChemAxon
pKa (Strongest Basic)3.07ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area79.73 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity94.49 m3·mol-1ChemAxon
Polarizability36.4 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring).
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassCamptothecins
Sub ClassNot Available
Direct ParentCamptothecins
Alternative Parents
Substituents
  • Camptothecin
  • Quinoline
  • Pyranopyridine
  • Pyridinone
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Tertiary alcohol
  • Lactone
  • Lactam
  • Carboxylic acid ester
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Poly(a) rna binding
Specific Function:
Releases the supercoiling and torsional tension of DNA introduced during the DNA replication and transcription by transiently cleaving and rejoining one strand of the DNA duplex. Introduces a single-strand break via transesterification at a target site in duplex DNA. The scissile phosphodiester is attacked by the catalytic tyrosine of the enzyme, resulting in the formation of a DNA-(3'-phosphot...
Gene Name:
TOP1
Uniprot ID:
P11387
Molecular Weight:
90725.19 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Teicher BA: Next generation topoisomerase I inhibitors: Rationale and biomarker strategies. Biochem Pharmacol. 2008 Mar 15;75(6):1262-71. Epub 2007 Oct 22. [PubMed:18061144 ]
  3. van der Merwe M, Bjornsti MA: Mutation of Gly721 alters DNA topoisomerase I active site architecture and sensitivity to camptothecin. J Biol Chem. 2008 Feb 8;283(6):3305-15. Epub 2007 Dec 4. [PubMed:18056711 ]
  4. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
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. Li D, Jang SH, Kim J, Wientjes MG, Au JL: Enhanced drug-induced apoptosis associated with P-glycoprotein overexpression is specific to antimicrotubule agents. Pharm Res. 2003 Jan;20(1):45-50. [PubMed:12608535 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both from mitochondria to cytosol and from cytosol to extracellular space, and cellular export of hemin, and heme. Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from t...
Gene Name:
ABCG2
Uniprot ID:
Q9UNQ0
Molecular Weight:
72313.47 Da
References
  1. Ma Y, Wink M: The beta-carboline alkaloid harmine inhibits BCRP and can reverse resistance to the anticancer drugs mitoxantrone and camptothecin in breast cancer cells. Phytother Res. 2010 Jan;24(1):146-9. doi: 10.1002/ptr.2860. [PubMed:19548284 ]
Comments
comments powered by Disqus
Drug created on September 11, 2007 11:49 / Updated on August 17, 2016 12:24