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Identification
NameIrinotecan
Accession NumberDB00762  (APRD00579)
TypeSmall Molecule
GroupsApproved, Investigational
Description

Irinotecan is an antineoplastic enzyme inhibitor primarily used in the treatment of colorectal cancer. It is a derivative of camptothecin that inhibits the action of topoisomerase I. Irinotecan prevents religation of the DNA strand by binding to topoisomerase I-DNA complex, and causes double-strand DNA breakage and cell death. It is a derivative of camptothecin. Irinotecan was approved for the treatment of advanced pancreatic cancer in October, 2015 (irinotecan liposome injection, trade name Onivyde).

Structure
Thumb
Synonyms
Biotecan
Camptothecin-11
External Identifiers
  • CPT-11
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Camptosarinjection, solution20 mg/mLintravenousPharmacia and Upjohn Company1996-06-142016-04-23Us
Camptosarinjection, solution20 mg/mLintravenousPharmacia And Upjohn Company Llc1996-06-142016-04-23Us
Camptosar Injectionsolution20 mgintravenousPfizer Canada Inc1997-08-27Not applicableCanada
Irinotecansolution20 mgintravenousPfizer Canada Inc2014-03-07Not applicableCanada
Irinotecan for Injectionsolution20 mgintravenousTeva Canada Limited2008-10-31Not applicableCanada
Irinotecan Hydrochloride Injectionsolution20 mgintravenousHospira Healthcare Corporation2006-02-01Not applicableCanada
Irinotecan Hydrochloride Injectionsolution20 mgintravenousAlveda Pharmaceuticals Inc2015-05-28Not applicableCanada
Irinotecan Hydrochloride Injection, USPsolution20 mgintravenousQilu Pharmaceuticals Co. LtdNot applicableNot applicableCanada
Irinotecan Hydrochloride Trihydrate for Injectionsolution20 mgintravenousAccord Healthcare Inc2013-05-06Not applicableCanada
Irinotecan Hydrochloride Trihydrate for Injectionsolution20 mgintravenousFresenius Kabi Canada Ltd2011-05-27Not applicableCanada
Irinotecan Hydrochloride Trihydrate Injectionsolution20 mgintravenousSandoz Canada Incorporated2008-01-30Not applicableCanada
Onivydeinjection4.3 mg/mLintravenousMerrimack Pharmaceuticals2015-10-222016-04-05Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Irinotecan Hydrochlorideinjection40 mg/2mLintravenousSun Pharma Global FZE2008-04-212016-04-05Us
Irinotecan Hydrochlorideinjection20 mg/mLintravenousWest ward Pharmaceutical Corp2010-12-202016-04-23Us
Irinotecan Hydrochlorideinjection, solution20 mg/mLintravenousActavis Pharma, Inc.2015-01-052016-04-05Us
Irinotecan Hydrochlorideinjection20 mg/mLintravenousAreva Pharmaceuticals,Inc.2008-02-202016-04-05Us
Irinotecan Hydrochlorideinjection, solution20 mg/mLintravenousSagent Pharmaceuticals2014-08-152016-04-05Us
Irinotecan Hydrochlorideinjection20 mg/mLintravenousWest Ward Pharmaceuticals Corp2010-12-202016-04-23Us
Irinotecan Hydrochlorideinjection, solution20 mg/mLintravenousSagent Pharmaceuticals2012-04-202016-04-05Us
Irinotecan Hydrochlorideinjection, solution20 mg/mLintravenousFresenius Kabi USA, LLC2009-04-012016-04-05Us
Irinotecan Hydrochlorideinjection20 mg/mLintravenousHeritage Pharmaceuticals Inc.2012-06-202016-04-05Us
Irinotecan Hydrochlorideinjection, solution20 mg/mLintravenousSandoz Inc2009-11-302016-04-05Us
Irinotecan Hydrochlorideinjection, solution100 mg/5mLintravenousTeva Parenteral Medicines, Inc.2008-02-272016-04-05Us
Irinotecan Hydrochlorideinjection, solution20 mg/mLintravenousHospira Worldwide, Inc.2008-02-272016-04-05Us
Irinotecan Hydrochlorideinjection, solution40 mg/2mLintravenousTeva Parenteral Medicines, Inc.2008-02-282016-04-05Us
Irinotecan Hydrochlorideinjection100 mg/5mLintravenousSun Pharma Global FZE2008-04-212016-04-05Us
Irinotecan Hydrochlorideinjection20 mg/mLintravenousWest ward Pharmaceutical Corp2010-12-202016-04-23Us
Over the Counter ProductsNot Available
International Brands
NameCompany
CamptoYakultHonsha Co. Ltd.
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Irinotecan Hydrochloride
Thumb
  • InChI Key: GURKHSYORGJETM-WAQYZQTGSA-N
  • Monoisotopic Mass: 622.255812707
  • Average Mass: 623.139
DBSALT000103
Categories
UNII7673326042
CAS number100286-90-6
WeightAverage: 586.678
Monoisotopic: 586.279134968
Chemical FormulaC33H38N4O6
InChI KeyInChIKey=UWKQSNNFCGGAFS-XIFFEERXSA-N
InChI
InChI=1S/C33H38N4O6/c1-3-22-23-16-21(43-32(40)36-14-10-20(11-15-36)35-12-6-5-7-13-35)8-9-27(23)34-29-24(22)18-37-28(29)17-26-25(30(37)38)19-42-31(39)33(26,41)4-2/h8-9,16-17,20,41H,3-7,10-15,18-19H2,1-2H3/t33-/m0/s1
IUPAC Name
(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaen-7-yl 4-(piperidin-1-yl)piperidine-1-carboxylate
SMILES
CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=C1C=C(OC(=O)N1CCC(CC1)N1CCCCC1)C=C2
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
  • Hydroxyquinoline
  • Quinoline
  • Pyranopyridine
  • Piperidinecarboxylic acid
  • Pyridinone
  • 4-aminopiperidine
  • Benzenoid
  • Pyridine
  • Piperidine
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Tertiary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Lactone
  • Lactam
  • Carboxylic acid ester
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of metastatic colorectal cancer (first-line therapy when administered with 5-fluorouracil and leucovorin). Also used in combination with cisplatin for the treatment of extensive small cell lung cancer. Irinotecan is currently under investigation for the treatment of metastatic or recurrent cervical cancer. Also used in combination with fluorouracil and leucovorin for the treatment of patients with metastatic adenocarcinoma of the pancreas after disease progression following gemcitabine-based therapy.
PharmacodynamicsIrinotecan is an antineoplastic enzyme inhibitor primarily used in the treatment of colorectal cancer. Irinotecan is a semisynthetic derivative of camptothecin. Camptothecins interact specifically with topoisomerase I, an enzyme in the cell nucleus that regulates DNA topology and facilitates nuclear processes such as DNA replication, recombination, and repair. During these processes, topoisomerase I relieves torsional strain in DNA by inducing reversible single-strand breaks, allowing single DNA strands to pass through the break. The 3'-DNA terminus of the broken DNA strands bind covalently with the topoisomerase enzyme to form a catalytic intermediate called a cleavable complex. After the DNA is sufficiently relaxed and the strand passage reaction is complete, DNA topoisomerase reattaches the broken DNA strands to form the chemically unaltered topoisomers that allow transcription to proceed. Irinotecan and its active metabolite SN-38 bind to the topoisomerase I-DNA complex and prevent religation of these single-strand breaks. Current research suggests that the cytotoxicity of irinotecan is due to double-strand DNA damage produced during DNA synthesis when replication enzymes interact with the ternary complex formed by topoisomerase I, DNA, and either Irinotecan or SN-38. Mammalian cells cannot efficiently repair these double-strand breaks. The precise contribution of SN-38 to the activity of irinotecan in humans is not known. Irinotecan is cell cycle phase-specific (S-phase).
Mechanism of actionIrinotecan inhibits the action of topoisomerase I. Irinotecan prevents religation of the DNA strand by binding to topoisomerase I-DNA complex. The formation of this ternary complex interferes with the moving replication fork, which induces replication arrest and lethal double-stranded breaks in DNA. As a result, DNA damage is not efficiently repaired and apoptosis (programmed cell death) occurs.
Related Articles
AbsorptionThe maximum plasma concentration (Cmax) when a dose of 125 mg/m^2 is given to patients with solid tumours is 1660 ng/mL. The AUC (0-24) is 10,200 ng·h/mL. The Cmax when a dose of 340 mg/m^2 is given to patients with solid tumours is 3392 ng/mL. The AUC (0-24) is 20,604 ng·h/mL.
Volume of distribution

The volume of distribution of terminal elimination phase is 110 L/m^2 when a dose of 125 mg/m^2 is given to patients with solid tumours. The volume of distribution of terminal elimination phase is 234 L/m^2 when a dose of 340 mg/m^2 is given to patients with solid tumours.

Protein binding30%-68% protein bound, mainly to albumin.
Metabolism

Hepatic. The metabolic conversion of irinotecan to the active metabolite SN-38 is mediated by carboxylesterase enzymes and primarily occurs in the liver. SN-38 is subsequently conjugated predominantly by the enzyme UDP-glucuronosyl transferase 1A1 (UGT1A1) to form a glucuronide metabolite.

SubstrateEnzymesProduct
Irinotecan
SN-38Details
Route of eliminationThe cumulative biliary and urinary excretion of irinotecan and its metabolites (SN-38 and SN-38 glucuronide) over a period of 48 hours following administration of irinotecan in two patients ranged from approximately 25% (100 mg/m2) to 50% (300 mg/m2).
Half lifeThe half life of irinotecan is about 6 - 12 hours. The terminal elimination half-life of the active metabolite, SN-38 is 10 - 20 hours.
Clearance
  • 13.3 L/h/m^2 [Dose of 125 mg/m^2, patients with solid tumours]
  • 13.9 L/h/m^2 [Dose of 340 mg/m^2, patients with solid tumours]
ToxicityGastrointestinal complications, such as nausea, vomiting, abdominal cramping, diarrhea, and infection.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Irinotecan Action PathwayDrug actionSMP00433
Irinotecan Metabolism PathwayDrug metabolismSMP00600
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug Reactions
Interacting Gene/EnzymeSNP RS IDAllele nameDefining changeAdverse ReactionReference(s)
Solute carrier organic anion transporter family member 1B1
Gene symbol: SLCO1B1
UniProt: Q9Y6L6
rs4149056 SLCO1B1*15C AlleleDiarrhea, leucopenia, neutropenia17898662
Solute carrier organic anion transporter family member 1B1
Gene symbol: SLCO1B1
UniProt: Q9Y6L6
rs2306283 SLCO1B1*15G AlleleDiarrhea, leucopenia, neutropenia17898662
UDP-glucuronosyltransferase 1-1
Gene symbol: UGT1A1
UniProt: P22309
rs8175347 UGT1A1*28 or UGT1A 7/7extra TA in promoterLeukopenia, thrombpocytopenia17681105
UDP-glucuronosyltransferase 1-7
Gene symbol: UGT1A7
UniProt: Q9HAW7
rs17868323 Not AvailableG alleleLeukopenia, thrombpocytopenia18349289
UDP-glucuronosyltransferase 1-7
Gene symbol: UGT1A7
UniProt: Q9HAW7
rs17863778 Not AvailableA alleleLeukopenia, thrombpocytopenia18349289
UDP-glucuronosyltransferase 1-7
Gene symbol: UGT1A7
UniProt: Q9HAW7
rs17868324 Not AvailableA alleleLeukopenia, thrombpocytopenia18349289
UDP-glucuronosyltransferase 1-1
Gene symbol: UGT1A1
UniProt: P22309
rs10929302 Not AvailableA AlleleHematological toxicity, neutropenia17510208
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.969
Blood Brain Barrier+0.6284
Caco-2 permeable-0.6065
P-glycoprotein substrateSubstrate0.7861
P-glycoprotein inhibitor IInhibitor0.7092
P-glycoprotein inhibitor IINon-inhibitor0.5337
Renal organic cation transporterNon-inhibitor0.8178
CYP450 2C9 substrateNon-substrate0.8174
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateSubstrate0.7407
CYP450 1A2 substrateNon-inhibitor0.8564
CYP450 2C9 inhibitorNon-inhibitor0.7377
CYP450 2D6 inhibitorNon-inhibitor0.7779
CYP450 2C19 inhibitorNon-inhibitor0.6625
CYP450 3A4 inhibitorInhibitor0.8295
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5081
Ames testNon AMES toxic0.6977
CarcinogenicityNon-carcinogens0.8045
BiodegradationNot ready biodegradable0.9956
Rat acute toxicity2.7960 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9457
hERG inhibition (predictor II)Inhibitor0.5413
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Pfizer inc
  • Accord healthcare inc
  • Actavis totowa llc
  • Akorn inc
  • App pharmaceuticals
  • Bedford laboratories
  • Dr reddys laboratories ltd
  • Ebewe pharma ges mbh nfg kg
  • Fresenius kabi oncology plc
  • Hospira inc
  • Pharmaforce inc
  • Pliva lachema as
  • Sandoz inc
  • Sun pharma global inc
  • Teva parenteral medicines inc
  • Watson laboratories inc
Packagers
Dosage forms
FormRouteStrength
Injection, solutionintravenous20 mg/mL
Solutionintravenous20 mg
Injectionintravenous100 mg/5mL
Injectionintravenous20 mg/mL
Injectionintravenous40 mg/2mL
Injection, solutionintravenous100 mg/5mL
Injection, solutionintravenous40 mg/2mL
Injectionintravenous4.3 mg/mL
Prices
Unit descriptionCostUnit
Irinotecan hcl 40 mg/2 ml inj138.07USD ml
Camptosar 20 mg/ml vial36.0USD ml
Irinotecan hcl 40 mg/2 ml vial22.2USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2202531 No2005-05-032015-10-11Canada
CA2294031 No2005-01-182018-07-27Canada
US6403569 Yes2000-10-282020-10-28Us
US6794370 Yes2000-11-012020-11-01Us
US8147867 No2008-08-292028-08-29Us
US8329213 No2005-05-022025-05-02Us
US8703181 No2005-05-022025-05-02Us
US8992970 No2005-05-022025-05-02Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point222-223 °CNot Available
water solubilitySolubleNot Available
logP3.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.107 mg/mLALOGPS
logP3.94ALOGPS
logP2.78ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)11.71ChemAxon
pKa (Strongest Basic)9.47ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area112.51 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity161.33 m3·mol-1ChemAxon
Polarizability65.27 Å3ChemAxon
Number of Rings7ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceUS4604463
General References
  1. Innocenti F, Undevia SD, Iyer L, Chen PX, Das S, Kocherginsky M, Karrison T, Janisch L, Ramirez J, Rudin CM, Vokes EE, Ratain MJ: Genetic variants in the UDP-glucuronosyltransferase 1A1 gene predict the risk of severe neutropenia of irinotecan. J Clin Oncol. 2004 Apr 15;22(8):1382-8. Epub 2004 Mar 8. [PubMed:15007088 ]
  2. O'Dwyer PJ, Catalano RB: Uridine diphosphate glucuronosyltransferase (UGT) 1A1 and irinotecan: practical pharmacogenomics arrives in cancer therapy. J Clin Oncol. 2006 Oct 1;24(28):4534-8. [PubMed:17008691 ]
  3. Ramesh M, Ahlawat P, Srinivas NR: Irinotecan and its active metabolite, SN-38: review of bioanalytical methods and recent update from clinical pharmacology perspectives. Biomed Chromatogr. 2010 Jan;24(1):104-23. doi: 10.1002/bmc.1345. [PubMed:19852077 ]
  4. Chabot GG: Clinical pharmacokinetics of irinotecan. Clin Pharmacokinet. 1997 Oct;33(4):245-59. [PubMed:9342501 ]
External Links
ATC CodesL01XX19
AHFS Codes
  • 10:00.00
PDB EntriesNot Available
FDA labelDownload (132 KB)
MSDSDownload (36.3 KB)
Interactions
Drug Interactions
Drug
AdenineThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Adenine.
AprepitantThe serum concentration of Irinotecan can be increased when it is combined with Aprepitant.
AtazanavirThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Atazanavir.
BevacizumabThe risk or severity of adverse effects can be increased when Bevacizumab is combined with Irinotecan.
BexaroteneThe serum concentration of Irinotecan can be decreased when it is combined with Bexarotene.
BoceprevirThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Boceprevir.
BosentanThe serum concentration of Irinotecan can be decreased when it is combined with Bosentan.
CarbamazepineThe serum concentration of the active metabolites of Irinotecan can be reduced when Irinotecan is used in combination with Carbamazepine resulting in a loss in efficacy.
CeritinibThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Ceritinib.
ClarithromycinThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Clarithromycin.
ClozapineThe risk or severity of adverse effects can be increased when Irinotecan is combined with Clozapine.
CobicistatThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Cobicistat.
ConivaptanThe serum concentration of Irinotecan can be increased when it is combined with Conivaptan.
DabrafenibThe serum concentration of Irinotecan can be decreased when it is combined with Dabrafenib.
DarunavirThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Darunavir.
DasatinibThe serum concentration of Irinotecan can be increased when it is combined with Dasatinib.
DeferasiroxThe serum concentration of Irinotecan can be decreased when it is combined with Deferasirox.
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Irinotecan.
EltrombopagThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Eltrombopag.
EnzalutamideThe serum concentration of the active metabolites of Irinotecan can be reduced when Irinotecan is used in combination with Enzalutamide resulting in a loss in efficacy.
ErlotinibThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Erlotinib.
FluconazoleThe metabolism of Irinotecan can be decreased when combined with Fluconazole.
FosaprepitantThe serum concentration of Irinotecan can be increased when it is combined with Fosaprepitant.
FosphenytoinThe serum concentration of the active metabolites of Irinotecan can be reduced when Irinotecan is used in combination with Fosphenytoin resulting in a loss in efficacy.
Fusidic AcidThe serum concentration of Irinotecan can be increased when it is combined with Fusidic Acid.
GemfibrozilThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Gemfibrozil.
IdelalisibThe serum concentration of Irinotecan can be increased when it is combined with Idelalisib.
IndinavirThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Indinavir.
ItraconazoleThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Itraconazole.
IvacaftorThe serum concentration of Irinotecan can be increased when it is combined with Ivacaftor.
KetoconazoleThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Ketoconazole.
LeflunomideThe risk or severity of adverse effects can be increased when Irinotecan is combined with Leflunomide.
LenvatinibThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Lenvatinib.
LuliconazoleThe serum concentration of Irinotecan can be increased when it is combined with Luliconazole.
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Irinotecan.
MifepristoneThe serum concentration of Irinotecan can be increased when it is combined with Mifepristone.
MitotaneThe serum concentration of the active metabolites of Irinotecan can be reduced when Irinotecan is used in combination with Mitotane resulting in a loss in efficacy.
NatalizumabThe risk or severity of adverse effects can be increased when Irinotecan is combined with Natalizumab.
NefazodoneThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Nefazodone.
NelfinavirThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Nelfinavir.
NetupitantThe serum concentration of Irinotecan can be increased when it is combined with Netupitant.
NevirapineThe metabolism of Irinotecan can be increased when combined with Nevirapine.
NilotinibThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Nilotinib.
PalbociclibThe serum concentration of Irinotecan can be increased when it is combined with Palbociclib.
PazopanibThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Pazopanib.
PhenobarbitalThe serum concentration of the active metabolites of Irinotecan can be reduced when Irinotecan is used in combination with Phenobarbital resulting in a loss in efficacy.
PhenytoinThe serum concentration of the active metabolites of Irinotecan can be reduced when Irinotecan is used in combination with Phenytoin resulting in a loss in efficacy.
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Irinotecan.
PosaconazoleThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Posaconazole.
PrimidoneThe serum concentration of the active metabolites of Irinotecan can be reduced when Irinotecan is used in combination with Primidone resulting in a loss in efficacy.
QuazepamThe serum concentration of Irinotecan can be increased when it is combined with Quazepam.
RanolazineThe serum concentration of Irinotecan can be increased when it is combined with Ranolazine.
RegorafenibThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Regorafenib.
RifabutinThe serum concentration of the active metabolites of Irinotecan can be reduced when Irinotecan is used in combination with Rifabutin resulting in a loss in efficacy.
RifampicinThe serum concentration of the active metabolites of Irinotecan can be reduced when Irinotecan is used in combination with Rifampicin resulting in a loss in efficacy.
RifapentineThe serum concentration of the active metabolites of Irinotecan can be reduced when Irinotecan is used in combination with Rifapentine resulting in a loss in efficacy.
RitonavirThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Ritonavir.
RoflumilastRoflumilast may increase the immunosuppressive activities of Irinotecan.
RolapitantThe serum concentration of Irinotecan can be increased when it is combined with Rolapitant.
SaquinavirThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Saquinavir.
SiltuximabThe serum concentration of Irinotecan can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Irinotecan can be increased when it is combined with Simeprevir.
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Irinotecan.
SorafenibThe serum concentration of Irinotecan can be increased when it is combined with Sorafenib.
St. John's WortThe therapeutic efficacy of Irinotecan can be decreased when used in combination with St. John's Wort.
StiripentolThe serum concentration of Irinotecan can be increased when it is combined with Stiripentol.
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Irinotecan.
TelaprevirThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Telaprevir.
TelithromycinThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Telithromycin.
TeriflunomideThe serum concentration of Irinotecan can be increased when it is combined with Teriflunomide.
TesmilifeneThe serum concentration of Irinotecan can be decreased when it is combined with Tesmilifene.
TiclopidineThe metabolism of Irinotecan can be decreased when combined with Ticlopidine.
TocilizumabThe serum concentration of Irinotecan can be decreased when it is combined with Tocilizumab.
TofacitinibIrinotecan may increase the immunosuppressive activities of Tofacitinib.
TrastuzumabTrastuzumab may increase the neutropenic activities of Irinotecan.
VerapamilThe serum concentration of Irinotecan can be increased when it is combined with Verapamil.
VoriconazoleThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Voriconazole.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Dna topoisomerase type ii (atp-hydrolyzing) activity
Specific Function:
Releases the supercoiling and torsional tension of DNA introduced during duplication of mitochondrial DNA 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'-phosphotyrosy...
Gene Name:
TOP1MT
Uniprot ID:
Q969P6
Molecular Weight:
69871.39 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. Yoshikawa M, Ikegami Y, Hayasaka S, Ishii K, Ito A, Sano K, Suzuki T, Togawa T, Yoshida H, Soda H, Oka M, Kohno S, Sawada S, Ishikawa T, Tanabe S: Novel camptothecin analogues that circumvent ABCG2-associated drug resistance in human tumor cells. Int J Cancer. 2004 Jul 20;110(6):921-7. [PubMed:15170677 ]
  4. Yoshikawa M, Ikegami Y, Sano K, Yoshida H, Mitomo H, Sawada S, Ishikawa T: Transport of SN-38 by the wild type of human ABC transporter ABCG2 and its inhibition by quercetin, a natural flavonoid. J Exp Ther Oncol. 2004 Apr;4(1):25-35. [PubMed:15255290 ]
  5. Yang X, Hu Z, Chan SY, Chan E, Goh BC, Duan W, Zhou S: Novel agents that potentially inhibit irinotecan-induced diarrhea. Curr Med Chem. 2005;12(11):1343-58. [PubMed:15975002 ]
  6. Nakagawa H, Saito H, Ikegami Y, Aida-Hyugaji S, Sawada S, Ishikawa T: Molecular modeling of new camptothecin analogues to circumvent ABCG2-mediated drug resistance in cancer. Cancer Lett. 2006 Mar 8;234(1):81-9. Epub 2005 Nov 23. [PubMed:16309825 ]
  7. Ishikawa T, Ikegami Y, Sano K, Nakagawa H, Sawada S: Transport mechanism-based drug molecular design: novel camptothecin analogues to circumvent ABCG2-associated drug resistance of human tumor cells. Curr Pharm Des. 2006;12(3):313-25. [PubMed:16454746 ]
  8. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  9. Ramesh M, Ahlawat P, Srinivas NR: Irinotecan and its active metabolite, SN-38: review of bioanalytical methods and recent update from clinical pharmacology perspectives. Biomed Chromatogr. 2010 Jan;24(1):104-23. doi: 10.1002/bmc.1345. [PubMed:19852077 ]
  10. Chabot GG: Clinical pharmacokinetics of irinotecan. Clin Pharmacokinet. 1997 Oct;33(4):245-59. [PubMed:9342501 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
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. Yoshikawa M, Ikegami Y, Hayasaka S, Ishii K, Ito A, Sano K, Suzuki T, Togawa T, Yoshida H, Soda H, Oka M, Kohno S, Sawada S, Ishikawa T, Tanabe S: Novel camptothecin analogues that circumvent ABCG2-associated drug resistance in human tumor cells. Int J Cancer. 2004 Jul 20;110(6):921-7. [PubMed:15170677 ]
  2. Yoshikawa M, Ikegami Y, Sano K, Yoshida H, Mitomo H, Sawada S, Ishikawa T: Transport of SN-38 by the wild type of human ABC transporter ABCG2 and its inhibition by quercetin, a natural flavonoid. J Exp Ther Oncol. 2004 Apr;4(1):25-35. [PubMed:15255290 ]
  3. Yang X, Hu Z, Chan SY, Chan E, Goh BC, Duan W, Zhou S: Novel agents that potentially inhibit irinotecan-induced diarrhea. Curr Med Chem. 2005;12(11):1343-58. [PubMed:15975002 ]
  4. Nakagawa H, Saito H, Ikegami Y, Aida-Hyugaji S, Sawada S, Ishikawa T: Molecular modeling of new camptothecin analogues to circumvent ABCG2-mediated drug resistance in cancer. Cancer Lett. 2006 Mar 8;234(1):81-9. Epub 2005 Nov 23. [PubMed:16309825 ]
  5. Ishikawa T, Ikegami Y, Sano K, Nakagawa H, Sawada S: Transport mechanism-based drug molecular design: novel camptothecin analogues to circumvent ABCG2-associated drug resistance of human tumor cells. Curr Pharm Des. 2006;12(3):313-25. [PubMed:16454746 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  7. Ramesh M, Ahlawat P, Srinivas NR: Irinotecan and its active metabolite, SN-38: review of bioanalytical methods and recent update from clinical pharmacology perspectives. Biomed Chromatogr. 2010 Jan;24(1):104-23. doi: 10.1002/bmc.1345. [PubMed:19852077 ]
  8. Chabot GG: Clinical pharmacokinetics of irinotecan. Clin Pharmacokinet. 1997 Oct;33(4):245-59. [PubMed:9342501 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Ramesh M, Ahlawat P, Srinivas NR: Irinotecan and its active metabolite, SN-38: review of bioanalytical methods and recent update from clinical pharmacology perspectives. Biomed Chromatogr. 2010 Jan;24(1):104-23. doi: 10.1002/bmc.1345. [PubMed:19852077 ]
  2. 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 ]
  3. Kuhn JG: Pharmacology of irinotecan. Oncology (Williston Park). 1998 Aug;12(8 Suppl 6):39-42. [PubMed:9726089 ]
  4. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 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 ]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular Weight:
56277.81 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular Weight:
57525.03 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid binding
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naph...
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular Weight:
59590.91 Da
References
  1. Kuhn JG: Pharmacology of irinotecan. Oncology (Williston Park). 1998 Aug;12(8 Suppl 6):39-42. [PubMed:9726089 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Retinoic acid binding
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks transferase activity but acts as a negative regulator of isoform 1.
Gene Name:
UGT1A9
Uniprot ID:
O60656
Molecular Weight:
59940.495 Da
References
  1. Chabot GG: Clinical pharmacokinetics of irinotecan. Clin Pharmacokinet. 1997 Oct;33(4):245-59. [PubMed:9342501 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Triglyceride lipase activity
Specific Function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity,...
Gene Name:
CES1
Uniprot ID:
P23141
Molecular Weight:
62520.62 Da
References
  1. Chabot GG: Clinical pharmacokinetics of irinotecan. Clin Pharmacokinet. 1997 Oct;33(4):245-59. [PubMed:9342501 ]
  2. Ramesh M, Ahlawat P, Srinivas NR: Irinotecan and its active metabolite, SN-38: review of bioanalytical methods and recent update from clinical pharmacology perspectives. Biomed Chromatogr. 2010 Jan;24(1):104-23. doi: 10.1002/bmc.1345. [PubMed:19852077 ]
  3. Kuhn JG: Pharmacology of irinotecan. Oncology (Williston Park). 1998 Aug;12(8 Suppl 6):39-42. [PubMed:9726089 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Methylumbelliferyl-acetate deacetylase activity
Specific Function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Shows high catalytic efficiency for hydrolysis of cocaine, 4-methylumbelliferyl acetate, heroin and 6-monoacetylmorphine.
Gene Name:
CES2
Uniprot ID:
O00748
Molecular Weight:
61806.41 Da
References
  1. Sanghani SP, Quinney SK, Fredenburg TB, Davis WI, Murry DJ, Bosron WF: Hydrolysis of irinotecan and its oxidative metabolites, 7-ethyl-10-[4-N-(5-aminopentanoic acid)-1-piperidino] carbonyloxycamptothecin and 7-ethyl-10-[4-(1-piperidino)-1-amino]-carbonyloxycamptothecin, by human carboxylesterases CES1A1, CES2, and a newly expressed carboxylesterase isoenzyme, CES3. Drug Metab Dispos. 2004 May;32(5):505-11. [PubMed:15100172 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Identical protein binding
Specific Function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular Weight:
68417.575 Da
References
  1. Link [Link]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Toxic substance binding
Specific Function:
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
Molecular Weight:
69365.94 Da
References
  1. FDA label

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Toxin transporter activity
Specific Function:
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain.
Gene Name:
SLC22A3
Uniprot ID:
O75751
Molecular Weight:
61279.485 Da
References
  1. Shnitsar V, Eckardt R, Gupta S, Grottker J, Muller GA, Koepsell H, Burckhardt G, Hagos Y: Expression of human organic cation transporter 3 in kidney carcinoma cell lines increases chemosensitivity to melphalan, irinotecan, and vincristine. Cancer Res. 2009 Feb 15;69(4):1494-501. doi: 10.1158/0008-5472.CAN-08-2483. Epub 2009 Feb 3. [PubMed:19190342 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. Involved in the clearance of bile acids and organic anions from the liver.
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6
Molecular Weight:
76447.99 Da
References
  1. Nozawa T, Minami H, Sugiura S, Tsuji A, Tamai I: Role of organic anion transporter OATP1B1 (OATP-C) in hepatic uptake of irinotecan and its active metabolite, 7-ethyl-10-hydroxycamptothecin: in vitro evidence and effect of single nucleotide polymorphisms. Drug Metab Dispos. 2005 Mar;33(3):434-9. Epub 2004 Dec 17. [PubMed:15608127 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Transporter activity
Specific Function:
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency.
Gene Name:
ABCC1
Uniprot ID:
P33527
Molecular Weight:
171589.5 Da
References
  1. Chen ZS, Furukawa T, Sumizawa T, Ono K, Ueda K, Seto K, Akiyama SI: ATP-Dependent efflux of CPT-11 and SN-38 by the multidrug resistance protein (MRP) and its inhibition by PAK-104P. Mol Pharmacol. 1999 May;55(5):921-8. [PubMed:10220571 ]
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. Wang X, Furukawa T, Nitanda T, Okamoto M, Sugimoto Y, Akiyama S, Baba M: Breast cancer resistance protein (BCRP/ABCG2) induces cellular resistance to HIV-1 nucleoside reverse transcriptase inhibitors. Mol Pharmacol. 2003 Jan;63(1):65-72. [PubMed:12488537 ]
  2. Maliepaard M, van Gastelen MA, Tohgo A, Hausheer FH, van Waardenburg RC, de Jong LA, Pluim D, Beijnen JH, Schellens JH: Circumvention of breast cancer resistance protein (BCRP)-mediated resistance to camptothecins in vitro using non-substrate drugs or the BCRP inhibitor GF120918. Clin Cancer Res. 2001 Apr;7(4):935-41. [PubMed:11309344 ]
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. Kroetz DL: Role for drug transporters beyond tumor resistance: hepatic functional imaging and genotyping of multidrug resistance transporters for the prediction of irinotecan toxicity. J Clin Oncol. 2006 Sep 10;24(26):4225-7. Epub 2006 Aug 8. [PubMed:16895999 ]
  2. Han JY, Lim HS, Park YH, Lee SY, Lee JS: Integrated pharmacogenetic prediction of irinotecan pharmacokinetics and toxicity in patients with advanced non-small cell lung cancer. Lung Cancer. 2009 Jan;63(1):115-20. doi: 10.1016/j.lungcan.2007.12.003. Epub 2008 Jan 24. [PubMed:18221820 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Organic anion transmembrane transporter activity
Specific Function:
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name:
ABCC2
Uniprot ID:
Q92887
Molecular Weight:
174205.64 Da
References
  1. Kroetz DL: Role for drug transporters beyond tumor resistance: hepatic functional imaging and genotyping of multidrug resistance transporters for the prediction of irinotecan toxicity. J Clin Oncol. 2006 Sep 10;24(26):4225-7. Epub 2006 Aug 8. [PubMed:16895999 ]
  2. Han JY, Lim HS, Park YH, Lee SY, Lee JS: Integrated pharmacogenetic prediction of irinotecan pharmacokinetics and toxicity in patients with advanced non-small cell lung cancer. Lung Cancer. 2009 Jan;63(1):115-20. doi: 10.1016/j.lungcan.2007.12.003. Epub 2008 Jan 24. [PubMed:18221820 ]
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Drug created on June 13, 2005 07:24 / Updated on May 01, 2016 03:12