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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL481
CHEMBL481
Compound Name IRINOTECAN
ChEMBL Synonyms U-101440E | Camptosar | irinotecan hydrochloride | Campto | IRINOTECAN HYDROCHLORIDE | IRINOTECAN | ONIVYDE | U-101,440E | CAMPTOSAR
Max Phase 4 (Approved)
Trade Names IRINOTECAN HYDROCHLORIDE | Camptosar | CAMPTOSAR | ONIVYDE | Campto
Molecular Formula C33H38N4O6

Additional synonyms for CHEMBL481 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CCc1c2CN3C(=O)C4=C(C=C3c2nc5ccc(OC(=O)N6CCC(CC6)N7CCCCC7)cc1 ...
Download SMILES
Standard InChI InChI=1S/C33H38N4O6/c1-3-22-23-16-21(43-32(40)36-14-10-20(11 ...
Download InChI
Standard InChI Key UWKQSNNFCGGAFS-XIFFEERXSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • DrugMatrix
  • Orange Book
  • Patent Bioactivity Data
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL481

Molecule Features

CHEMBL481 compound icon
Drug Type:Natural Product-derived Rule of Five:N First In Class:N Chirality:Single Stereoisomer Prodrug:Y Oral:N Parenteral:Y Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
DNA topoisomerase I inhibitor DNA topoisomerase I DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Biliary Tract NeoplasmsD001661EFO:0003891biliary tract neoplasm2ClinicalTrials
CholangiocarcinomaD018281EFO:0005221cholangiocarcinoma2ClinicalTrials
Choroid Plexus NeoplasmsD016545EFO:0007206choroid plexus cancer3ClinicalTrials
Stomach NeoplasmsD013274EFO:0000503gastric adenocarcinoma3ClinicalTrials
Uterine Cervical NeoplasmsD002583EFO:0001061cervical carcinoma2ClinicalTrials
Uterine Cervical NeoplasmsD002583EFO:0001416cervical adenocarcinoma2ClinicalTrials
Carcinoma, HepatocellularD006528EFO:0000182hepatocellular carcinoma2ClinicalTrials
Colonic NeoplasmsD003110EFO:1001950colon carcinoma3ClinicalTrials
Colorectal NeoplasmsD015179EFO:0000365colorectal adenocarcinoma3ClinicalTrials
Colorectal NeoplasmsD015179EFO:0005842colorectal cancer3ClinicalTrials
NeoplasmsD009369EFO:0000311cancer4ClinicalTrials
NeuroblastomaD009447EFO:0000621neuroblastoma2ClinicalTrials
OligodendrogliomaD009837EFO:0002501anaplastic oligodendroglioma1ClinicalTrials
RhabdomyosarcomaD012208EFO:0002918rhabdomyosarcoma2ClinicalTrials
Lymphoma, Non-HodgkinD008228EFO:0005952non-Hodgkins lymphoma2ClinicalTrials
Neuroendocrine TumorsD018358EFO:1001901neuroendocrine neoplasm2ClinicalTrials
Rectal NeoplasmsD012004EFO:1000657rectum cancer3ClinicalTrials
Brain NeoplasmsD001932EFO:0003833brain neoplasm2ClinicalTrials
Breast NeoplasmsD001943EFO:0003869breast neoplasm3ClinicalTrials
CarcinomaD002277EFO:0000313carcinoma2ClinicalTrials
GliosarcomaD018316EFO:1001465gliosarcoma2ClinicalTrials
LeukemiaD007938EFO:0000565leukemia2ClinicalTrials
Pancreatic NeoplasmsD010190EFO:0003860pancreatic neoplasm3ClinicalTrials
SarcomaD012509EFO:0000691sarcoma2ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma3ClinicalTrials
Carcinoma, Non-Small-Cell LungD002289EFO:0003060non-small cell lung carcinoma2ClinicalTrials
Colorectal NeoplasmsD015179EFO:0004142colorectal neoplasm3ClinicalTrials
GlioblastomaD005909EFO:0000519glioblastoma multiforme2ClinicalTrials
Lung NeoplasmsD008175EFO:0001071lung carcinoma3ClinicalTrials
Pancreatic NeoplasmsD010190EFO:0002618pancreatic carcinoma3ClinicalTrials
PinealomaD010871EFO:1000475Pineoblastoma2ClinicalTrials
Carcinoma, Squamous CellD002294EFO:0000707squamous cell carcinoma2ClinicalTrials
Colonic NeoplasmsD003110EFO:0004288colonic neoplasm3ClinicalTrials
Esophageal NeoplasmsD004938EFO:0002916esophageal carcinoma3ClinicalTrials
GliomaD005910EFO:0000326central nervous system cancer2ClinicalTrials
LymphomaD008223EFO:0000574lymphoma2ClinicalTrials
MedulloblastomaD008527EFO:0002939medulloblastoma2ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm4ATC
ClinicalTrials
Small Cell Lung CarcinomaD055752EFO:0000702small cell lung carcinoma3ClinicalTrials
Stomach NeoplasmsD013274EFO:0000178gastric carcinoma3ClinicalTrials
Esophageal NeoplasmsD004938EFO:0005922esophageal squamous cell carcinoma3ClinicalTrials
Stomach NeoplasmsD013274EFO:0003897stomach neoplasm3ClinicalTrials
AstrocytomaD001254EFO:0002499anaplastic astrocytoma1ClinicalTrials
Carcinoma, Pancreatic DuctalD021441EFO:0002517pancreatic ductal adenocarcinoma2ClinicalTrials
Colorectal NeoplasmsD015179EFO:1001951colorectal carcinoma3ClinicalTrials
Sarcoma, EwingD012512EFO:0000174Ewing sarcoma2ClinicalTrials

Clinical Data

ClinicalTrials.gov IRINOTECAN
The Cochrane Collaboration IRINOTECAN

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
586.7 586.2791 4.09 4 114.2 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
9 1 1 10 1 1


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
11.2 9.33 3.73 2.08 3 43 0.36

Structural Alerts

There are 3 structural alerts for CHEMBL481. To view alerts please click here.

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L01 - ANTINEOPLASTIC AGENTS
L01X - OTHER ANTINEOPLASTIC AGENTS
L01XX - Other antineoplastic agents
L01XX19 - irinotecan

ChemSpider ChemSpider:UWKQSNNFCGGAFS-XIFFEERXSA-N
DailyMed irinotecan hydrochloride
PubChem SID: 124893595
Wikipedia Irinotecan

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL481



ACToR 97682-44-5
BindingDB 50128267
Brenda 161387 159474 139378 14217 25961 31924 4670 20080 17312
ChEBI 80630
ChemicalBook CB1124156
DrugBank DB00762
DrugCentral 1482
eMolecules 901988 31588824
EPA CompTox Dashboard DTXSID1041051
FDA SRS 7673326042
Guide to Pharmacology 6823
Human Metabolome Database HMDB0014900
IBM Patent System 9D5D7AFCAE213A6642D9AD402410F75B
KEGG Ligand C16641
LINCS LSM-2167
Mcule MCULE-1702653278
MolPort MolPort-003-848-231
Nikkaji J261.801J
PDBe CP0
PharmGKB PA450085
PubChem 60838
PubChem: Thomson Pharma 14911520 14764625
Selleck Irinotecan
SureChEMBL SCHEMBL4034
ZINC ZINC000001612996

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/UWKQSNNFCGGAFS-XIFFEERXSA-N spacer
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