IRINOTECAN

Search structure
Synonyms:
Status: Approved (1996)
Entry Type: Small molecule
Molecule Category: Parent Prodrug
ATC: L01CE02
UNII: 7673326042

Structure
InChI Key UWKQSNNFCGGAFS-XIFFEERXSA-N
Smile CCc1c2c(nc3ccc(OC(=O)N4CCC(N5CCCCC5)CC4)cc13)-c1cc3c(c(=O)n1C2)COC(=O)[C@]3(O)CC
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C33H38N4O6
Molecular Weight 586.69
AlogP 4.09
Hydrogen Bond Acceptor 9.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 4.0
Polar Surface Area 114.2
Molecular species BASE
Aromatic Rings 3.0
Heavy Atoms 43.0

Pharmacology

Primary Target
DNA topoisomerase I
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- - - 24000 -
Enzyme Hydrolase
- - - 26 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 27-34
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- 20800 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC47 family of multidrug and toxin extrusion transporters
- 2100-7900 - - 49

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Neoplasms 4 D009369 ClinicalTrials
Colorectal Neoplasms 3 D015179 ClinicalTrials
Uterine Cervical Neoplasms 3 D002583 ClinicalTrials
Uterine Cervical Neoplasms 3 D002583 ClinicalTrials
Rectal Neoplasms 3 D012004 ClinicalTrials
Colonic Neoplasms 3 D003110 ClinicalTrials
Neoplasm Metastasis 3 D009362 ClinicalTrials
Adenocarcinoma, Mucinous 3 D002288 ClinicalTrials
Lung Neoplasms 3 D008175 ClinicalTrials
Choroid Plexus Neoplasms 3 D016545 ClinicalTrials
Stomach Neoplasms 3 D013274 ClinicalTrials
Pancreatic Neoplasms 3 D010190 ClinicalTrials
Lung Neoplasms 3 D008175 ClinicalTrials
Esophageal Neoplasms 3 D004938 ClinicalTrials
Hepatoblastoma 3 D018197 ClinicalTrials
Esophageal Neoplasms 3 D004938 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Cholangiocarcinoma 3 D018281 ClinicalTrials
Carcinoma, Hepatocellular 3 D006528 ClinicalTrials
Stomach Neoplasms 3 D013274 ClinicalTrials
Brain Neoplasms 3 D001932 ClinicalTrials
Sarcoma, Ewing 3 D012512 ClinicalTrials
Brain Neoplasms 3 D001932 ClinicalTrials
Rectal Neoplasms 3 D012004 ClinicalTrials
Uterine Cervical Neoplasms 3 D002583 ClinicalTrials
Pancreatic Neoplasms 3 D010190 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Stomach Neoplasms 3 D013274 ClinicalTrials
Colorectal Neoplasms 3 D015179 ClinicalTrials
Colonic Neoplasms 3 D003110 ClinicalTrials
Cholangiocarcinoma 3 D018281 ClinicalTrials
Colorectal Neoplasms 3 D015179 ClinicalTrials
Esophageal Neoplasms 3 D004938 ClinicalTrials
Stomach Neoplasms 3 D013274 ClinicalTrials
Rectal Neoplasms 3 D012004 ClinicalTrials
Small Cell Lung Carcinoma 3 D055752 ClinicalTrials
Colorectal Neoplasms 3 D015179 ClinicalTrials
Pulmonary Disease, Chronic Obstructive 2 D029424 ClinicalTrials
Carcinoma 2 D002277 ClinicalTrials
Glioma 2 D005910 ClinicalTrials
Glioblastoma 2 D005909 ClinicalTrials
Leukemia 2 D007938 ClinicalTrials
Lymphoma 2 D008223 ClinicalTrials
Neuroblastoma 2 D009447 ClinicalTrials
Carcinoma, Squamous Cell 2 D002294 ClinicalTrials
Carcinoma, Pancreatic Ductal 2 D021441 ClinicalTrials
Rhabdomyosarcoma 2 D012208 ClinicalTrials
Medulloblastoma 2 D008527 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 2 D002289 ClinicalTrials
Biliary Tract Neoplasms 2 D001661 ClinicalTrials
Lymphoma, Non-Hodgkin 2 D008228 ClinicalTrials
Pinealoma 2 D010871 ClinicalTrials
Gliosarcoma 2 D018316 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Head and Neck Neoplasms 2 D006258 ClinicalTrials
Ganglioneuroblastoma 2 D018305 ClinicalTrials
Hemangiosarcoma 2 D006394 ClinicalTrials
Carcinoma, Islet Cell 2 D018273 ClinicalTrials
Central Nervous System Neoplasms 2 D016543 ClinicalTrials
Sarcoma 2 D012509 ClinicalTrials
Peritoneal Neoplasms 2 D010534 ClinicalTrials
Carcinoma, Neuroendocrine 2 D018278 ClinicalTrials
Fallopian Tube Neoplasms 2 D005185 ClinicalTrials
Biliary Tract Neoplasms 2 D001661 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Wilms Tumor 2 D009396 ClinicalTrials
Glioma 2 D005910 ClinicalTrials
Sarcoma 2 D012509 ClinicalTrials
Lymphoma, Large B-Cell, Diffuse 1 D016403 ClinicalTrials
Diffuse Intrinsic Pontine Glioma 1 D000080443 ClinicalTrials
Mesothelioma 1 D008654 ClinicalTrials
Bone Neoplasms 1 D001859 ClinicalTrials
Digestive System Neoplasms 1 D004067 ClinicalTrials
Oligodendroglioma 1 D009837 ClinicalTrials
Carcinoid Tumor 1 D002276 ClinicalTrials
Liver Neoplasms 1 D008113 ClinicalTrials
Kidney Neoplasms 1 D007680 ClinicalTrials
Astrocytoma 1 D001254 ClinicalTrials
Endometrial Neoplasms 1 D016889 ClinicalTrials
Desmoplastic Small Round Cell Tumor 0 D058405 ClinicalTrials

Related Entries

Scaffolds

Salt

Cross References

Resources Reference
CAS NUMBER 97682-44-5
ChEBI 80630
ChEMBL CHEMBL481
DrugBank DB00762
DrugCentral 1482
EPA CompTox DTXSID1041051
FDA SRS 7673326042
Human Metabolome Database HMDB0014900
Guide to Pharmacology 6823
KEGG C16641
PDB CP0
PharmGKB PA450085
PubChem 60838
SureChEMBL SCHEMBL4034
ZINC ZINC000001612996
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