IRINOTECAN HYDROCHLORIDE

Search structure
Trade Names:
Synonyms:
Status: Approved (1996)
Entry Type: Small molecule
Molecule Category: Salt Prodrug
UNII: 042LAQ1IIS
Parent Compound: IRINOTECAN

Structure
InChI Key GURKHSYORGJETM-WAQYZQTGSA-N
Smile CCc1c2c(nc3ccc(OC(=O)N4CCC(N5CCCCC5)CC4)cc13)-c1cc3c(c(=O)n1C2)COC(=O)[C@]3(O)CC.Cl
InChI
InChI=1S/C33H38N4O6.ClH/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;1H/t33-;/m0./s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C33H45ClN4O9
Molecular Weight 677.19
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

Action Mechanism of Action Reference
INHIBITOR DNA topoisomerase I inhibitor DailyMed

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Colorectal Neoplasms 3 D015179 ClinicalTrials
Sarcoma 3 D012509 ClinicalTrials
Colonic Neoplasms 3 D003110 ClinicalTrials
Hepatoblastoma 3 D018197 ClinicalTrials
Colorectal Neoplasms 3 D015179 ClinicalTrials
Lung Neoplasms 3 D008175 ClinicalTrials
Colorectal Neoplasms 3 D015179 ClinicalTrials
Rhabdomyosarcoma, Alveolar 3 D018232 ClinicalTrials
Rectal Neoplasms 3 D012004 ClinicalTrials
Mesenchymoma 3 D008637 ClinicalTrials
Diarrhea 3 D003967 ClinicalTrials
Lung Neoplasms 3 D008175 ClinicalTrials
Stomach Neoplasms 3 D013274 ClinicalTrials
Stomach Neoplasms 3 D013274 ClinicalTrials
Rectal Neoplasms 3 D012004 ClinicalTrials
Carcinoma, Pancreatic Ductal 3 D021441 ClinicalTrials
Rhabdomyosarcoma, Embryonal 3 D018233 ClinicalTrials
Pancreatic Neoplasms 3 D010190 ClinicalTrials
Stomach Neoplasms 3 D013274 ClinicalTrials
Peritoneal Neoplasms 2 D010534 ClinicalTrials
Fallopian Tube Neoplasms 2 D005185 ClinicalTrials
Neuroectodermal Tumors, Primitive, Peripheral 2 D018241 ClinicalTrials
Glioma 2 D005910 ClinicalTrials
Pinealoma 2 D010871 ClinicalTrials
Neuroblastoma 2 D009447 ClinicalTrials
Oligodendroglioma 2 D009837 ClinicalTrials
Osteosarcoma 2 D012516 ClinicalTrials
Gliosarcoma 2 D018316 ClinicalTrials
Carcinoma, Merkel Cell 2 D015266 ClinicalTrials
Small Cell Lung Carcinoma 2 D055752 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Carcinoma, Squamous Cell 2 D002294 ClinicalTrials
Ganglioneuroblastoma 2 D018305 ClinicalTrials
Astrocytoma 2 D001254 ClinicalTrials
Central Nervous System Neoplasms 2 D016543 ClinicalTrials
Oligodendroglioma 2 D009837 ClinicalTrials
Urinary Bladder Neoplasms 2 D001749 ClinicalTrials
Penile Neoplasms 2 D010412 ClinicalTrials
Lymphoma 2 D008223 ClinicalTrials
Carcinoma, Neuroendocrine 2 D018278 ClinicalTrials
Fallopian Tube Neoplasms 2 D005185 ClinicalTrials
Kidney Neoplasms 2 D007680 ClinicalTrials
Rhabdomyosarcoma 2 D012208 ClinicalTrials
Liver Neoplasms 2 D008113 ClinicalTrials
Medulloblastoma 2 D008527 ClinicalTrials
Biliary Tract Neoplasms 2 D001661 ClinicalTrials
Urethral Neoplasms 2 D014523 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 2 D002289 ClinicalTrials
Gallbladder Neoplasms 2 D005706 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Esophageal Neoplasms 2 D004938 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Choroid Plexus Neoplasms 2 D016545 ClinicalTrials
Meningioma 2 D008579 ClinicalTrials
Astrocytoma 2 D001254 ClinicalTrials
Glioblastoma 2 D005909 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Head and Neck Neoplasms 2 D006258 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Gastrointestinal Stromal Tumors 1 D046152 ClinicalTrials
Hodgkin Disease 1 D006689 ClinicalTrials
Immunoblastic Lymphadenopathy 1 D007119 ClinicalTrials
Burkitt Lymphoma 1 D002051 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
Lymphoma, Large B-Cell, Diffuse 1 D016403 ClinicalTrials
Leukemia 1 D007938 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
Lymphoma, Large-Cell, Anaplastic 1 D017728 ClinicalTrials
Carcinoma, Basal Cell 1 D002280 ClinicalTrials
Carcinoid Tumor 1 D002276 ClinicalTrials
Nasopharyngeal Neoplasms 1 D009303 ClinicalTrials
Triple Negative Breast Neoplasms 1 D064726 ClinicalTrials
Carcinoma, Verrucous 1 D018289 ClinicalTrials
Esthesioneuroblastoma, Olfactory 1 D018304 ClinicalTrials
Sezary Syndrome 1 D012751 ClinicalTrials
Mycosis Fungoides 1 D009182 ClinicalTrials
Lymphoma, AIDS-Related 1 D016483 ClinicalTrials
Lymphoma, Mantle-Cell 1 D020522 ClinicalTrials
Endometrial Neoplasms 1 D016889 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 1 D015451 ClinicalTrials
Hypopharyngeal Neoplasms 1 D007012 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 1 D054198 ClinicalTrials
Neutropenia 1 D009503 ClinicalTrials
Anus Neoplasms 1 D001005 ClinicalTrials
Papilloma, Inverted 1 D018308 ClinicalTrials
Uterine Cervical Neoplasms 1 D002583 ClinicalTrials
Appendiceal Neoplasms 1 D001063 ClinicalTrials
Salivary Gland Neoplasms 1 D012468 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 1 D064129 ClinicalTrials
Lymphoma, Follicular 1 D008224 ClinicalTrials
Leukemia-Lymphoma, Adult T-Cell 1 D015459 ClinicalTrials
Oropharyngeal Neoplasms 1 D009959 ClinicalTrials
Melanoma 1 D008545 ClinicalTrials
Carcinoma, Renal Cell 1 D002292 ClinicalTrials
Melanoma 1 D008545 ClinicalTrials
Squamous Cell Carcinoma of Head and Neck 1 D000077195 ClinicalTrials
Granuloma, Lethal Midline 1 D006103 ClinicalTrials

Related Entries

Scaffolds

Parent

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Gastrointestinal disorders
18.0
General disorders and administration site conditions
14.19
Blood and lymphatic system disorders
7.24
Nervous system disorders
7.05
Vascular disorders
6.76
Investigations
5.76
Respiratory, thoracic and mediastinal disorders
5.7
Infections and infestations
5.08
Metabolism and nutrition disorders
4.9
Skin and subcutaneous tissue disorders
4.1
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
3.62
Injury, poisoning and procedural complications
3.59
Cardiac disorders
2.68
Hepatobiliary disorders
2.39

Cross References

Resources Reference
ChEBI 90881
ChEMBL CHEMBL3989514
FDA SRS 042LAQ1IIS
Guide to Pharmacology 6823
KEGG C16641
PDB CP0
PubChem 60837
SureChEMBL SCHEMBL359364
ZINC ZINC01612996
CONTENTS