IRINOTECAN SUCROSOFATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	4C33H38N4O6.C12H22O35S8
Molecular Weight	3329.5285
Optical Activity	UNSPECIFIED
Defined Stereocenters	13 / 13
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCc1c2cc(ccc2nc-3c1Cn4c3cc5c(COC(=O)[C@@]5(CC)O)c4=O)OC(=O)N6CCC(CC6)N7CCCCC7.CCc1c2cc(ccc2nc-3c1Cn4c3cc5c(COC(=O)[C@@]5(CC)O)c4=O)OC(=O)N6CCC(CC6)N7CCCCC7.CCc1c2cc(ccc2nc-3c1Cn4c3cc5c(COC(=O)[C@@]5(CC)O)c4=O)OC(=O)N6CCC(CC6)N7CCCCC7.CCc1c2cc(ccc2nc-3c1Cn4c3cc5c(COC(=O)[C@@]5(CC)O)c4=O)OC(=O)N6CCC(CC6)N7CCCCC7.C([C@]1([H])[C@]([H])([C@@]([H])([C@]([H])([C@]([H])(O1)O[C@@]2(COS(=O)(=O)O)[C@]([H])([C@@]([H])([C@@]([H])(COS(=O)(=O)O)O2)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O

InChI

InChIKey=BCPSLKYBXGKPIW-RTXWKGGWSA-N

InChI=1S/4C33H38N4O6.C12H22O35S8/c4*1-3-22-23-16-21(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;13-48(14,15)37-1-4-6(43-51(22,23)24)8(45-53(28,29)30)9(46-54(31,32)33)11(40-4)42-12(3-39-50(19,20)21)10(47-55(34,35)36)7(44-52(25,26)27)5(41-12)2-38-49(16,17)18/h4*8-9,16-17,20,41H,3-7,10-15,18-19H2,1-2H3;4-11H,1-3H2,(H,13,14,15)(H,16,17,18)(H,19,20,21)(H,22,23,24)(H,25,26,27)(H,28,29,30)(H,31,32,33)(H,34,35,36)/t4*33-;4-,5-,6-,7-,8+,9-,10+,11-,12+/m00001/s1

HIDE SMILES / InChI

Molecular Formula	C33H38N4O6
Molecular Weight	586.6793
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	C12H22O35S8
Molecular Weight	982.8114
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020571s048lbl.pdf | https://www.drugs.com/cdi/irinotecan.html | https://www.ncbi.nlm.nih.gov/pubmed/14988754

breaks.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA topoisomerase I 54 Target ID: CHEMBL1781 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020571s048lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/9655905 \| https://www.ncbi.nlm.nih.gov/pubmed/8182764 \| https://www.ncbi.nlm.nih.gov/pubmed/8388965 \| https://www.ncbi.nlm.nih.gov/pubmed/14988754	Inhibitor 7701	Metastatic carcinoma of the colon or rectum

Conditions

Condition	Modality	Targets	Highest Phase	Product
Metastatic carcinoma of the colon or rectum 5 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020571s048lbl.pdf	Primary	DNA topoisomerase I	Approved 7997	CAMPTOSAR Approved Use CAMPTOSAR is a topoisomerase inhibitor indicated for: • First-line therapy in combination with 5-fluorouracil and leucovorin for patients with metastatic carcinoma of the colon or rectum. (1) • Patients with metastatic carcinoma of the colon or rectum whose disease has recurred or progressed following initial fluorouracil-based therapy. Launch Date 834710400000

C_max

Value	Dose	Co-administered	Analyte	Population
3392 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020571s051lbl.pdf	340 mg/m² single, intravenous dose: 340 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		IRINOTECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
1660 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020571s051lbl.pdf	125 mg/m² single, intravenous dose: 125 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		IRINOTECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
20604 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020571s051lbl.pdf	340 mg/m² single, intravenous dose: 340 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		IRINOTECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
10200 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020571s051lbl.pdf	125 mg/m² single, intravenous dose: 125 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		IRINOTECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
11.7 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020571s051lbl.pdf	340 mg/m² single, intravenous dose: 340 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		IRINOTECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
5.8 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020571s051lbl.pdf	125 mg/m² single, intravenous dose: 125 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		IRINOTECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
51% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020571s051lbl.pdf	125 mg/m² single, intravenous dose: 125 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		IRINOTECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
21 mg/m2 1 times / day multiple, oral MTD Dose: 21 mg/m2, 1 times / day Route: oral Route: multiple Dose: 21 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/30406838/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/30406838/	Other AEs: Fatigue, Weight loss... Other AEs: Fatigue (grade 1-2, 33.3%) Weight loss (grade 1-2, 33.3%) Diarrhea (grade 1-2, 50%) Nausea (grade 1-2, 58.3%) Vomiting (grade 1-2, 50%) Cholinergic syndrome (grade 1-2, 33.3%) Mucositis (grade 1-2, 33.3%) Dyspnea (grade 1-2, 8.3%) Fever (grade 1-2, 8.3%) Fatigue (grade 3, 8.3%) Diarrhea (grade 3, 8.3%) Nausea (grade 3, 8.3%) Vomiting (grade 3, 8.3%) Cholinergic syndrome (grade 3, 33.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/30406838/
290 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 290 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 290 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/10873073/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10873073/	Other AEs: Leukopenia, Leukopenia... Other AEs: Leukopenia (grade 2, 1 patient) Leukopenia (grade 3, 2 patients) Leukopenia (grade 4, 1 patient) Neutropenia (grade 2, 2 patients) Neutropenia (grade 3, 2 patients) Neutropenia (grade 4, 1 patient) Nausea (grade 1, 4 patients) Nausea (grade 3, 1 patient) Vomiting (grade 4, 1 patient) Diarrhea (grade 1, 2 patients) Diarrhea (grade 2, 3 patients) Diarrhea (grade 4, 1 patient) Anorexia (grade 1, 3 patients) Anorexia (grade 2, 2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/10873073/
320 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 320 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 320 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/10873073/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10873073/	Other AEs: Leukopenia, Leukopenia... Other AEs: Leukopenia (grade 1, 4 patients) Leukopenia (grade 2, 1 patient) Leukopenia (grade 3, 2 patients) Neutropenia (grade 1, 2 patients) Neutropenia (grade 2, 2 patients) Neutropenia (grade 4, 2 patients) Thrombocytopenia (grade 1, 2 patients) Nausea (grade 1, 3 patients) Nausea (grade 2, 3 patients) Nausea (grade 3, 2 patients) Vomiting (grade 1, 2 patients) Vomiting (grade 2, 2 patients) Vomiting (grade 3, 1 patient) Vomiting (grade 4, 1 patient) Diarrhea (grade 1, 3 patients) Diarrhea (grade 2, 2 patients) Diarrhea (grade 3, 1 patient) Diarrhea (grade 4, 1 patient) Anorexia (grade 1, 3 patients) Anorexia (grade 2, 2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/10873073/

AEs

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:80630	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:80630
MolPort	MolPort-003-848-231	https://www.molport.com/shop/molecule-link/MolPort-003-848-231
ZINC	ZINC000001612996	http://zinc15.docking.org/substances/ZINC000001612996

PubMed

Title	Date	PubMed
Management of chemotherapy-induced adverse effects in the treatment of colorectal cancer.	2001	11419562
A dose-finding study of irinotecan (CPT-11) plus a four-day continuous 5-fluorouracil infusion in advanced colorectal cancer.	2001	11340371
Factors affecting the pharmacokinetics of CPT-11: the body mass index, age and sex are independent predictors of pharmacokinetic parameters of CPT-11.	2001	11291833
Irinotecan and mitomycin C in 5-fluorouracil-refractory colorectal cancer patients. A phase I/II study of the Southern Italy Cooperative Oncology Group.	2001	11244327
Treatment of extensive stage small cell lung cancer.	2001	11224990
Lung cancer: therapeutic options for stage IV and recurrent NSCLC.	2001	11224988
[Home chemotherapy and/or outpatient chemotherapy for patient with advanced gastric cancer].	2001 Apr	11424453
[Irinotecan (CPT-11) therapy for advanced gastric cancer].	2001 Apr	11424411
[Chemotherapy of irinotecan (CPT-11) combined with cisplatin in patients with advanced gastric cancer].	2001 Apr	11424409
Safe administration of irinotecan, oxaliplatin and raltitrexed in a DPD-deficient patient with metastatic colon cancer.	2001 Apr	11398894
A phase II trial of irinotecan (CPT-11) for unresectable biliary tree carcinoma.	2001 Apr	11398883
The role of irinotecan and oxaliplatin in the treatment of advanced colorectal cancer.	2001 Apr	11346931
Human plasma carboxylesterase and butyrylcholinesterase enzyme activity: correlations with SN-38 pharmacokinetics during a prolonged infusion of irinotecan.	2001 Apr	11345644
Antitumor activity of XR5944, a novel and potent topoisomerase poison.	2001 Apr	11335793
Pharmacogenetics of anticancer agents: lessons from amonafide and irinotecan.	2001 Apr	11259359
Subcellular localization and distribution of the breast cancer resistance protein transporter in normal human tissues.	2001 Apr 15	11309308
Prevention of irinotecan (CPT-11)-induced diarrhea by oral alkalization combined with control of defecation in cancer patients.	2001 Apr 15	11291056
26S proteasome inhibition induces apoptosis and limits growth of human pancreatic cancer.	2001 Apr 2-27	11400168
The current status of docetaxel for advanced non-small cell lung cancer.	2001 Feb	11340898
[Medical treatment of pulmonary neoplasms].	2001 Feb	11294106
North Central Cancer Treatment Group--Mayo Clinic trials in colon cancer.	2001 Feb	11273589
Modulation of camptothecin analogs in the treatment of cancer: a review.	2001 Feb	11261892
[Weekly low dose CPT-11 for multiple lung metastases of colon cancer on an out-patient treatment: a case report].	2001 Feb	11235190
Effect of bile acids on the uptake of irinotecan and its active metabolite, SN-38, by intestinal cells.	2001 Feb 16	11342261
New state of the art in small-cell lung cancer.	2001 Jan	11221023
Current status of irinotecan in lung cancer.	2001 Jan	11221022
Irinotecan: summary and future directions.	2001 Jan	11221021
Rationale and dose-finding studies of the combination of irinotecan and a taxane on a weekly schedule.	2001 Jan	11221018
[Irinotecan in colorectal cancer].	2001 Jan-Feb	11300023
Topoisomerase I-DNA covalent complexes in human colorectal cancer xenografts with different p53 and microsatellite instability status: relation with their sensitivity to CTP-11.	2001 Jan-Feb	11299781
Perioperative radiotherapy and concurrent radiochemotherapy in rectal cancer.	2001 Jan-Feb	11291127
New chemotherapy approaches in colorectal cancer.	2001 Jul	11429486
Control of irinotecan-induced diarrhea by octreotide after loperamide failure.	2001 Jun	11430421
Phase I-II study of irinotecan in combination with mitomycin C in patients with advanced gastrointestinal cancer.	2001 Jun	11404495
Active transepithelial transport of irinotecan (CPT-11) and its metabolites by human intestinal Caco-2 cells.	2001 Jun	11395570
Hepatic extraction, metabolism, and biliary excretion of irinotecan in the isolated perfused rat liver.	2001 Jun	11357175
Irinotecan/gemcitabine combination chemotherapy in pancreatic cancer.	2001 Mar	11301841
Cisplatin and irinotecan in upper gastrointestinal malignancies.	2001 Mar	11301840
[A case of AFP-producing gastric cancer responding to low-dose CPT-11 and low-dose cisplatin combination chemotherapy].	2001 Mar	11265410
Irinotecan in the treatment of colorectal cancer: clinical overview.	2001 Mar 1	11230497
[Chemotherapy of colonic carcinoma in the year 2001].	2001 Mar 22	11324309
Preliminary study of fortnightly irinotecan hydrochloride plus cisplatin therapy in patients with advanced gastric and colorectal cancer.	2001 May	11391851
[A modified administrated schedule for combination therapy with irinotecan and cisplatin as a neoadjuvant chemotherapy in locally advanced cervical cancer--a report of 2 cases as a pilot study].	2001 May	11383222
[Platinum compounds in cancer therapy--past, present, and future].	2001 May	11383210
CPT-11 alters the circadian rhythm of dihydropyrimidine dehydrogenase mRNA in mouse liver.	2001 May	11376565
Modulation of irinotecan-induced diarrhea by cotreatment with neomycin in cancer patients.	2001 May	11350876
Potentiation of antitumor activity of irinotecan by chemically modified oligonucleotides.	2001 May	11295057
Enhanced chemosensitivity to CPT-11 with proteasome inhibitor PS-341: implications for systemic nuclear factor-kappaB inhibition.	2001 May 1	11325813
Phase I study of hepatic arterial infusion of floxuridine and dexamethasone with systemic irinotecan for unresectable hepatic metastases from colorectal cancer.	2001 May 15	11352961
Advances in chemotherapy for small cell lung cancer: single-agent activity of newer agents.	2001 May-Jun	11419031

Patents

Sample Use Guides

In Vivo Use Guide

Usual Adult Dose for Colorectal Cancer

Route of Administration: Intravenous

In Vitro Use Guide

The sensitivity to CPT-11 (Irinotecan) alone, of 5 human colon-cancer cell lines, expressed as IC50 values, varied between 2.5 and 6.1uM. The anti-proliferative effectsof the active metabolite SN-38 showed IC50 values between 5.6 and 38 nM, 130 to 570 times lower than those measured for CPT-11 alone. The sensitivity to SN-38 was highest in LS174T and COLO320 cells, intermediate in SW1398 cells and lowest in COLO 205 and WiDr cells.

Substance Class	Chemical Created by `admin` on `Sat Jun 26 15:52:39 UTC 2021` Edited by `admin` on `Sat Jun 26 15:52:39 UTC 2021`
Record UNII	OL741S3N8B
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

IRINOTECAN SUCROSOFATE

Official Name

English

IRINOTECAN SUCROSOFATE [USAN]

Common Name

English

MM-398

Code

English

IRINOTECAN SUCROSOFATE [WHO-DD]

Common Name

English

PEP-02

Code

English

SULFATE OF SUCROSE (ESTER) AND OF IRINOTECAN (SALT): SUCROSE OCTAKIS(HYDROGEN SULFATE) SALT WITH (4S)-4,11-DIETHYL-4-HYDROXY-3,14-DIOXO-3,4,12,14-TETRAHYDRO-1H-PYRANO(3',4':6,7)INDOLIZINO(1,2-B)QUINOLIN-9-YL (1,4'-BIPIPERIDINE)-1'-CARBOXYLATE

Systematic Name

English

Code System Code Type Description

PUBCHEM

76964235