CAS 100286-90-6|Irinotecan hydrochloride

Introduction：Basic information about CAS 100286-90-6|Irinotecan hydrochloride, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Irinotecan hydrochloride BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Articles123
7. Synonyms

Common Name	Irinotecan hydrochloride
CAS Number	100286-90-6	Molecular Weight	623.139
Density	/	Boiling Point	257 °C
Molecular Formula	C₃₃H₃₉ClN₄O₆	Melting Point	250-256°C (dec.)
MSDS	ChineseUSA	Flash Point	482ºC
Symbol	GHS07	Signal Word	Warning

Names

Name	Irinotecan hydrochloride
Synonym	More Synonyms

Irinotecan hydrochloride BiologicalActivity

Description	Irinotecan hydrochloride is a water soluble topoisomerase I inhibitor mainly used to treat colon cancer and rectal cancer.
Related Catalog	Signaling Pathways >>Autophagy >>AutophagySignaling Pathways >>Cell Cycle/DNA Damage >>TopoisomeraseResearch Areas >>Cancer
Target	Topoisomerase I
In Vitro	Irinotecan hydrochloride is a topoisomerase I inhibitor. Irinotecan inhibits the growth of LoVo and HT-29 cells, with IC50s of 15.8 ± 5.1 and 5.17 ± 1.4 μM, respectively, and induces similar amounts of cleavable complexes in both in LoVo and HT-29 cells[2]. Irinotecan suppresses the proliferation of human umbilical vein endothelial cells (HUVEC), with an IC50 of 1.3 μM[3].
In Vivo	Irinotecan (CPT-11, 5 mg/kg) significantly inhibits the growth of tumors by intratumoral injection daily for 5 days, on two consecutive weeks in rats, and such effects also occur via continuous intraperitoneal infusion by osmotic minipump into mice. However, Irinotecan (10 mg/kg) shows no effect on the growth of tumor by i.p[1]. Irinotecan (CPT-11, 100-300 mg/kg, i.p.) apparently suppresses tumor growth of HT-29 xenografts in athymic female mice by day 21. The two groups of Irinotecan (125 mg/kg) plus TSP-1 (10 mg/kg per day) or Irinotecan (150 mg/kg) in combination TSP-1 (20 mg/kg per day) are nearly equally effective and inhibit tumor growth 84% and 89%, respectively, and both are more effective than Irinotecan alone at doses of 250 and 300 mg/kg[3].
Cell Assay	Exponentially growing cells are seeded in 20 cm2 dishes with an optimal cell number for each cell line (20,000 for LoVo cells, 100,000 for HT-29 cells). They are treated 2 days later with increasing concentrations of irinotecan or SN-38 for one cell doubling time (24 h for LoVo cells, 40 h for HT-29 cells). After washing with 0.15 M NaCl, the cells are further grown for two doubling times in normal medium, detached from the support with trypsin-EDTA and counted in a hemocytometer. The IC50 values are then estimated as the drug concentrations responsible for 50% growth inhibition as compared with cells incubated without drug[2].
Animal Admin	Irinotecan has been administered by intratumoral injection at 0.1 cc volume of the appropriate solution, for a doses of 5 mg/kg daily for 5 days, on two consecutive weeks, followed by a 7-days rest period, referred to as one cycle of therapy. Rats receive three cycles over a period of 8 weeks. Control animals receive 0.1 cc of sterile 0.9% sodium chloride solution by intratumoral injection in the same rule of administration as that of animals of group II[1].
References	[1]. Morales C, et al. Antitumoral effect of irinotecan (CPT-11) on an experimental model of malignant neuroectodermal tumor. J Neurooncol. 2002 Feb;56(3):219-26. [2]. Pavillard V, et al. Determinants of the cytotoxicity of irinotecan in two human colorectal tumor cell lines. Cancer Chemother Pharmacol. 2002 Apr;49(4):329-35. Epub 2002 Jan 30. [3]. Allegrini G, et al. Thrombospondin-1 plus irinotecan: a novel antiangiogenic-chemotherapeutic combination that inhibits the growth of advanced human colon tumor xenografts in mice. Cancer Chemother Pharmacol. 2004 Mar;53(3):261-6. Epub 2003 Dec 5.

Chemical & Physical Properties

Boiling Point	257 °C
Melting Point	250-256°C (dec.)
Molecular Formula	C₃₃H₃₉ClN₄O₆
Molecular Weight	623.139
Flash Point	482ºC
Exact Mass	622.255798
PSA	114.20000
LogP	4.76890
Vapour Pressure	1.31E-32mmHg at 25°C
Index of Refraction	67.7 ° (C=1, H2O)
InChIKey	GURKHSYORGJETM-WAQYZQTGSA-N
SMILES	CCc1c2c(nc3ccc(OC(=O)N4CCC(N5CCCCC5)CC4)cc13)-c1cc3c(c(=O)n1C2)COC(=O)C3(O)CC.Cl
Storage condition	Refrigerator

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DW1061000

CAS REGISTRY NUMBER :: 100286-90-6

LAST UPDATED :: 199806

DATA ITEMS CITED :: 20

MOLECULAR FORMULA :: C33-H38-N4-O6.Cl-H

MOLECULAR WEIGHT :: 623.21

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 867 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - effect, not otherwise specified Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 83600 ug/kg

TOXIC EFFECTS :: Tumorigenic - active as anti-cancer agent

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 765 mg/kg

TOXIC EFFECTS :: Tumorigenic - active as anti-cancer agent

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 177 mg/kg

TOXIC EFFECTS :: Tumorigenic - active as anti-cancer agent

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 132 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - effect, not otherwise specified Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 40 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Gastrointestinal - hypermotility, diarrhea Gastrointestinal - nausea or vomiting

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 728 mg/kg/26W-C

TOXIC EFFECTS :: Endocrine - other changes Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Blood - changes in other cell count (unspecified)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 112 mg/kg/4W-I

TOXIC EFFECTS :: Endocrine - changes in thymus weight Blood - pigmented or nucleated red blood cells Blood - other changes

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 700 mg/kg/14D-I

TOXIC EFFECTS :: Gastrointestinal - ulceration or bleeding from small intestine Gastrointestinal - hypermotility, diarrhea Gastrointestinal - other changes

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 44800 ug/kg/28D-C

TOXIC EFFECTS :: Endocrine - changes in spleen weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Blood - changes in other cell count (unspecified)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 66 mg/kg

SEX/DURATION :: female 7-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - Central Nervous System

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 66 mg/kg

SEX/DURATION :: female 7-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 66 mg/kg

SEX/DURATION :: female 7-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - skin and skin appendages Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 66 mg/kg

SEX/DURATION :: female 7-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - live birth index (measured after birth) Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 78 mg/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 78 mg/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 78 mg/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 78 mg/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Rodent - mouse Leukocyte

DOSE/DURATION :: 100 umol/L

REFERENCE :: CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 51,4187,1991

Safety Information

Symbol	GHS07
Signal Word	Warning
Hazard Statements	H302
Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes	Xn
Risk Phrases	R22
RIDADR	NONH for all modes of transport
RTECS	DW1060750

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Synonyms

Campto hydrochloride

Campto

[1,4'-Bipiperidine]-1'-carboxylic acid, (4S)-4,11-diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl ester, hydrochloride (1:1)

[1,4'-bipiperidine]-1'-carboxylic acid, (4S)-4,11-diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl ester, monohydrochloride

1,4'-bipipéridine-1'-carboxylate de (4S)-4,11-diéthyl-4-hydroxy-3,14-dioxo-3,4,12,14-tétrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoléin-9-yle chlorhydrate

Camptothecin 11 hydrochloride

Irinotecan hydrochloride

CPT-11 hydrochloride

Topotecin

(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 hydrochloride

irinotecan hydrochloride (anhydrous)

Irinotecan Hcl

CPT 11

(4s)-4,11-diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1h-pyrano[3',4':6,7]indolizino[1,2-b]chinolin-9-yl-1,4'-bipiperidin-1'-carboxylathydrochlorid

(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 hydrochloride (1:1)

Camptothecin analog

MFCD01862255

Irinotecan (hydrochloride)

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