CAS No.100286-90-6,Irinotecan hydrochloride Suppliers

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Basic Information

Molecular Structure:
CAS No.:	100286-90-6
Name:	Irinotecan hydrochloride
Article Data:	24

Formula:	C₃₃H₃₈N₄O₆^.HCl
Molecular Weight:	623.149
Synonyms:	[1,4'-Bipiperidine]-1'-carboxylicacid,(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(9CI);[1,4'-Bipiperidine]-1'-carboxylic acid,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,(S)-;1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline, [1,4'-bipiperidine]-1'-carboxylic acid deriv.;7-Ethyl-10-[[4-(1-piperidyl)-1-piperidyl]carbonyloxy]camptothecin hydrochloride;CPT 11;Campto;Camptosar;Camptothecin 11;Camptothecin 11 hydrochloride;Topotecin;U 101440E;
EINECS:	600-054-0
Melting Point:	250-256 ºC (dec.)
Boiling Point:	873.4 ºC at 760 mmHg
Flash Point:	482 ºC
Solubility:	Soluble in DMSO at 100mg/ml. Soluble in water at 25mg/ml with warming
Appearance:	Yellow crystalline powder
Hazard Symbols:	Xn
Risk Codes:	22
PSA:	114.20000
LogP:	4.76890

Synthetic route

: 97682-44-5, 130144-33-1
irinotecan

: 100286-90-6
irinotecan hydrochloirde

Conditions

Conditions	Yield
With hydrogenchloride In dichloromethane; water at 0℃; for 2 - 3h; Product distribution / selectivity;	100%
With hydrogenchloride In tetrahydrofuran; water Product distribution / selectivity;	100%
With hydrogenchloride In water Product distribution / selectivity;	95%

: 4897-50-1
4-piperidinopiperidin

: 86639-52-3, 110714-48-2, 130144-34-2
7-ethyl-10-hydroxycamptothecin

: 100286-90-6
irinotecan hydrochloirde

Conditions

Conditions	Yield
Stage #1: 4-piperidinopiperidine-1-carbonyl chloride hydrochloride; 7-ethyl-10-hydroxycamptothecin With triethylamine In pyridine; dichloromethane at 30 - 40℃; for 1.5h; Stage #2: 4-piperidinopiperidin In pyridine; dichloromethane for 0.5h;	90%

: 1-chloroformyl-4-piperidinylpiperidine monohydrochloride

: 86639-52-3, 110714-48-2, 130144-34-2
7-ethyl-10-hydroxycamptothecin

: 100286-90-6
irinotecan hydrochloirde

Conditions

Conditions	Yield
Stage #1: 4-piperidinopiperidine-1-carbonyl chloride hydrochloride; 7-ethyl-10-hydroxycamptothecin With pyridine; triethylamine In dichloromethane at 30 - 40℃; for 1.5h; Stage #2: With 4-piperidinopiperidin In dichloromethane at 0 - 80℃; for 0.5h; pH=4.0; Stage #3: With hydrogenchloride In water; acetonitrile at 20℃; for 20h; Product distribution / selectivity;	90%
Stage #1: 4-piperidinopiperidine-1-carbonyl chloride hydrochloride; 7-ethyl-10-hydroxycamptothecin With pyridine; triethylamine In dichloromethane at 20℃; for 2h; Stage #2: With hydrogenchloride In water at 0 - 80℃; for 20h; pH=4.0; Product distribution / selectivity;	80%
With triethylamine In pyridine; dichloromethane; water at 20℃; for 2h;	80%

: irinotecan carboxylate

: 100286-90-6
irinotecan hydrochloirde

Conditions

Conditions	Yield
With Britton-Robinson's buffer pH 6.0; water at 37℃; Equilibrium constant; Kinetics; Thermodynamic data; Ea, A, var. pH, var. temp., var. time;

: 7-ethyl-10-[4-(1-piperidino)-1-piperidino]carboxyoxycamptothecin acetic acid salt

: 100286-90-6
irinotecan hydrochloirde

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; n-heptane; water at 0 - 10℃; for 1h; pH=< 4;
With hydrogenchloride In ethanol; water; ethyl acetate at 0 - 10℃; for 1h; pH=< 4;
With hydrogenchloride In ethanol; water; ethyl acetate at 0 - 10℃; for 1h; pH=< 4;
With hydrogenchloride In methanol; water; ethyl acetate at 0 - 10℃; for 1h; pH=< 4;
With hydrogenchloride In methanol at 50℃;

: (S)-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 [1,4'bipiperidine]-1'-carboxylate acetate

: 100286-90-6
irinotecan hydrochloirde

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 50℃;

: 4897-50-1
4-piperidinopiperidin

: 100286-90-6
irinotecan hydrochloirde

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: dichloromethane; acetonitrile / 20 - 70 °C 1.2: 20 °C 2.1: triethylamine; pyridine; acetamide / dichloromethane / 2 h / 30 - 40 °C / Inert atmosphere 3.1: hydrogenchloride / water View Scheme
Multi-step reaction with 3 steps 1.1: dichloromethane; hexane; acetonitrile / 20 - 25 °C 1.2: 20 °C 2.1: pyridine / dichloromethane; acetamide / 2 h / 30 - 40 °C / Inert atmosphere 3.1: hydrogenchloride / water / 20 h / 2 - 70 °C View Scheme
Multi-step reaction with 3 steps 1: dichloromethane / 0 - 20 °C 2: 1-Methylpyrrolidine / dichloromethane / 20 - 45 °C 3: hydrogenchloride / water / 3 h / 70 °C View Scheme
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 3 h / 60 - 65 °C 2: dichloromethane / 6 h / 45 - 50 °C 3: hydrogenchloride / water / 12 h / 20 °C View Scheme

: 86639-52-3, 110714-48-2, 130144-34-2
7-ethyl-10-hydroxycamptothecin

: 100286-90-6
irinotecan hydrochloirde

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; pyridine; acetamide / dichloromethane / 2 h / 30 - 40 °C / Inert atmosphere 2: hydrogenchloride / water View Scheme
Multi-step reaction with 2 steps 1: pyridine / dichloromethane; acetamide / 2 h / 30 - 40 °C / Inert atmosphere 2: hydrogenchloride / water / 20 h / 2 - 70 °C View Scheme

: 103816-19-9
4-piperidinopiperidine-1-carbonyl chloride

: 100286-90-6
irinotecan hydrochloirde

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; pyridine; acetamide / dichloromethane / 2 h / 30 - 40 °C / Inert atmosphere 2: hydrogenchloride / water View Scheme
Multi-step reaction with 2 steps 1: pyridine / dichloromethane; acetamide / 2 h / 30 - 40 °C / Inert atmosphere 2: hydrogenchloride / water / 20 h / 2 - 70 °C View Scheme

: 110351-94-5
(4S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione

: 100286-90-6
irinotecan hydrochloirde

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: trifluoroacetic acid / toluene / 20 h / 85 - 90 °C / Industry scale 2: 1-Methylpyrrolidine / dichloromethane / 20 - 45 °C 3: hydrogenchloride / water / 3 h / 70 °C View Scheme

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Consensus Reports

In 2004, a clinical study was performed that both validated prospectively the association of the variant with greater toxicity and the ability of genetic testing in predicting that toxicity before chemotherapy administration.
In 2005, the FDA made changes to the labelling of irinotecan to add pharmacogenomics recommendations that patients with polymorphisms in UGT1A1 gene, specifically the variant, should perhaps receive reduced drug doses. Irinotecan is one of the first widely-used chemotherapy agents that is dosed for each patient according to his genotype.

Specification

1. Introduction of Irinotecan hydrochloride
Irinotecan hydrochloride is yellow crystalline powder or white or off-white crystalline powder. Its systematic name is called (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). Irinotecan hydrochloride belongs to product categories of Active Pharmaceutical Ingredients; Antineoplastic; Antitumors for Research and Experimental Use; Biochemistry; Chiral Reagents; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals; Irinotecan.

This chemical is a yellow crystalline powder and should be sealed in a cool, dry place at the temperature of 2-8 °C. Besides, its Classification Code is Antineoplastic Agents; Antineoplastic Agents, Phytogenic; Drug / Therapeutic Agent; Enzyme Inhibitors; Mutation data; Radiation-Sensitizing Agents; Reproductive Effect; Topoisomerase I Inhibitors; Topoisomerase Inhibitors. Irinotecan hydrochloride Solubility is DMSO (50 mg/ml).

2. Properties of Irinotecan hydrochloride
Physical properties about Irinotecan hydrochloride are:
(1)ACD/LogP: 4.18; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 1.09; (4)ACD/LogD (pH 7.4): 2.53; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 19.89; (7)ACD/KOC (pH 5.5): 3.63; (8)ACD/KOC (pH 7.4): 100.73; (9)#H bond acceptors: 10; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 101.51 Å²; (13)Flash Point: 482 °C; (14)Enthalpy of Vaporization: 132.98 kJ/mol; (15)Boiling Point: 873.4 °C at 760 mmHg; (16)Vapour Pressure: 1.31E-32 mmHg at 25 °C.

3. Structure Descriptors of Irinotecan hydrochloride
You can still convert the following datas into molecular structure:
(1) SMILES: Cl.O=C7OCC=6C(=O)N2C(\c1nc5c(c(c1C2)CC)cc(OC(=O)N4CCC(N3CCCCC3)CC4)cc5)=C/C=6[C@@]7(O)CC
(2) 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
(3) InChIKey: GURKHSYORGJETM-WAQYZQTGSA-N

4. Toxicity of Irinotecan hydrochloride
The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LD50	intravenous	40mg/kg (40mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" GASTROINTESTINAL: NAUSEA OR VOMITING	Kiso to Rinsho. Clinical Report. Vol. 24, Pg. 7185, 1990.
mouse	LD50	intraperitoneal	177mg/kg (177mg/kg)		Cancer Research. Vol. 47, Pg. 5944, 1987.
mouse	LD50	intravenous	132mg/kg (132mg/kg)	SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Kiso to Rinsho. Clinical Report. Vol. 24, Pg. 7185, 1990.
mouse	LD50	oral	765mg/kg (765mg/kg)		Cancer Research. Vol. 47, Pg. 5944, 1987.
rat	LD50	intravenous	83600ug/kg (83.6mg/kg)		Cancer Research. Vol. 47, Pg. 5944, 1987.
rat	LD50	oral	867mg/kg (867mg/kg)	SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Kiso to Rinsho. Clinical Report. Vol. 24, Pg. 7185, 1990.

5. Preparation of Irinotecan hydrochloride
Irinotecan hydrochloride is prepared by irinotecan with HCl. The reaction needs solvent ethanol at the temperature of 20 °C. Product is obtained by concentration and recrystallization. The yield is about 65.2%.

Irinotecan hydrochloride is prepared by reaction of irinotecan with HCl.

6. Uses of Irinotecan hydrochloride
Irinotecan hydrochloride is a DNA topoisomerase inhibitor. What's more, Irinotecan hydrochloride is used as DNA topoisomerase inhibitor and antineoplastic. It can inhibitor of DNA topoisomerase I that displays antitumor activity against a range of tumor types.