Irinotecan hydrochloride trihydrate

Molecular Weight：677.192

Modify Date.: 2022-10-28 03:01

Introduction: White powderChEBI: A hydrate that is the trihydrate form of irinotecan hydrochloride. Onivyde is used in combination with fluorouracil and leucovorin, for the treatment of patients with metastatic adenocarcinoma of the pancreas after disease progression following gemcitabinebased therapy. It is converted via hydrolysis of the carbamate linkage to its active metabolite, SN-38, which is ~1000 times more active. View more+

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1. Names and Identifiers

1.1 Name: Irinotecan hydrochloride trihydrate
1.2 Synonyms: (+)-(4S)-4,11-Diethyl-4-hydroxy-9--1H-pyranoindolizinoquinoline-3,14-(4H,12H)-dione hydrochloride trihydrate (1,4’-bipiperidine)-1’-carboxylicacid,4,11-diethyl-3,4,12,14-tetrahydro-4-hyd (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 trihydrate [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, hydrate (1:1:3) CPT-11 Trihydrate Irinotecan (hydrochloride trihydrate) Irinotecan HCL 3H2O IRINOTECAN HCL TRIHYDRATE IRINOTECAN MONOHYDROCHLORIDE TRIHYDRATE MFCD01765731 roxy-3,14-dioxo-1h-pyrano(3’,4’:6,7)indolizino(1,2-b)quinolin-9-ylester,mono trihydrate,(s)-hydrochlorid

1.3 CAS No.: 136572-09-3

1.4 CID: 60837

1.5 EINECS(EC#): 603-967-2

1.6 Molecular Formula: C33H45ClN4O9 (isomer)

1.7 Inchi: InChI=1S/C33H38N4O6.ClH.3H2O/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;3*1H2/t33-;;;;/m0..../s1

1.8 InChkey: KLEAIHJJLUAXIQ-JDRGBKBRSA-N

1.9 Canonical Smiles: CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)C4(CC)O)C2=NC5=C1C=C(C=C5)OC(=O)N6CCC(CC6)N7CCCCC7.O.O.O.Cl

1.10 Isomers Smiles: CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)[C@@]4(CC)O)C2=NC5=C1C=C(C=C5)OC(=O)N6CCC(CC6)N7CCCCC7.O.O.O.Cl

2. Properties

2.1 Density: ==

2.1 Melting point: 250-256℃ (dec.)

2.1 Boiling point: 873.4 °C at 760 mmHg

2.1 Flash Point: 482 °C

2.1 Precise Quality: 676.28800

2.1 PSA: 141.89000

2.1 logP: 4.57600

2.1 Appearance: Pale yellow to yellow crystalline powder

2.2 Storage: Keep Cold.

2.3 Chemical Properties: White powder

2.4 Water Solubility: Soluble in DMSO at 100mg/ml. Soluble in water at 25mg/ml with warming

2.5 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A hydrate that is the trihydrate form of irinotecan hydrochloride. Onivyde is used in combination with fluorouracil and leucovorin, for the treatment of patients with metastatic adenocarcinoma of the pancreas after disease progression following gemcitabinebased therapy. It is converted via hydrolysis of the carbamate linkage to its active metabolite, SN-38, which is ~1000 times more active.

3.2 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 11 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
H341 (36.36%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]
H360 (90.91%): May damage fertility or the unborn child [Danger Reproductive toxicity]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P264, P270, P281, P301+P312, P308+P313, P330, P405, and P501

3.3 Usage: A DNA topoisomerase inhibitor.

4. Safety and Handling

4.1 Risk Statements: 22

4.1 Safety Statements: 20/21-22

4.1 RTECS: DW1060750

4.1 Safety: A poison by intravenous route. Moderately toxic by ingestion. When heated to decomposition it emits toxic vapors of NO_x, HCl, and Cl^?.

4.2 Specification: ?Irinotecan hydrochloride trihydrate , its cas register number is 136572-09-3. It also can be called (S)-[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 hydrochloride trihydrate ;?Irinotecan hydrochloride [USAN:JAN]?; (+)-7-Ethyl-10-hydroxycamptothecine 10-(1,4'-bipiperidine)-1'-carboxylate, monohydrochloride, trihydrate ; Camptosar?; Irinotecan HCl ; (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, trihydrate, (S)- .

4.3 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LD50	intravenous	40mg/kg (40mg/kg)	?	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 953, 1995.
mouse	LD50	intravenous	132mg/kg (132mg/kg)	?	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 953, 1995.
mouse	LD50	oral	1045mg/kg (1045mg/kg)	?	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 953, 1995.
rat	LD50	intravenous	83600ug/kg (83.6mg/kg)	?	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 953, 1995.
rat	LD50	oral	867mg/kg (867mg/kg)	?	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 953, 1995.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Reproductive toxicity, Category 1B

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H302 Harmful if swallowed H360 May damage fertility or the unborn child
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P308+P313 IF exposed or concerned: Get medical advice/ attention.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. Synthesis Route

136572-09-3Total: 1 Synthesis Route

100286-90-6 283 Suppliers

136572-09-3 287 Suppliers

Literatures:
FERMION OY Patent: WO2006/84941 A2, 2006 ; Location in patent: Page/Page column 6 ;
Yield: ~85%

7. Precursor and Product

precursor:

100286-90-6

8. Other Information

8.0 Target: Value

8.1 Uses: Irinotecan Hydrochloride Trihydrate is a DNA topoisomerase inhibitor.

8.2 Brand name: Camptosar (Pharmacia &Upjohn) .

8.3 Merck: 14,5091

8.4 Chemical Properties: White powder

8.5 Uses: A DNA topoisomerase inhibitor.

8.6 Definition: ChEBI: A hydrate that is the trihydrate form of irinotecan hydrochloride. Onivyde is used in combination with fluorouracil and leucovorin, for the treatment of patients with metastatic adenocarcinoma of the pancreas after disease progression following gemcitabine based therapy. It is converted via hydrolysis of the carbamate linkage to its active metabolite, SN-38, which is ~1000 times more active.

8.7 Brand name: Camptosar (Pharmacia &Upjohn) .

8.8 Hazard: Moderately toxic by ingestion.

8.9 Usage: Topoisomerase I inhibitor

9. Computational chemical data

Molecular Weight: 677.192g/mol
Molecular Formula: C₃₃H₄₅ClN₄O₉
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 676.2875067
Monoisotopic Mass: 676.2875067
Complexity: 1200
Rotatable Bond Count: 5
Hydrogen Bond Donor Count: 5
Hydrogen Bond Acceptor Count: 11
Topological Polar Surface Area: 116
Heavy Atom Count: 47
Defined Atom Stereocenter Count: 1
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 5
CACTVS Substructure Key Fingerprint: AAADcfB/vAAEAAAAAAAAAAAAAAAAAWAAAAA8WLECAAAAAFix8AAAHgAACAAADGzhngYyzvMIFgCoAyXyXAKCiCAhIiAImCF+bNgNZvbE8Zuecihm5hHL+QewwPAOgEABAAACAAAAgAIAAAQAAAAAAAAAAA==

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Irinotecan hydrochloride trihydrateCAS NO.: 136572-09-3

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Price: 1 USD/kilogram
Time: 2023/05/11

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Irinotecan hydrochloride trihydrate