ChemicalBook > CAS DataBase List > Irinotecan

Irinotecan

Product Name: Irinotecan
CAS No.: 97682-44-5
Chemical Name: Irinotecan
Synonyms: CPT-11;IRINOTECAN HCL;CAMPTOSAR;Irinotecan(TECANS);Irinotecan (free Base);[1,4'-BIPIPERIDINE]-1'-CARBOXYLIC ACID;(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaen-7-yl 4-(piperidin-1-yl)piperidine-1-carboxylate;DQ-2805;SN-38-11;IRINOTECAN
CBNumber: CB1124156
Molecular Formula: C33H38N4O6
Formula Weight: 586.68
MOL File: 97682-44-5.mol

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Irinotecan Property

Melting point:: 222-223°
Boiling point:: 873.4±65.0 °C(Predicted)
Density: 1.40±0.1 g/cm3(Predicted)
storage temp.: Sealed in dry,2-8°C
solubility: Acetonitrile (Slightly, Heated, Sonicated), DMSO (Slightly), Methanol (Slightly)
pka: 11.20±0.20(Predicted)
form: Solid
color: White to Brown
InChIKey: UWKQSNNFCGGAFS-XIFFEERXSA-N
SMILES: N1(C2CCN(C(OC3=CC=C4C(=C3)C(CC)=C3CN5C(C3=N4)=CC3[C@](CC)(O)C(=O)OCC=3C5=O)=O)CC2)CCCCC1
CAS DataBase Reference: 97682-44-5(CAS DataBase Reference)

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Safety

Hazard Codes: Xn
Risk Statements: 22
RTECS: DW1061000
Hazardous Substances Data: 97682-44-5(Hazardous Substances Data)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H318Causes serious eye damage

H361Suspected of damaging fertility or the unborn child

H373May cause damage to organs through prolonged or repeated exposure

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P281Use personal protective equipment as required.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

P310Immediately call a POISON CENTER or doctor/physician.

P314Get medical advice/attention if you feel unwell.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Tocris

Product number: 2688
Product name: CPT11
Purity: ≥99%(HPLC)
Packaging: 10
Price: $229
Updated: 2021/12/16

Tocris

Product number: 2688
Product name: CPT11
Purity: ≥99%(HPLC)
Packaging: 50
Price: $960
Updated: 2021/12/16

Usbiological

Product number: 255047
Product name: CPT 11
Packaging: 10mg
Price: $480
Updated: 2021/12/16

TRC

Product number: I767523
Product name: (+)-Irinotecan
Packaging: 50mg
Price: $60
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FI33814
Product name: Irinotecan
Packaging: 100mg
Price: $60
Updated: 2021/12/16

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Irinotecan Chemical Properties,Usage,Production

Uses

(+)-Irinotecan is a Topo I inhibitor.

Uses

Irinotecan is a topoisomerase I inhibitor for LoVo cells and HT-29 cells with IC50 of 15.8 μM and 5.17 μM, respectively

Definition

ChEBI: A member of the class of pyranoindolizinoquinolines that is the carbamate ester obtained by formal condensation of the carboxy group of [1,4'-bipiperidine]-1'-carboxylic acid with the phenolic hydroxy group of (4S)-4,11-diethyl-4,9-dihydro y-1H-pyrano[3',4':6,7]indolizino[1,2- hydrochloride]quinoline-3,14-dione. Used (in the form of its hydrochloride salt trihydrate) in combination with fluorouracil and leucovorin, for the treatment of patients with metastatic adenocarcino a 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.

brand name

Camptosar (Pharmacia &Upjohn) .

Biological Activity

irinotecan (cpt-11), a prodrug for treating metastatic colorectal cancer, is a topoisomerase i inhibitor for lovo cells and ht-29 cells with ic50 of 15.8 μm and 5.17 μm, respectively [1].in vivo, irinotecan is converted to sn-38, its most active metabolite, by carboxylesterase converting enzyme (cce) [2].

Synthesis

103816-19-9

86639-52-3

97682-44-5

(S)-4,11-diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione was synthesized using piperidinyl piperidine carbonyl chloride and (S)-4,11-diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[ 3',4':6,7]indolo[1,2-b]quinolin-9-yl [1,4'-bipiperidin]-1'-carboxylate was prepared in the following general steps: under nitrogen protection, (S)-4,11-diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolo[1,2-b]quinolin-3,14(4H,12H)-dione (20 g ) was suspended in dichloromethane and acetamide (3 g) and pyridine (60 ml) were added. Subsequently, piperidinyl piperidine carbonyl chloride (17.6 g) was dissolved in dichloromethane and triethylamine (20 ml) was added and this solution was slowly added to the above suspension. The reaction mixture was stirred at 30-40°C for 2 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure at 50°C and hexane was added as a counter-solvent to promote crystallization. The crystalline product was collected by filtration, washed with hexane and dried under reduced pressure at 50 °C to give 28.4 g of the target product in 95% yield.HPLC analysis showed 99.9% purity of the product.

in vitro

irinotecan induced similar amounts of cleavable complexes in lovocells and ht-29 cell lines with the ic50 of 15.8 μm and 5.17 μm, respectively [1].after addition of 157 mm irinotecan to plasma, sn-38 concentration showed linear increase during the first 60-min period, followed by a plateau.in the first 60 min, mean and standard deviation of the conversion rate were 515.9 ± 50.1 pmol/ml/h (n = 69), with a coefficient of variation of 0.097 [2]. irinotecan (cpt-11) was significantly more active in sclc than in nsclccelllines (p = 0.0036). ce activity appeared to be associated with higher sensitivity to cpt-11 in human lung cancercelllines and may partly explain the difference in the in vitro sensitivity to cpt-11 between sclc and nsclccells [3].in vitro, the sensitivity to cpt-11 and sn-38 was highest in ls174t and colo 320cells, intermediate in sw1398cellsand lowest in colo 205 and widr cells. the activity of sn-38 was 130 to 570 times than cpt-11[4].

in vivo

in colo 320 xenografts, irinotecan induced a maximum growth inhibition of 92% [4].a single dose of irinotecan significantly increased amounts of topoisomerase i covalently bound to dna in stomach, duodenum, colon and liver. concomitantly, the irinotecan-treated group exihibited significantly higher amounts of dna strand breaks in colon mucosa cells compared to the control group [5].

References

[1]. tobin p, clarke s, seale j p, et al. the in vitro metabolism of irinotecan (cpt‐11) by carboxylesterase and β‐glucuronidase in human colorectal tumours[j]. british journal of clinical pharmacology, 2006, 62(1): 122-129.
[2]. shingyoji m, takiguchi y, watanabe‐uruma r, et al. in vitro conversion of irinotecan to sn‐38 in human plasma[j]. cancer science, 2004, 95(6): 537-540.
[3]. van ark-otte j, kedde m a, van der vijgh w j, et al. determinants of cpt-11 and sn-38 activities in human lung cancer cells[j]. british journal of cancer, 1998, 77(12): 2171.
[4]. jansen w j m, zwart b, hulscher s t m, et al. cpt-11 in human colon-cancer cell lines and xenografts: characterization of cellular sensitivity determinants[j]. international journal of cancer, 1997, 70(3): 335-340.
[5]. na y s, jung k a, kim s m, et al. the histone deacetylase inhibitor pxd101 increases the efficacy of irinotecan in in vitro and in vivo colon cancer models[j]. cancer chemotherapy and pharmacology, 2011, 68(2): 389-398.

Irinotecan Preparation Products And Raw materials

Raw materials

Nitrogen (+)-Camptothecin 7-Ethyl camptothecin 7-Ethyl-10-hydroxycamptothecin N-ACETYL-D-GALACTOSAMINE(GALACTOSE-13C6, 99%)

Preparation Products

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View Lastest Price from Irinotecan manufacturers

Baoji Guokang Healthchem Co., Ltd.

Product: Irinotecan 97682-44-5
Price: US $825.00/g/Bag
Min. Order: 10g
Purity: 99%
Supply Ability: 1kg
Release date: 2021-06-03

Shaanxi Dideu New Materials Co. Ltd

Product: Irinotecan 97682-44-5
Price: US $0.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 10000KGS
Release date: 2025-02-22

Shaanxi Haibo Biotechnology Co., Ltd

Product: lrinotecan 97682-44-5
Price: US $0.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 2000ton
Release date: 2023-09-07

97682-44-5, IrinotecanRelated Search:

IRINOTECAN HCL,IRINOTECAN HYDROCHLORIDE Mefenpyr-diethyl Diethyl phthalate Diethyl malonate Diethyl carbonate Paclitaxel Docetaxel (+)-Camptothecin 7,11-Diethyl-10-hydroxycaMptothecin sodium:(2S)-2-[12-ethyl-8-(hydroxymethyl)-9-oxo-2-(4-piperidin-1-ylpiperidine-1-carbonyl)oxy-11H-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoate Irinotecan Impurity 6 Irinotecan EP Impurity H 12-Hydroxy Irinotecan SN-38 GLUCURONIDE 10-Hydroxycamptothecin 7-Ethylcamptothecin 7-Ethyl-10-hydroxycamptothecin Irinotecan IMpurity G

Irinotecan (free Base)

Irinotecan(TECANS)

1,4'-Bipiperidine-1'-carboxylic acid (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 ester

DQ-2805

(4S)-4,11-Diethyl-4-hydroxy-9-[[(4-piperidinopiperidino)carbonyl]oxy]-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione

SN-38-11

(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaen-7-yl 4-(piperidin-1-yl)piperidine-1-carboxylate

[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, (S)-

1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline, [1,4'-bipiperidine]-1'-carboxylic acid deriv.

Irinotecan base

Irinotecanum

Irinotecan Monomer

Irinotecan EP Impurity L

(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-[1,4'-bipiperidine]-1'-carboxylic acid

(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

(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 ESTER

Irinotecan Labeled d10

(S)-4,11-Diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-

TOPOTECIN HYDROCHLORIDE

[1,4'-BIPIPERIDINE]-1'-CARBOXYLIC ACID

CPT-11

IRINOTECAN

IRINOTECAN HCL

CAMPTOSAR

CAMPTOTHECIN 11 HYDROCHLORIDE

CAMPTOTHECIN 11 HYDROCHLORIDE,TOPOTECIN

Irinotecan(Cpt-11)

(1,4'-Bipiperidine)-1'-carboxylicacid(S)-4,11-di]

Irinotecane

[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

IRINOTECAN HCL(P)

[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 (9CI)

(S)-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

Irinotecan USP/EP/BP

IrinotecanQ: What is Irinotecan Q: What is the CAS Number of Irinotecan Q: What is the storage condition of Irinotecan Q: What are the applications of Irinotecan

Propanamide,N-(3-bromophenyl)-8-chloro-

Irinotecan, 10 mM in DMSO

97682-44-5

97682-44-8

C33H38N4O6

Camptothecin series

APIs

Natural Anti-cancer Medical Materials and It's Derivatives

API's

chemical reagent

pharmaceutical intermediate

phytochemical

reference standards from Chinese medicinal herbs (TCM).

standardized herbal extract

API

Anti cancer

Inhibitors

Camptosar, Campto

Anti-cancer&immunity