TOP
Nav Bar
  1. General Info
  2. Effects Info
  3. Reference
Drug Details
01. General Information
Name Irinotecan
PubChem CID 60838
Molecular Weight 586.7g/mol
Synonyms

irinotecan, 97682-44-5, (+)-Irinotecan, Camptosar, Irinophore C, Irinotecanum, Biotecan, Irinotecan lactone, Irinotecan mylan, Irinotecanum [INN-Latin], Campto, Irinotecan Free base, CPT-11, (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, HSDB 7607, Irinotecan (INN), NSC-728073, CHEBI:80630, CHEMBL481, UNII-7673326042, DTXSID1041051, 97682-44-5 (Free base), NSC728073, NSC 728073, (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, 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, IRINOTECAN [INN], Irinotecanum (INN-Latin), Irinotecan [INN:BAN], (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)-, CPT-11 hydrochloride;Camptothecin 11 hydrochloride, Irrinotecan, Biotecan (TN), (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, [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, 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, Irinotecan?, MFCD00866307, (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, (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, IRINOTECAN [MI], IRINOTECAN [HSDB], IRINOTECAN [VANDF], SCHEMBL4034, IRINOTECAN [WHO-DD], IRINOTECAN; CPT-11, BSPBio_002346, GTPL6823, DTXCID9021051, AMY4227, L01XX19, 1u65, BCP02860, BDBM50128267, s1198, AKOS015894969, AB07527, AC-7469, BCP9000793, CS-1138, DB00762, NCGC00178697-02, NCGC00178697-05, (4S)-4,11-Diethyl-4-hydroxy-3,14-dioxo-4,12-dihydro-1H-pyrano[3,4-f]quinolino[2,3-a]indolizin-9-yl 4-piperidylpiperidinecarboxylate, AS-14323, HY-16562, NCI60_005051, NS00004943, D08086, EN300-708800, AB00698464-07, AB00698464-09, AB00698464-10, AB00698464-11, AB00698464_12, AB00698464_13, AB00698464_14, A845740, Q412197, BRD-K08547377-003-02-4, (diethyl-hydroxy-dioxo-[?]yl) 4-(1-piperidyl)piperidine-1-carboxylate, (+)-7-ethyl-10-hydroxycamptothecine 10-(1,4'-bipiperidine)-1'-carboxylate, 2-methoxy-5-[2-(3-sulfophenyl)-5-(4-sulfophenyl)pyrylium-4-yl]benzenesulfonic acid, (+)-(4S)-4,11-diethyl-4-hydroxy-9-((4-piperidino-piperidino)carbonyloxy)-1H-pyrano(3',4':6,7)indolizino(1,2-b)quinol-3,14,(4H,12H)-dione, (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, (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(11),3,5,7,9,15(20)-heptaen-7-yl 4-(piperidin-1-yl)piperidine-1-carboxylate, (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(11),3,5,7,9,15(20)-heptaen-7-yl [1,4'-bipiperidine]-1'-carboxylate, (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(11),3,5,7,9,15(20)-heptaen-7-yl 4-(piperidin-1-yl)piperidine-1-carboxylate, (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, (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, [(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaen-7-yl] 4-piperidin-1-ylpiperidine-1-carboxylate, [1,4'']bipiperidinyl-1''-carboxylic acid (S)-4,11-diethyl-4-hydroxy-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yl ester, [1,4'']Bipiperidinyl-1''-carboxylic acid 4,11-diethyl-4-hydroxy-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yl ester
Drug Type Small molecule
Formula C₃₃H₃₈N₄O₆
SMILES CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)C4(CC)O)C2=NC5=C1C=C(C=C5)OC(=O)N6CCC(CC6)N7CCCCC7
InChI 1S/C33H38N4O6/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/t33-/m0/s1
InChIKey UWKQSNNFCGGAFS-XIFFEERXSA-N
CAS Number 97682-44-5
ChEMBL ID CHEMBL481
ChEBI ID CHEBI:80630
TTD ID D07HOB
Drug Bank ID DB00762
KEGG ID D01061
Toxicity Organism Test Type Route(Dose)
rat LD50 intraperitoneal(165 mg/kg)
mouse LD50 intraperitoneal(254 mg/kg)
rat LD50 oral(322 mg/kg)
Structure 2D-img
Download
2D MOL 3D MOL
02. Combinatorial Therapeutic Effect(s)
Synergistic Effect
Hide/Show
Enhancing Drug Efficacy
Hide/Show
Combination Pair ID: 221
Ref_4
Pair Name Toosendanin, Irinotecan
Partner Name Toosendanin
Disease Info [ICD-11: 2C60] Breast cancer Investigative
Biological Phenomena Induction-->Autophagy
Gene Regulation Up-regulation Expression CASP3 hsa836
Down-regulation Expression CTSB hsa1508
Down-regulation Expression CTSD hsa1509
In Vitro Model MDA-MB-231 Breast adenocarcinoma Homo sapiens (Human) CVCL_0062
MDA-MB-436 Invasive breast carcinoma Homo sapiens (Human) CVCL_0623
In Vivo Model MDA-MB-231 cells stably expressing RFP-GFP-LC3 were suspended in a 1:1 ratio in serum-free DMEM medium with a matrigel basement membrane matrix and inoculated subcutaneously (5×10⁶/site) in the right armpit.
Result The data showed that TSN blocked 7-ethyl-10-hydroxycamptothecin (SN-38)/irinotecan-induced protective autophagy, and significantly induced apoptosis in TNBC cells and tumor xenograft models when compared to SN-38/irinotecan alone group.
Combination Pair ID: 949
Ref_5
Pair Name Phenethyl isothiocyanate, Irinotecan
Partner Name Phenethyl isothiocyanate
Disease Info [ICD-11: 2B90] Colon cancer Investigative
Biological Phenomena Induction-->Endoplasmic reticulum stress
Gene Regulation Up-regulation Expression BAD hsa572
Up-regulation Expression BAK1 hsa578
Down-regulation Expression BCL2 hsa596
Up-regulation Phosphorylation CAMK2G hsa818
Up-regulation Expression CASP3 hsa836
Up-regulation Expression CASP8 hsa841
Up-regulation Expression CASP9 hsa842
Up-regulation Expression CYCS hsa54205
Up-regulation Phosphorylation EIF2AK3 hsa9451
Up-regulation Expression EIF2S1 hsa1965
Up-regulation Expression FAS hsa355
Up-regulation Expression HSPA5 hsa3309
Up-regulation Expression PARP1 hsa142
Down-regulation Expression XIAP hsa331
In Vitro Model HCT 116 Colon carcinoma Homo sapiens (Human) CVCL_0291
Result PEITC potentiates IRI anticancer activity by promoting cell apoptosis in the human colon HCT 116 cells. Thus, PEITC may be a potential enhancer for IRI in humans as an anticolon cancer drug in the future.
Combination Pair ID: 262
Ref_6
Pair Name Panaxadiol, Irinotecan
Partner Name Panaxadiol
Disease Info [ICD-11: 2B91] Colorectal cancer Investigative
Biological Phenomena Induction-->Apoptosis
Gene Regulation Up-regulation Activity CASP3 hsa836
Up-regulation Activity CASP9 hsa842
In Vitro Model HCT 116 Colon carcinoma Homo sapiens (Human) CVCL_0291
Result Data from this study suggested that caspase-3- and caspase-9-mediated apoptosis may play an important role in the panaxadiol enhanced antiproliferative effects of irinotecan on human colorectal cancer cells.
Combination Pair ID: 455
Ref_7
Pair Name Epigallocatechin gallate, Irinotecan
Partner Name Epigallocatechin gallate
Disease Info [ICD-11: 2B91] Colorectal cancer Investigative
Biological Phenomena Induced-->GRP78-mediated endoplasmic reticulum stress
Gene Regulation Down-regulation Expression BCL2 hsa596
Up-regulation Expression GRP78 KEGG ID N.A.
Down-regulation Expression ROS1 hsa6098
In Vitro Model HCT 116 Colon carcinoma Homo sapiens (Human) CVCL_0291
RKO Colon carcinoma Homo sapiens (Human) CVCL_0504
In Vivo Model The concentration of HCT116 cells in the logarithmic phase was adjusted to 2.5×10⁷/mL, and the 200 μL cell suspension was inoculated subcutaneously on the right dorsal side of the mouse. When the average tumor volume reached 100 mm3, animals were randomized into 4 groups (5 mice for each group), control (Control, normal saline, 1 time per day, ip), irinotecan (IRI, 4 mg/kg irinotecan, 2 times per week, ip), EGCG (EGCG, 5 mg/kg, 1 time per day, ip), and irinotecan in combination with EGCG (IRI + EGCG).
Result These reults confirmed that EGCG alone or in combination with irinotecan could up-regulate the GRP78, activate ERS of colorectal cancer cells, reduce intracellular reactive oxygen species and mitochondrial membrane potential, and induce apoptosis. The mouse xenograft experiment also confirmed the synergistic effect of EGCG and irinotecan on ERS and tumor cell.EGCG can induce GRP78-mediated endoplasmic reticulum stress and enhance the chemo-sensitivity of colorectal cancer cells when coadministered with irinotecan.
Combination Pair ID: 761
Ref_8
Pair Name Aloin, Irinotecan
Partner Name Aloin
Disease Info [ICD-11: 2B91] Colorectal cancer Investigative
Biological Phenomena Induction-->Apoptosis
Gene Regulation Down-regulation Phosphorylation AKT1 hsa207
Up-regulation Cleavage CASP3 hsa836
Up-regulation Cleavage CASP9 hsa842
Down-regulation Expression IGF1R hsa3480
Down-regulation Phosphorylation MTOR hsa2475
Up-regulation Cleavage PARP1 hsa142
Down-regulation Phosphorylation PIK3CA hsa5290
In Vitro Model LoVo Colon adenocarcinoma Homo sapiens (Human) CVCL_0399
In Vivo Model 4×10⁶ LoVo cells were suspended in serum-free Matrigel medium.Control (DMSO), CPT-11(2 mg/Kg), Aloin (20 mg/Kg), and combination (2 mg/Kg CPT-11 + 20 mg/Kg Aloin). The mice were treated via intratumor injection, every 48 h for four weeks.
Result Our findings suggests that CPT-11 and Aloin are potential combination treatment partners against colorectal cancer. MicroRNA-133b may serve as a co-therapeutic target with IGF1R against colorectal cancer, which might overcome the existing treatment limitations.
Reversing Drug Resistance
Hide/Show
Combination Pair ID: 820
Ref_9
Pair Name Curcumin, Irinotecan
Partner Name Curcumin
Disease Info [ICD-11: 2B90] Colon cancer Investigative
Biological Phenomena Induction-->Apoptosis
Gene Regulation Down-regulation Expression CD24 hsa100133941
Down-regulation Expression CD44 hsa960
Down-regulation Expression EPCAM hsa4072
Down-regulation Expression PROM1 hsa8842
In Vitro Model LoVo Colon adenocarcinoma Homo sapiens (Human) CVCL_0399
Result The present data demonstrated that curcumin attenuated resistance to chemotherapeutic drugs through induction of apoptosis of CSCs among colon cancer cells. These findings may provide novel evidence for the therapeutic application of curcumin in CRC intervention.
Decreasing Drug Toxicity
Hide/Show
Combination Pair ID: 126
Ref_2
Pair Name Epigallocatechin gallate, Irinotecan
Partner Name Epigallocatechin gallate
Disease Info [ICD-11: 2B91] Colorectal cancer Investigative
Biological Phenomena Induction-->DNA damage
Gene Regulation Down-regulation Expression CCNB1 hsa891
Down-regulation Expression CCND1 hsa595
Down-regulation Expression CDK4 hsa1019
Up-regulation Expression MAP1LC3A hsa84557
Up-regulation Phosphorylation RB1 hsa5925
Down-regulation Expression TOP1 hsa7150
In Vitro Model RKO Colon carcinoma Homo sapiens (Human) CVCL_0504
HCT 116 Colon carcinoma Homo sapiens (Human) CVCL_0291
Result EGCG synergizes the therapeutic effect of irinotecan through enhanced DNA damage in human colorectal cancer cells
Combination Pair ID: 423
Ref_3
Pair Name Cianidanol, Irinotecan
Partner Name Cianidanol
Disease Info [ICD-11: 2B90] Colon cancer Investigative
In Vivo Model It was investigated the antitumor effects of GT alone or in combination with IRN in inflammation-associated colon cancer mouse model induced by azoxymethane (AOM) and dextran sulfate sodium (DSS).
Result GT significantly reduced the toxicity induced by IRN in terms of diarrhea, neutropenia, leucopenia, and NAFLD and works as an effective anticancer agent as it mitigates histopathology of colon adenocarcinoma.
Antagonistic Effect
Hide/Show
Reducing Drug Efficacy
Hide/Show
Combination Pair ID: 1091
Ref_1
Pair Name Epigallocatechin gallate, Irinotecan
Partner Name Epigallocatechin gallate
Disease Info [ICD-11: 2A00-2F9Z] Solid tumour or cancer Investigative
Biological Phenomena Inhibition-->P-gp expression
In Vivo Model Adult, male Sprague–Dawley rats (300 ± 20 g body weight) were provided by the Laboratory Animal Center at National Yang-Ming University, the rats were initially anaesthetized with urethane 1 g/mL and α-chloralose 0.1 g/mL (1 mL/kg, i.p.), and remained anaesthetized throughout the experimental period. The femoral vein was exposed for further drug administration.
Result EGCG was found to inhibit the transport of CPT-11 and SN-38 into the biliary elimination and their half-lives in plasma could be substantially prolonged. Based on the food-drug interaction, persons taking daily nutritional supplements should be warned of this interaction possibility.
03. Reference
No. Title Href
1 Food-drug interaction of (-)-epigallocatechin-3-gallate on the pharmacokinetics of irinotecan and the metabolite SN-38. Chem Biol Interact. 2008;174(3):177-182. doi:10.1016/j.cbi.2008.05.033 Click
2 EGCG synergizes the therapeutic effect of irinotecan through enhanced DNA damage in human colorectal cancer cells. J Cell Mol Med. 2021 Aug;25(16):7913-7921. doi: 10.1111/jcmm.16718. Click
3 Green tea catechins in combination with irinotecan attenuates tumorigenesis and treatment-associated toxicity in an inflammation-associated colon cancer mice model. J Egypt Natl Canc Inst. 2021 Jul 26;33(1):17. doi: 10.1186/s43046-021-00074-4. Click
4 Toosendanin, a late-stage autophagy inhibitor, sensitizes triple-negative breast cancer to irinotecan chemotherapy. Chin Med. 2022 May 6;17(1):55. doi: 10.1186/s13020-022-00605-8. Click
5 Phenethyl isothiocyanate and irinotecan synergistically induce cell apoptosis in colon cancer HCT 116 cells in vitro. Environ Toxicol. 2024 Jan;39(1):457-469. doi: 10.1002/tox.23993. Click
6 Caspase-mediated pro-apoptotic interaction of panaxadiol and irinotecan in human colorectal cancer cells. J Pharm Pharmacol. 2012 May;64(5):727-34. doi: 10.1111/j.2042-7158.2012.01463.x. Epub 2012 Feb 21. Click
7 EGCG Enhances the Chemosensitivity of Colorectal Cancer to Irinotecan through GRP78-MediatedEndoplasmic Reticulum Stress. J Oncol. 2022;2022:7099589. Published 2022 Sep 13. doi:10.1155/2022/7099589 Click
8 Aloin and CPT-11 combination activates miRNA-133b and downregulates IGF1R- PI3K/AKT/mTOR and MEK/ERK pathways to inhibit colorectal cancer progression. Biomed Pharmacother. 2023 Dec 31;169:115911. doi: 10.1016/j.biopha.2023.115911. Click
9 Curcumin attenuates resistance to irinotecan via induction of apoptosis of cancer stem cells in chemoresistant colon cancer cells. Int J Oncol. 2018 Sep;53(3):1343-1353. doi: 10.3892/ijo.2018.4461. Click
It has been 26438 visits since 2024.08
If you find any error in data or bug in web service, please kindly report it to Dr. Zhang
TOP