Compound: irinotecan
SMILES: O=c1n2c(-c3nc4ccc(cc4c(c3C2)CC)OC(=O)N5CCC(N6CCCCC6)CC5)cc7c1COC([C@]7(O)CC)=O
InChIKey: UWKQSNNFCGGAFS-XIFFEERXSA-N
Synonyms: irinotecan, 97682-44-5, (+)-Irinotecan, Irinophore C, Irinotecanum, Biotecan, Irinotecan lactone, Irinotecan mylan, HSDB 7607, NSC-728073, DTXSID1041051, CHEBI:80630, NSC728073, camptothecin-11, [(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'-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, Irrinotecan, ((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'-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, (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 4-(piperidin-1-yl)piperidine-1-carboxylate, SN-38-11, RefChem:56366, DTXCID9021051, L01XX19, SN3811, (+)-7-ethyl-10-hydroxycamptothecine 10-(1,4'-bipiperidine)-1'-carboxylate, (+)-(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, 691-567-9, 7-ethyl-10-(4-(1-piperidino)-1-piperidino)carbonyloxycamptothecin, 7673326042, Camptothecin 11, NSC616348, Irinotecanum [INN-Latin], Irinotecan Free base, (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, MFCD00866307, Irinotecan (INN), 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, CHEMBL481, Irinotecan (hydrochloride), IRINOTECAN [INN], Irinotecan [INN:BAN], (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, CPT-11 hydrochloride;Camptothecin 11 hydrochloride, MLS001401366, Biotecan (TN), (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, SMR000469166, Irinotecan?, Camptetin;, Camptosar;, s1198, Campto;, 97682-44-5 (Free base), Irinotecan (Standard), (diethyl-hydroxy-dioxo-[?]yl) 4-(1-piperidyl)piperidine-1-carboxylate, UNII-7673326042, IRINOTECAN [MI], IRINOTECAN [HSDB], IRINOTECAN [VANDF], SCHEMBL4034, IRINOTECAN [WHO-DD], IRINOTECAN; CPT-11, BSPBio_002346, GTPL6823, orb1300959, orb3141204, SCHEMBL29356918, SCHEMBL29367581, BDBM51762, 1u65, cid_23581792, (S)-4,11-Diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3 inverted exclamation mark ,4 inverted exclamation mark :6,7]indolizino[1,2-b]quinolin-9-yl [1,4 inverted exclamation mark -bipiperidine]-1 inverted exclamation mark -carboxylate, ARD162722, BDBM50128267, EBC-17160, HY-16562R, MSK162722, UBI-10002, AKOS015894969, AB07527, AC-7469, CS-1138, DB00762, FI33814, NSC 728073, NCGC00178697-02, NCGC00178697-05, (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)-, (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, BP-42974, HY-16562, NCI60_005051, SY105303, NS00004943, D08086, EN300-708800, AB00698464-07, AB00698464-09, AB00698464-10, AB00698464-11, AB00698464_12, AB00698464_13, AB00698464_14, Q412197, BRD-K08547377-001-04-4, BRD-K08547377-003-02-4, BRD-K08547377-003-04-0, BRD-K08547377-003-05-7, BRD-K08547377-003-07-3, BRD-K08547377-394-03-5, (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, (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-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)-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-(1-piperidyl)piperidine-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
Theoretical properties:
molecular_formula: C33H38N4O6
molecular_weight: 586.7 g/mol
exact_mass: 586.27913494 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 8
rotatable_bond_count: 5
heavy_atom_count: 43
topological_polar_surface_area: 113 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Pale yellow powder
color: Pale yellow powder
melting_point: 222-223 °C
solubility: 1.07e-01 g/L
Descriptions:
{"pubchem": "Irinotecan is 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-dihydroxy-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 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. It has a role as an antineoplastic agent, a prodrug, an EC 5.99.1.2 (DNA topoisomerase) inhibitor and an apoptosis inducer. It is a delta-lactone, a carbamate ester, a tertiary alcohol, a ring assembly, a N-acylpiperidine, a pyranoindolizinoquinoline and a tertiary amino compound. It is functionally related to a SN-38. It is a conjugate base of an irinotecan(1+).", "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 (4<i>S</i>)-4,11-diethyl-4,9-dihydroxy-1<em>H</em>-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 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.", "chembl": "IRINOTECAN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Irinotecan, sold under the brand name Camptosar among others, is an anti-cancer medication used to treat colon cancer and small cell lung cancer. For colon cancer it is used either alone or with fluorouracil. For small cell lung cancer it is used with cisplatin. It is given intravenously.\nCommon side effects include diarrhea, vomiting, bone marrow suppression, hair loss, shortness of breath, and fever. Other severe side effects include blood clots, colon inflammation, and allergic reactions. Those with two copies of the UGT1A1*28 gene variant are at higher risk for side effects. Use during pregnancy can result in harm to the baby. Irinotecan is a topoisomerase inhibitor\u2014it blocks the topoisomerase I enzyme, resulting in DNA damage and cell death.\nIrinotecan was approved for medical use in the United States in 1996. It is on the World Health Organization's List of Essential Medicines. It is made from the natural compound camptothecin which is found in the Chinese ornamental tree Camptotheca acuminata."}