Compound: 7-Ethyl-10-hydroxycamptothecin
SMILES: O=c1n2c(-c3nc4ccc(cc4c(c3C2)CC)O)cc5c1COC([C@]5(O)CC)=O
InChIKey: FJHBVJOVLFPMQE-QFIPXVFZSA-N
Synonyms: 7-Ethyl-10-hydroxycamptothecin, 86639-52-3, SN-38, SN 38 lactone, SN 38, 10-Hydroxy-7-ethylcamptothecin, NK-012, 7-Ethyl-10-hydroxy-20(S)-camptothecin, NK 012, NK012, 0H43101T0J, CAMPTOTHECIN, 7-ETHYL-10-HYDROXY-, CHEBI:8988, DTXSID4040399, (4S)-4,11-Diethyl-4,9-dihydroxy-1H-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, (4S)-4,11-diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, (19S)-10,19-diethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione, (1S,2S,3R)-1-(3,4-dihydroxy-5-methoxy-phenyl)-2,3,7-trihydroxy-3-(hydroxymethyl)-6-methoxy-tetralin-2-carboxylic acid, 1H-PYRANO(3',4':6,7)INDOLIZINO(1,2-B)QUINOLINE-3,14(4H,12H)-DIONE, 4,11-DIETHYL-4,9-DIHYDROXY-, (4S)-, H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4,11-diethyl-4,9-dihydroxy-, (S)-, (19S)-10,19-diethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo(11.8.0.02,11.04,9.015,20)henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione, 1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4,11-diethyl-4,9-dihydroxy-, (4S)-, RefChem:914300, 7 Ethyl 10 hydroxycamptothecin, DTXCID2020399, 7-Ethyl-10-hydroxy-camptothecin, (S)-4,11-Diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, MFCD00871873, SN38, C22H20N2O5, (19S)-10,19-diethyl-7,19-dihydroxy-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)-heptaene-14,18-dione, IT-141, NSC673596, 113015-38-6, LE-SN38, Captothecin, 7-ethyl-10-hydroxy-, UNII-0H43101T0J, 7-Ethyl-10-hydroxycamptothecin ((S)-4,11-Diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione), AvaChem1025, SN-38 (Standard), 7-10-hydroxycamptothecin, (+)-7-ETHYL-10-HYDROXYCAMPTOTHECIN, diethyl(dihydroxy)[?]dione, SCHEMBL34018, GTPL6925, orb1307686, orb3141304, SN 38 [WHO-DD], SCHEMBL29354078, SCHEMBL29359781, 10-hydroxy-7-ethyl camptothecin, 10-hydroxy-7-ethyl-camptothecin, EX-A989, HMS3413B12, HMS3652P12, HMS3677B12, HMS3753E15, 7-Ethyl-10-hydroxy-20(S)-CPT, BDBM50418088, EBC-11025, HY-13704R, MSK162382, s4908, AKOS015920433, AC-1357, CCG-264764, CS-1579, DB05482, FE29579, NSC-673596, SN-38(NK-012)?, NCGC00167831-01, NCGC00167831-05, 110714-48-2, AS-13533, BP-24513, Camptothecin 7-Ethyl-10-Hydroxy Impurity, HY-13704, NCI60_026056, SY013197, E0748, NS00069821, SW219948-1, S-(+)-7-ETHYL-10-HYDROXYCAMPOTHECIN, EN300-122379, F046379, Q1750127, BRD-K89561498-001-01-7, BRD-K89561498-001-02-5, 7-Ethyl-10-hydroxycamptothecin, >=98% (HPLC), powder, Z1541759909, Irinotecan EP Impurity E; Camptothecin 7-Ethyl-10-Hydroxy Impurity, (19S)-10,19-diethyl-7,19-dihydroxy-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)-heptaene-14,18-dione, (4S)-4,11-Diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)dione, AldrichCPR, (S)-4,11-Diethyl-4,9-di-OH-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione, 1H-Pyrano[3',7]indolizino[1,2-b]quinoline- 3,14(4H,12H)-dione, 4,11-diethyl-4,9-dihydroxy-, (4S)-, RS4
Theoretical properties:
molecular_formula: C22H20N2O5
molecular_weight: 392.4 g/mol
exact_mass: 392.13722174 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 2
heavy_atom_count: 29
topological_polar_surface_area: 100 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: SN-38 is a member of the class of pyranoindolizinoquinolines that is (4S)-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione bearing two additional ethyl substituents at positions 4 and 11 as well as two additional hydroxy substituents at positions 4 and 9. It is the active metabolite of irinotecan and is ~1000 times more active than irinotecan itself. It has a role as an antineoplastic agent, a drug metabolite, an EC 5.99.1.2 (DNA topoisomerase) inhibitor and an apoptosis inducer. It is a delta-lactone, a tertiary alcohol, a member of phenols and a pyranoindolizinoquinoline.
chebi: A member of the class of pyranoindolizinoquinolines that is (4<i>S</i>)-pyrano[3',4':6,7]indolizino[1,2-<em>b</em>]quinoline-3,14-dione bearing two additional ethyl substituents at positions 4 and 11 as well as two additional hydroxy substituents at positions 4 and 9. It is the active metabolite of irinotecan and is ~1000 times more active than irinotecan itself.
chembl: 7-ETHYL-10-HYDROXYCAMPTOTHECIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: SN-38 is an antineoplastic drug. It is the active metabolite of irinotecan (an analog of camptothecin - a topoisomerase I inhibitor) but has 1000 times more activity than irinotecan itself. In vitro cytotoxicity assays show that the potency of SN-38 relative to irinotecan varies from 2- to 2000-fold.
SN38 is formed via hydrolysis of irinotecan by carboxylesterases and metabolized via glucuronidation by UGT1A1.
The variant of UGT1A1 in ~10% of Caucasians which leads to poor metabolism of SN-38 predicts irinotecan toxicity, as it is then less easily excreted from the body in its SN-38 glucuronide form.
SN-38 and its glucuronide are lost into the bile and intestines.  It can cause the symptoms of diarrhoea and myelosuppression experienced by ~25% of the patients administered irinotecan.