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136572-09-3 molecular structure
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(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),2,4,6,8,10,15(20)-heptaen-7-yl 4-(piperidin-1-yl)piperidine-1-carboxylate trihydrate hydrochloride

ChemBase ID: 72905
Molecular Formular: C33H45ClN4O9
Molecular Mass: 677.1848
Monoisotopic Mass: 676.28750672
SMILES and InChIs

SMILES:
C1CCN(CC1)C1CCN(CC1)C(=O)Oc1ccc2c(c1)c(c1c(n2)c2n(C1)c(=O)c1c(c2)[C@](C(=O)OC1)(CC)O)CC.O.O.O.Cl
Canonical SMILES:
CC[C@@]1(O)C(=O)OCc2c1cc1c3nc4ccc(cc4c(c3Cn1c2=O)CC)OC(=O)N1CCC(CC1)N1CCCCC1.O.O.O.Cl
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
InChIKey:
KLEAIHJJLUAXIQ-JDRGBKBRSA-N

Cite this record

CBID:72905 http://www.chembase.cn/molecule-72905.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(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),2,4,6,8,10,15(20)-heptaen-7-yl 4-(piperidin-1-yl)piperidine-1-carboxylate trihydrate hydrochloride
(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),2,4,6,8,10,15(20)-heptaen-7-yl 4-(piperidin-1-yl)piperidine-1-carboxylate trihydrate hydrochloride
IUPAC Traditional name
(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),2,4,6,8,10,15(20)-heptaen-7-yl 4-(piperidin-1-yl)piperidine-1-carboxylate trihydrate hydrochloride
(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),2,4,6,8,10,15(20)-heptaen-7-yl 4-(piperidin-1-yl)piperidine-1-carboxylate trihydrate hydrochloride
Synonyms
CPT 11
Camptosar
Campto
Irinotecan
Irinotecan Hcl Trihydrate
Irinotecan hydrochloride trihydrate
CAS Number
136572-09-3
MDL Number
MFCD01765731
PubChem SID
162037825
PubChem CID
60837

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 60837 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 11.713039  H Acceptors
H Donor LogD (pH = 5.5) -0.6070732 
LogD (pH = 7.4) 0.7157881  Log P 2.776473 
Molar Refractivity 161.3303 cm3 Polarizability 63.005684 Å3
Polar Surface Area 112.51 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Storage Condition
-20°C expand Show data source
Target
Topoisomerase expand Show data source
Purity
95+% expand Show data source
Salt Data
hydrate expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals
Selleck Chemicals - S2217 external link
Biological Activity:
Irinotecan hydrochloride trihydrate is a hydrochloride trihydrate of irinotecan (Camptosar, Campto, CPT-11) which is a topoisomerase I inhibitor with IC50 of 15.8 and 5.17 μM for LoVo cells and HT-29 cells, respectively. As a Topo I inhibitor, Irinotecan (Camptosar, Campto, CPT-11) inhibits the religation step of the enzyme’s normal action, inducing single stranded DNA breaks. These single stranded breaks are then converted to double-stranded breaks within the course of DNA replication which is reported to induce apoptosis or repair mechanisms as a result. Irinotecan is activated by esterases to produce the activated metabolite and has been reported to be associated with cleavage of poly (ADP-ribose) polymerase (PARP) in colon carcinoma cells. Irinotecan’s active metabolite is additionally noted to activate p53 in the Huh7 cell line. [1][2][3]

REFERENCES

REFERENCES

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  • • Hofmann C et al. Anticancer Res. 2005 Mar-Apr;25(2A):795-804.
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PATENTS

PATENTS

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INTERNET

INTERNET

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