Compounds > 7-ethyl-7-hydroxy-10h-1,3-dioxolo(4,5-g)pyrano(3',4':6,7)indolizino(1,2-b)quinoline-8,11(7h,12h)-dione
Page last updated: 2024-12-08

7-ethyl-7-hydroxy-10h-1,3-dioxolo(4,5-g)pyrano(3',4':6,7)indolizino(1,2-b)quinoline-8,11(7h,12h)-dione

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

7-ethyl-7-hydroxy-10H-1,3-Dioxolo(4,5-g)pyrano(3',4':6,7)indolizino(1,2-b)quinoline-8,11(7H,12H)-dione: an antineoplastic agent that inhibits survivin, Mcl-1, and cIAP2; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID366358
CHEMBL ID52057
SCHEMBL ID9563404
MeSH IDM0581727

Synonyms (30)

Synonym
(20s)-7-ethyl-7-hydroxy-7,8,11,13-tetrahydro-10h-[1,3]dioxolo[5,4-g]pyrano[3'',4'':6,7]indolizino[1,2-b]quinoline-8,11-dione
(20r)-7-ethyl-7-hydroxy-7,8,11,13-tetrahydro-10h-[1,3]dioxolo[5,4-g]pyrano[3'',4'':6,7]indolizino[1,2-b]quinoline-8,11-dione
20(rs)-7-ethyl-7-hydroxy-7,8,11,13-tetrahydro-10h-[1,3]dioxolo[5,4-g]pyrano[3'',4'':6,7]indolizino[1,2-b]quinoline-8,11-dione
7-ethyl-7-hydroxy-7,8,11,13-tetrahydro-10h-[1,3]dioxolo[5,4-g]pyrano[3'',4'':6,7]indolizino[1,2-b]quinoline-8,11-dione
(20rs)-7-ethyl-7-hydroxy-7,8,11,13-tetrahydro-10h-[1,3]dioxolo[5,4-g]pyrano[3'',4'':6,7]indolizino[1,2-b]quinoline-8,11-dione
bdbm50045377
7-ethyl-7-hydroxy-10h-[1,3]dioxolo[4,5-g]pyrano[3',4':6,7]indolizino[1,2-b]quinoline-8,11(7h,13h)-dione
{10h,12h-1,3-dioxolo[4,} {5-g]pyrano[3',4':6,7]indolizino} {[1,2-b]quinoline-8,11(7h,} 10h)-dione, 7-ethyl-7-hydroxy-, (+-)
NCI60_004656
10,11-methylenedioxy-20(rs)-camptothecin
nsc606174
10h,3-dioxolo[4,5-g]pyrano[3',4':6,7]indolizino [1,2-b]quinoline-8,11(7h,10h)-dione, 7-ethyl-7-hydroxy-, (+-)
nsc-606174
CHEMBL52057 ,
nsc 634724
151636-76-9
fl118 ,
SCHEMBL9563404
94898-61-0
glycoside-o-4
cid 72403
7-ethyl-7-hydroxy-10h-1,3-dioxolo(4,5-g)pyrano(3',4':6,7)indolizino(1,2-b)quinoline-8,11(7h,12h)-dione
EX-A525
glycosideo-4
FT-0700213
fl-118;fl 118;(r)-fl-118
BCP12571
5-ethyl-5-hydroxy-7,18,20-trioxa-11,24-diazahexacyclo[11.11.0.02,11.04,9.015,23.017,21]tetracosa-1(13),2,4(9),14,16,21,23-heptaene-6,10-dione
SY283015
(s)-7-ethyl-7-hydroxy-7h-[1,3]dioxolo[4,5-g]pyrano[3 inverted exclamation mark ,4 inverted exclamation mark :6,7]indolizino[1,2-b]quinoline-8,11(10h,13h)-dione
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
DNA topoisomerase 1Homo sapiens (human)IC50 (µMol)0.05250.02101.862610.0000AID210946; AID210947
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (11)

Processvia Protein(s)Taxonomy
DNA topological changeDNA topoisomerase 1Homo sapiens (human)
chromatin remodelingDNA topoisomerase 1Homo sapiens (human)
circadian rhythmDNA topoisomerase 1Homo sapiens (human)
response to xenobiotic stimulusDNA topoisomerase 1Homo sapiens (human)
programmed cell deathDNA topoisomerase 1Homo sapiens (human)
phosphorylationDNA topoisomerase 1Homo sapiens (human)
peptidyl-serine phosphorylationDNA topoisomerase 1Homo sapiens (human)
circadian regulation of gene expressionDNA topoisomerase 1Homo sapiens (human)
embryonic cleavageDNA topoisomerase 1Homo sapiens (human)
chromosome segregationDNA topoisomerase 1Homo sapiens (human)
DNA replicationDNA topoisomerase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (13)

Processvia Protein(s)Taxonomy
RNA polymerase II cis-regulatory region sequence-specific DNA bindingDNA topoisomerase 1Homo sapiens (human)
DNA bindingDNA topoisomerase 1Homo sapiens (human)
chromatin bindingDNA topoisomerase 1Homo sapiens (human)
double-stranded DNA bindingDNA topoisomerase 1Homo sapiens (human)
single-stranded DNA bindingDNA topoisomerase 1Homo sapiens (human)
RNA bindingDNA topoisomerase 1Homo sapiens (human)
DNA topoisomerase type I (single strand cut, ATP-independent) activityDNA topoisomerase 1Homo sapiens (human)
protein serine/threonine kinase activityDNA topoisomerase 1Homo sapiens (human)
protein bindingDNA topoisomerase 1Homo sapiens (human)
ATP bindingDNA topoisomerase 1Homo sapiens (human)
DNA binding, bendingDNA topoisomerase 1Homo sapiens (human)
protein domain specific bindingDNA topoisomerase 1Homo sapiens (human)
supercoiled DNA bindingDNA topoisomerase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
nuclear chromosomeDNA topoisomerase 1Homo sapiens (human)
P-bodyDNA topoisomerase 1Homo sapiens (human)
fibrillar centerDNA topoisomerase 1Homo sapiens (human)
male germ cell nucleusDNA topoisomerase 1Homo sapiens (human)
nucleusDNA topoisomerase 1Homo sapiens (human)
nucleoplasmDNA topoisomerase 1Homo sapiens (human)
nucleolusDNA topoisomerase 1Homo sapiens (human)
perikaryonDNA topoisomerase 1Homo sapiens (human)
protein-DNA complexDNA topoisomerase 1Homo sapiens (human)
nucleolusDNA topoisomerase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (31)

Assay IDTitleYearJournalArticle
AID223505Relative survival in L1210 lymphoid leukemic mice after subcutaneous administration on days 1,4,6,8 at dose of 3 mg/kg1993Journal of medicinal chemistry, Sep-03, Volume: 36, Issue:18
Plant antitumor agents. 30. Synthesis and structure activity of novel camptothecin analogs.
AID223513Relative survival in RAW117-H10 cells implanted mice in comparison to control at dose of 3 mg/kg1993Journal of medicinal chemistry, Sep-03, Volume: 36, Issue:18
Plant antitumor agents. 30. Synthesis and structure activity of novel camptothecin analogs.
AID91477Association constant for the binding of the carboxylate form to human serum albumin;(M aa)e-11994Journal of medicinal chemistry, Jan-07, Volume: 37, Issue:1
The structural basis of camptothecin interactions with human serum albumin: impact on drug stability.
AID91476Binding parameter of the lactone form to human serum albumin; n value1994Journal of medicinal chemistry, Jan-07, Volume: 37, Issue:1
The structural basis of camptothecin interactions with human serum albumin: impact on drug stability.
AID91478Association constant for the binding of the lactone form to human serum albumin;(M aa)e-11994Journal of medicinal chemistry, Jan-07, Volume: 37, Issue:1
The structural basis of camptothecin interactions with human serum albumin: impact on drug stability.
AID22193Excited-state lifetime value for free lactone form of compound in solution1994Journal of medicinal chemistry, Jan-07, Volume: 37, Issue:1
The structural basis of camptothecin interactions with human serum albumin: impact on drug stability.
AID221120Toxic dose in L1210 lymphoid leukemic mice1993Journal of medicinal chemistry, Sep-03, Volume: 36, Issue:18
Plant antitumor agents. 30. Synthesis and structure activity of novel camptothecin analogs.
AID99053Log of initial tumor cell population minus log of tumor cell population at end of treatment in L1210 lymphoid leukemic mice1993Journal of medicinal chemistry, Sep-03, Volume: 36, Issue:18
Plant antitumor agents. 30. Synthesis and structure activity of novel camptothecin analogs.
AID94454Number of metastases in K1735-M2 murine melanoma cells after subcutaneous administration on days1,4,6,8 at dose of 3 mg/kg1993Journal of medicinal chemistry, Sep-03, Volume: 36, Issue:18
Plant antitumor agents. 30. Synthesis and structure activity of novel camptothecin analogs.
AID96203In vitro cytotoxic activity against KB cell culture.1987Journal of medicinal chemistry, Oct, Volume: 30, Issue:10
Plant antitumor agents. 25. Total synthesis and antileukemic activity of ring A substituted camptothecin analogues. Structure-activity correlations.
AID91475Binding parameter of the carboxylate form to human serum albumin; n value1994Journal of medicinal chemistry, Jan-07, Volume: 37, Issue:1
The structural basis of camptothecin interactions with human serum albumin: impact on drug stability.
AID94907Toxic dose against L1210 mouse leukemia cells was determined1987Journal of medicinal chemistry, Oct, Volume: 30, Issue:10
Plant antitumor agents. 25. Total synthesis and antileukemic activity of ring A substituted camptothecin analogues. Structure-activity correlations.
AID210946Inhibition of Topoisomerase I by cleavage complex formation in human HL-60 cells1993Journal of medicinal chemistry, Sep-03, Volume: 36, Issue:18
Plant antitumor agents. 30. Synthesis and structure activity of novel camptothecin analogs.
AID152104Compound was evaluated for antitumor activity against P-338 leukemia in mice at the dose of 2 mg/kg; T/C=Survival time of treated/control animals*1001986Journal of medicinal chemistry, Nov, Volume: 29, Issue:11
Plant antitumor agents. 23. Synthesis and antileukemic activity of camptothecin analogues.
AID152247Antitumor activity against P-338 leukemia in mice.1986Journal of medicinal chemistry, Nov, Volume: 29, Issue:11
Plant antitumor agents. 23. Synthesis and antileukemic activity of camptothecin analogues.
AID136564In vivo antileukemic activity against L-1210 mouse leukemia cells expressed as KE (log10 of initial tumor cell population minus log10 of tumor cell population at end of treatment)1987Journal of medicinal chemistry, Oct, Volume: 30, Issue:10
Plant antitumor agents. 25. Total synthesis and antileukemic activity of ring A substituted camptothecin analogues. Structure-activity correlations.
AID221383Highest active dose in L1210 lymphoid leukemic mice at dose range of 2-4 mg/kg1993Journal of medicinal chemistry, Sep-03, Volume: 36, Issue:18
Plant antitumor agents. 30. Synthesis and structure activity of novel camptothecin analogs.
AID210947Inhibition of Topoisomerase I by cleavage complex formation in intact human HL-60 cells1993Journal of medicinal chemistry, Sep-03, Volume: 36, Issue:18
Plant antitumor agents. 30. Synthesis and structure activity of novel camptothecin analogs.
AID152112Antitumor activity against P-338 leukemia in mice 1986Journal of medicinal chemistry, Nov, Volume: 29, Issue:11
Plant antitumor agents. 23. Synthesis and antileukemic activity of camptothecin analogues.
AID152245Antitumor activity against P-338 leukemia in mice.1986Journal of medicinal chemistry, Nov, Volume: 29, Issue:11
Plant antitumor agents. 23. Synthesis and antileukemic activity of camptothecin analogues.
AID152118Compound was evaluated for antitumor activity against P-338 leukemia in mice, active dose range of the compound; Lowest dose administered, dose range was 2.0-4.0 mg/kg1986Journal of medicinal chemistry, Nov, Volume: 29, Issue:11
Plant antitumor agents. 23. Synthesis and antileukemic activity of camptothecin analogues.
AID135487In vivo antileukemic activity against L-1210 mouse leukemia cells given as number of animals cured out of 61987Journal of medicinal chemistry, Oct, Volume: 30, Issue:10
Plant antitumor agents. 25. Total synthesis and antileukemic activity of ring A substituted camptothecin analogues. Structure-activity correlations.
AID26144Half-life in PBS buffer solution in the absence of human serum albumin1994Journal of medicinal chemistry, Jan-07, Volume: 37, Issue:1
The structural basis of camptothecin interactions with human serum albumin: impact on drug stability.
AID136426In vivo antileukemic activity against L-1210 mouse leukemia cells expressed as % T/C (median survival time of treated/control animals) x 100 after 2 mg/kg administration of dose1987Journal of medicinal chemistry, Oct, Volume: 30, Issue:10
Plant antitumor agents. 25. Total synthesis and antileukemic activity of ring A substituted camptothecin analogues. Structure-activity correlations.
AID26145Half-life in PBS buffer solution in the presence of human serum albumin1994Journal of medicinal chemistry, Jan-07, Volume: 37, Issue:1
The structural basis of camptothecin interactions with human serum albumin: impact on drug stability.
AID223493Percent median survival time of treated leukemic mice compared to control1993Journal of medicinal chemistry, Sep-03, Volume: 36, Issue:18
Plant antitumor agents. 30. Synthesis and structure activity of novel camptothecin analogs.
AID22192Excited-state lifetime value for free carboxylate form of compound in solution1994Journal of medicinal chemistry, Jan-07, Volume: 37, Issue:1
The structural basis of camptothecin interactions with human serum albumin: impact on drug stability.
AID222958Number of L1210 lymphoid leukemic mice cured out of 61993Journal of medicinal chemistry, Sep-03, Volume: 36, Issue:18
Plant antitumor agents. 30. Synthesis and structure activity of novel camptothecin analogs.
AID22190Excited-state lifetime value for carboxylate form of compound bound to human serum albumin1994Journal of medicinal chemistry, Jan-07, Volume: 37, Issue:1
The structural basis of camptothecin interactions with human serum albumin: impact on drug stability.
AID22191Excited-state lifetime value for lactone form of compound bound to human serum albumin1994Journal of medicinal chemistry, Jan-07, Volume: 37, Issue:1
The structural basis of camptothecin interactions with human serum albumin: impact on drug stability.
AID94898Active dose range for antileukemic activity against L1210 mouse leukemia cells was reported 2 to 41987Journal of medicinal chemistry, Oct, Volume: 30, Issue:10
Plant antitumor agents. 25. Total synthesis and antileukemic activity of ring A substituted camptothecin analogues. Structure-activity correlations.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (20)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (10.00)18.7374
1990's2 (10.00)18.2507
2000's0 (0.00)29.6817
2010's9 (45.00)24.3611
2020's7 (35.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.33

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.33 (24.57)
Research Supply Index3.04 (2.92)
Research Growth Index4.38 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.33)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (5.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other19 (95.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
LSM-1442
[no description available]		1.9810pyranoindolizinoquinoline
camptothecin
NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source		3.6690delta-lactone;
pyranoindolizinoquinoline;
quinoline alkaloid;
tertiary alcohol		antineoplastic agent;
EC 5.99.1.2 (DNA topoisomerase) inhibitor;
genotoxin;
plant metabolite
topotecan
Topotecan: An antineoplastic agent used to treat ovarian cancer. It works by inhibiting DNA TOPOISOMERASES, TYPE I.. topotecan : A pyranoindolizinoquinoline used as an antineoplastic agent. It is a derivative of camptothecin and works by binding to the topoisomerase I-DNA complex and preventing religation of these 328 single strand breaks.		2.3920pyranoindolizinoquinolineantineoplastic agent;
EC 5.99.1.2 (DNA topoisomerase) inhibitor
irinotecan
[no description available]		2.5720carbamate ester;
delta-lactone;
N-acylpiperidine;
pyranoindolizinoquinoline;
ring assembly;
tertiary alcohol;
tertiary amino compound		antineoplastic agent;
apoptosis inducer;
EC 5.99.1.2 (DNA topoisomerase) inhibitor;
prodrug
9-aminocamptothecin
[no description available]		2.8940pyranoindolizinoquinoline
10,11-methylenedioxy-20-camptothecin
10,11-methylenedioxy-20-camptothecin: structure given in first source		1.9810
10-hydroxycamptothecin
[no description available]		2.6730pyranoindolizinoquinoline
9-methoxycamptothecin
10-methoxycamptothecin: a radiotracer; structure in first source		1.9610
sn 38
SN-38 : 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.		1.9810delta-lactone;
phenols;
pyranoindolizinoquinoline;
tertiary alcohol		antineoplastic agent;
apoptosis inducer;
drug metabolite;
EC 5.99.1.2 (DNA topoisomerase) inhibitor
resveratrol
trans-resveratrol : A resveratrol in which the double bond has E configuration.		2.3110resveratrolantioxidant;
phytoalexin;
plant metabolite;
quorum sensing inhibitor;
radical scavenger
rubitecan
rubitecan: RN refers to (+-)-isomer; anti-HIV agent; DNA Topoisomerases, Type I inhibitor. rubitecan : A pyranoindolizinoquinoline that is camptothecin in which the hydrogen at position 9 has been replaced by a nitro group. It is a prodrug for 9-aminocamptothecin.		1.9610C-nitro compound;
delta-lactone;
pyranoindolizinoquinoline;
semisynthetic derivative;
tertiary alcohol		antineoplastic agent;
EC 5.99.1.2 (DNA topoisomerase) inhibitor;
prodrug
es-285
spisulosine: from marine organism, Spisula polynyma; structure in first source. 1-deoxysphinganine : A bioactive sphingoid, sphinganine, in which the terminal hydroxy group has been replaced by a hydrogen.		2.2510amino alcohol;
sphingoid		antineoplastic agent
nsc 100880
[no description available]		1.9810
ConditionIndicatedRelationship StrengthStudiesTrials
Leukemia L 1210
[description not available]		02.6630
Cancer of Pancreas
[description not available]		03.4350
Colorectal Cancer
[description not available]		03.2750
Carcinoma, Ductal, Pancreatic
[description not available]		02.4110
Pancreatic Neoplasms
Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).		03.4350
Colorectal Neoplasms
Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.		03.2750
Carcinoma, Pancreatic Ductal
Carcinoma that arises from the PANCREATIC DUCTS. It accounts for the majority of cancers derived from the PANCREAS.		02.4110
Benign Neoplasms
[description not available]		03.0840
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		03.0840
Metastase
[description not available]		02.2510
Invasiveness, Neoplasm
[description not available]		02.9330
Neoplasm Metastasis
The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.		02.2510
ER-Negative PR-Negative HER2-Negative Breast Cancer
[description not available]		02.3110
Triple Negative Breast Neoplasms
Breast neoplasms that do not express ESTROGEN RECEPTORS; PROGESTERONE RECEPTORS; and do not overexpress the NEU RECEPTOR/HER-2 PROTO-ONCOGENE PROTEIN.		02.3110
Breast Cancer
[description not available]		02.1710
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.1710
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.1710
Kahler Disease
[description not available]		02.2510
Multiple Myeloma
A malignancy of mature PLASMA CELLS engaging in monoclonal immunoglobulin production. It is characterized by hyperglobulinemia, excess Bence-Jones proteins (free monoclonal IMMUNOGLOBULIN LIGHT CHAINS) in the urine, skeletal destruction, bone pain, and fractures. Other features include ANEMIA; HYPERCALCEMIA; and RENAL INSUFFICIENCY.		02.2510
Disease Exacerbation
[description not available]		02.1110
Carcinoma, Non-Small Cell Lung
[description not available]		02.1110
Cancer of Lung
[description not available]		02.1110
Carcinoma, Non-Small-Cell Lung
A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.		02.1110
Lung Neoplasms
Tumors or cancer of the LUNG.		02.1110