RUBITECAN

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H15N3O6
Molecular Weight	393.3496
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC[C@@]1(O)C(=O)OCC2=C1C=C3N(CC4=C3N=C5C=CC=C(C5=C4)[N+]([O-])=O)C2=O

InChI

InChIKey=VHXNKPBCCMUMSW-FQEVSTJZSA-N

InChI=1S/C20H15N3O6/c1-2-20(26)13-7-16-17-10(8-22(16)18(24)12(13)9-29-19(20)25)6-11-14(21-17)4-3-5-15(11)23(27)28/h3-7,26H,2,8-9H2,1H3/t20-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C20H15N3O6
Molecular Weight	393.3496
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11193898http://www.fda.gov/downloads/Drugs/GuidanceComplianceRegulatoryInformation/EnforcementActivitiesbyFDA/WarningLettersandNoticeofViolationLetterstoPharmaceuticalCompanies/UCM166470.pdf
Curator's Comment: Description was created based on several sources, including http://www.ema.europa.eu/docs/en_GB/document_library/Application_withdrawal_assessment_report/2010/01/WC500069806.pdf

Rubitecan [Orathecin™] is a topoisomerase I inhibitor extracted from the bark and leaves of the Camptotheca acuminata tree, which is native to China. Rubitecan is an oral compound being developed for the treatment of pancreatic cancer and other solid tumours by SuperGen. Rubitecan binds to and inhibits the enzyme topoisomerase I and induces protein-linked DNA single-strand breaks, thereby blocking DNA and RNA synthesis in dividing cells; this agent also prevents repair of reversible single-strand DNA breaks.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
cell proliferation 28 Target ID: GO:0008283 Sources: http://www.ncbi.nlm.nih.gov/pubmed/21695227	Inhibitor 8504	0.17 µM [IC50]
Topoisomerase I 4 Target ID: CHEMBL6023 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1846923	Inhibitor 8504	12.0 nM [IC50]
DNA topoisomerase I 60 Target ID: CHEMBL1781 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Application_withdrawal_assessment_report/2010/01/WC500069806.pdf	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Colorectal cancer 102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11042563	Primary	Phase II 1147	Unknown Approved Use Unknown
Non-small cell lung cancer 211 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11561694	Primary	Phase II 1147	Unknown Approved Use Unknown
Ovarian cancer 160 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15589582	Primary	Phase II 1147	Unknown Approved Use Unknown
Kidney cancer 10 Sources: https://clinicaltrials.gov/ct2/show/NCT00003551	Primary	Phase II 1147	Unknown Approved Use Unknown
Lymphoma 60 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18648813	Primary	Phase II 1147	Unknown Approved Use Unknown
Pancreatic cancer 98 Sources: http://www.ncbi.nlm.nih.gov/pubmed/15793221	Primary	Withdrawn	Unknown Approved Use Unknown
Hepatocellular carcinoma 83 Sources: http://www.ncbi.nlm.nih.gov/pubmed/21695227	Primary	Basic research	Unknown Approved Use Unknown
Melanoma 88 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11901310	Primary	Phase II 1147	Unknown Approved Use Unknown
Ovarian cancer 160 Sources: http://www.ncbi.nlm.nih.gov/pubmed/10378672	Primary	Phase II 1147	Unknown Approved Use Unknown
Peritoneal cancer 11 Sources: http://www.ncbi.nlm.nih.gov/pubmed/10378672	Primary	Phase II 1147	Unknown Approved Use Unknown
Chronic myelomonocytic leukemia 5 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16955510	Primary	Preclinical	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
147.57 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21191594	1.75 mg/m² single, oral dose: 1.75 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	9-AMINOCAMPTOTHECIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
85.98 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21191594	1.5 mg/m² 1 times / day multiple, oral dose: 1.5 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	9-AMINOCAMPTOTHECIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
52.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16205924	1.5 mg/m² single, oral dose: 1.5 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	RUBITECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
26.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16205924	1.5 mg/m² single, oral dose: 1.5 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	RUBITECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
115.56 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21191594	1.5 mg/m² single, oral dose: 1.5 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	RUBITECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
85.98 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21191594	1.5 mg 1 times / day steady-state, oral dose: 1.5 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	RUBITECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
1385.39 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21191594	1.75 mg/m² single, oral dose: 1.75 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	9-AMINOCAMPTOTHECIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2214.92 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21191594	1.5 mg/m² 1 times / day multiple, oral dose: 1.5 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	9-AMINOCAMPTOTHECIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
557 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16205924	1.5 mg/m² single, oral dose: 1.5 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	RUBITECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
330 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16205924	1.5 mg/m² single, oral dose: 1.5 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	RUBITECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
1047.35 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21191594	1.5 mg/m² single, oral dose: 1.5 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	RUBITECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2214.92 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21191594	1.5 mg 1 times / day steady-state, oral dose: 1.5 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	RUBITECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
8.65 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21191594	1.75 mg/m² single, oral dose: 1.75 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	9-AMINOCAMPTOTHECIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
21.25 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21191594	1.5 mg/m² 1 times / day multiple, oral dose: 1.5 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered:	9-AMINOCAMPTOTHECIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
9.17 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21191594	1.5 mg/m² single, oral dose: 1.5 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	RUBITECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
21.25 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21191594	1.5 mg 1 times / day steady-state, oral dose: 1.5 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	RUBITECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
1.5 mg/m2 1 times / day multiple, oral MTD Dose: 1.5 mg/m2, 1 times / day Route: oral Route: multiple Dose: 1.5 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9491790	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/9491790	DLT: Anemia, Neutropenia... Dose limiting toxicities: Anemia (grade 4, 10%) Neutropenia (grade 4, 10%) Sources: https://pubmed.ncbi.nlm.nih.gov/9491790
2 mg/m2 1 times / day multiple, oral Studied dose Dose: 2 mg/m2, 1 times / day Route: oral Route: multiple Dose: 2 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9491790	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/9491790	DLT: Neutropenic sepsis, Thrombocytopenia... Dose limiting toxicities: Neutropenic sepsis (grade 4, 23%) Thrombocytopenia (grade 4, 19.2%) Anemia (grade 4, 26.9%) Nausea (grade 3, 18%) Vomiting (grade 3, 18%) Diarrhea (grade 3, 14%) Chemical cystitis (grade 3, 14%) Sources: https://pubmed.ncbi.nlm.nih.gov/9491790
0.7 mg/m2 1 times / day multiple, oral Highest studied dose Dose: 0.7 mg/m2, 1 times / day Route: oral Route: multiple Dose: 0.7 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12796369	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12796369	DLT: anemia, neutropenia... Dose limiting toxicities: anemia (grade 3, 33.3%) neutropenia (grade 4, 33.3%) thrombocytopenia (grade 4, 33.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/12796369
60 ug/m2 1 times / day multiple, intravenous Highest studied dose Dose: 60 ug/m2, 1 times / day Route: intravenous Route: multiple Dose: 60 ug/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9815982	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9815982	DLT: neutropenia... Dose limiting toxicities: neutropenia (grade 4) Sources: https://pubmed.ncbi.nlm.nih.gov/9815982
0.63 mg/m2 1 times / day multiple, oral MTD Dose: 0.63 mg/m2, 1 times / day Route: oral Route: multiple Dose: 0.63 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12796369	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12796369	Sources: https://pubmed.ncbi.nlm.nih.gov/12796369
1.3 mg/m2 1 times / day multiple, intravenous MTD Dose: 1.3 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1.3 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10561232	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/10561232	DLT: thrombocytopenia... Dose limiting toxicities: thrombocytopenia (grade 3, 50%) Sources: https://pubmed.ncbi.nlm.nih.gov/10561232
45 ug/m2 1 times / day multiple, intravenous MTD Dose: 45 ug/m2, 1 times / day Route: intravenous Route: multiple Dose: 45 ug/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9815982	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9815982	DLT: neutropenia... Dose limiting toxicities: neutropenia Sources: https://pubmed.ncbi.nlm.nih.gov/9815982
1.1 mg/m2 1 times / day multiple, intravenous RP2D Dose: 1.1 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 1.1 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10561232	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/10561232	Sources: https://pubmed.ncbi.nlm.nih.gov/10561232

AEs

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY113540	https://www.001chemical.com/chem/search?q=DY113540
1PlusChem LLC	1P003O0O	https://www.1pchem.com/search?query=1P003O0O
A2B Chem	AB70296	http://a2bchem.com/prod/AB70296
AK Scientific	K664	https://aksci.com/item_detail.php?cat=K664
001 Chemical	DY115137	https://www.001chemical.com/chem/search?q=DY115137
Alfa Chemistry	31614	http://www.alfa-chemistry.com/search.aspx?q=31614
Alfa Chemistry	ACM104195611	http://www.alfa-chemistry.com/search.aspx?q=ACM104195611
Angene	AGN-PC-0VSCS4	http://www.angenechemical.com/productshow/AGN-PC-0VSCS4.html
ApexBio Technology	C5790	https://www.apexbt.com/catalogsearch/result/?q=C5790
AstaTech	F11420	http://astatechinc.com/CPSResult.php?CRNO=F11420
BioSynth	J-504140	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/J-504140
BOC Sciences	104195-61-1	http://www.bocsci.com/description.asp?cas=104195-61-1
Cayman Chemical	17232	http://www.caymanchem.com/app/template/Product.vm/catalog/17232
Chem-Impex International	32444	http://www.chemimpex.com/category/search/32444/2?filter=&search=32444&type=q&keywordoption=ANY&cid=2&fltrdesc=
Chem Scene	CS-7784	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-7784
1PlusChem LLC	1P003O27	https://www.1pchem.com/search?query=1P003O27
ChemShuttle	185617	https://www.chemshuttle.com/catalogsearch/result/?q=185617
eMolecules	300481891	https://orderbb.emolecules.com/search/#?query=300481891
eMolecules	30315901	https://orderbb.emolecules.com/search/#?query=30315901
eNovation Chemicals	K78245	https://www.enovationchem.com/Products.asp?SEARCHTEXT=K78245&searchbtn.x=0&searchbtn.y=0
Fluorochem	213672	http://www.fluorochem.co.uk/Products/Product?code=213672
Hairui	HR128618	http://www.hairuichem.com/en/product/search.do?q=HR128618
KeyOrganics	AS-14292	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-14292
KeyOrganics	STR09285	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=STR09285
Lab Network	LN00189862	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00189862
Matrix Scientific	90901	http://www.matrixscientific.com/090901.html
A2B Chem	AB70351	http://a2bchem.com/prod/AB70351
mcule	MCULE-7175414234	https://mcule.com/MCULE-7175414234/
mcule	MCULE-9765473112	https://mcule.com/MCULE-9765473112/
MedChem Express	HY-100309	https://www.medchemexpress.com/search.html?q=HY-100309&ft=&fa=&fp=
Molcore	MC113540	http://www.molcore.com/CatMC113540.html
MolPort	MolPort-009-684-196	https://www.molport.com/shop/molecule-link/MolPort-009-684-196
MolPort	MolPort-046-763-095	https://www.molport.com/shop/molecule-link/MolPort-046-763-095
MuseChem	M117058	https://www.musechem.com/product/M117058.html
PI Chemicals	PI-36649	http://www.pipharm.com/catalog_products/PI-36649.html
ShangHai Biochempartner	BCP09002	http://www.biochempartner.com/search_BCP09002
Tetrahedron	TS66532	http://www.thsci.com/search.do?q=TS66532
Achemo Scientific Limited	AC-64432	http://www.achemo.com/search/?Keyword=AC-64432
Toronto Research Chemicals	A603125	https://www.trc-canada.com/product-detail/?CatNum=A603125
Toronto Research Chemicals	M224955	https://www.trc-canada.com/product-detail/?CatNum=M224955
W&J PharmaChem	50C776311	http://wjpharmachem.com/new/searcht.php?keyword=50C776311
Wonderchem	WD06ZPC	http://www.wonder-chem.com/search.html?text=WD06ZPC
AK Scientific	M884	https://aksci.com/item_detail.php?cat=M884
Angene	AGN-PC-0VSCRR	http://www.angenechemical.com/productshow/AGN-PC-0VSCRR.html
AstaTech	42333	http://astatechinc.com/CPSResult.php?CRNO=42333
Biopurify Phytochemicals	BP1229	https://www.phytopurify.com/search.do?a=s&searchtype=3&psize=10&q=BP1229&searchhtmp=simplesearch&t=1
BioSynth	Q-100889	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-100889
BOC Sciences	91421-42-0	http://www.bocsci.com/description.asp?cas=91421-42-0
Chem-Impex International	32498	http://www.chemimpex.com/category/search/32498/2?filter=&search=32498&type=q&keywordoption=ANY&cid=2&fltrdesc=
Chem Scene	CS-0007769	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0007769
eMolecules	29542673	https://orderbb.emolecules.com/search/#?query=29542673
eMolecules	300455233	https://orderbb.emolecules.com/search/#?query=300455233
eNovation Chemicals	D379858	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D379858&searchbtn.x=0&searchbtn.y=0
Hairui	HR123221	http://www.hairuichem.com/en/product/search.do?q=HR123221
Hairui	HR144753	http://www.hairuichem.com/en/product/search.do?q=HR144753
KeyOrganics	AS-14856	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-14856
Lab Network	LN00199918	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00199918
Lab Seeker	SC-54565	http://www.labseeker.com/search.php?keywords=SC-54565&category=0
LabSeeker	SC-54565	http://www.labseeker.com/search.php?keywords=SC-54565&category=0
Matrix Scientific	99302	http://www.matrixscientific.com/099302.html
mcule	MCULE-1551776158	https://mcule.com/MCULE-1551776158/
mcule	MCULE-6404718274	https://mcule.com/MCULE-6404718274/
MedChem Express	HY-13744	https://www.medchemexpress.com/search.html?q=HY-13744&ft=&fa=&fp=
Molcore	MC115137	http://www.molcore.com/CatMC115137.html
MolPort	MolPort-003-850-214	https://www.molport.com/shop/molecule-link/MolPort-003-850-214
MuseChem	R007201	https://www.musechem.com/product/R007201.html
ShangHai Biochempartner	BCP06207	http://www.biochempartner.com/search_BCP06207
TargetMol	T5853	https://www.targetmol.com/search?keyword=T5853
Tetrahedron	TS80808	http://www.thsci.com/search.do?q=TS80808
Toronto Research Chemicals	B410878	https://www.trc-canada.com/product-detail/?CatNum=B410878
Toronto Research Chemicals	R701500	https://www.trc-canada.com/product-detail/?CatNum=R701500
Toronto Research Chemicals	R701525	https://www.trc-canada.com/product-detail/?CatNum=R701525
W&J PharmaChem	50C163574	http://wjpharmachem.com/new/searcht.php?keyword=50C163574
Wonderchem	WD06ZPB	http://www.wonder-chem.com/search.html?text=WD06ZPB

PubMed

Title	Date	PubMed
In vitro antitrypanosomal and antileishmanial activity of plants used in Benin in traditional medicine and bio-guided fractionation of the most active extract.	2011-09-02	21782916
Preparation and in vitro characterization of 9-nitrocamptothecin-loaded long circulating nanoparticles for delivery in cancer patients.	2010-08-09	20957168
Antitumor efficacy of colon-specific HPMA copolymer/9-aminocamptothecin conjugates in mice bearing human-colon carcinoma xenografts.	2009-11-10	19685500
Safety and feasibility of switching from phenytoin to levetiracetam monotherapy for glioma-related seizure control following craniotomy: a randomized phase II pilot study.	2009-07	19169651
The role side effects play in the choice of antiepileptic therapy in brain tumor-related epilepsy: a comparative study on traditional antiepileptic drugs versus oxcarbazepine.	2009-05-06	19419544
Gateways to clinical trials.	2009-04	19536362
Phase II study of 9-aminocamptothecin in previously treated lymphomas: results of Cancer and Leukemia Group B 9551.	2009-04	18648813
Tumor, tissue, and plasma pharmacokinetic studies and antitumor response studies of docetaxel in combination with 9-nitrocamptothecin in mice bearing SKOV-3 human ovarian xenografts.	2008-08	17957368
Tumor-targeting prodrug-activating bacteria for cancer therapy.	2008-06	18369382
Key role of topoisomerase I inhibitors in the treatment of recurrent and refractory epithelial ovarian carcinoma.	2008-05	18471053
Benzyl ether-linked glucuronide derivative of 10-hydroxycamptothecin designed for selective camptothecin-based anticancer therapy.	2008-03-27	18318465
Pharmacokinetic modeling of absorption behavior of 9-aminocamptothecin (9-AC) released from colon-specific HPMA copolymer-9-AC conjugate in rats.	2008-01	17929146
Effect of pH and human serum albumin on the cytotoxicity of a glucuronide prodrug of 9-aminocamptothecin.	2007-06	16983566
Biodistribution and pharmacokinetics of colon-specific HPMA copolymer--9-aminocamptothecin conjugate in mice.	2007-02-12	17150276
Membrane-localized activation of glucuronide prodrugs by beta-glucuronidase enzymes.	2007-02	16977328
Gateways to clinical trials.	2006-12	17235418
Disposition of 9-nitrocamptothecin and its 9-aminocamptothecin metabolite in relation to ABC transporter genotypes.	2006-09	16505951
Phase I trial of continuous infusion 9-aminocamptothecin in patients with advanced solid tumors: 21-day infusion is an active well-tolerated regimen.	2006-06	16702815
Clinical and pharmacokinetic study evaluating the effect of food on the disposition of 9-nitrocamptothecin and its 9-aminocamptothecin metabolite in patients with solid tumors.	2006-05	16205924
Identification of a small topoisomerase I-binding peptide that has synergistic antitumor activity with 9-aminocamptothecin.	2006-03	16546989
Risk assessment of human myelotoxicity of anticancer drugs: a predictive model and the in vitro colony forming unit granulocyte/macrophage (CFU-GM) assay.	2006-02	16526561
Colon-specific 9-aminocamptothecin-HPMA copolymer conjugates containing a 1,6-elimination spacer.	2006-01-10	16290118
Rubitecan.	2006-01	16370935
Relationship between plasma exposure of 9-nitrocamptothecin and its 9-aminocamptothecin metabolite and antitumor response in mice bearing human colon carcinoma xenografts.	2005-07-01	16000585
Alternative administration of camptothecin analogues.	2005-03	16296757
Gateways to clinical trials.	2005-03	15834466
Topoisomerases in the treatment of metastatic or recurrent squamous carcinoma of the head and neck.	2005-01	15709886
Phase II evaluation of 9-aminocamptothecin (9-AC, NSC #603071) in platinum-resistant ovarian and primary peritoneal carcinoma: a Gynecologic Oncology Group Study.	2005-01	15589582
Pharmacokinetic studies of 9-nitrocamptothecin on intermittent and continuous schedules of administration in patients with solid tumors.	2004-12	15322760
Phase I and pharmacokinetic study of XR11576, an oral topoisomerase I and II inhibitor, administered on days 1-5 of a 3-weekly cycle in patients with advanced solid tumours.	2004-10-18	15452551
A predictive model of human myelotoxicity using five camptothecin derivatives and the in vitro colony-forming unit granulocyte/macrophage assay.	2004-10-01	15475463
Topoisomerase I inhibitors in the treatment of gastrointestinal cancer: from intravenous to oral administration.	2004-09	15377400
Phase I and pharmacologic study of intermittently administered 9-nitrocamptothecin in patients with advanced solid tumors.	2004-08-01	15297407
9-Aminocamptothecin (9-AC) given as a 120-hour continuous infusion in patients with advanced adenocarcinomas of the stomach and gastroesophageal junction: A phase II trial of the University of Chicago phase II consortium.	2004-08	15122080
Plasma and cerebrospinal fluid pharmacokinetic study of BNP1350 in nonhuman primates.	2004-06	14997342
Membrane transport of camptothecin: facilitation by human P-glycoprotein (ABCB1) and multidrug resistance protein 2 (ABCC2).	2004-05-04	15125776
Gateways to clinical trials.	2004-03	15071612
Development of a bioanalytical liquid chromatography method for quantitation of 9-nitrocamptothecin in human plasma.	2004-01-05	14659436
Biweekly 72-hour 9-aminocamptothecin infusion as second-line therapy for ovarian carcinoma: phase II study of the New York Gynecologic Oncology Group and the Eastern Cooperative Oncology Group.	2004-01-01	14701774
Ex vivo analysis of topotecan: advancing the application of laboratory-based clinical therapeutics.	2003-11-03	14583785
Gateways to clinical trials.	2003-11	14685303
Determination of 9-nitrocamptothecin by precolumn derivatization and its metabolite 9-aminocamptothecin in a biological fluid using reversed-phase high-performance liquid chromatography with fluorescence detection.	2003-10-05	14522035
Stability of the new prodrug 9-aminocamptothecin glucuronide (9ACG) in the presence of human serum albumin.	2003-10-01	14505797
Are there any better camptothecins than the ones we have?	2003-10	16258452
A phase I study of 9-aminocamptothecin as a colloidal dispersion formulation given as a fortnightly 72-h infusion.	2003-10	12819941
The anti-neoplastic and novel topoisomerase II-mediated cytotoxicity of neoamphimedine, a marine pyridoacridine.	2003-08-01	12907244
Differential effects of the breast cancer resistance protein on the cellular accumulation and cytotoxicity of 9-aminocamptothecin and 9-nitrocamptothecin.	2003-06-15	12810652
Intravenous administration of 9-aminocamptothecin to dogs with lymphoma.	2003-06	19379320
Phase I and pharmacological study of oral 9-aminocamptothecin colloidal dispersion (NSC 603071) in patients with advanced solid tumors.	2003-06	12796369
Inhibitors of human immunodeficiency virus integrase.	1993-03-15	8460151

Patents

Sample Use Guides

In Vivo Use Guide

In phase I clinical trial 9-aminocamptothecin was administered intravenously as a 72-hour infusion. Different administration schedules were investigated in phase II trials.

Route of Administration: Intravenous

In Vitro Use Guide

In vitro anti-tumor efficacy of 9-aminocamptothecin (9-AC) was measured using growth inhibition assay in L1210 murine leukemia cells. 9-AC inhibited the proliferation of L1210 cells by 50% upon continues exposure at a concentration of 0.9 uM.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 06:59:37 GMT 2025` Edited by `admin` on `Wed Apr 02 06:59:37 GMT 2025`
Record UNII	H19C446XXB
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RFS-2000

Preferred Name

English

RUBITECAN

Official Name

English

9-NITRO-20-(S)-CAMPTOTHECIN

Common Name

English

9-NC

Common Name

English

rubitecan [INN]

Common Name

English

RFS2000

Code

English

Rubitecan [WHO-DD]

Common Name

English

RUBITECAN [USAN]

Common Name

English

1H-PYRANO(3',4':6,7)INDOLIZINO(1,2-B)QUINOLINE-3,14(4H,12H)-DIONE, 4-ETHYL-4-HYDROXY-10-NITRO-, (4S)-

Systematic Name

English

RUBITECAN [MI]

Common Name

English

RUBITECAN [MART.]

Common Name

English

9-NITRO-20(S)-CAMPTOTHECIN

Common Name

English

9-Nitrocamptothecin

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

100196