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91421-42-0,MFCD06656294
Catalog No.:AA003NIR

91421-42-0 | Rubitecan

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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA003NIR
Chemical Name:
Rubitecan
CAS Number:
91421-42-0
Molecular Formula:
C20H15N3O6
Molecular Weight:
393.3496
MDL Number:
MFCD06656294
SMILES:
CC[C@@]1(O)C(=O)OCc2c1cc1c3nc4cccc(c4cc3Cn1c2=O)[N+](=O)[O-]
Properties
Properties
 
Form:
Solid  
MP:
>255℃ (dec.)  
Storage:
-20 ℃;  

Computed Properties
 
Complexity:
861  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
29  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
1  
XLogP3:
0.8  

Literature

Title: Utilization of human nuclear receptors as an early counter screen for off-target activity: a case study with a compendium of 615 known drugs.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20150601

Title: Synergism of cyclin-dependent kinase inhibitors with camptothecin derivatives in small cell lung cancer cell lines.

Journal: Molecules (Basel, Switzerland) 20140217

Title: Anticancer activity of new haloalkyl camptothecin esters against human cancer cell lines and human tumor xenografts grown in nude mice.

Journal: Anti-cancer agents in medicinal chemistry 20120901

Title: Nano-advantage in enhanced drug delivery with biodegradable nanoparticles: contribution of reduced clearance.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20120701

Title: Inhaled chemotherapy in lung cancer: future concept of nanomedicine.

Journal: International journal of nanomedicine 20120101

Title: Targeted therapy in Ewing sarcoma.

Journal: ISRN oncology 20120101

Title: Enhanced anti-tumor effect of 9-nitro-camptothecin complexed by hydroxypropyl-β-cyclodextrin and safety evaluation.

Journal: International journal of pharmaceutics 20110830

Title: Increasing tumoral 5-fluorouracil concentrations during a 5-day continuous infusion: a microdialysis study.

Journal: Cancer chemotherapy and pharmacology 20110501

Title: Expect the unexpected-screen your screens.

Journal: Journal of pharmaceutical sciences 20110501

Title: A phase I pharmacokinetics study of 9-nitrocamptothecin in patients with advanced solid tumors.

Journal: Cancer chemotherapy and pharmacology 20110401

Title: α-Tocopheryloxyacetic acid: a novel chemotherapeutic that stimulates the antitumor immune response.

Journal: Breast cancer research : BCR 20110101

Title: Development and optimization of solid lipid nanoparticle formulation for ophthalmic delivery of chloramphenicol using a Box-Behnken design.

Journal: International journal of nanomedicine 20110101

Title: Identification and replication of loci involved in camptothecin-induced cytotoxicity using CEPH pedigrees.

Journal: PloS one 20110101

Title: Characterization of 9-nitrocamptothecin liposomes: anticancer properties and mechanisms on hepatocellular carcinoma in vitro and in vivo.

Journal: PloS one 20110101

Title: In vitro characterization of cells derived from chordoma cell line U-CH1 following treatment with X-rays, heavy ions and chemotherapeutic drugs.

Journal: Radiation oncology (London, England) 20110101

Title: Anti-MUC1 monoclonal antibody (C595) and docetaxel markedly reduce tumor burden and ascites, and prolong survival in an in vivo ovarian cancer model.

Journal: PloS one 20110101

Title: The vitamin E analog, alpha-tocopheryloxyacetic acid enhances the anti-tumor activity of trastuzumab against HER2/neu-expressing breast cancer.

Journal: BMC cancer 20110101

Title: New surface-modified solid lipid nanoparticles using N-glutaryl phosphatidylethanolamine as the outer shell.

Journal: International journal of nanomedicine 20110101

Title: Polymeric micelles in anticancer therapy: targeting, imaging and triggered release.

Journal: Pharmaceutical research 20101201

Title: Complex of 9-nitro-camptothecin in hydroxypropyl-beta-cyclodextrin: in vitro and in vivo evaluation.

Journal: International journal of pharmaceutics 20100915

Title: Chordoma: clinical characteristics, management and prognosis of a case series of 25 patients.

Journal: BMC cancer 20100101

Title: Downregulation of Epidermal Growth Factor Receptor Expression Contributes to alpha-TEA's Proapoptotic Effects in Human Ovarian Cancer Cell Lines.

Journal: Journal of oncology 20100101

Title: Anti-tumor activity of N-trimethyl chitosan-encapsulated camptothecin in a mouse melanoma model.

Journal: Journal of experimental & clinical cancer research : CR 20100101

Title: Preparation and in vitro characterization of 9-nitrocamptothecin-loaded long circulating nanoparticles for delivery in cancer patients.

Journal: International journal of nanomedicine 20100101

Title: α-TEA-induced death receptor dependent apoptosis involves activation of acid sphingomyelinase and elevated ceramide-enriched cell surface membranes.

Journal: Cancer cell international 20100101

Title: Molecular characterization of putative chordoma cell lines.

Journal: Sarcoma 20100101

Title: Application of prolonged microdialysis sampling in carboplatin-treated cancer patients.

Journal: Cancer chemotherapy and pharmacology 20090701

Title: 9-NC-loaded folate-conjugated polymer micelles as tumor targeted drug delivery system: preparation and evaluation in vitro.

Journal: International journal of pharmaceutics 20090508

Title: Synthesis of new camptothecin analogs with improved antitumor activities.

Journal: Bioorganic & medicinal chemistry letters 20090401

Title: Preparation of large monodisperse vesicles.

Journal: PloS one 20090101

Title: Optimization of the preparation process of vinblastine sulfate (VBLS)-loaded folate-conjugated bovine serum albumin (BSA) nanoparticles for tumor-targeted drug delivery using response surface methodology (RSM).

Journal: International journal of nanomedicine 20090101

Title: The role of Fas/FasL in the metastatic potential of osteosarcoma and targeting this pathway for the treatment of osteosarcoma lung metastases.

Journal: Cancer treatment and research 20090101

Title: Optimal modeling for phase I design of a two drug combination-results of a phase I study of cisplatin with 9-nitrocamptothecin.

Journal: Investigational new drugs 20081201

Title: [Investigations on preparation and release behavior in vitro of 9-nitro camptothecin encapsulated micelles].

Journal: Sheng wu yi xue gong cheng xue za zhi = Journal of biomedical engineering = Shengwu yixue gongchengxue zazhi 20081201

Title: 9-nitrocamptothecin polymeric nanoparticles: cytotoxicity and pharmacokinetic studies of lactone and total forms of drug in rats.

Journal: Anti-cancer drugs 20080901

Title: 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.

Journal: Cancer chemotherapy and pharmacology 20080801

Title: Self-microemulsifying drug delivery system (SMEDDS) improves anticancer effect of oral 9-nitrocamptothecin on human cancer xenografts in nude mice.

Journal: European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V 20080801

Title: Lactone stability and tissue distribution of free and liposomal encapsulated 9-nitrocamptothecin in rats following intravenous injection.

Journal: Drug development and industrial pharmacy 20080801

Title: Preparation and characterization of novel polymeric micelles for 9-nitro-20(S)-camptothecin delivery.

Journal: European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20080703

Title: Phase II study of rubitecan in recurrent or metastatic head and neck cancer.

Journal: Cancer chemotherapy and pharmacology 20080701

Title: Key role of topoisomerase I inhibitors in the treatment of recurrent and refractory epithelial ovarian carcinoma.

Journal: Expert review of anticancer therapy 20080501

Title: Synthesis and antitumor activity of aromatic camptothecin esters.

Journal: International journal of molecular medicine 20080401

Title: Controlled release of 9-nitro-20(S)-camptothecin from methoxy poly(ethylene glycol)-poly(D,L-lactide) micelles.

Journal: Biomedical materials (Bristol, England) 20080301

Title: Nanocarriers as pulmonary drug delivery systems to treat and to diagnose respiratory and non respiratory diseases.

Journal: International journal of nanomedicine 20080301

Title: Aerosolized chemotherapy.

Journal: Journal of aerosol medicine and pulmonary drug delivery 20080301

Title: Biodistribution in mice and severity of damage in rat lungs following pulmonary delivery of 9-nitrocamptothecin liposomes.

Journal: Pulmonary pharmacology & therapeutics 20080101

Title: Induced differentiation of hepatocellular carcinoma by natural products.

Journal: African journal of traditional, complementary, and alternative medicines : AJTCAM 20080101

Title: Effect of injection routes on pharmacokinetics and lactone/carboxylate equilibrium of 9-Nitrocamptothecin in rats.

Journal: International journal of pharmaceutics 20070801

Title: Encapsulation of 9-nitrocamptothecin, a novel anticancer drug, in biodegradable nanoparticles: factorial design, characterization and release kinetics.

Journal: European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V 20070401

Title: Activity of 9-nitro-camptothecin, an oral topoisomerase I inhibitor, in myelodysplastic syndrome and chronic myelomonocytic leukemia.

Journal: Cancer 20061001

Title: Treatment of neoplastic meningitis with intrathecal 9-nitro-camptothecin.

Journal: Neurologia medico-chirurgica 20061001

Title: Disposition of 9-nitrocamptothecin and its 9-aminocamptothecin metabolite in relation to ABC transporter genotypes.

Journal: Investigational new drugs 20060901

Title: Sequential oral 9-nitrocamptothecin and etoposide: a pharmacodynamic- and pharmacokinetic-based phase I trial.

Journal: Molecular cancer therapeutics 20060801

Title: Phase II study of rubitecan, an oral camptothecin in patients with advanced colorectal cancer who have failed previous 5-fluorouracil based chemotherapy.

Journal: Investigational new drugs 20060701

Title: Effect of phospholipid composition on characterization of liposomes containing 9-nitrocamptothecin.

Journal: Drug development and industrial pharmacy 20060701

Title: Novel therapeutic approaches in pediatric and young adult sarcomas.

Journal: Current oncology reports 20060701

Title: 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.

Journal: Cancer chemotherapy and pharmacology 20060501

Title: Minimal clinical benefit of single agent Orathecin (Rubitecan) in heavily pretreated metastatic breast cancer.

Journal: Cancer chemotherapy and pharmacology 20060401

Title: Raltitrexed-eloxatin salvage chemotherapy in gemcitabine-resistant metastatic pancreatic cancer.

Journal: British journal of cancer 20060327

Title: Pharmacokinetics of lactone, carboxylate and total 9-nitrocamptothecin with different doses and administration routes in rats.

Journal: Biopharmaceutics & drug disposition 20060301

Title: Rubitecan.

Journal: Expert opinion on investigational drugs 20060101

Title: [9-nitrocamptothecin nanostructured lipid carrier system: in vitro releasing characteristics, uptake by cells, and tissue distribution in vivo].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20051101

Title: [In vitro and in vivo stability of 9-nitrocamptothecin lactone form in rats].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20051001

Title: A phase I study of concurrent 9-nitro-20(s)-camptothecin (9NC/Orathecin) and radiation therapy in the treatment of locally advanced adenocarcinoma of the pancreas.

Journal: Radiotherapy and oncology : journal of the European Society for Therapeutic Radiology and Oncology 20050701

Title: Relationship between plasma exposure of 9-nitrocamptothecin and its 9-aminocamptothecin metabolite and antitumor response in mice bearing human colon carcinoma xenografts.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20050701

Title: A phase II trial with RFS2000 (rubitecan) in patients with advanced non-small cell lung cancer.

Journal: European journal of cancer (Oxford, England : 1990) 20050701

Title: Phase II study of 9-nitro-camptothecin in patients with advanced chordoma or soft tissue sarcoma.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20050520

Title: Liquid chromatographic quantitation of the lactone and the total of lactone and carboxylate forms of 9-nitrocamptothecin in human plasma.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20050425

Title: Herceptin down-regulates HER-2/neu and vascular endothelial growth factor expression and enhances taxol-induced cytotoxicity of human Ewing's sarcoma cells in vitro and in vivo.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20050301

Title: Phase II trial of oral rubitecan in previously treated pancreatic cancer patients.

Journal: The oncologist 20050301

Title: Alternative administration of camptothecin analogues.

Journal: Expert opinion on drug delivery 20050301

Title: Synthesis and anti-tumor activity of alkenyl camptothecin esters.

Journal: Acta pharmacologica Sinica 20050201

Title: Control-relevant modeling of the antitumor effects of 9-nitrocamptothecin in SCID mice bearing HT29 human colon xenografts.

Journal: Journal of pharmacokinetics and pharmacodynamics 20050201

Title: Pharmacokinetic studies of 9-nitrocamptothecin on intermittent and continuous schedules of administration in patients with solid tumors.

Journal: Cancer chemotherapy and pharmacology 20041201

Title: Analysis of ATP-binding cassette transporter expression in drug-selected cell lines by a microarray dedicated to multidrug resistance.

Journal: Molecular pharmacology 20041201

Title: Novel vitamin E analogue and 9-nitro-camptothecin administered as liposome aerosols decrease syngeneic mouse mammary tumor burden and inhibit metastasis.

Journal: Cancer chemotherapy and pharmacology 20041101

Title: 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.

Journal: British journal of cancer 20041018

Title: [The in vitro kinetics of uptake, transport and efflux of 9-nitrocamptothecin in Caco-2 cell model].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20041001

Title: Phase II study on 9-nitrocamptothecin (RFS 2000) in patients with advanced or metastatic urothelial tract tumors.

Journal: Investigational new drugs 20040801

Title: Reduction of 9-nitrocamptothecin-triggered apoptosis in DU-145 human prostate cancer cells by ectopic expression of 14-3-3zeta.

Journal: International journal of oncology 20040801

Title: Phase I and pharmacologic study of intermittently administered 9-nitrocamptothecin in patients with advanced solid tumors.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20040801

Title: Current and future strategies for treating metastatic pancreatic cancer.

Journal: Clinical advances in hematology & oncology : H&O 20040801

Title: RFS2000 (9-nitrocamptothecin) in advanced small cell lung cancer, a phase II study of the EORTC New Drug Development Group.

Journal: European journal of cancer (Oxford, England : 1990) 20040601

Title: Clinical evaluation of the delivery and safety of aerosolized liposomal 9-nitro-20(s)-camptothecin in patients with advanced pulmonary malignancies.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20040401

Title: Transport characteristics of 9-nitrocamptothecin in the human intestinal cell line Caco-2 and everted gut sacs.

Journal: International journal of pharmaceutics 20040319

Title: Development of a bioanalytical liquid chromatography method for quantitation of 9-nitrocamptothecin in human plasma.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20040105

Title: A novel approach to develop anti-HIV drugs: adapting non-nucleoside anticancer chemotherapeutics.

Journal: Antiviral research 20040101

Title: A phase II study of 9-nitro-camptothecin in patients with previously treated metastatic breast cancer.

Journal: Investigational new drugs 20040101

Title: Membrane transport of camptothecin: facilitation by human P-glycoprotein (ABCB1) and multidrug resistance protein 2 (ABCC2).

Journal: BMC medicine 20040101

Title: Rubitecan: 9-NC, 9-Nitro-20(S)-camptothecin, 9-nitro-camptothecin, 9-nitrocamptothecin, RFS 2000, RFS2000.

Journal: Drugs in R&D 20040101

Title: 9-Nitrocamptothecin as second line chemotherapy for men with progressive, metastatic, hormone refractory prostate cancer: Results of the CALGB 99901.

Journal: Urologic oncology 20040101

Title: 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.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20031005

Title: Advanced pancreatic cancer: is there a role for combination therapy?

Journal: Expert review of anticancer therapy 20031001

Title: Are there any better camptothecins than the ones we have?

Journal: Clinical advances in hematology & oncology : H&O 20031001

Title: Differential susceptibility to 9-nitrocamptothecin (9-NC)-induced apoptosis in clones derived from a human ovarian cancer cell line: possible implications in the treatment of ovarian cancer patients with 9-NC.

Journal: Anti-cancer drugs 20030701

Title: Differential effects of the breast cancer resistance protein on the cellular accumulation and cytotoxicity of 9-aminocamptothecin and 9-nitrocamptothecin.

Journal: Cancer research 20030615

Title: Identification of the metabolites of 9-nitro-20(S)-camptothecin in rats.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20030601

Title: Results of a 2-arm Phase II study of 9-nitrocamptothecin in patients with advanced soft-tissue sarcomas.

Journal: Cancer 20030601

Title: Irinotecan plus raltitrexed vs raltitrexed alone in patients with gemcitabine-pretreated advanced pancreatic adenocarcinoma.

Journal: British journal of cancer 20030422

Title: Pharmacokinetics of 9-nitro-20(S)-camptothecin in rats.

Journal: Acta pharmacologica Sinica 20030301

Title: [A symphony for the camptothecins].

Journal: Bulletin du cancer 20030301

Title: Structure-activity relationship of alkyl 9-nitrocamptothecin esters.

Journal: Acta pharmacologica Sinica 20030201

Title: [Determination of 9-nitrocamptothecin in rat plasma and tissues by high performance liquid chromatography].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20030201

Title: A Phase I study of 9-nitrocamptothecin given concurrently with capecitabine in patients with refractory, metastatic solid tumors.

Journal: Cancer 20030101

Title: GoMiner: a resource for biological interpretation of genomic and proteomic data.

Journal: Genome biology 20030101

Title: Camptothecin and 9-nitrocamptothecin (9NC) as anti-cancer, anti-HIV and cell-differentiation agents. Development of resistance, enhancement of 9NC-induced activities and combination treatments in cell and animal models.

Journal: Anticancer research 20030101

Title: Development of an optimal pharmacokinetic sampling schedule for rubitecan administered orally in a daily times five schedule.

Journal: Cancer chemotherapy and pharmacology 20021201

Title: New drugs for patients with pancreatic cancer.

Journal: Current opinion in oncology 20021101

Title: Phase I study of rubitecan and gemcitabine in patients with advanced malignancies.

Journal: Annals of oncology : official journal of the European Society for Medical Oncology 20021101

Title: Preclinical activity of an i.v. formulation of rubitecan in IDD-P against human solid tumor xenografts.

Journal: Anti-cancer drugs 20021001

Title: Determination of 9-nitrocamptothecin and its metabolite 9-aminocamptothecin in human plasma using high-performance liquid chromatography with ultraviolet and fluorescence detection.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20020805

Title: Adaptive dose finding for phase I clinical trials of drugs used for chemotherapy of cancer.

Journal: Statistics in medicine 20020715

Title: Multicentre phase II and pharmacokinetic study of RFS2000 (9-nitro-camptothecin) administered orally 5 days a week in patients with glioblastoma multiforme.

Journal: European journal of cancer (Oxford, England : 1990) 20020701

Title: Clinical phase II study and pharmacological evaluation of rubitecan in non-pretreated patients with metastatic colorectal cancer-significant effect of food intake on the bioavailability of the oral camptothecin analogue.

Journal: European journal of cancer (Oxford, England : 1990) 20020401

Title: Current perspectives on the clinical experience, pharmacology, and continued development of the camptothecins.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20020301

Title: Growth inhibition of established B16-F10 lung metastases by sequential aerosol delivery of p53 gene and 9-nitrocamptothecin.

Journal: Gene therapy 20020301

Title: Phase II trial of 9-nitrocamptothecin (RFS 2000) for patients with metastatic cutaneous or uveal melanoma.

Journal: Anti-cancer drugs 20020201

Title: 9-nitrocamptothecin liposome aerosol: lack of subacute toxicity in dogs.

Journal: Inhalation toxicology 20020201

Title: Preclinical evaluation of the anticancer activity and toxicity of 9-nitro-20(S)-camptothecin (Rubitecan).

Journal: International journal of oncology 20020101

Title: Radiation enhancement by the combined use of topoisomerase I inhibitors, RFS-2000 or CPT-11, and topoisomerase II inhibitor etoposide in human lung cancer cells.

Journal: Radiotherapy and oncology : journal of the European Society for Therapeutic Radiology and Oncology 20020101

Title: A phase II study of 9-nitrocamptothecin in patients with advanced pancreatic adenocarcinoma.

Journal: Cancer chemotherapy and pharmacology 20011101

Title: Induction of apoptosis in 9-nitrocamptothecin-treated DU145 human prostate carcinoma cells correlates with de novo synthesis of CD95 and CD95 ligand and down-regulation of c-FLIP(short).

Journal: Cancer research 20011001

Title: Cellular, pharmacokinetic, and pharmacodynamic aspects of response to camptothecins: can we improve it?

Journal: Drug resistance updates : reviews and commentaries in antimicrobial and anticancer chemotherapy 20010801

Title: 9-Nitrocamptothecin inhibits HIV-1 replication in human peripheral blood lymphocytes: a potential alternative for HIV-infection/AIDS therapy.

Journal: Journal of medical virology 20010701

Title: Cellular, pharmacokinetic, and pharmacodynamic aspects of response to camptothecins: can we improve it?

Journal: Drug resistance updates : reviews and commentaries in antimicrobial and anticancer chemotherapy 20010601

Title: 9-Nitrocamptothecin is an effective drug for the treatment of human lung tumors: comparison of in vitro and in vivo studies.

Journal: Anticancer research 20010101

Title: 9-nitrocamptothecin selectively inhibits human immunodeficiency virus type 1 replication in freshly infected parental but not 9-nitrocamptothecin-resistant U937 monocytoid cells.

Journal: AIDS research and human retroviruses 19990210

Title: Burris HA 3rd, et al. Phase II trial of oral rubitecan in previously treated pancreatic cancer patients. Oncologist. 2005 Mar;10(3):183-90.

Title: Rubitecan: 9-NC, 9-Nitro-20(S)-camptothecin, 9-nitro-camptothecin, 9-nitrocamptothecin, RFS 2000, RFS2000. Drugs R D. 2004;5(5):305-11.

Title: Rubitecan

Title: Xia M, et al. Identification of repurposed small molecule drugs for chordoma therapy. Cancer Biol Ther. 2013 Jul;14(7):638-47.

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