Rubitecan
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This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Generic Name
- Rubitecan
- DrugBank Accession Number
- DB06159
- Background
Not Available
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 393.355
Monoisotopic: 393.096085215 - Chemical Formula
- C20H15N3O6
- Synonyms
- 1H-PYRANO(3',4':6,7)INDOLIZINO(1,2-B)QUINOLINE-3,14(4H,12H)-DIONE, 4-ETHYL-4-HYDROXY-10-NITRO-, (4S)-
- 9-NC
- 9-nitro-(20S)-camptothecin
- 9-nitro-20-(S)-camptothecin
- 9-nitro-20(S)-camptothecin
- 9-nitrocamptothecin
- 9NC
- Rubitecan
- Rubitecán
- Rubitécan
- Rubitecanum
- External IDs
- RF-2000
- RFS 2000
- RFS-2000
- RFS2000
Pharmacology
- Indication
Investigated for use/treatment in pancreatic cancer, leukemia (unspecified), melanoma, ovarian cancer, and cancer/tumors (unspecified).
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- Pharmacodynamics
Not Available
- Mechanism of action
Rubitecan prevents DNA from unwinding during replication via DNA topoisomerase 1, therefore interfering with tumor growth.
Target Actions Organism UDNA topoisomerase 1 Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAmbroxol The risk or severity of methemoglobinemia can be increased when Rubitecan is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Rubitecan is combined with Articaine. Benzocaine The risk or severity of methemoglobinemia can be increased when Rubitecan is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Rubitecan is combined with Benzyl alcohol. Bupivacaine The risk or severity of methemoglobinemia can be increased when Rubitecan is combined with Bupivacaine. - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- International/Other Brands
- Camptogen / Orathecin (Supergen)
Categories
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- H19C446XXB
- CAS number
- 91421-42-0
- InChI Key
- VHXNKPBCCMUMSW-FQEVSTJZSA-N
- InChI
- 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
- IUPAC Name
- (19S)-19-ethyl-19-hydroxy-8-nitro-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
- SMILES
- CC[C@@]1(O)C(=O)OCC2=C1C=C1N(CC3=C1N=C1C=CC=C(C1=C3)[N+]([O-])=O)C2=O
References
- General References
- Not Available
- External Links
- KEGG Drug
- D04031
- PubChem Compound
- 11954380
- ChemSpider
- 414807
- BindingDB
- 50248354
- ChEBI
- 90225
- ChEMBL
- CHEMBL77305
- ZINC
- ZINC000003827362
- Wikipedia
- Rubitecan
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 3 Unknown Status Treatment Pancreatic Cancer 3 2 Completed Treatment Bladder Cancer / Cancer of the Urethra / Transitional Cell Cancer of the Renal Pelvis and Ureter 1 2 Completed Treatment Brain and Central Nervous System Tumors 1 2 Completed Treatment Breast Cancer 1 2 Completed Treatment Cancer / Lung Disorder 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.239 mg/mL ALOGPS logP 1.88 ALOGPS logP 1.16 Chemaxon logS -3.2 ALOGPS pKa (Strongest Acidic) 11.71 Chemaxon pKa (Strongest Basic) 0.29 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 122.87 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 100.81 m3·mol-1 Chemaxon Polarizability 38.87 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.7977 Blood Brain Barrier - 0.6125 Caco-2 permeable - 0.8307 P-glycoprotein substrate Substrate 0.5853 P-glycoprotein inhibitor I Non-inhibitor 0.7775 P-glycoprotein inhibitor II Non-inhibitor 0.9611 Renal organic cation transporter Non-inhibitor 0.8838 CYP450 2C9 substrate Non-substrate 0.8475 CYP450 2D6 substrate Non-substrate 0.8388 CYP450 3A4 substrate Substrate 0.6054 CYP450 1A2 substrate Inhibitor 0.6135 CYP450 2C9 inhibitor Non-inhibitor 0.647 CYP450 2D6 inhibitor Non-inhibitor 0.8503 CYP450 2C19 inhibitor Non-inhibitor 0.6043 CYP450 3A4 inhibitor Inhibitor 0.6262 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6372 Ames test AMES toxic 0.7389 Carcinogenicity Non-carcinogens 0.6422 Biodegradation Not ready biodegradable 0.9971 Rat acute toxicity 2.7520 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9616 hERG inhibition (predictor II) Non-inhibitor 0.862
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 209.2462128 predictedDarkChem Lite v0.1.0 [M-H]- 186.86237 predictedDeepCCS 1.0 (2019) [M+H]+ 209.4304128 predictedDarkChem Lite v0.1.0 [M+H]+ 189.25793 predictedDeepCCS 1.0 (2019) [M+Na]+ 195.20232 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
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1. DetailsDNA topoisomerase 1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Poly(a) rna binding
- Specific Function
- Releases the supercoiling and torsional tension of DNA introduced during the DNA replication and transcription by transiently cleaving and rejoining one strand of the DNA duplex. Introduces a singl...
- Gene Name
- TOP1
- Uniprot ID
- P11387
- Uniprot Name
- DNA topoisomerase 1
- Molecular Weight
- 90725.19 Da
References
- Chedid S, Rivera E, Frye DK, Ibrahim N, Esteva F, Valero V, Hortobagyi G, Mettinger KL, Cristofanilli M: Minimal clinical benefit of single agent Orathecin (Rubitecan) in heavily pretreated metastatic breast cancer. Cancer Chemother Pharmacol. 2006 Apr;57(4):540-4. Epub 2005 Sep 29. [Article]
Drug created at March 19, 2008 16:14 / Updated at July 18, 2023 22:56