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
  • 9-NC
  • 9-nitro-(20S)-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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Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
UDNA topoisomerase 1Not AvailableHumans
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
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
Darbepoetin alfaThe risk or severity of Thrombosis can be increased when Darbepoetin alfa is combined with Rubitecan.
ErythropoietinThe risk or severity of Thrombosis can be increased when Erythropoietin is combined with Rubitecan.
Methoxy polyethylene glycol-epoetin betaThe risk or severity of Thrombosis can be increased when Methoxy polyethylene glycol-epoetin beta is combined with Rubitecan.
PeginesatideThe risk or severity of Thrombosis can be increased when Peginesatide is combined with Rubitecan.
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Food Interactions
Not Available

Products

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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
KEGG Drug
D04031
PubChem Compound
11954380
ChemSpider
414807
ChEBI
90225
ChEMBL
CHEMBL77305
ZINC
ZINC000003827362
Wikipedia
Rubitecan

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3Unknown StatusTreatmentMalignant Neoplasm of Pancreas3
2CompletedTreatmentBladder Cancer, Cancer / Transitional Cell Cancer of the Renal Pelvis and Ureter / Urethral Cancer1
2CompletedTreatmentBrain and Central Nervous System Tumors1
2CompletedTreatmentBreast Cancer1
2CompletedTreatmentCorpus Uteri / Endometrial Cancer1
2CompletedTreatmentGastrointestinal Stromal Tumor (GIST) / Sarcomas / Small Intestine Cancer1
2CompletedTreatmentLung Cancers2
2CompletedTreatmentLung Disorder / Malignancies1
2CompletedTreatmentMelanoma1
2CompletedTreatmentOvarian Cancer1

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
PropertyValueSource
Water Solubility0.239 mg/mLALOGPS
logP1.88ALOGPS
logP1.16ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)11.71ChemAxon
pKa (Strongest Basic)0.29ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area122.87 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity100.81 m3·mol-1ChemAxon
Polarizability38.87 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7977
Blood Brain Barrier-0.6125
Caco-2 permeable-0.8307
P-glycoprotein substrateSubstrate0.5853
P-glycoprotein inhibitor INon-inhibitor0.7775
P-glycoprotein inhibitor IINon-inhibitor0.9611
Renal organic cation transporterNon-inhibitor0.8838
CYP450 2C9 substrateNon-substrate0.8475
CYP450 2D6 substrateNon-substrate0.8388
CYP450 3A4 substrateSubstrate0.6054
CYP450 1A2 substrateInhibitor0.6135
CYP450 2C9 inhibitorNon-inhibitor0.647
CYP450 2D6 inhibitorNon-inhibitor0.8503
CYP450 2C19 inhibitorNon-inhibitor0.6043
CYP450 3A4 inhibitorInhibitor0.6262
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6372
Ames testAMES toxic0.7389
CarcinogenicityNon-carcinogens0.6422
BiodegradationNot ready biodegradable0.9971
Rat acute toxicity2.7520 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9616
hERG inhibition (predictor II)Non-inhibitor0.862
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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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
  1. 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 February 21, 2021 18:52