This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Gimatecan
Accession Number
DB06721
Type
Small Molecule
Groups
Investigational
Description

Gimatecan is an orally available 7-t-butoxyiminomethyl-substituted lipophilic camptothecin derivative.

Structure
Thumb
Synonyms
Not Available
Categories
UNII
7KKS9R192F
CAS number
292618-32-7
Weight
Average: 447.491
Monoisotopic: 447.179420917
Chemical Formula
C25H25N3O5
InChI Key
UIVFUQKYVFCEKJ-OPTOVBNMSA-N
InChI
InChI=1S/C25H25N3O5/c1-5-25(31)18-10-20-21-16(12-28(20)22(29)17(18)13-32-23(25)30)15(11-26-33-24(2,3)4)14-8-6-7-9-19(14)27-21/h6-11,31H,5,12-13H2,1-4H3/b26-11+/t25-/m0/s1
IUPAC Name
(19S)-10-[(1E)-[(tert-butoxy)imino]methyl]-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione
SMILES
[H]\C(=N/OC(C)(C)C)C1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=CC=C12

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
ApalutamideThe serum concentration of Gimatecan can be decreased when it is combined with Apalutamide.
Conjugated estrogensThe excretion of Gimatecan can be decreased when combined with Conjugated estrogens.
DiclofenacThe excretion of Gimatecan can be decreased when combined with Diclofenac.
DipyridamoleThe excretion of Gimatecan can be decreased when combined with Dipyridamole.
EltrombopagThe serum concentration of Gimatecan can be increased when it is combined with Eltrombopag.
ErythromycinThe excretion of Gimatecan can be decreased when combined with Erythromycin.
EstradiolThe excretion of Gimatecan can be decreased when combined with Estradiol.
FluvastatinThe excretion of Gimatecan can be decreased when combined with Fluvastatin.
IndinavirThe excretion of Gimatecan can be decreased when combined with Indinavir.
IndomethacinThe excretion of Gimatecan can be decreased when combined with Indomethacin.
Food Interactions
Not Available

References

General References
Not Available
External Links
ChemSpider
7851565
ChEMBL
CHEMBL113051

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentAdvanced Solid Tumors3
1CompletedTreatmentMyelodysplastic Syndromes / Smith-Magenis Syndrome1
1CompletedTreatmentSolid Malignancies1
1CompletedTreatmentTumors, Solid1
1, 2CompletedTreatmentBrain and Central Nervous System Tumors1
1, 2CompletedTreatmentMalignant Gliomas1

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 Solubility0.0427 mg/mLALOGPS
logP2.91ALOGPS
logP2.37ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)11.71ChemAxon
pKa (Strongest Basic)3.06ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area101.32 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity123.19 m3·mol-1ChemAxon
Polarizability48.57 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

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

Taxonomy

Description
This compound belongs to the class of organic compounds known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring).
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Camptothecins
Sub Class
Not Available
Direct Parent
Camptothecins
Alternative Parents
Quinolines and derivatives / Pyranopyridines / Pyridinones / Benzenoids / Tertiary alcohols / Heteroaromatic compounds / Carboxylic acid esters / Lactams / Lactones / Azacyclic compounds
show 7 more
Substituents
Camptothecin / Pyranopyridine / Quinoline / Pyridinone / Pyridine / Benzenoid / Heteroaromatic compound / Tertiary alcohol / Carboxylic acid ester / Lactam
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. Oostendorp RL, van de Steeg E, van der Kruijssen CM, Beijnen JH, Kenworthy KE, Schinkel AH, Schellens JH: Organic anion-transporting polypeptide 1B1 mediates transport of Gimatecan and BNP1350 and can be inhibited by several classic ATP-binding cassette (ABC) B1 and/or ABCG2 inhibitors. Drug Metab Dispos. 2009 Apr;37(4):917-23. doi: 10.1124/dmd.108.024901. Epub 2009 Jan 12. [PubMed:19139163]

Drug created on June 25, 2010 16:01 / Updated on August 02, 2018 05:38