Gimatecan

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

Identification

Generic Name
Gimatecan
DrugBank Accession Number
DB06721
Background

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

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 447.491
Monoisotopic: 447.179420917
Chemical Formula
C25H25N3O5
Synonyms
  • Gimatecan

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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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

Adverse Effects
Adverseeffects
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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
AcetylcysteineThe excretion of Gimatecan can be decreased when combined with Acetylcysteine.
Aminohippuric acidThe excretion of Gimatecan can be decreased when combined with Aminohippuric acid.
AmprenavirThe excretion of Gimatecan can be decreased when combined with Amprenavir.
ApalutamideThe excretion of Gimatecan can be increased when combined with Apalutamide.
AsunaprevirThe excretion of Gimatecan can be decreased when combined with Asunaprevir.
AtazanavirThe excretion of Gimatecan can be decreased when combined with Atazanavir.
AtorvastatinThe excretion of Gimatecan can be decreased when combined with Atorvastatin.
AxitinibThe excretion of Gimatecan can be decreased when combined with Axitinib.
Beclomethasone dipropionateThe excretion of Gimatecan can be decreased when combined with Beclomethasone dipropionate.
BelumosudilThe excretion of Gimatecan can be decreased when combined with Belumosudil.
Interactions
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Alcohol / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Camptothecin / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Heteroaromatic compound / Hydrocarbon derivative
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
7KKS9R192F
CAS number
292618-32-7
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

References

General References
Not Available
ChemSpider
7851565
ChEMBL
CHEMBL113051
ZINC
ZINC000003993519

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2Not Yet RecruitingTreatmentFallopian Tubes Cancer / Malignant Peritoneal Neoplasm / Ovarian Cancer (Epithelial)1
2Not Yet RecruitingTreatmentMalignant Neoplasm of Pancreas1
2Not Yet RecruitingTreatmentSmall Cell Lung Cancer (SCLC)1
1CompletedTreatmentMDS / Myelodysplastic Syndromes (MDS)1
1CompletedTreatmentSolid Malignancies1
1CompletedTreatmentSolid Tumors, Advanced Solid Tumors3
1CompletedTreatmentTumors, Solid1
1RecruitingTreatmentFallopian Tubes Cancer / Ovarian Cancer (Epithelial) / Primary Peritoneal Cancer1
1, 2CompletedTreatmentBrain and Central Nervous System Tumors1
1, 2CompletedTreatmentGliomas, Malignant1

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

Transporters

Kind
Protein
Organism
Humans
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. [Article]

Drug created on June 25, 2010 22:01 / Updated on February 21, 2021 18:52