Gimatecan
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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
- Gimatecan
- DrugBank Accession Number
- DB06721
- Background
Gimatecan is an orally available 7-t-butoxyiminomethyl-substituted lipophilic camptothecin derivative.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 447.491
Monoisotopic: 447.179420917 - Chemical Formula
- C25H25N3O5
- Synonyms
- (4S)-11-[(E)-(tert-butoxyimino)methyl]-4-ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
- (4S)-4-ethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1-H-pyrano[3',4':6,7]-indolizino-[1,2-b]-quinoline-11-carbaldehyde O-(tert-butyl)-(E)-oxime
- 1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-11-carboxaldehyde, 4-ethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-, 11-[O-(1,1-dimethylethyl)oxime], (4S)-
- Gimatecan
- External IDs
- CPT 184
- LBQ 707
- LBQ707
- ST 1481
- ST1481
Pharmacology
- Indication
Not Available
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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
- 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
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcetylcysteine The excretion of Gimatecan can be decreased when combined with Acetylcysteine. Aminohippuric acid The excretion of Gimatecan can be decreased when combined with Aminohippuric acid. Amprenavir The excretion of Gimatecan can be decreased when combined with Amprenavir. Apalutamide The serum concentration of Gimatecan can be decreased when it is combined with Apalutamide. Asunaprevir The excretion of Gimatecan can be decreased when combined with Asunaprevir. - 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
- External Links
- ChemSpider
- 7851565
- ChEMBL
- CHEMBL113051
- ZINC
- ZINC000003993519
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Not Yet Recruiting Treatment Epithelial Ovarian Cancer / Fallopian Tube Cancer / Peritoneal Cancer 1 2 Not Yet Recruiting Treatment Pancreatic Cancer 1 2 Not Yet Recruiting Treatment Small Cell Lung Cancer (SCLC) 1 1 Completed Treatment Advanced Solid Tumors 3 1 Completed Treatment Myelodysplastic Syndrome 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 0.0427 mg/mL ALOGPS logP 2.91 ALOGPS logP 2.37 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 11.71 Chemaxon pKa (Strongest Basic) 3.06 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 101.32 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 123.19 m3·mol-1 Chemaxon Polarizability 48.57 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
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0005900000-c9966e7cc9c56902fc46 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0f6t-0009600000-06884fc5b3b2ae512605 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-1009000000-fd60b9bfcd9650a5aebd Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0019300000-c6826c47725b88c454de Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0007-2039100000-61324354339f8a154e4d Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-014j-0339600000-bebaacada6378c9b8929 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]- 235.1712383 predictedDarkChem Lite v0.1.0 [M-H]- 207.43575 predictedDeepCCS 1.0 (2019) [M+H]+ 234.0965383 predictedDarkChem Lite v0.1.0 [M+H]+ 209.83131 predictedDeepCCS 1.0 (2019) [M+Na]+ 235.4991383 predictedDarkChem Lite v0.1.0 [M+Na]+ 215.74649 predictedDeepCCS 1.0 (2019)
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
- 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 at June 25, 2010 22:01 / Updated at December 23, 2022 00:49