Identification
- Generic Name
- Elacytarabine
- DrugBank Accession Number
- DB05494
- Background
Elacytarabine is a fatty acid derivative of cytarabine, an approved cytotoxic cancer drug. Cytarabine has limitations such as minimal uptake in solid tumours and is only used to treat leukaemia. Elacytarabine is designed to overcome this limitation and has shown considerable uptake in solid tumour cells. Elacytarabine is a patented new chemical entity of the nucleoside analog class, with improved biological properties and the potential to treat solid tumours such as non-small cell lung cancer, malignant melanoma and ovarian cancer.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Elacytarabine (DB05494)
- Weight
- Average: 507.672
Monoisotopic: 507.330836181 - Chemical Formula
- C27H45N3O6
- Synonyms
- Elacytarabine
- External IDs
- CP 4055
- CP-4055
- P-4055
Pharmacology
- Indication
Investigated for use/treatment in leukemia (unspecified) and melanoma.
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CP-4055 is a fatty acid derivative of cytarabine, an approved cytotoxic cancer drug. Cytarabine has limitations such as minimal uptake in solid tumours and is only used to treat leukaemia. CP-4055 is designed to overcome this limitation and has shown considerable uptake in solid tumour cells. CP-4055 is a patented new chemical entity of the nucleoside analog class, with improved biological properties and the potential to treat solid tumours such as non-small cell lung cancer, malignant melanoma and ovarian cancer.
- Mechanism of action
CP-4055 is the lipophilic 5'-elaidic acid ester of the deoxycytidine analog cytosine arabinoside (cytarabine; Ara-C) with potential antineoplastic activity. As a prodrug, CP-4055 is converted intracellularly into cytarabine triphosphate by deoxycytidine kinase and subsequently competes with cytidine for incorporation into DNA, thereby inhibiting DNA synthesis. Compared to cytarabine, CP-4055 shows increased cellular uptake and retention, resulting in increased activation by deoxycytidine kinase to cytarabine triphosphate, decreased deamination and deactivation by deoxycytidine deaminase, and increased inhibition of DNA synthesis. This agent also inhibits RNA synthesis, an effect not seen with cytarabine.
Target Actions Organism UDeoxycytidine kinase 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
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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.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as pyrimidine nucleosides. These are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety.
- Kingdom
- Organic compounds
- Super Class
- Nucleosides, nucleotides, and analogues
- Class
- Pyrimidine nucleosides
- Sub Class
- Not Available
- Direct Parent
- Pyrimidine nucleosides
- Alternative Parents
- Glycosylamines / Pentoses / Aminopyrimidines and derivatives / Pyrimidones / Fatty acid esters / Hydropyrimidines / Imidolactams / Tetrahydrofurans / Heteroaromatic compounds / 1,2-diols show 11 more
- Substituents
- 1,2-diol / Alcohol / Amine / Amino acid or derivatives / Aminopyrimidine / Aromatic heteromonocyclic compound / Azacycle / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester show 25 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- TA7WJG93AR
- CAS number
- 188181-42-2
- InChI Key
- FLFGNMFWNBOBGE-FNNZEKJRSA-N
- InChI
- InChI=1S/C27H45N3O6/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23(31)35-20-21-24(32)25(33)26(36-21)30-19-18-22(28)29-27(30)34/h9-10,18-19,21,24-26,32-33H,2-8,11-17,20H2,1H3,(H2,28,29,34)/b10-9+/t21-,24-,25+,26-/m1/s1
- IUPAC Name
- [(2R,3S,4S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl (9E)-octadec-9-enoate
- SMILES
- CCCCCCCC\C=C\CCCCCCCC(=O)OC[C@H]1O[C@H]([C@@H](O)[C@@H]1O)N1C=CC(N)=NC1=O
References
- General References
- Bergman AM, Kuiper CM, Voorn DA, Comijn EM, Myhren F, Sandvold ML, Hendriks HR, Peters GJ: Antiproliferative activity and mechanism of action of fatty acid derivatives of arabinofuranosylcytosine in leukemia and solid tumor cell lines. Biochem Pharmacol. 2004 Feb 1;67(3):503-11. [Article]
- External Links
- PubChem Compound
- 6438895
- PubChem Substance
- 175427021
- ChemSpider
- 4943338
- BindingDB
- 50004746
- ChEMBL
- CHEMBL2105665
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 Completed Treatment Acute Myeloid Leukemia 1 2 Completed Treatment Acute Myeloid Leukemia 1 2 Completed Treatment Advanced Colorectal Cancer / Colorectal Cancer 1 2 Completed Treatment Malignant Melanoma 1 2 Completed Treatment Malignant Melanoma / Metastatic Cancer 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 0.00419 mg/mL ALOGPS logP 5.52 ALOGPS logP 4.65 Chemaxon logS -5.1 ALOGPS pKa (Strongest Acidic) 12.56 Chemaxon pKa (Strongest Basic) 4.07 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 134.68 Å2 Chemaxon Rotatable Bond Count 19 Chemaxon Refractivity 138.45 m3·mol-1 Chemaxon Polarizability 59.02 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9623 Blood Brain Barrier + 0.9465 Caco-2 permeable - 0.8887 P-glycoprotein substrate Non-substrate 0.798 P-glycoprotein inhibitor I Non-inhibitor 0.9686 P-glycoprotein inhibitor II Non-inhibitor 0.9532 Renal organic cation transporter Non-inhibitor 0.9519 CYP450 2C9 substrate Non-substrate 0.793 CYP450 2D6 substrate Non-substrate 0.8613 CYP450 3A4 substrate Non-substrate 0.6203 CYP450 1A2 substrate Non-inhibitor 0.9543 CYP450 2C9 inhibitor Non-inhibitor 0.9638 CYP450 2D6 inhibitor Non-inhibitor 0.9497 CYP450 2C19 inhibitor Non-inhibitor 0.9489 CYP450 3A4 inhibitor Non-inhibitor 0.9609 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.981 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.9158 Biodegradation Not ready biodegradable 0.7807 Rat acute toxicity 1.7184 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.983 hERG inhibition (predictor II) Non-inhibitor 0.911
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 218.805 predictedDeepCCS 1.0 (2019) [M+H]+ 220.62997 predictedDeepCCS 1.0 (2019) [M+Na]+ 226.2358 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Protein homodimerization activity
- Specific Function
- Required for the phosphorylation of the deoxyribonucleosides deoxycytidine (dC), deoxyguanosine (dG) and deoxyadenosine (dA). Has broad substrate specificity, and does not display selectivity based...
- Gene Name
- DCK
- Uniprot ID
- P27707
- Uniprot Name
- Deoxycytidine kinase
- Molecular Weight
- 30518.315 Da
Drug created at November 18, 2007 18:25 / Updated at January 14, 2023 19:03