Sapacitabine

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

Identification

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Name
Sapacitabine
Accession Number
DB06365
Type
Small Molecule
Groups
Investigational
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
CS-682 / CYC-682 / CYC682
Categories
UNII
W335P73C3L
CAS number
151823-14-2
Weight
Average: 490.645
Monoisotopic: 490.315520468
Chemical Formula
C26H42N4O5
InChI Key
LBGFKUUHOPIEMA-PEARBKPGSA-N
InChI
InChI=1S/C26H42N4O5/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-23(32)28-22-16-17-30(26(34)29-22)25-20(18-27)24(33)21(19-31)35-25/h16-17,20-21,24-25,31,33H,2-15,19H2,1H3,(H,28,29,32,34)/t20-,21+,24-,25+/m0/s1
IUPAC Name
N-{1-[(2R,3S,4S,5R)-3-cyano-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl}hexadecanamide
SMILES
CCCCCCCCCCCCCCCC(=O)NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1C#N

Pharmacology

Indication

Investigated for use/treatment in solid tumors, cutaneous t-cell lymphoma, myelodysplastic syndrome, and leukemia (lymphoid).

Pharmacodynamics
Not Available
Mechanism of action

Sapacitabine appears to act through a dual mechanism. It interferes with DNA synthesis by causing single-strand DNA breaks and also induces arrest of cell cycle progression mainly at G2/M-Phase. Both sapacitabine and CNDAC, its major metabolite or a substance into which the drugs converts after ingestion by patients, have demonstrated potent anti-tumor activity in preclinical studies.

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
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

References

General References
Not Available
External Links
ChemSpider
135703
ChEMBL
CHEMBL2105681
Wikipedia
Sapacitabine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentLeukemias / Myelodysplastic Syndromes1
1RecruitingTreatmentAdvanced Solid Tumors1
1, 2RecruitingTreatmentCancer, Breast1
1, 2RecruitingTreatmentLeukemia Acute Myeloid Leukemia (AML) / Myelodysplastic Syndromes1
2CompletedTreatmentLeukemia Acute Myeloid Leukemia (AML)1
2TerminatedTreatmentCutaneous T-Cell Lymphoma (CTCL)1
2TerminatedTreatmentLeukemias1
2TerminatedTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
3CompletedTreatmentLeukemia Acute Myeloid Leukemia (AML)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
PropertyValueSource
Water Solubility0.00915 mg/mLALOGPS
logP4.83ALOGPS
logP3.97ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)11.14ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area135.25 Å2ChemAxon
Rotatable Bond Count17ChemAxon
Refractivity132.29 m3·mol-1ChemAxon
Polarizability56.94 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
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 pyrimidine 2'-deoxyribonucleosides. These are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Pyrimidine nucleosides
Sub Class
Pyrimidine 2'-deoxyribonucleosides
Direct Parent
Pyrimidine 2'-deoxyribonucleosides
Alternative Parents
N-arylamides / Pyrimidones / Fatty amides / Imidolactams / Hydropyrimidines / Tetrahydrofurans / Heteroaromatic compounds / Secondary carboxylic acid amides / Secondary alcohols / Azacyclic compounds
show 7 more
Substituents
Pyrimidine 2'-deoxyribonucleoside / N-arylamide / Pyrimidone / Fatty amide / Hydropyrimidine / Pyrimidine / Fatty acyl / Imidolactam / Heteroaromatic compound / Tetrahydrofuran
show 20 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Drug created on March 19, 2008 10:27 / Updated on September 02, 2019 18:19