NAV

Sapacitabine

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

Identification

Generic Name
Sapacitabine
DrugBank Accession Number
DB06365
Background

Not Available

Type
Small Molecule
Groups
Investigational
Structure
Similar Structures
Weight
Average: 490.645
Monoisotopic: 490.315520468
Chemical Formula
C26H42N4O5
Synonyms
  • 1-(2-C-cyano-2-deoxy- ß-D-arabino-pentafuranosyl)-N4-palmitoylcytosine
  • Sapacitabine
External IDs
  • CS-682
  • CYC-682
  • CYC682
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Pharmacology

Indication

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

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Contraindications & Blackbox Warnings
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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

Adverse Effects
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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
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interactions in your software
AmbroxolThe risk or severity of methemoglobinemia can be increased when Sapacitabine is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Sapacitabine is combined with Articaine.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Sapacitabine is combined with Benzocaine.
Benzyl alcoholThe risk or severity of methemoglobinemia can be increased when Sapacitabine is combined with Benzyl alcohol.
BupivacaineThe risk or severity of methemoglobinemia can be increased when Sapacitabine is combined with Bupivacaine.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Alcohol / Aromatic heteromonocyclic compound / Azacycle / Carbonitrile / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Fatty acyl / Fatty amide / Heteroaromatic compound
show 20 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
W335P73C3L
CAS number
151823-14-2
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

References

General References
Not Available
ChemSpider
135703
ChEBI
145429
ChEMBL
CHEMBL2105681
ZINC
ZINC000014263648
Wikipedia
Sapacitabine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentAcute Myeloid Leukemia1
2CompletedTreatmentAcute Myeloid Leukemia1
2TerminatedTreatmentCutaneous T-Cell Lymphoma (CTCL)1
2TerminatedTreatmentLeukemias1
2TerminatedTreatmentNon-Small Cell Lung Cancer (NSCLC)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/MSsplash10-0006-3014900000-f8a64728377a9a9e8e31
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0041-1003900000-16ae5b599adad02eab86
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-6628900000-1d4065541e6abb9284f7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-06r2-2019700000-2f4feb872b1b8609b49b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dr-1934100000-bb6438052a206be680a0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9413300000-f7a81dd1ab5425d4e3bc
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-272.8654059
predicted
DarkChem Lite v0.1.0
[M-H]-212.29256
predicted
DeepCCS 1.0 (2019)
[M+H]+273.8417059
predicted
DarkChem Lite v0.1.0
[M+H]+214.68813
predicted
DeepCCS 1.0 (2019)
[M+Na]+273.9702059
predicted
DarkChem Lite v0.1.0
[M+Na]+221.68819
predicted
DeepCCS 1.0 (2019)

Drug created at March 19, 2008 16:27 / Updated at November 16, 2022 21:59