NAV

Guadecitabine

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

Identification

Generic Name
Guadecitabine
DrugBank Accession Number
DB11918
Background

Guadecitabine is under investigation for the treatment of Previously Treated Metastatic Colorectal Cancer.

Type
Small Molecule
Groups
Investigational
Structure
Similar Structures
Weight
Average: 557.417
Monoisotopic: 557.138375007
Chemical Formula
C18H24N9O10P
Synonyms
  • Guadecitabine
External IDs
  • SGI-110
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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
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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 Guadecitabine is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Guadecitabine is combined with Articaine.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Guadecitabine is combined with Benzocaine.
Benzyl alcoholThe risk or severity of methemoglobinemia can be increased when Guadecitabine is combined with Benzyl alcohol.
BupivacaineThe risk or severity of methemoglobinemia can be increased when Guadecitabine is combined with Bupivacaine.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Guadecitabine Sodium0RB89YH367929904-85-8XLHBNJPXFOZFNJ-BYKQGDNKSA-M

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside monophosphates. These are purine nucleotides with monophosphate group linked to the ribose moiety lacking a hydroxyl group at position 2.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleotides
Sub Class
Purine deoxyribonucleotides
Direct Parent
Purine 2'-deoxyribonucleoside monophosphates
Alternative Parents
6-oxopurines / Hypoxanthines / Triazinones / Pyrimidones / Aminopyrimidines and derivatives / Aminotriazines / Dialkyl phosphates / 1,3,5-triazines / N-substituted imidazoles / Vinylogous amides
show 9 more
Substituents
1,3,5-triazine / 6-oxopurine / Alcohol / Alkyl phosphate / Amine / Amino-1,3,5-triazine / Aminopyrimidine / Aminotriazine / Aromatic heteropolycyclic compound / Azacycle
show 28 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
2KT4YN1DP7
CAS number
929901-49-5
InChI Key
GUWXKKAWLCENJA-WGWHJZDNSA-N
InChI
InChI=1S/C18H24N9O10P/c19-16-22-6-27(18(31)25-16)12-2-8(9(3-28)35-12)37-38(32,33)34-4-10-7(29)1-11(36-10)26-5-21-13-14(26)23-17(20)24-15(13)30/h5-12,28-29H,1-4H2,(H,32,33)(H2,19,25,31)(H3,20,23,24,30)/t7-,8-,9+,10+,11+,12+/m0/s1
IUPAC Name
{[(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydro-1,3,5-triazin-1-yl)-2-(hydroxymethyl)oxolan-3-yl]oxy}({[(2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy})phosphinic acid
SMILES
NC1=NC(=O)C2=C(N1)N(C=N2)[C@H]1C[C@H](O)[C@@H](COP(O)(=O)O[C@H]2C[C@@H](O[C@@H]2CO)N2C=NC(N)=NC2=O)O1

References

General References
Not Available
PubChem Compound
71587872
PubChem Substance
347828249
ChemSpider
32701891
ChEMBL
CHEMBL3544916
ZINC
ZINC000043203165

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentAcute Myeloid Leukemia2
3CompletedTreatmentChronic Myelomonocytic Leukemia / Myelodysplastic Syndrome1
2Active Not RecruitingTreatmentAcute Myeloid Leukemia / Chronic Myelomonocytic Leukemia / Myelodysplastic Syndrome / Recurrent Acute Myeloid Leukemia / Recurrent Myelodysplastic Syndrome1
2Active Not RecruitingTreatmentHigh-risk Myelodysplastic Syndrome (MDS)1
2Active Not RecruitingTreatmentUrothelial Carcinoma1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.89 mg/mLALOGPS
logP-2ALOGPS
logP-3.6Chemaxon
logS-2.3ALOGPS
pKa (Strongest Acidic)1.79Chemaxon
pKa (Strongest Basic)2.67Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count15Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area271.03 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity120.45 m3·mol-1Chemaxon
Polarizability49.74 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
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/MSsplash10-0a4i-0300090000-78b539dea52a8d7c9312
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0bvi-0000090000-ca1f3960822dfc1bfddf
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0704390000-b9f4d21909dc0c3f93c5
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-06ri-3040390000-416f65d0ba1b45d26af3
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0zfr-0942140000-981b15560a6a68c7423b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0404-9110250000-7464a65306c4e3a13a6c
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-203.0946
predicted
DeepCCS 1.0 (2019)
[M+H]+204.91948
predicted
DeepCCS 1.0 (2019)
[M+Na]+210.55591
predicted
DeepCCS 1.0 (2019)

Drug created at October 20, 2016 21:00 / Updated at February 21, 2021 18:53