NAV

Tiazofurine

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

Identification

Generic Name
Tiazofurine
DrugBank Accession Number
DB13243
Background

Tiazofurine has potential clinical use in cancer treatment as it is a potential inhibitor of Inosine- 5’-monophosphate (IMP) dehydrogenase 1.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 260.267
Monoisotopic: 260.046692194
Chemical Formula
C9H12N2O5S
Synonyms
  • 2-(β-D-ribofuranosyl)-4-thiazolecarboxamide
  • 2-Beta-D-ribofuranosyl-4-thiazolecarboxamide
  • 2-β-D-ribofuranosyl-4-thiazolecarboxamide
  • TCAR
  • Tiazofurin
  • Tiazofurina
  • Tiazofurine
  • Tiazofurinum
External IDs
  • CI-909
  • NSC-286193
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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 Tiazofurine is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Tiazofurine is combined with Articaine.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Tiazofurine is combined with Benzocaine.
Benzyl alcoholThe risk or severity of methemoglobinemia can be increased when Tiazofurine is combined with Benzyl alcohol.
BupivacaineThe risk or severity of methemoglobinemia can be increased when Tiazofurine is combined with Bupivacaine.
Food Interactions
Not Available

Categories

ATC Codes
L01XX18 — Tiazofurine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
C-glycosyl compounds
Alternative Parents
Pentoses / Thiazolecarboxamides / 2-heteroaryl carboxamides / 2,4-disubstituted thiazoles / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols / Primary carboxylic acid amides / Dialkyl ethers / Azacyclic compounds
show 6 more
Substituents
2,4-disubstituted 1,3-thiazole / 2-heteroaryl carboxamide / Alcohol / Aromatic heteromonocyclic compound / Azacycle / Azole / C-glycosyl compound / Carboxamide group / Carboxylic acid derivative / Dialkyl ether
show 18 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
ULJ82834RE
CAS number
60084-10-8
InChI Key
FVRDYQYEVDDKCR-DBRKOABJSA-N
InChI
InChI=1S/C9H12N2O5S/c10-8(15)3-2-17-9(11-3)7-6(14)5(13)4(1-12)16-7/h2,4-7,12-14H,1H2,(H2,10,15)/t4-,5-,6-,7-/m1/s1
IUPAC Name
2-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-thiazole-4-carboxamide
SMILES
NC(=O)C1=CSC(=N1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

References

General References
  1. Melink TJ, Von Hoff DD, Kuhn JG, Hersh MR, Sternson LA, Patton TF, Siegler R, Boldt DH, Clark GM: Phase I evaluation and pharmacokinetics of tiazofurin (2-beta-D-ribofuranosylthiazole-4-carboxamide, NSC 286193). Cancer Res. 1985 Jun;45(6):2859-65. [Article]
KEGG Drug
D06130
ChemSpider
403014
BindingDB
50368057
ChEBI
90239
ChEMBL
CHEMBL108358
ZINC
ZINC000004217560
PDBe Ligand
TIZ
Wikipedia
Tiazofurin
PDB Entries
2p0e / 2ql6

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility5.85 mg/mLALOGPS
logP-1.4ALOGPS
logP-2Chemaxon
logS-1.6ALOGPS
pKa (Strongest Acidic)12.55Chemaxon
pKa (Strongest Basic)-1.4Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area125.9 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity56.53 m3·mol-1Chemaxon
Polarizability24.08 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 GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0006-9740000000-9e41e789e31555147c0a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0190000000-2ae3d4353764cc73af09
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0296-0590000000-6bd25101f8ce6528a6f4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0980000000-68a21768f0750fca6df0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-05my-3900000000-e4231f27a32d9df4044d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fvj-1920000000-a465f6f686968121d8ac
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9700000000-ca95e84a4d29d425a68e
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]-164.247
predicted
DarkChem Lite v0.1.0
[M-H]-152.9472
predicted
DeepCCS 1.0 (2019)
[M+H]+165.1638
predicted
DarkChem Lite v0.1.0
[M+H]+155.34276
predicted
DeepCCS 1.0 (2019)
[M+Na]+164.7266
predicted
DarkChem Lite v0.1.0
[M+Na]+163.0198
predicted
DeepCCS 1.0 (2019)

Drug created at June 23, 2017 20:38 / Updated at July 18, 2023 22:57