ContaminantDB: Tolrestat

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 06:44:35 UTC

Update Date

2016-11-09 01:16:07 UTC

Accession Number

CHEM020054

Identification

Common Name

Tolrestat

Class

Small Molecule

Description

Tolrestat (INN) (AY-27773) is an aldose reductase inhibitor which was approved for the control of certain diabetic complications. While it was approved for marketed in several countries, it failed a Phase III trial in the U.S. due to toxicity and never received FDA approval. It was sold under the tradename Tolrestat but was discontinued by Wyeth in 1997 because of the risk of severe liver toxicity and death.

Contaminant Sources

ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Alredase	ChEBI
N-((6-Methoxy-5-(trifluoromethyl)-1-naphthalenyl)thioxomethyl)-N-methylglycine	ChEBI
N-{[6-methoxy-5-(trifluoromethyl)-1-naphthyl]carbonothioyl}-N-methylglycine	ChEBI
Tolrestatum	ChEBI
N-5-Trifluoromethyl-6-methoxy-1-thionaphthoyl-N-methylglycine	MeSH
N-((5-(Trifluoromethyl)-6-methoxy-1-naphthalenyl)thioxomethyl)-N-methylglycine	MeSH

Chemical Formula

C₁₆H₁₄F₃NO₃S

Average Molecular Mass

357.347 g/mol

Monoisotopic Mass

357.065 g/mol

CAS Registry Number

75820-08-5

IUPAC Name

2-{1-[6-methoxy-5-(trifluoromethyl)naphthalen-1-yl]-N-methylmethanethioamido}acetic acid

Traditional Name

tolrestat

SMILES

COC1=C(C2=CC=CC(C(=S)N(C)CC(O)=O)=C2C=C1)C(F)(F)F

InChI Identifier

InChI=1S/C16H14F3NO3S/c1-20(8-13(21)22)15(24)11-5-3-4-10-9(11)6-7-12(23-2)14(10)16(17,18)19/h3-7H,8H2,1-2H3,(H,21,22)

InChI Key

LUBHDINQXIHVLS-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Naphthalene
Anisole
Alkyl aryl ether
Thioamide
Carboxylic acid derivative
Carboxylic acid
Thiocarboxylic acid amide
Ether
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Organooxygen compound
Organosulfur compound
Thiocarbonyl group
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Alkyl halide
Alkyl fluoride
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

naphthalenes (CHEBI:48549 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0076 g/L	ALOGPS
logP	3.25	ALOGPS
logP	3.35	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	3.95	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	87.89 m³·mol⁻¹	ChemAxon
Polarizability	32.08 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0009000000-cdb60e9fd89615b1a947	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0009000000-4c4926a981bad06db733	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uka-1392000000-4622aad9b6867474fc04	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0009000000-912dea387e54fea52989	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bt9-0019000000-199075fceff9450fc215	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-029b-1098000000-a69bcc8c18e3fefa66b5	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB02383

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Tolrestat

Chemspider ID

Not Available

ChEBI ID

48549

PubChem Compound ID

53359

Kegg Compound ID

C01621

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Tolrestat (CHEM020054)

Structure for CHEM020054: Tolrestat