ChemFOnt: Showing chemical card for Riluzole (CFc000009211)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:16 UTC

Chemfont ID

CFc000009211

Molecule Identification

Common Name

Riluzole

Definition

Riluzole is only found in individuals that have used or taken this drug. It is a glutamate antagonist (receptors, glutamate) used as an anticonvulsant (anticonvulsants) and to prolong the survival of patients with amyotrophic lateral sclerosis. [PubChem]The mode of action of riluzole is unknown. Its pharmacological properties include the following, some of which may be related to its effect: 1) an inhibitory effect on glutamate release (activation of glutamate reuptake), 2) inactivation of voltage-dependent sodium channels, and 3) ability to interfere with intracellular events that follow transmitter binding at excitatory amino acid receptors.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Rilutek	Kegg
Riluzole impax brand	HMDB
2 Amino 6 trifluoromethoxybenzothiazole	HMDB
2-Amino-6-trifluoromethoxybenzothiazole	HMDB
Aventis brand OF riluzole	HMDB
Riluzole aventis brand	HMDB
Impax brand OF riluzole	HMDB
Rhone-poulenc rorer brand OF riluzole	HMDB
Aventis behring brand OF riluzole	HMDB
Rhone poulenc rorer brand OF riluzole	HMDB

Chemical Formula

C₈H₅F₃N₂OS

Average Molecular Weight

234.198

Monoisotopic Molecular Weight

234.007468097

IUPAC Name

6-(trifluoromethoxy)-1,3-benzothiazol-2-amine

Traditional Name

riluzole

CAS Registry Number

1744-22-5

SMILES

NC1=NC2=C(S1)C=C(OC(F)(F)F)C=C2

InChI Identifier

InChI=1S/C8H5F3N2OS/c9-8(10,11)14-4-1-2-5-6(3-4)15-7(12)13-5/h1-3H,(H2,12,13)

InChI Key

FTALBRSUTCGOEG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzothiazoles. These are organic compounds containing a benzene fused to a thiazole ring (a five-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiazoles

Sub Class

Not Available

Direct Parent

Benzothiazoles

Alternative Parents

Substituents

1,3-benzothiazole
Benzenoid
1,3-thiazol-2-amine
Azole
Thiazole
Heteroaromatic compound
Trihalomethane
Azacycle
Amine
Organopnictogen compound
Organic oxygen compound
Alkyl halide
Primary amine
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Organic nitrogen compound
Alkyl fluoride
Hydrocarbon derivative
Halomethane
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzothiazoles (CHEBI:8863 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014878)

Source

Exogenous

Exogenous (HMDB: HMDB0014878)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.04 g/L	ALOGPS
logP	2.83	ALOGPS
logP	3.4	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	16.44	ChemAxon
pKa (Strongest Basic)	4.57	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	48.14 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	44.37 m³·mol⁻¹	ChemAxon
Polarizability	18.59 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon