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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4)transporters (1) Show 5 proteins XML

enzymes (4)transporters (1) Show 5 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:46 UTC

HMDB ID

HMDB0014878

Secondary Accession Numbers

HMDB14878

Metabolite Identification

Common Name

Riluzole

Description

Riluzole, also known as rilutek, 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). Riluzole is a medication used to treat amyotrophic lateral sclerosis. However, the action of riluzole on glutamate receptors has been controversial, as no binding of the drug to any known sites has been shown for them. Riluzole is a drug which is used for the treatment of amyotrophic lateral sclerosis (als, lou gehrig's disease). A reformulation of riluzole that originated at Yale University and is known by the code name BHV-0223 is under development for the treatment of generalized anxiety disorder and mood disorders now by Biohaven Pharmaceuticals. Riluzole is a strong basic compound (based on its pKa). CYP1A2 substrates, inhibitors and inducers would probably interact with riluzole, due its dependency on this cytochrome for metabolism. Riluzole is a potentially toxic compound. Very common (>10% frequency): nausea; weakness; decreased lung functionCommon (1–10% frequency): headache; dizziness; drowsiness; vomiting; abdominal pain; increased aminotransferasesUncommon (0.1-1% frequency): pancreatitis; interstitial lung diseaseRare (<0.1% frequency): neutropenia; allergic reaction (including angiooedema, anaphylactoid reaction)Symptoms of overdose include: neurological and psychiatric symptoms, acute toxic encephalopathy with stupor, coma and methemoglobinemia. A Cochrane Library review states a 9% gain in the probability of surviving one year. In addition, as its antiglutamatergic action is still detectable in the presence of sodium channel blockers, it is also uncertain whether or not it acts via this way.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

740
  Mrv0541 02231214582D          

 15 16  0  0  0  0            999 V2000
    6.0031    0.5129    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.4529    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.1510    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.9760    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.6740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0031   -0.8149    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3097   -0.1510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4846   -0.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1 14  1  0  0  0  0
  2 15  1  0  0  0  0
  3 15  1  0  0  0  0
  4 15  1  0  0  0  0
  5 11  1  0  0  0  0
  5 15  1  0  0  0  0
  6  9  1  0  0  0  0
  6 14  2  0  0  0  0
  7 14  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  2  0  0  0  0
 11 13  1  0  0  0  0
 12 13  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014878

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C8H5F3N2OS

> <MOLECULAR_WEIGHT>
234.198

> <EXACT_MASS>
234.007468097

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
18.58773356890207

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-(trifluoromethoxy)-1,3-benzothiazol-2-amine

> <ALOGPS_LOGP>
2.83

> <JCHEM_LOGP>
3.3999074026666665

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.44059219702281

> <JCHEM_PKA_STRONGEST_BASIC>
4.573084910451721

> <JCHEM_POLAR_SURFACE_AREA>
48.14

> <JCHEM_REFRACTIVITY>
44.3727

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.95e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
riluzole

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 740                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      11.206   0.957   0.000  0.00  0.00           S+0
HETATM    2  F   UNK     0       5.184  -0.845   0.000  0.00  0.00           F+0
HETATM    3  F   UNK     0       3.080  -0.282   0.000  0.00  0.00           F+0
HETATM    4  F   UNK     0       3.644   1.822   0.000  0.00  0.00           F+0
HETATM    5  O   UNK     0       5.748   1.258   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      11.206  -1.521   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      13.645  -0.282   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       9.748   0.488   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.748  -1.052   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415   1.258   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081   0.488   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.415  -1.822   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081  -1.052   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.105  -0.282   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414   0.488   0.000  0.00  0.00           C+0
CONECT    1    8   14                                                       
CONECT    2   15                                                            
CONECT    3   15                                                            
CONECT    4   15                                                            
CONECT    5   11   15                                                       
CONECT    6    9   14                                                       
CONECT    7   14                                                            
CONECT    8    1    9   10                                                  
CONECT    9    6    8   12                                                  
CONECT   10    8   11                                                       
CONECT   11    5   10   13                                                  
CONECT   12    9   13                                                       
CONECT   13   11   12                                                       
CONECT   14    1    6    7                                                  
CONECT   15    2    3    4    5                                             
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol View Stereo Labels

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 )

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

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	119 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.04 g/L	Not Available
LogP	2.3	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	146.211	30932474
DeepCCS	[M-H]-	143.853	30932474
DeepCCS	[M-2H]-	177.589	30932474
DeepCCS	[M+Na]+	152.462	30932474
AllCCS	[M+H]+	145.5	32859911
AllCCS	[M+H-H2O]+	141.6	32859911
AllCCS	[M+NH4]+	149.1	32859911
AllCCS	[M+Na]+	150.2	32859911
AllCCS	[M-H]-	139.3	32859911
AllCCS	[M+Na-2H]-	139.0	32859911
AllCCS	[M+HCOO]-	138.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.9 minutes	32390414
Predicted by Siyang on May 30, 2022	11.6701 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.96 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	68.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1523.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	403.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	127.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	262.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	221.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	357.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	738.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	95.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	859.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	308.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1026.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	356.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	423.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	361.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	102.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	47.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Riluzole	NC1=NC2=C(S1)C=C(OC(F)(F)F)C=C2	2301.7	Standard polar	33892256
Riluzole	NC1=NC2=C(S1)C=C(OC(F)(F)F)C=C2	1558.2	Standard non polar	33892256
Riluzole	NC1=NC2=C(S1)C=C(OC(F)(F)F)C=C2	1623.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Riluzole,1TMS,isomer #1	C[Si](C)(C)NC1=NC2=CC=C(OC(F)(F)F)C=C2S1	1646.6	Semi standard non polar	33892256
Riluzole,1TMS,isomer #1	C[Si](C)(C)NC1=NC2=CC=C(OC(F)(F)F)C=C2S1	1702.0	Standard non polar	33892256
Riluzole,1TMS,isomer #1	C[Si](C)(C)NC1=NC2=CC=C(OC(F)(F)F)C=C2S1	2100.8	Standard polar	33892256
Riluzole,2TMS,isomer #1	C[Si](C)(C)N(C1=NC2=CC=C(OC(F)(F)F)C=C2S1)[Si](C)(C)C	1681.4	Semi standard non polar	33892256
Riluzole,2TMS,isomer #1	C[Si](C)(C)N(C1=NC2=CC=C(OC(F)(F)F)C=C2S1)[Si](C)(C)C	1845.7	Standard non polar	33892256
Riluzole,2TMS,isomer #1	C[Si](C)(C)N(C1=NC2=CC=C(OC(F)(F)F)C=C2S1)[Si](C)(C)C	1912.0	Standard polar	33892256
Riluzole,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC2=CC=C(OC(F)(F)F)C=C2S1	1839.0	Semi standard non polar	33892256
Riluzole,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC2=CC=C(OC(F)(F)F)C=C2S1	1886.1	Standard non polar	33892256
Riluzole,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC2=CC=C(OC(F)(F)F)C=C2S1	2202.2	Standard polar	33892256
Riluzole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NC2=CC=C(OC(F)(F)F)C=C2S1)[Si](C)(C)C(C)(C)C	2047.8	Semi standard non polar	33892256
Riluzole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NC2=CC=C(OC(F)(F)F)C=C2S1)[Si](C)(C)C(C)(C)C	2224.9	Standard non polar	33892256
Riluzole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NC2=CC=C(OC(F)(F)F)C=C2S1)[Si](C)(C)C(C)(C)C	2156.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Riluzole GC-MS (Non-derivatized) - 70eV, Positive	splash10-00li-2940000000-00c484cbc92e6a94bae0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riluzole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riluzole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riluzole , positive-QTOF	splash10-000i-2590000000-5a9d0f7cdad7e4f2ec6b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riluzole , positive-QTOF	splash10-000i-0390000000-4bd44ae3d25f047943e8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riluzole , positive-QTOF	splash10-000i-3940000000-1da38288b84e863a64e5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riluzole 35V, Positive-QTOF	splash10-000i-0590000000-79d300cfd2b43692d963	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riluzole 35V, Negative-QTOF	splash10-001i-0190000000-63069bec4e00478eb380	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Riluzole 10V, Positive-QTOF	splash10-000i-0190000000-f0b481a2910122ad9bdc	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Riluzole 20V, Positive-QTOF	splash10-000i-0090000000-d6a855ead1f5f5fe1a37	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Riluzole 40V, Positive-QTOF	splash10-014i-0900000000-b797bc65c27579651949	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Riluzole 10V, Negative-QTOF	splash10-001i-0090000000-4caa5c429c103b56c151	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Riluzole 20V, Negative-QTOF	splash10-001i-0090000000-78bd33541d87ef645303	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Riluzole 40V, Negative-QTOF	splash10-03di-0900000000-6f96de4ddfa58b872d2e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Riluzole 10V, Positive-QTOF	splash10-000i-0090000000-77cd58803ff632c89002	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Riluzole 20V, Positive-QTOF	splash10-000i-0090000000-77cd58803ff632c89002	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Riluzole 40V, Positive-QTOF	splash10-0a4r-0490000000-ab117c07a1f16bb2d5f8	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Riluzole 10V, Negative-QTOF	splash10-001i-0090000000-9f868134c3a763fd526e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Riluzole 20V, Negative-QTOF	splash10-001i-0090000000-9f868134c3a763fd526e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Riluzole 40V, Negative-QTOF	splash10-0a4i-9320000000-2312256d22d9ca57d014	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00740	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00740	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00740

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4892

KEGG Compound ID

C07937

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Riluzole

METLIN ID

Not Available

PubChem Compound

5070

PDB ID

Not Available

ChEBI ID

138898

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Song JH, Huang CS, Nagata K, Yeh JZ, Narahashi T: Differential action of riluzole on tetrodotoxin-sensitive and tetrodotoxin-resistant sodium channels. J Pharmacol Exp Ther. 1997 Aug;282(2):707-14. [PubMed:9262334 ]
Zarate CA Jr, Payne JL, Quiroz J, Sporn J, Denicoff KK, Luckenbaugh D, Charney DS, Manji HK: An open-label trial of riluzole in patients with treatment-resistant major depression. Am J Psychiatry. 2004 Jan;161(1):171-4. [PubMed:14702270 ]
van Kan HJ, Groeneveld GJ, Kalmijn S, Spieksma M, van den Berg LH, Guchelaar HJ: Association between CYP1A2 activity and riluzole clearance in patients with amyotrophic lateral sclerosis. Br J Clin Pharmacol. 2005 Mar;59(3):310-3. [PubMed:15752377 ]
Coric V, Taskiran S, Pittenger C, Wasylink S, Mathalon DH, Valentine G, Saksa J, Wu YT, Gueorguieva R, Sanacora G, Malison RT, Krystal JH: Riluzole augmentation in treatment-resistant obsessive-compulsive disorder: an open-label trial. Biol Psychiatry. 2005 Sep 1;58(5):424-8. [PubMed:15993857 ]
Mathew SJ, Manji HK, Charney DS: Novel drugs and therapeutic targets for severe mood disorders. Neuropsychopharmacology. 2008 Aug;33(9):2080-92. doi: 10.1038/sj.npp.1301652. Epub 2008 Jan 2. [PubMed:18172433 ]
Lamanauskas N, Nistri A: Riluzole blocks persistent Na+ and Ca2+ currents and modulates release of glutamate via presynaptic NMDA receptors on neonatal rat hypoglossal motoneurons in vitro. Eur J Neurosci. 2008 May;27(10):2501-14. doi: 10.1111/j.1460-9568.2008.06211.x. Epub 2008 Apr 26. [PubMed:18445055 ]

Enzymes

Enzyme Details

1. Cytochrome P450 1A1

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP1A1
Uniprot ID:: P04798
Molecular weight:: 58164.815

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Wang B, Zhou SF: Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218. [PubMed:19754423 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cystine/glutamate transporter

General function:: Involved in transport
Specific function:: Sodium-independent, high-affinity exchange of anionic amino acids with high specificity for anionic form of cystine and glutamate.
Gene Name:: SLC7A11
Uniprot ID:: Q9UPY5
Molecular weight:: 55422.44

References

Wokke J: Riluzole. Lancet. 1996 Sep 21;348(9030):795-9. [PubMed:8813989 ]
Azbill RD, Mu X, Springer JE: Riluzole increases high-affinity glutamate uptake in rat spinal cord synaptosomes. Brain Res. 2000 Jul 21;871(2):175-80. [PubMed:10899284 ]
Dunlop J, Beal McIlvain H, She Y, Howland DS: Impaired spinal cord glutamate transport capacity and reduced sensitivity to riluzole in a transgenic superoxide dismutase mutant rat model of amyotrophic lateral sclerosis. J Neurosci. 2003 Mar 1;23(5):1688-96. [PubMed:12629173 ]
Gosselin RD, O'Connor RM, Tramullas M, Julio-Pieper M, Dinan TG, Cryan JF: Riluzole normalizes early-life stress-induced visceral hypersensitivity in rats: role of spinal glutamate reuptake mechanisms. Gastroenterology. 2010 Jun;138(7):2418-25. doi: 10.1053/j.gastro.2010.03.003. Epub 2010 Mar 10. [PubMed:20226190 ]
Hayashida K, Parker RA, Eisenach JC: Activation of glutamate transporters in the locus coeruleus paradoxically activates descending inhibition in rats. Brain Res. 2010 Mar 4;1317:80-6. doi: 10.1016/j.brainres.2009.12.086. Epub 2010 Jan 6. [PubMed:20059984 ]

Enzyme Details

4. Sodium channel protein type 5 subunit alpha

General function:: Involved in ion channel activity
Specific function:: This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential in the electrocardiogram
Gene Name:: SCN5A
Uniprot ID:: Q14524
Molecular weight:: 226937.5

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Schwartz G, Fehlings MG: Secondary injury mechanisms of spinal cord trauma: a novel therapeutic approach for the management of secondary pathophysiology with the sodium channel blocker riluzole. Prog Brain Res. 2002;137:177-90. [PubMed:12440368 ]
Song JH, Huang CS, Nagata K, Yeh JZ, Narahashi T: Differential action of riluzole on tetrodotoxin-sensitive and tetrodotoxin-resistant sodium channels. J Pharmacol Exp Ther. 1997 Aug;282(2):707-14. [PubMed:9262334 ]
Weiss S, Benoist D, White E, Teng W, Saint DA: Riluzole protects against cardiac ischaemia and reperfusion damage via block of the persistent sodium current. Br J Pharmacol. 2010 Jul;160(5):1072-82. doi: 10.1111/j.1476-5381.2010.00766.x. [PubMed:20590601 ]

Transporters

Enzyme Details

1. ATP-binding cassette sub-family G member 2

General function:: Involved in ATP binding
Specific function:: Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123
Gene Name:: ABCG2
Uniprot ID:: Q9UNQ0
Molecular weight:: 72313.5

References

Milane A, Vautier S, Chacun H, Meininger V, Bensimon G, Farinotti R, Fernandez C: Interactions between riluzole and ABCG2/BCRP transporter. Neurosci Lett. 2009 Mar 6;452(1):12-6. doi: 10.1016/j.neulet.2008.12.061. Epub 2009 Jan 6. [PubMed:19146924 ]

Showing metabocard for Riluzole (HMDB0014878)

MOL for HMDB0014878 (Riluzole)

3D MOL for HMDB0014878 (Riluzole)

3D SDF for HMDB0014878 (Riluzole)

3D-SDF for HMDB0014878 (Riluzole)

PDB for HMDB0014878 (Riluzole)

3D PDB for HMDB0014878 (Riluzole)

SMILES for HMDB0014878 (Riluzole)

INCHI for HMDB0014878 (Riluzole)

Structure for HMDB0014878 (Riluzole)

3D Structure for HMDB0014878 (Riluzole)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

Transporters

References