Riluzole

Identification

Summary

Riluzole is a glutamate antagonist used to treat amyotrophic lateral sclerosis.

Brand Names
Exservan, Rilutek, Tiglutik
Generic Name
Riluzole
DrugBank Accession Number
DB00740
Background

A glutamate antagonist (receptors, glutamate) used as an anticonvulsant (anticonvulsants) and to prolong the survival of patients with amyotrophic lateral sclerosis. Riluzole is marketed as Rilutek by Sanofi.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 234.198
Monoisotopic: 234.007468097
Chemical Formula
C8H5F3N2OS
Synonyms
  • Riluzol
  • Riluzole
  • Riluzolum
External IDs
  • PK 26124
  • RP 54274
  • RPR 202

Pharmacology

Indication

For the treatment of amyotrophic lateral sclerosis (ALS, Lou Gehrig's Disease)

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofAmyotrophic lateral sclerosis••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Riluzole, a member of the benzothiazole class, is indicated for the treatment of patients with amyotrophic lateral sclerosis (ALS). Riluzole extends survival and/or time to tracheostomy. It is also neuroprotective in various in vivo experimental models of neuronal injury involving excitotoxic mechanisms. The etiology and pathogenesis of amyotrophic lateral sclerosis (ALS) are not known, although a number of hypotheses have been advanced. One hypothesis is that motor neurons, made vulnerable through either genetic predisposition or environmental factors, are injured by glutamate. In some cases of familial ALS the enzyme superoxide dismutase has been found to be defective.

Mechanism of action

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.

TargetActionsOrganism
ASodium channel protein type 5 subunit alpha
inhibitor
Humans
ACystine/glutamate transporter
inducer
Humans
Absorption

Riluzole is well-absorbed (approximately 90%), with average absolute oral bioavailability of about 60% (CV=30%). A high fat meal decreases absorption, reducing AUC by about 20% and peak blood levels by about 45%.

Volume of distribution

Not Available

Protein binding

96% bound to plasma proteins, mainly to albumin and lipoprotein over the clinical concentration range.

Metabolism

Riluzole is extensively metabolized to six major and a number of minor metabolites, which have not all been identified to date. Metabolism is mostly hepatic, consisting of cytochrome P450–dependent hydroxylation and glucuronidation. CYP1A2 is the primary isozyme involved in N-hydroxylation; CYP2D6, CYP2C19, CYP3A4, and CYP2E1 are considered unlikely to contribute significantly to riluzole metabolism in humans.

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Route of elimination

Not Available

Half-life

The mean elimination half-life of riluzole is 12 hours (CV=35%) after repeated doses.

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
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Riluzole is combined with 1,2-Benzodiazepine.
AbametapirThe serum concentration of Riluzole can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Riluzole can be increased when combined with Abatacept.
AbemaciclibAbemaciclib may decrease the excretion rate of Riluzole which could result in a higher serum level.
AbirateroneThe serum concentration of Riluzole can be increased when it is combined with Abiraterone.
Food Interactions
  • Take on an empty stomach. Take at least 1 hour before or 2 hours after meals.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Riluzole HydrochlorideNot AvailableNot AvailableQEAOELIJQRYJJS-UHFFFAOYSA-N
Product Images
International/Other Brands
Fanizan (Actavis) / Laidec (Sun Pro) / Lizolorol (Actavis) / Lizorolol (ratiopharm) / Rilustad (STADA) / Sclefic (Actavis) / Xie Yi Li (Lunan Pharm) / Zolerilis (Actavis)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ExservanFilm50 mg/1OralMitsubishi Tanabe Pharma America, Inc.2021-05-01Not applicableUS flag
ExservanFilm50 mg/1OralAquestive Therapeutics2019-01-24Not applicableUS flag
ExservanFilm50 mg/1OralMitsubishi Tanabe Pharma America, Inc.2021-05-01Not applicableUS flag
RilutekTablet, film coated50 mg/1Oralsanofi-aventis U.S. LLC1995-12-122015-06-30US flag
RilutekTablet50 mg/1OralCovis Pharma US, Inc2016-08-01Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-riluzoleTablet50 mgOralApotex Corporation2012-09-25Not applicableCanada flag
Mylan-riluzoleTablet50 mgOralMylan Pharmaceuticals2012-10-23Not applicableCanada flag
RiluzoleTablet, film coated50 mg/1OralGlenmark Pharmaceuticals Inc., USA2013-06-18Not applicableUS flag
RiluzoleTablet, film coated50 mg/1OralQuinn Pharmaceuticals2020-01-01Not applicableUS flag
RiluzoleTablet, film coated50 mg/1OralRising Pharmaceuticals, Inc.2013-05-15Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
TeglutikRiluzole (5 mg/1mL)LiquidOralEDW PHARMA2024-03-08Not applicableUS flag
TeglutikRiluzole (50 mg/10mL)LiquidOralEDW PHARMA, INC2024-01-19Not applicableUS flag

Categories

ATC Codes
N07XX02 — Riluzole
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound 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
Benzenoids / 2-amino-1,3-thiazoles / Heteroaromatic compounds / Trihalomethanes / Azacyclic compounds / Primary amines / Organopnictogen compounds / Organooxygen compounds / Organofluorides / Hydrocarbon derivatives
show 1 more
Substituents
1,3-benzothiazole / 1,3-thiazol-2-amine / Alkyl fluoride / Alkyl halide / Amine / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Halomethane
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
benzothiazoles (CHEBI:8863)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
7LJ087RS6F
CAS number
1744-22-5
InChI Key
FTALBRSUTCGOEG-UHFFFAOYSA-N
InChI
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)
IUPAC Name
6-(trifluoromethoxy)-1,3-benzothiazol-2-amine
SMILES
NC1=NC2=C(S1)C=C(OC(F)(F)F)C=C2

References

Synthesis Reference

Pratap Padi, Madhusudhan Ganta, Satyanarayana Bollikonda, Sridhar Chaganti, Ramulu Akula, Loka Maheshwari Dommati, "PROCESS FOR PREPARING RILUZOLE." U.S. Patent US20080108827, issued May 08, 2008.

US20080108827
General References
  1. 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. [Article]
  2. 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. [Article]
  3. 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. [Article]
  4. 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. [Article]
  5. 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. [Article]
  6. 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. [Article]
  7. FDA Approved Drug Products: RILUTEK (riluzole) tablets [Link]
  8. FDA Approved Drug Products: EXSERVAN (riluzole) film [Link]
  9. FDA Approved Drug Products: TIGLUTIK (riluzole) suspension [Link]
Human Metabolome Database
HMDB0014878
KEGG Drug
D00775
KEGG Compound
C07937
PubChem Compound
5070
PubChem Substance
46508094
ChemSpider
4892
BindingDB
30705
RxNav
35623
ChEBI
8863
ChEMBL
CHEMBL744
ZINC
ZINC000000006481
Therapeutic Targets Database
DAP000527
PharmGKB
PA451251
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
657
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Riluzole
PDB Entries
5v02 / 7bnj / 7wdb / 8thg
FDA label
Download (125 KB)
MSDS
Download (29.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentAmyotrophic Lateral Sclerosis (ALS)1
4CompletedTreatmentFatigue / Inflammation1
4CompletedTreatmentFragile X Syndrome1
4CompletedTreatmentGilles de la Tourette's Syndrome1
4CompletedTreatmentMajor Depressive Disorder (MDD)1

Pharmacoeconomics

Manufacturers
  • Sanofi aventis us llc
  • Impax laboratories inc
Packagers
  • Inyx Usa Ltd.
  • Kaiser Foundation Hospital
  • Sanofi-Aventis Inc.
  • Southwood Pharmaceuticals
Dosage Forms
FormRouteStrength
FilmOral50 MG
TabletOral
FilmOral50 mg/1
TabletOral50.00 mg
Tablet, coatedOral50 mg
Tablet, film coatedOral50 mg
Tablet, coatedOral5000000 mg
TabletOral50 mg
Tablet, film coatedOral
TabletOral50 mg/1
Tablet, film coatedOral50 mg/1
LiquidOral5 mg/1mL
SuspensionOral5 MG/ML
SuspensionOral
SuspensionOral0.5 mg
LiquidOral50 mg/10mL
Prices
Unit descriptionCostUnit
Rilutek 50 mg tablet18.77USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5527814No1996-06-182013-06-18US flag
CA2151604No2005-09-202013-12-10Canada flag
CA2117466No2000-01-252012-10-22Canada flag
US8603514No2013-12-102024-04-03US flag
US8765150No2014-07-012029-03-12US flag
US8765167No2014-07-012024-02-20US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)119 °CNot Available
logP2.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0395 mg/mLALOGPS
logP2.83ALOGPS
logP3.4Chemaxon
logS-3.8ALOGPS
pKa (Strongest Acidic)16.44Chemaxon
pKa (Strongest Basic)4.57Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area48.14 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity44.37 m3·mol-1Chemaxon
Polarizability18.59 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.995
Blood Brain Barrier+0.9799
Caco-2 permeable-0.5377
P-glycoprotein substrateNon-substrate0.8045
P-glycoprotein inhibitor INon-inhibitor0.8245
P-glycoprotein inhibitor IINon-inhibitor0.6998
Renal organic cation transporterNon-inhibitor0.859
CYP450 2C9 substrateNon-substrate0.8679
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7032
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorNon-inhibitor0.9072
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8332
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6647
Ames testAMES toxic0.6799
CarcinogenicityNon-carcinogens0.9001
BiodegradationNot ready biodegradable1.0
Rat acute toxicity3.6843 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9775
hERG inhibition (predictor II)Non-inhibitor0.8734
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-00li-2940000000-00c484cbc92e6a94bae0
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-2590000000-5a9d0f7cdad7e4f2ec6b
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-0390000000-4bd44ae3d25f047943e8
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-3940000000-1da38288b84e863a64e5
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-7843c01132bccbbab8fa
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-2972f1ebcacdf4db0736
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-82f022cd37921d0ac71e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-f522253a86d418326dd0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0bt9-1690000000-3f361795c0ce2867a1ca
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9210000000-ebd8914ee14afccf5af7
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]-137.8325092
predicted
DarkChem Lite v0.1.0
[M-H]-143.85353
predicted
DeepCCS 1.0 (2019)
[M+H]+137.5397092
predicted
DarkChem Lite v0.1.0
[M+H]+146.21153
predicted
DeepCCS 1.0 (2019)
[M+Na]+138.5174092
predicted
DarkChem Lite v0.1.0
[M+Na]+152.46223
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Voltage-gated sodium channel activity involved in sa node cell action potential
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 pr...
Gene Name
SCN5A
Uniprot ID
Q14524
Uniprot Name
Sodium channel protein type 5 subunit alpha
Molecular Weight
226937.475 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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. [Article]
  3. 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. [Article]
  4. 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. [Article]
  5. 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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inducer
General Function
Cystine:glutamate antiporter activity
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
Uniprot Name
Cystine/glutamate transporter
Molecular Weight
55422.44 Da
References
  1. Wokke J: Riluzole. Lancet. 1996 Sep 21;348(9030):795-9. [Article]
  2. 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. [Article]
  3. 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. [Article]
  4. 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. [Article]
  5. 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. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d 24-hydroxylase 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 un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
  2. Sanderink GJ, Bournique B, Stevens J, Petry M, Martinet M: Involvement of human CYP1A isoenzymes in the metabolism and drug interactions of riluzole in vitro. J Pharmacol Exp Ther. 1997 Sep;282(3):1465-72. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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 un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Ajroud-Driss S, Saeed M, Khan H, Siddique N, Hung WY, Sufit R, Heller S, Armstrong J, Casey P, Siddique T, Lukas TJ: Riluzole metabolism and CYP1A1/2 polymorphisms in patients with ALS. Amyotroph Lateral Scler. 2007 Oct;8(5):305-9. doi: 10.1080/17482960701500650. [Article]
  2. 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. [Article]
  3. Flockhart Table of Drug Interactions [Link]
  4. Riluzole FDA label [File]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. 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. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48