Identification

Name
Ledipasvir
Accession Number
DB09027
Type
Small Molecule
Groups
Approved
Description

Ledipasvir is a direct acting antiviral (DAA) medication used as part of combination therapy to treat chronic Hepatitis C, an infectious liver disease caused by infection with Hepatitis C Virus (HCV). HCV is a single-stranded RNA virus that is categorized into nine distinct genotypes, with genotype 1 being the most common in the United States, and affecting 72% of all chronic HCV patients [9]. Treatment options for chronic Hepatitis C have advanced significantly since 2011, with the development of Direct Acting Antivirals (DAAs) such as ledipasvir. More specifically, ledipasvir is an inhibitor of the Hepatitis C Virus (HCV) Non-Structural Protein 5A (NS5A), which is required for viral RNA replication and assembly of HCV virions. Although its exact mechanism of action is unknown, it is postulated to prevent hyperphosphorylation of NS5A which is required for viral protein production. It is effective against genotypes 1a, 1b, 4a, and 5a and with a lesser activity against genotypes 2a and 3a of HCV. Ledipasvir and other direct acting antivirals are very potent options for the treatment of Hepatitis C, as they exhibit a high barrier to the development of resistance [8]. This is an important advantage relative to HCV drugs that target other viral enzymes such as the protease, for which rapid development of resistance has proven to be an important cause of therapeutic failure.

In a joint recommendation published in 2016, the American Association for the Study of Liver Diseases (AASLD) and the Infectious Diseases Society of America (IDSA) recommend ledipasvir as a first line therapy option in combination with Sofosbuvir for the treatment of HCV genotypes 1a, 1b, 4, 5, and 6 [9]. Treatment with ledipasvir is used with the intent to cure, or achieve a sustained virologic response (SVR), after 12 weeks of daily therapy. SVR and eradication of HCV infection is associated with significant long-term health benefits including reduced liver-related damage, improved quality of life, reduced incidence of Hepatocellular Carcinoma, and reduced all-cause mortality [6]. Treatment with direct acting antivirals such as ledipasvir is associated with very minimal side effects, with the most common being headache and fatigue [FDA Label]. Lack of significant side effects and short duration of therapy is a considerable advantage over older interferon- and ribavirin-based regimens, which were limited by infusion site reactions, reduced blood count, and neuropsychiatric effects [7].

Since 2014, ledipasvir has been available as a fixed dose combination product with Sofosbuvir (tradename Harvoni) used for the treatment of chronic Hepatitis C. Approved in October 2014 by the FDA, Harvoni is indicated for the treatment of HCV genotypes 1, 4, 5, and 6 with or without Ribavirin depending on the level of liver damage or cirrhosis [FDA Label]. When combined together, ledipasvir and sofosbuvir as the combination product Harvoni has been shown to achieve a SVR between 93 and 99% after 12 weeks of treatment [FDA Label]. Its use has also proven successful in the treatment of HCV in patients co-infected with HIV [5].

Structure
Thumb
Synonyms
  • methyl [(2S)-1-{(6S)-6-[4-(9,9-difluoro-7-{2-[(1R,3S,4S)-2-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-azabicyclo[2.2.1]hept-3-yl]-1H-benzimidazol-5-yl}-9H-fluoren-2-yl)-1H-imidazol-2-yl]-5-azaspiro[2.4]hept-5-yl}-3-methyl-1-oxobutan-2-yl]carbamate
External IDs
GS 5885 / GS-5885 / GS5885 / WHO 9796
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
HarvoniLedipasvir (90 mg) + Sofosbuvir (400 mg)TabletOralGilead Sciences2014-10-16Not applicableCanada
HarvoniLedipasvir (90 mg/1) + Sofosbuvir (400 mg/1)Tablet, film coatedOralGilead Sciences2014-10-10Not applicableUs
Categories
UNII
013TE6E4WV
CAS number
1256388-51-8
Weight
Average: 888.9999
Monoisotopic: 888.41343791
Chemical Formula
C49H54F2N8O6
InChI Key
VRTWBAAJJOHBQU-KMWAZVGDSA-N
InChI
InChI=1S/C49H54F2N8O6/c1-24(2)39(56-46(62)64-5)44(60)58-23-48(15-16-48)21-38(58)42-52-22-37(55-42)28-9-13-32-31-12-8-26(18-33(31)49(50,51)34(32)19-28)27-10-14-35-36(20-27)54-43(53-35)41-29-7-11-30(17-29)59(41)45(61)40(25(3)4)57-47(63)65-6/h8-10,12-14,18-20,22,24-25,29-30,38-41H,7,11,15-17,21,23H2,1-6H3,(H,52,55)(H,53,54)(H,56,62)(H,57,63)/t29-,30+,38-,39-,40-,41-/m0/s1
IUPAC Name
(2S)-1-[(6S)-6-[5-(9,9-difluoro-7-{2-[(1R,3S,4S)-2-[(2S)-2-{[hydroxy(methoxy)methylidene]amino}-3-methylbutanoyl]-2-azabicyclo[2.2.1]heptan-3-yl]-1H-1,3-benzodiazol-6-yl}-9H-fluoren-2-yl)-1H-imidazol-2-yl]-5-azaspiro[2.4]heptan-5-yl]-2-{[hydroxy(methoxy)methylidene]amino}-3-methylbutan-1-one
SMILES
[H][[email protected]](N=C(O)OC)(C(C)C)C(=O)N1CC2(CC2)C[[email protected]@]1([H])C1=NC=C(N1)C1=CC2=C(C=C1)C1=C(C=C(C=C1)C1=CC3=C(C=C1)N=C(N3)[[email protected]@]1([H])N(C(=O)[[email protected]@]([H])(N=C(O)OC)C(C)C)[[email protected]]3([H])CC[[email protected]@]1([H])C3)C2(F)F

Pharmacology

Indication

When used in combination with the antiviral medication Sofosbuvir as the commercially available product Harvoni, ledipasvir is indicated for the treatment of HCV genotypes 1, 4, 5, and 6 with or without Ribavirin depending on the level of liver damage or cirrhosis [FDA Label]. Its use has also proven successful in the treatment of HCV in patients co-infected with HIV [5].

Structured Indications
Pharmacodynamics

Ledipasvir acts against HCV and is categorized as a direct-acting antiviral agent (DAA).

At a dose of 120 mg twice daily (2.67 times the maximum recommended dosage), ledipasvir does not prolong QTc interval to any clinically relevant extent [FDA Label].

Mechanism of action

Ledipasvir is an inhibitor of the Hepatitis C Virus (HCV) NS5A protein required for viral RNA replication and assembly of HCV virions. Although its exact mechanism of action is unknown, it is postulated to prevent hyperphosphorylation of NS5A which is required for viral production.

TargetActionsOrganism
ANonstructural protein 5A
inhibitor
Hepatitis C virus
Absorption

When given orally, ledipasvir reaches its maximum plasma concentration in about 4 to 4.5 hours with a maximum concentration (Cmax) of 323 ng/mL [FDA Label].

Volume of distribution
Not Available
Protein binding

Ledipasvir is >99.8% bound to human plasma proteins [FDA Label].

Metabolism

In vitro, no detectable metabolism of ledipasvir was observed by human CYP1A2, CYP2C8, CYP2C9, CYP2C19, CYP2D6, and CYP3A4. Evidence of slow oxidative metabolism via an unknown mechanism has been observed. Following a single dose of 90 mg [14C]-ledipasvir, systemic exposure was almost exclusively to the parent drug (>98%). Unchanged ledipasvir is the major species present in feces [FDA Label].

Route of elimination

Following a single 90 mg oral dose of [14C]-ledipasvir, mean total recovery of the [14C]-radioactivity in feces and urine was approximately 87%, with most of the radioactive dose recovered from feces (approximately 86%). Unchanged ledipasvir excreted in feces accounted for a mean of 70% of the administered dose and the oxidative metabolite M19 accounted for 2.2% of the dose. These data indicate that biliary excretion of unchanged ledipasvir is a major route of elimination, with renal excretion being a minor pathway (approximately 1%) [FDA Label].

Half life

The median terminal half-life of ledipasvir is 47 hours [FDA Label].

Clearance
Not Available
Toxicity

There is very little toxicity associated with the use of ledipasvir in combination products. The most common adverse reactions are headache and fatigue.

Affected organisms
  • Hepatitis C Virus
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcetaminophenThe serum concentration of Ledipasvir can be increased when it is combined with Acetaminophen.Approved
AfatinibThe serum concentration of Ledipasvir can be increased when it is combined with Afatinib.Approved
AlbendazoleThe serum concentration of Ledipasvir can be increased when it is combined with Albendazole.Approved, Vet Approved
AldosteroneThe serum concentration of Ledipasvir can be decreased when it is combined with Aldosterone.Experimental, Investigational
AlectinibThe serum concentration of Ledipasvir can be increased when it is combined with Alectinib.Approved
AlfentanilThe serum concentration of Ledipasvir can be increased when it is combined with Alfentanil.Approved, Illicit
AlgeldrateThe serum concentration of Ledipasvir can be decreased when it is combined with Algeldrate.Approved, Experimental
AlmagateThe serum concentration of Ledipasvir can be decreased when it is combined with Almagate.Experimental
AlmasilateThe serum concentration of Ledipasvir can be decreased when it is combined with Almasilate.Approved, Experimental
AloglutamolThe serum concentration of Ledipasvir can be decreased when it is combined with Aloglutamol.Experimental
AluminiumThe serum concentration of Ledipasvir can be decreased when it is combined with Aluminium.Approved
Aluminium acetoacetateThe serum concentration of Ledipasvir can be decreased when it is combined with Aluminium acetoacetate.Experimental
Aluminium glycinateThe serum concentration of Ledipasvir can be decreased when it is combined with Aluminium glycinate.Experimental
Aluminum hydroxideThe serum concentration of Ledipasvir can be decreased when it is combined with Aluminum hydroxide.Approved
AmantadineThe serum concentration of Ledipasvir can be increased when it is combined with Amantadine.Approved
Aminohippuric acidThe serum concentration of Ledipasvir can be increased when it is combined with Aminohippuric acid.Approved, Investigational
AmiodaroneThe serum concentration of Ledipasvir can be increased when it is combined with Amiodarone.Approved, Investigational
AmitriptylineThe serum concentration of Ledipasvir can be increased when it is combined with Amitriptyline.Approved
AmlodipineThe serum concentration of Ledipasvir can be increased when it is combined with Amlodipine.Approved
AmprenavirThe serum concentration of Ledipasvir can be increased when it is combined with Amprenavir.Approved
AmsacrineThe serum concentration of Ledipasvir can be increased when it is combined with Amsacrine.Approved
AsenapineThe serum concentration of Ledipasvir can be decreased when it is combined with Asenapine.Approved
AstemizoleThe serum concentration of Ledipasvir can be increased when it is combined with Astemizole.Approved, Withdrawn
AtazanavirThe serum concentration of Ledipasvir can be increased when it is combined with Atazanavir.Approved, Investigational
AtenololThe serum concentration of Ledipasvir can be increased when it is combined with Atenolol.Approved
AtorvastatinThe serum concentration of Ledipasvir can be increased when it is combined with Atorvastatin.Approved
AzelastineThe serum concentration of Ledipasvir can be increased when it is combined with Azelastine.Approved
AzithromycinThe serum concentration of Ledipasvir can be increased when it is combined with Azithromycin.Approved
BenzocaineThe serum concentration of Ledipasvir can be increased when it is combined with Benzocaine.Approved
BepridilThe serum concentration of Ledipasvir can be increased when it is combined with Bepridil.Approved, Withdrawn
BiperidenThe serum concentration of Ledipasvir can be increased when it is combined with Biperiden.Approved, Investigational
Bismuth SubcitrateThe serum concentration of Ledipasvir can be decreased when it is combined with Bismuth Subcitrate.Approved
Bismuth subnitrateThe serum concentration of Ledipasvir can be decreased when it is combined with Bismuth subnitrate.Experimental
BoceprevirThe serum concentration of Ledipasvir can be increased when it is combined with Boceprevir.Approved, Withdrawn
BosutinibThe serum concentration of Ledipasvir can be increased when it is combined with Bosutinib.Approved
BromocriptineThe serum concentration of Ledipasvir can be increased when it is combined with Bromocriptine.Approved, Investigational
BuprenorphineThe serum concentration of Ledipasvir can be increased when it is combined with Buprenorphine.Approved, Illicit, Investigational, Vet Approved
BuspironeThe serum concentration of Ledipasvir can be increased when it is combined with Buspirone.Approved, Investigational
CabazitaxelThe serum concentration of Ledipasvir can be increased when it is combined with Cabazitaxel.Approved
CaffeineThe serum concentration of Ledipasvir can be increased when it is combined with Caffeine.Approved
Calcium CarbonateThe serum concentration of Ledipasvir can be decreased when it is combined with Calcium Carbonate.Approved
Calcium silicateThe serum concentration of Ledipasvir can be decreased when it is combined with Calcium silicate.Experimental
CanagliflozinThe serum concentration of Ledipasvir can be increased when it is combined with Canagliflozin.Approved
Candesartan cilexetilThe serum concentration of Ledipasvir can be increased when it is combined with Candesartan.Approved
CaptoprilThe serum concentration of Ledipasvir can be increased when it is combined with Captopril.Approved
CarbamazepineThe serum concentration of Ledipasvir can be increased when it is combined with Carbamazepine.Approved, Investigational
CarvedilolThe serum concentration of Ledipasvir can be increased when it is combined with Carvedilol.Approved, Investigational
CaspofunginThe serum concentration of Ledipasvir can be increased when it is combined with Caspofungin.Approved
ChloroquineThe serum concentration of Ledipasvir can be increased when it is combined with Chloroquine.Approved, Vet Approved
ChlorpromazineThe serum concentration of Ledipasvir can be increased when it is combined with Chlorpromazine.Approved, Vet Approved
ChlorpropamideThe serum concentration of Ledipasvir can be increased when it is combined with Chlorpropamide.Approved
ChlorprothixeneThe serum concentration of Ledipasvir can be increased when it is combined with Chlorprothixene.Approved, Investigational, Withdrawn
CholesterolThe serum concentration of Ledipasvir can be increased when it is combined with Cholesterol.Experimental, Investigational
Cholic AcidThe serum concentration of Ledipasvir can be decreased when it is combined with Cholic Acid.Approved
CilazaprilThe serum concentration of Ledipasvir can be increased when it is combined with Cilazapril.Approved
CiprofloxacinThe serum concentration of Ledipasvir can be increased when it is combined with Ciprofloxacin.Approved, Investigational
CitalopramThe serum concentration of Ledipasvir can be increased when it is combined with Citalopram.Approved
ClarithromycinThe serum concentration of Ledipasvir can be increased when it is combined with Clarithromycin.Approved
ClofazimineThe serum concentration of Ledipasvir can be increased when it is combined with Clofazimine.Approved, Investigational
ClomipramineThe serum concentration of Ledipasvir can be increased when it is combined with Clomipramine.Approved, Vet Approved
ClotrimazoleThe serum concentration of Ledipasvir can be increased when it is combined with Clotrimazole.Approved, Vet Approved
CobicistatThe serum concentration of Ledipasvir can be increased when it is combined with Cobicistat.Approved
ColchicineThe serum concentration of Ledipasvir can be increased when it is combined with Colchicine.Approved
ColforsinThe serum concentration of Ledipasvir can be increased when it is combined with Colforsin.Experimental, Investigational
CrizotinibThe serum concentration of Ledipasvir can be increased when it is combined with Crizotinib.Approved
CyclophosphamideThe serum concentration of Ledipasvir can be increased when it is combined with Cyclophosphamide.Approved, Investigational
CyclosporineThe serum concentration of Ledipasvir can be increased when it is combined with Cyclosporine.Approved, Investigational, Vet Approved
DaclatasvirThe serum concentration of Ledipasvir can be increased when it is combined with Daclatasvir.Approved
DactinomycinThe serum concentration of Ledipasvir can be increased when it is combined with Dactinomycin.Approved
DasatinibThe serum concentration of Ledipasvir can be increased when it is combined with Dasatinib.Approved, Investigational
DaunorubicinThe serum concentration of Ledipasvir can be increased when it is combined with Daunorubicin.Approved
DesipramineThe serum concentration of Ledipasvir can be increased when it is combined with Desipramine.Approved
DesloratadineThe serum concentration of Ledipasvir can be increased when it is combined with Desloratadine.Approved, Investigational
DexamethasoneThe serum concentration of Ledipasvir can be increased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DexlansoprazoleThe serum concentration of Ledipasvir can be decreased when it is combined with Dexlansoprazole.Approved
DexrabeprazoleThe serum concentration of Ledipasvir can be decreased when it is combined with Dexrabeprazole.Experimental
DextromethorphanThe serum concentration of Ledipasvir can be increased when it is combined with Dextromethorphan.Approved
DiclofenacThe serum concentration of Ledipasvir can be increased when it is combined with Diclofenac.Approved, Vet Approved
DigoxinThe serum concentration of Ledipasvir can be increased when it is combined with Digoxin.Approved
DihydroergotamineThe serum concentration of Ledipasvir can be increased when it is combined with Dihydroergotamine.Approved
DiltiazemThe serum concentration of Ledipasvir can be increased when it is combined with Diltiazem.Approved
DipyridamoleThe serum concentration of Ledipasvir can be increased when it is combined with Dipyridamole.Approved
DoxazosinThe serum concentration of Ledipasvir can be increased when it is combined with Doxazosin.Approved
DoxepinThe serum concentration of Ledipasvir can be decreased when it is combined with Doxepin.Approved
DoxorubicinThe serum concentration of Ledipasvir can be increased when it is combined with Doxorubicin.Approved, Investigational
DronabinolThe serum concentration of Ledipasvir can be increased when it is combined with Dronabinol.Approved, Illicit
DronedaroneThe serum concentration of Ledipasvir can be increased when it is combined with Dronedarone.Approved
ElbasvirThe serum concentration of Ledipasvir can be increased when it is combined with Elbasvir.Approved
EnalaprilThe serum concentration of Ledipasvir can be increased when it is combined with Enalapril.Approved, Vet Approved
EnasidenibThe serum concentration of Ledipasvir can be increased when it is combined with Enasidenib.Approved
EnzalutamideThe serum concentration of Ledipasvir can be increased when it is combined with Enzalutamide.Approved
EpinastineThe serum concentration of Ledipasvir can be decreased when it is combined with Epinastine.Approved, Investigational
ErgonovineThe serum concentration of Ledipasvir can be increased when it is combined with Ergonovine.Approved
ErgotamineThe serum concentration of Ledipasvir can be increased when it is combined with Ergotamine.Approved
ErythromycinThe serum concentration of Ledipasvir can be increased when it is combined with Erythromycin.Approved, Vet Approved
EsomeprazoleThe serum concentration of Ledipasvir can be decreased when it is combined with Esomeprazole.Approved, Investigational
EstramustineThe serum concentration of Ledipasvir can be increased when it is combined with Estramustine.Approved
EstriolThe serum concentration of Ledipasvir can be decreased when it is combined with Estriol.Approved, Investigational, Vet Approved
EstroneThe serum concentration of Ledipasvir can be decreased when it is combined with Estrone.Approved
EtoposideThe serum concentration of Ledipasvir can be increased when it is combined with Etoposide.Approved
EtravirineThe serum concentration of Ledipasvir can be increased when it is combined with Etravirine.Approved
FamotidineThe serum concentration of Ledipasvir can be decreased when it is combined with Famotidine.Approved
FelodipineThe serum concentration of Ledipasvir can be increased when it is combined with Felodipine.Approved, Investigational
FentanylThe serum concentration of Ledipasvir can be increased when it is combined with Fentanyl.Approved, Illicit, Investigational, Vet Approved
FexofenadineThe serum concentration of Ledipasvir can be increased when it is combined with Fexofenadine.Approved
FidaxomicinThe serum concentration of Ledipasvir can be increased when it is combined with Fidaxomicin.Approved
FluconazoleThe serum concentration of Ledipasvir can be increased when it is combined with Fluconazole.Approved
FluoxetineThe serum concentration of Ledipasvir can be increased when it is combined with Fluoxetine.Approved, Vet Approved
FlupentixolThe serum concentration of Ledipasvir can be increased when it is combined with Flupentixol.Approved, Withdrawn
FluphenazineThe serum concentration of Ledipasvir can be increased when it is combined with Fluphenazine.Approved
FlurazepamThe serum concentration of Ledipasvir can be increased when it is combined with Flurazepam.Approved, Illicit
FluvoxamineThe serum concentration of Ledipasvir can be increased when it is combined with Fluvoxamine.Approved, Investigational
GefitinibThe serum concentration of Ledipasvir can be increased when it is combined with Gefitinib.Approved, Investigational
GenisteinThe serum concentration of Ledipasvir can be increased when it is combined with Genistein.Investigational
GlecaprevirThe serum concentration of Ledipasvir can be increased when it is combined with Glecaprevir.Approved
GlyburideThe serum concentration of Ledipasvir can be increased when it is combined with Glyburide.Approved
GlycerinThe serum concentration of Ledipasvir can be increased when it is combined with Glycerin.Approved, Investigational
Gramicidin DThe serum concentration of Ledipasvir can be increased when it is combined with Gramicidin D.Approved
GrepafloxacinThe serum concentration of Ledipasvir can be increased when it is combined with Grepafloxacin.Investigational, Withdrawn
HaloperidolThe serum concentration of Ledipasvir can be increased when it is combined with Haloperidol.Approved
HydrocortisoneThe serum concentration of Ledipasvir can be increased when it is combined with Hydrocortisone.Approved, Vet Approved
HydrotalciteThe serum concentration of Ledipasvir can be decreased when it is combined with Hydrotalcite.Experimental, Investigational
IdelalisibThe serum concentration of Ledipasvir can be increased when it is combined with Idelalisib.Approved
ImatinibThe serum concentration of Ledipasvir can be increased when it is combined with Imatinib.Approved
ImipramineThe serum concentration of Ledipasvir can be increased when it is combined with Imipramine.Approved
IndinavirThe serum concentration of Ledipasvir can be increased when it is combined with Indinavir.Approved
IndomethacinThe serum concentration of Ledipasvir can be increased when it is combined with Indomethacin.Approved, Investigational
IsavuconazoniumThe serum concentration of Ledipasvir can be increased when it is combined with Isavuconazonium.Approved, Investigational
ItraconazoleThe serum concentration of Ledipasvir can be increased when it is combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Ledipasvir can be increased when it is combined with Ivacaftor.Approved
IvermectinThe serum concentration of Ledipasvir can be increased when it is combined with Ivermectin.Approved, Vet Approved
KetamineThe serum concentration of Ledipasvir can be increased when it is combined with Ketamine.Approved, Vet Approved
KetoconazoleThe serum concentration of Ledipasvir can be increased when it is combined with Ketoconazole.Approved, Investigational
LansoprazoleThe serum concentration of Ledipasvir can be decreased when it is combined with Lansoprazole.Approved, Investigational
LapatinibThe serum concentration of Ledipasvir can be increased when it is combined with Lapatinib.Approved, Investigational
LevofloxacinThe serum concentration of Ledipasvir can be increased when it is combined with Levofloxacin.Approved, Investigational
LevothyroxineThe serum concentration of Ledipasvir can be decreased when it is combined with Levothyroxine.Approved
LidocaineThe serum concentration of Ledipasvir can be increased when it is combined with Lidocaine.Approved, Vet Approved
LiothyronineThe serum concentration of Ledipasvir can be decreased when it is combined with Liothyronine.Approved, Vet Approved
LiotrixThe serum concentration of Ledipasvir can be decreased when it is combined with Liotrix.Approved
LisinoprilThe serum concentration of Ledipasvir can be increased when it is combined with Lisinopril.Approved, Investigational
LomitapideThe serum concentration of Ledipasvir can be increased when it is combined with Lomitapide.Approved
LoperamideThe serum concentration of Ledipasvir can be increased when it is combined with Loperamide.Approved
LopinavirThe serum concentration of Ledipasvir can be increased when it is combined with Lopinavir.Approved
LoratadineThe serum concentration of Ledipasvir can be increased when it is combined with Loratadine.Approved
LosartanThe serum concentration of Ledipasvir can be increased when it is combined with Losartan.Approved
LovastatinThe serum concentration of Ledipasvir can be increased when it is combined with Lovastatin.Approved, Investigational
LumacaftorThe serum concentration of Ledipasvir can be increased when it is combined with Lumacaftor.Approved
MagaldrateThe serum concentration of Ledipasvir can be decreased when it is combined with Magaldrate.Approved, Withdrawn
Magnesium HydroxideThe serum concentration of Ledipasvir can be decreased when it is combined with Magnesium Hydroxide.Approved
Magnesium oxideThe serum concentration of Ledipasvir can be decreased when it is combined with Magnesium oxide.Approved
Magnesium peroxideThe serum concentration of Ledipasvir can be decreased when it is combined with Magnesium peroxide.Experimental
Magnesium silicateThe serum concentration of Ledipasvir can be decreased when it is combined with Magnesium silicate.Approved, Experimental
Magnesium TrisilicateThe serum concentration of Ledipasvir can be decreased when it is combined with Magnesium Trisilicate.Approved
MaprotilineThe serum concentration of Ledipasvir can be increased when it is combined with Maprotiline.Approved
MebendazoleThe serum concentration of Ledipasvir can be increased when it is combined with Mebendazole.Approved, Vet Approved
MefloquineThe serum concentration of Ledipasvir can be increased when it is combined with Mefloquine.Approved
Megestrol acetateThe serum concentration of Ledipasvir can be increased when it is combined with Megestrol acetate.Approved, Vet Approved
MeprobamateThe serum concentration of Ledipasvir can be increased when it is combined with Meprobamate.Approved, Illicit
MethadoneThe serum concentration of Ledipasvir can be increased when it is combined with Methadone.Approved
MethanthelineThe serum concentration of Ledipasvir can be decreased when it is combined with Methantheline.Approved, Investigational
MetiamideThe serum concentration of Ledipasvir can be decreased when it is combined with Metiamide.Experimental
MetoprololThe serum concentration of Ledipasvir can be increased when it is combined with Metoprolol.Approved, Investigational
MibefradilThe serum concentration of Ledipasvir can be increased when it is combined with Mibefradil.Investigational, Withdrawn
MiconazoleThe serum concentration of Ledipasvir can be increased when it is combined with Miconazole.Approved, Investigational, Vet Approved
MidazolamThe serum concentration of Ledipasvir can be increased when it is combined with Midazolam.Approved, Illicit
MifepristoneThe serum concentration of Ledipasvir can be increased when it is combined with Mifepristone.Approved, Investigational
MitomycinThe serum concentration of Ledipasvir can be increased when it is combined with Mitomycin.Approved
MitoxantroneThe serum concentration of Ledipasvir can be increased when it is combined with Mitoxantrone.Approved, Investigational
MorphineThe serum concentration of Ledipasvir can be increased when it is combined with Morphine.Approved, Investigational
NaltrexoneThe serum concentration of Ledipasvir can be increased when it is combined with Naltrexone.Approved, Investigational, Vet Approved
NaringeninThe serum concentration of Ledipasvir can be increased when it is combined with Naringenin.Experimental
NefazodoneThe serum concentration of Ledipasvir can be decreased when it is combined with Nefazodone.Approved, Withdrawn
NelfinavirThe serum concentration of Ledipasvir can be increased when it is combined with Nelfinavir.Approved
NeostigmineThe serum concentration of Ledipasvir can be increased when it is combined with Neostigmine.Approved, Vet Approved
NicardipineThe serum concentration of Ledipasvir can be increased when it is combined with Nicardipine.Approved
NifedipineThe serum concentration of Ledipasvir can be increased when it is combined with Nifedipine.Approved
NilotinibThe serum concentration of Ledipasvir can be increased when it is combined with Nilotinib.Approved, Investigational
NisoldipineThe serum concentration of Ledipasvir can be increased when it is combined with Nisoldipine.Approved
NitrazepamThe serum concentration of Ledipasvir can be increased when it is combined with Nitrazepam.Approved
NitrendipineThe serum concentration of Ledipasvir can be increased when it is combined with Nitrendipine.Approved, Investigational
NizatidineThe serum concentration of Ledipasvir can be decreased when it is combined with Nizatidine.Approved
NorethisteroneThe serum concentration of Ledipasvir can be decreased when it is combined with Norethisterone.Approved
OlanzapineThe serum concentration of Ledipasvir can be decreased when it is combined with Olanzapine.Approved, Investigational
OmeprazoleThe serum concentration of Ledipasvir can be decreased when it is combined with Omeprazole.Approved, Investigational, Vet Approved
OxcarbazepineThe serum concentration of Ledipasvir can be decreased when it is combined with Oxcarbazepine.Approved
P-NitrophenolThe serum concentration of Ledipasvir can be increased when it is combined with P-Nitrophenol.Experimental
PaclitaxelThe serum concentration of Ledipasvir can be increased when it is combined with Paclitaxel.Approved, Vet Approved
Palmitic AcidThe serum concentration of Ledipasvir can be increased when it is combined with Palmitic Acid.Approved, Experimental
PantoprazoleThe serum concentration of Ledipasvir can be decreased when it is combined with Pantoprazole.Approved
ParoxetineThe serum concentration of Ledipasvir can be increased when it is combined with Paroxetine.Approved, Investigational
PerindoprilThe serum concentration of Ledipasvir can be increased when it is combined with Perindopril.Approved
PhenobarbitalThe serum concentration of Ledipasvir can be decreased when it is combined with Phenobarbital.Approved
PibrentasvirThe serum concentration of Ledipasvir can be increased when it is combined with Pibrentasvir.Approved
PimozideThe serum concentration of Ledipasvir can be increased when it is combined with Pimozide.Approved
Platelet Activating FactorThe serum concentration of Ledipasvir can be decreased when it is combined with Platelet Activating Factor.Experimental
PonatinibThe serum concentration of Ledipasvir can be increased when it is combined with Ponatinib.Approved
PosaconazoleThe serum concentration of Ledipasvir can be increased when it is combined with Posaconazole.Approved, Investigational, Vet Approved
PravastatinThe serum concentration of Ledipasvir can be increased when it is combined with Pravastatin.Approved
PrazosinThe serum concentration of Ledipasvir can be increased when it is combined with Prazosin.Approved
PrednisoneThe serum concentration of Ledipasvir can be increased when it is combined with Prednisone.Approved, Vet Approved
ProbenecidThe serum concentration of Ledipasvir can be increased when it is combined with Probenecid.Approved
ProgesteroneThe serum concentration of Ledipasvir can be increased when it is combined with Progesterone.Approved, Vet Approved
PromethazineThe serum concentration of Ledipasvir can be decreased when it is combined with Promethazine.Approved
PropafenoneThe serum concentration of Ledipasvir can be increased when it is combined with Propafenone.Approved
PropranololThe serum concentration of Ledipasvir can be increased when it is combined with Propranolol.Approved, Investigational
ProtriptylineThe serum concentration of Ledipasvir can be increased when it is combined with Protriptyline.Approved
QuercetinThe serum concentration of Ledipasvir can be increased when it is combined with Quercetin.Experimental, Investigational
QuinacrineThe serum concentration of Ledipasvir can be increased when it is combined with Quinacrine.Approved, Investigational
QuinidineThe serum concentration of Ledipasvir can be increased when it is combined with Quinidine.Approved
QuinineThe serum concentration of Ledipasvir can be increased when it is combined with Quinine.Approved
RabeprazoleThe serum concentration of Ledipasvir can be decreased when it is combined with Rabeprazole.Approved, Investigational
RanitidineThe serum concentration of Ledipasvir can be decreased when it is combined with Ranitidine.Approved
ReboxetineThe serum concentration of Ledipasvir can be increased when it is combined with Reboxetine.Approved, Investigational
RegorafenibThe serum concentration of Ledipasvir can be increased when it is combined with Regorafenib.Approved
ReserpineThe serum concentration of Ledipasvir can be increased when it is combined with Reserpine.Approved, Investigational
RifabutinThe serum concentration of Ledipasvir can be decreased when it is combined with Rifabutin.Approved
RifampicinThe serum concentration of Ledipasvir can be increased when it is combined with Rifampicin.Approved
RifapentineThe serum concentration of Ledipasvir can be decreased when it is combined with Rifapentine.Approved
RilpivirineThe serum concentration of Ledipasvir can be increased when it is combined with Rilpivirine.Approved
RitonavirThe serum concentration of Ledipasvir can be increased when it is combined with Ritonavir.Approved, Investigational
RolapitantThe serum concentration of Ledipasvir can be increased when it is combined with Rolapitant.Approved
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Ledipasvir.Approved
Roxatidine acetateThe serum concentration of Ledipasvir can be decreased when it is combined with Roxatidine acetate.Approved, Investigational
SaquinavirThe serum concentration of Ledipasvir can be increased when it is combined with Saquinavir.Approved, Investigational
ScopolamineThe serum concentration of Ledipasvir can be increased when it is combined with Scopolamine.Approved
SelegilineThe serum concentration of Ledipasvir can be increased when it is combined with Selegiline.Approved, Investigational, Vet Approved
SertralineThe serum concentration of Ledipasvir can be increased when it is combined with Sertraline.Approved
SimeprevirThe serum concentration of Ledipasvir can be increased when it is combined with Simeprevir.Approved
SimvastatinThe serum concentration of Ledipasvir can be increased when it is combined with Simvastatin.Approved
SirolimusThe serum concentration of Ledipasvir can be increased when it is combined with Sirolimus.Approved, Investigational
SorafenibThe serum concentration of Ledipasvir can be increased when it is combined with Sorafenib.Approved, Investigational
SpironolactoneThe serum concentration of Ledipasvir can be increased when it is combined with Spironolactone.Approved
St. John's WortThe serum concentration of Ledipasvir can be decreased when it is combined with St. John's Wort.Investigational, Nutraceutical
StaurosporineThe serum concentration of Ledipasvir can be increased when it is combined with Staurosporine.Experimental
StreptozocinThe serum concentration of Ledipasvir can be decreased when it is combined with Streptozocin.Approved
SulfinpyrazoneThe serum concentration of Ledipasvir can be increased when it is combined with Sulfinpyrazone.Approved
SumatriptanThe serum concentration of Ledipasvir can be increased when it is combined with Sumatriptan.Approved, Investigational
SunitinibThe serum concentration of Ledipasvir can be increased when it is combined with Sunitinib.Approved, Investigational
TacrineThe serum concentration of Ledipasvir can be increased when it is combined with Tacrine.Investigational, Withdrawn
TacrolimusThe serum concentration of Ledipasvir can be increased when it is combined with Tacrolimus.Approved, Investigational
TamoxifenThe serum concentration of Ledipasvir can be increased when it is combined with Tamoxifen.Approved
Taurocholic AcidThe serum concentration of Ledipasvir can be increased when it is combined with Taurocholic Acid.Experimental
TelaprevirThe serum concentration of Ledipasvir can be increased when it is combined with Telaprevir.Approved, Withdrawn
TelmisartanThe serum concentration of Ledipasvir can be increased when it is combined with Telmisartan.Approved, Investigational
TemsirolimusThe serum concentration of Ledipasvir can be increased when it is combined with Temsirolimus.Approved
Tenofovir disoproxilThe serum concentration of Tenofovir disoproxil can be increased when it is combined with Ledipasvir.Approved, Investigational
TerazosinThe serum concentration of Ledipasvir can be increased when it is combined with Terazosin.Approved
TerfenadineThe serum concentration of Ledipasvir can be increased when it is combined with Terfenadine.Withdrawn
TesmilifeneThe serum concentration of Ledipasvir can be decreased when it is combined with Tesmilifene.Investigational
TestosteroneThe serum concentration of Ledipasvir can be increased when it is combined with Testosterone.Approved, Investigational
TicagrelorThe serum concentration of Ledipasvir can be increased when it is combined with Ticagrelor.Approved
TolvaptanThe serum concentration of Ledipasvir can be increased when it is combined with Tolvaptan.Approved
TrazodoneThe serum concentration of Ledipasvir can be decreased when it is combined with Trazodone.Approved, Investigational
TrifluoperazineThe serum concentration of Ledipasvir can be increased when it is combined with Trifluoperazine.Approved
TriflupromazineThe serum concentration of Ledipasvir can be increased when it is combined with Triflupromazine.Approved, Vet Approved
TrimethoprimThe serum concentration of Ledipasvir can be increased when it is combined with Trimethoprim.Approved, Vet Approved
TrimipramineThe serum concentration of Ledipasvir can be increased when it is combined with Trimipramine.Approved
TroleandomycinThe serum concentration of Ledipasvir can be increased when it is combined with Troleandomycin.Approved
VelpatasvirThe serum concentration of Ledipasvir can be increased when it is combined with Velpatasvir.Approved
VenlafaxineThe serum concentration of Ledipasvir can be increased when it is combined with Venlafaxine.Approved
VerapamilThe serum concentration of Ledipasvir can be increased when it is combined with Verapamil.Approved
VinblastineThe serum concentration of Ledipasvir can be increased when it is combined with Vinblastine.Approved
VincristineThe serum concentration of Ledipasvir can be increased when it is combined with Vincristine.Approved, Investigational
VinorelbineThe serum concentration of Ledipasvir can be increased when it is combined with Vinorelbine.Approved, Investigational
VoxilaprevirThe serum concentration of Ledipasvir can be increased when it is combined with Voxilaprevir.Approved
ZimelidineThe serum concentration of Ledipasvir can be increased when it is combined with Zimelidine.Withdrawn
Food Interactions
Not Available

References

Synthesis Reference

Henderson JA, Bilimoria D, Bubenik M, Cadilhac C, Cottrell KM, Denis F, Dietrich E, Ewing N, Falardeau G, Giroux S, L'Heureux L, Liu B, Mani N, Morris M, Nicolas O, Pereira OZ, Poisson C, Reddy TJ, Selliah S, Shawgo RS, Vaillancourt L, Wang J, Xu J, Chauret N, Berlioz-Seux F, Chan LC, Das SK, Grillot AL, Bennani YL, Maxwell JP: Synthesis and evaluation of NS5A inhibitors containing diverse heteroaromatic cores. Bioorg Med Chem Lett. 2015 Feb 15;25(4):948-51. doi: 10.1016/j.bmcl.2014.12.042. Epub 2014 Dec 22. Pubmed

General References
  1. Kumari R, Nguyen MH: Fixed-dose combination of sofosbuvir and ledipasvir for the treatment of chronic hepatitis C genotype 1. Expert Opin Pharmacother. 2015 Apr;16(5):739-48. doi: 10.1517/14656566.2015.1013938. Epub 2015 Feb 13. [PubMed:25676581]
  2. Younossi ZM, Stepanova M, Marcellin P, Afdhal N, Kowdley KV, Zeuzem S, Hunt SL: Treatment with ledipasvir and sofosbuvir improves patient-reported outcomes: Results from the ION-1, -2, and -3 clinical trials. Hepatology. 2015 Jun;61(6):1798-808. doi: 10.1002/hep.27724. Epub 2015 Mar 18. [PubMed:25627448]
  3. Waheed Y: Ledipasvir and sofosbuvir: Interferon free therapy for hepatitis C virus genotype 1 infection. World J Virol. 2015 Feb 12;4(1):33-5. doi: 10.5501/wjv.v4.i1.33. [PubMed:25674516]
  4. Osinusi A, Townsend K, Kohli A, Nelson A, Seamon C, Meissner EG, Bon D, Silk R, Gross C, Price A, Sajadi M, Sidharthan S, Sims Z, Herrmann E, Hogan J, Teferi G, Talwani R, Proschan M, Jenkins V, Kleiner DE, Wood BJ, Subramanian GM, Pang PS, McHutchison JG, Polis MA, Fauci AS, Masur H, Kottilil S: Virologic response following combined ledipasvir and sofosbuvir administration in patients with HCV genotype 1 and HIV co-infection. JAMA. 2015 Mar 24-31;313(12):1232-9. doi: 10.1001/jama.2015.1373. [PubMed:25706232]
  5. Naggie S, Cooper C, Saag M, Workowski K, Ruane P, Towner WJ, Marks K, Luetkemeyer A, Baden RP, Sax PE, Gane E, Santana-Bagur J, Stamm LM, Yang JC, German P, Dvory-Sobol H, Ni L, Pang PS, McHutchison JG, Stedman CA, Morales-Ramirez JO, Brau N, Jayaweera D, Colson AE, Tebas P, Wong DK, Dieterich D, Sulkowski M: Ledipasvir and Sofosbuvir for HCV in Patients Coinfected with HIV-1. N Engl J Med. 2015 Aug 20;373(8):705-13. doi: 10.1056/NEJMoa1501315. Epub 2015 Jul 21. [PubMed:26196665]
  6. Myers RP, Shah H, Burak KW, Cooper C, Feld JJ: An update on the management of chronic hepatitis C: 2015 Consensus guidelines from the Canadian Association for the Study of the Liver. Can J Gastroenterol Hepatol. 2015 Jan-Feb;29(1):19-34. Epub 2015 Jan 13. [PubMed:25585348]
  7. Dusheiko G: Side effects of alpha interferon in chronic hepatitis C. Hepatology. 1997 Sep;26(3 Suppl 1):112S-121S. [PubMed:9305675]
  8. Bagaglio S, Uberti-Foppa C, Morsica G: Resistance Mechanisms in Hepatitis C Virus: implications for Direct-Acting Antiviral Use. Drugs. 2017 May 12. doi: 10.1007/s40265-017-0753-x. [PubMed:28497432]
  9. American Association for the Study of Liver Diseases; Infectious Diseases Society of America. HCV guidance. http://hcvguidelines.org. Accessed June 12, 2017. [Link]
External Links
KEGG Drug
D10442
PubChem Compound
67505836
PubChem Substance
310264981
ChemSpider
29271894
ChEBI
85089
ChEMBL
CHEMBL2374220
PharmGKB
PA166128166
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Ledipasvir
ATC Codes
J05AX65 — Sofosbuvir and ledipasvir
FDA label
Download (486 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedPreventionChronic Hepatitis C Virus (HCV) Infection1
1CompletedNot AvailableHealthy Volunteers1
1CompletedTreatmentHCV Infections1
1CompletedTreatmentHepatitis / Infection, Human Immunodeficiency Virus I1
1RecruitingTreatmentChronic Hepatitis C Infection / Pregnancy1
2Active Not RecruitingTreatmentChronic Hepatitis C Infection / Human Immunodeficiency Virus (HIV) Infections1
2CompletedNot AvailableHepatitis C, Chronic1
2CompletedTreatmentChronic Genotype 1a or 1b HCV Infection1
2CompletedTreatmentChronic Genotype 4 HCV / Chronic Genotype 5 HCV1
2CompletedTreatmentChronic HCV Infection4
2CompletedTreatmentChronic Hepatitis C Infection4
2CompletedTreatmentChronic Hepatitis C Infection / Human Immunodeficiency Virus (HIV)1
2CompletedTreatmentChronic Hepatitis C Infection / Infection, Human Immunodeficiency Virus I1
2CompletedTreatmentChronic Hepatitis C Virus1
2CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection2
2CompletedTreatmentHCV Infections3
2CompletedTreatmentHepatitis C Infection With HIV Co-Infection1
2CompletedTreatmentHepatitis C Virus Infection6
2CompletedTreatmentHepatitis C, Chronic4
2CompletedTreatmentTreatment of Hepatitis C1
2Not Yet RecruitingTreatmentIndolent Lymphoma1
2Not Yet RecruitingTreatmentViral Hepatitis B1
2RecruitingTreatmentChronic Hepatitis C Infection1
2RecruitingTreatmentChronic Hepatitis C Infection / Indolent B-cell Lymphoma1
2RecruitingTreatmentChronic Hepatitis C Infection / Porphyria Cutanea Tarda1
2RecruitingTreatmentChronic Hepatitis C Virus (HCV) Infection1
2RecruitingTreatmentHepatitis C Virus Infection2
2TerminatedTreatmentChronic Hepatitis C Virus (HCV) Infection1
2, 3RecruitingTreatmentChronic Hepatitis C Infection / Cryoglobulinemia1
2, 3RecruitingTreatmentChronic Hepatitis C Infection / HBV Coinfection / Hepatitis B Reactivation1
3Active Not RecruitingTreatmentChronic Hepatitis C Infection / Liver Cirrhosis1
3Active Not RecruitingTreatmentHepatitis C Virus Infection2
3Active Not RecruitingTreatmentHepatitis C, Chronic / Human Immunodeficiency Virus (HIV)1
3CompletedTreatmentChronic HCV Infection2
3CompletedTreatmentChronic Hepatitis C Virus3
3CompletedTreatmentHCV Infections / Infection, Human Immunodeficiency Virus I1
3CompletedTreatmentHepatitis C Infection1
3CompletedTreatmentHepatitis C Virus (HCV) / Human Immunodeficiency Virus (HIV)1
3CompletedTreatmentHepatitis C Virus Infection2
3Enrolling by InvitationTreatmentCirrhosis, Decompensated / Hepatitis C, Chronic1
3RecruitingTreatmentChronic Hepatitis C Infection1
3RecruitingTreatmentHepatitis C, Chronic / Hepatocellular,Carcinoma1
3TerminatedTreatmentHepatitis C Viral Infection1
4Active Not RecruitingTreatmentChronic Hepatitis C Infection1
4Active Not RecruitingTreatmentHCV HIV1
4CompletedTreatmentChronic Hepatitis C Infection1
4CompletedTreatmentPT-NANBH1
4RecruitingTreatmentChronic Hepatitis C Infection1
4RecruitingTreatmentChronic Hepatitis C Infection / HCV1
4RecruitingTreatmentChronic Hepatitis C Infection / Human Immunodeficiency Virus (HIV)1
4RecruitingTreatmentChronic Hepatitis C Infection / Human Immunodeficiency Virus (HIV) / Liver Cirrhosis1
4RecruitingTreatmentChronic Hepatitis C Virus (HCV) Infection3
4RecruitingTreatmentGenotype 1 Hepatitis C Virus1
4RecruitingTreatmentHeart Failure, Unspecified / Hepatitis C, Chronic / Lung Diseases, Interstitial / Pulmonary Disease, Chronic Obstructive1
4RecruitingTreatmentHematopoietic Stem Cell Transplantation (HSCT)1
4TerminatedTreatmentLiver Diseases1
Not AvailableActive Not RecruitingNot AvailableChronic Hepatitis C Infection1
Not AvailableActive Not RecruitingNot AvailableChronic Hepatitis C Virus (HCV) Infection / Liver Cirrhosis1
Not AvailableCompletedNot AvailableChronic Hepatitis C (Disorder)1
Not AvailableEnrolling by InvitationNot AvailableChronic Hepatitis C Infection1
Not AvailableEnrolling by InvitationNot AvailableHepatitis C Virus Infection1
Not AvailableNot Yet RecruitingTreatmentChronic Hepatitis C Infection1
Not AvailableRecruitingNot AvailableChronic Hepatitis C Infection1
Not AvailableRecruitingNot AvailableHepatitis C Virus (HCV)1
Not AvailableRecruitingNot AvailableHepatitis C, Chronic / Human Immunodeficiency Virus (HIV)1
Not AvailableRecruitingBasic ScienceInsulin Resistance1
Not AvailableRecruitingScreeningHepatitis C, Chronic1
Not AvailableRecruitingTreatmentChronic Hepatitis C Infection / Chronic Kidney Disease (CKD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral
Tablet, film coatedOral
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8841278No2010-05-122030-05-12Us
US7964580No2009-03-262029-03-26Us
US8334270No2008-03-212028-03-21Us
US8822430No2010-05-122030-05-12Us
US8633309No2009-03-262029-03-26Us
US8273341No2010-05-122030-05-12Us
US8618076No2010-12-112030-12-11Us
US8735372No2008-03-212028-03-21Us
US8580765No2008-03-212028-03-21Us
US8889159No2009-03-262029-03-26Us
US9085573No2008-03-212028-03-21Us
US9284342No2010-09-132030-09-13Us
US8088368No2010-05-122030-05-12Us
US9393256No2012-09-142032-09-14Us
US9511056No2010-05-122030-05-12Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP3.8FDA Label
pKapka1 = 4.0, pka2 = 5.0FDA Label
Predicted Properties
PropertyValueSource
Water Solubility0.00182 mg/mLALOGPS
logP5.92ALOGPS
logP6.11ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)3.76ChemAxon
pKa (Strongest Basic)5.85ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area181.62 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity237.3 m3·mol-1ChemAxon
Polarizability98.91 Å3ChemAxon
Number of Rings10ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as fluorenes. These are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Fluorenes
Sub Class
Not Available
Direct Parent
Fluorenes
Alternative Parents
Valine and derivatives / Alpha amino acid amides / Benzimidazoles / N-acylpiperidines / N-acylpyrrolidines / Tertiary carboxylic acid amides / Heteroaromatic compounds / Methylcarbamates / Imidazoles / Organic carbonic acids and derivatives
show 8 more
Substituents
Fluorene / Valine or derivatives / Alpha-amino acid amide / Alpha-amino acid or derivatives / N-acyl-piperidine / Benzimidazole / N-acylpyrrolidine / Piperidine / Heteroaromatic compound / Methylcarbamate
show 23 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organofluorine compound, carbamate ester, imidazoles, N-acylpyrrolidine, bridged compound, ring assembly, fluorenes, carboxamide, L-valine derivative, benzimidazole, azaspiro compound (CHEBI:85089)

Targets

Kind
Protein
Organism
Hepatitis C virus
Pharmacological action
Yes
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Not Available
Gene Name
NS5A
Uniprot ID
Q5L478
Uniprot Name
Nonstructural protein 5A
Molecular Weight
48598.34 Da

Transporters

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Transporter
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Transporter
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

Drug created on November 26, 2014 16:19 / Updated on November 09, 2017 04:44