Identification

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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 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 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 Label. Its use has also proven successful in the treatment of HCV in patients co-infected with HIV 5.

Structure
Thumb
Synonyms
  • Ledipasvir
  • 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 (45 mg/1) + Sofosbuvir (200 mg/1)Tablet, film coatedOralGilead Sciences, Inc2019-08-28Not applicableUs
HarvoniLedipasvir (90 mg/1) + Sofosbuvir (400 mg/1)Tablet, film coatedOralGilead Sciences, Inc2014-10-10Not applicableUs
HarvoniLedipasvir (90 mg) + Sofosbuvir (400 mg)TabletOralGilead Sciences2014-10-16Not applicableCanada
HarvoniLedipasvir (45 mg/1) + Sofosbuvir (200 mg/1)PelletOralGilead Sciences, Inc2019-08-28Not applicableUs
HarvoniLedipasvir (33.75 mg/1) + Sofosbuvir (150 mg/1)PelletOralGilead Sciences, Inc2019-08-28Not applicableUs
Ledipasvir and SofosbuvirLedipasvir (90 mg/1) + Sofosbuvir (400 mg/1)Tablet, film coatedOralAsegua Therapeutics LLC2019-01-01Not 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
methyl N-[(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]heptan-3-yl]-1H-1,3-benzodiazol-5-yl}-9H-fluoren-2-yl)-1H-imidazol-2-yl]-5-azaspiro[2.4]heptan-5-yl]-3-methyl-1-oxobutan-2-yl]carbamate
SMILES
COC(=O)N[C@@H](C(C)C)C(=O)N1CC2(CC2)C[C@H]1C1=NC(=CN1)C1=CC=C2C3=CC=C(C=C3C(F)(F)C2=C1)C1=CC=C2NC(=NC2=C1)[C@@H]1[C@H]2CC[C@H](C2)N1C(=O)[C@@H](NC(=O)OC)C(C)C

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 Label. Its use has also proven successful in the treatment of HCV in patients co-infected with HIV 5.

Associated Conditions
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 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
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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 Label.

Volume of distribution
Not Available
Protein binding

Ledipasvir is >99.8% bound to human plasma proteins 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 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%) Label.

Half life

The median terminal half-life of ledipasvir is 47 hours 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
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
AbacavirAbacavir may decrease the excretion rate of Ledipasvir which could result in a higher serum level.
AbemaciclibThe serum concentration of Ledipasvir can be increased when it is combined with Abemaciclib.
AcarboseAcarbose may decrease the excretion rate of Ledipasvir which could result in a higher serum level.
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Ledipasvir.
AceclofenacAceclofenac may decrease the excretion rate of Ledipasvir which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Ledipasvir which could result in a higher serum level.
AcetaminophenThe serum concentration of Ledipasvir can be increased when it is combined with Acetaminophen.
AcetazolamideAcetazolamide may increase the excretion rate of Ledipasvir which could result in a lower serum level and potentially a reduction in efficacy.
AcetyldigoxinLedipasvir may decrease the excretion rate of Acetyldigoxin which could result in a higher serum level.
Acetylsalicylic acidThe serum concentration of Ledipasvir can be decreased when it is combined with Acetylsalicylic acid.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

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  • Action
    Action

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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
J05AP51 — Sofosbuvir and ledipasvir
FDA label
Download (486 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedPreventionChronic Hepatitis C Virus (HCV) Infection1
1Active Not RecruitingTreatmentHepatitis C Viral Infection / Pregnancy1
1CompletedNot AvailableHealthy Volunteers1
1CompletedOtherHealthy Volunteers1
1CompletedTreatmentHepatitis C Virus (HCV) Infection1
1CompletedTreatmentHepatitis / Human Immunodeficiency Virus Type 1 (HIV-1) Infection1
1, 2RecruitingTreatmentChronic Hepatitis C Virus (HCV) Infection / Malignancies, Hematologic1
2CompletedOtherChronic Hepatitis C Virus (HCV) Infection1
2CompletedTreatmentChronic Genotype 1a or 1b HCV Infection1
2CompletedTreatmentChronic Genotype 4 HCV / Chronic Genotype 5 HCV1
2CompletedTreatmentChronic HCV Infection4
2CompletedTreatmentChronic Hepatitis C Virus1
2CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection10
2CompletedTreatmentHepatitis C Infection With HIV Co-Infection1
2CompletedTreatmentHepatitis C Viral Infection2
2CompletedTreatmentHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV)2
2CompletedTreatmentHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentHepatitis C Virus (HCV) Infection3
2CompletedTreatmentHepatitis C Virus Infection8
2CompletedTreatmentTreatment of Hepatitis C1
2Not Yet RecruitingTreatmentIndolent Lymphoma1
2RecruitingTreatmentChronic Hepatitis C Virus (HCV) Infection1
2RecruitingTreatmentHepatitis C Viral Infection / Indolent B-cell Lymphoma1
2RecruitingTreatmentHepatitis C Viral Infection / Porphyria Cutanea Tarda1
2RecruitingTreatmentViral Hepatitis B1
2TerminatedTreatmentChronic Hepatitis C Virus (HCV) Infection1
2TerminatedTreatmentHepatitis C Viral Infection / Human Immunodeficiency Virus Type 1 (HIV-1) Infection1
2, 3RecruitingTreatmentChronic Hepatitis C Virus (HCV) Infection / HBV Coinfection / Reactivation of hepatitis B virus infection1
2, 3RecruitingTreatmentCryoglobulinemia / Hepatitis C Viral Infection1
3Active Not RecruitingTreatmentChronic Hepatitis C Virus (HCV) Infection / Human Immunodeficiency Virus (HIV)1
3CompletedTreatmentChronic HCV Infection2
3CompletedTreatmentChronic Hepatitis C Virus3
3CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection1
3CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection / Cirrhosis, Decompensated1
3CompletedTreatmentHepatitis C Infection / Hepatitis C Virus Infection1
3CompletedTreatmentHepatitis C Viral Infection / Liver Cirrhosis1
3CompletedTreatmentHepatitis C Virus (HCV) Infection / Human Immunodeficiency Virus (HIV)1
3CompletedTreatmentHepatitis C Virus (HCV) Infection / Human Immunodeficiency Virus Type 1 (HIV-1) Infection1
3CompletedTreatmentHepatitis C Virus Infection3
3Enrolling by InvitationTreatmentHepatitis C Virus Infection, Response to Therapy of1
3Not Yet RecruitingTreatmentHepatitis C Viral Infection1
3RecruitingTreatmentChronic Hepatitis C Virus (HCV) Infection / Hepatocellular,Carcinoma1
3TerminatedTreatmentHepatitis C Viral Infection1
3TerminatedTreatmentHepatitis C Virus Infection1
4Active Not RecruitingTreatmentChronic Hepatitis C Virus (HCV) Infection1
4Active Not RecruitingTreatmentGenotype 1 Hepatitis C Virus1
4Active Not RecruitingTreatmentHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV) / Liver Cirrhosis1
4CompletedTreatmentBeta-Thalassemia / Hepatitis C Viral Infection1
4CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection2
4CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection / Chronic Obstructive Pulmonary Disease (COPD) / Heart Failure / Lung Diseases, Interstitial1
4CompletedTreatmentHepatitis C Infection With HIV Co-Infection1
4CompletedTreatmentHepatitis C Viral Infection3
4CompletedTreatmentHepatitis C Viral Infection / Hepatitis C Virus (HCV) Infection1
4CompletedTreatmentPT-NANBH1
4Not Yet RecruitingPreventionHepatocellular,Carcinoma1
4RecruitingBasic ScienceCardiovascular Disease (CVD) / Hepatitis C Viral Infection / Human Immunodeficiency Virus (HIV)1
4RecruitingOtherHepatitis C Viral Infection / HIV Coinfection1
4RecruitingTreatmentChronic Hepatitis C Virus (HCV) Infection1
4RecruitingTreatmentGaucher's Disease / Hepatitis C Virus (HCV) Infection1
4RecruitingTreatmentHepatitis C Genotype 41
4RecruitingTreatmentHepatitis C Viral Infection1
4TerminatedTreatmentLiver Diseases1
4WithdrawnTreatmentHematopoietic Stem Cell Transplantation (HSCT)1
Not AvailableCompletedNot AvailableChronic Hepatitis C (Disorder)1
Not AvailableCompletedNot AvailableChronic Hepatitis C Virus (HCV) Infection / Liver Cirrhosis1
Not AvailableCompletedNot AvailableHepatitis C Viral Infection1
Not AvailableCompletedNot AvailableHepatitis C Virus (HCV) Infection1
Not AvailableCompletedBasic ScienceInsulin Resistance1
Not AvailableCompletedTreatmentChronic Kidney Disease (CKD) / Hepatitis C Viral Infection1
Not AvailableEnrolling by InvitationNot AvailableHepatitis C Viral Infection1
Not AvailableEnrolling by InvitationNot AvailableHepatitis C Virus Infection1
Not AvailableNot Yet RecruitingNot AvailableAntiviral Drug1
Not AvailableRecruitingNot AvailableChronic Hepatitis C Virus (HCV) Infection1
Not AvailableRecruitingNot AvailableChronic Hepatitis C Virus (HCV) Infection / Human Immunodeficiency Virus (HIV)1
Not AvailableRecruitingNot AvailableHepatitis C Viral Infection / Substance Use Disorder (SUD)1
Not AvailableRecruitingNot AvailableHepatitis C Virus (HCV) Infection1
Not AvailableRecruitingHealth Services ResearchChronic Hepatitis C Virus (HCV) Infection1
Not AvailableRecruitingScreeningChronic Hepatitis C Virus (HCV) Infection1
Not AvailableRecruitingTreatmentHepatitis C Viral Infection1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
PelletOral
TabletOral
Tablet, film coatedOral
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8841278Yes2014-09-232030-11-12Us
US7964580Yes2011-06-212029-09-26Us
US8334270Yes2012-12-182028-09-21Us
US8822430Yes2014-09-022030-11-12Us
US8633309Yes2014-01-212029-09-26Us
US8273341Yes2012-09-252030-11-12Us
US8618076Yes2013-12-312031-06-11Us
US8735372Yes2014-05-272028-09-21Us
US8580765Yes2013-11-122028-09-21Us
US8889159Yes2014-11-182029-09-26Us
US9085573Yes2015-07-212028-09-21Us
US9284342Yes2016-03-152031-03-13Us
US8088368Yes2012-01-032030-11-12Us
US9393256Yes2016-07-192033-03-14Us
US9511056Yes2016-12-062030-11-12Us
US10039779Yes2018-08-072034-07-30Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
logP3.8FDA Label
pKapka1 = 4.0, pka2 = 5.0FDA Label
Predicted Properties
PropertyValueSource
Water Solubility0.00388 mg/mLALOGPS
logP5.98ALOGPS
logP7.18ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)11.33ChemAxon
pKa (Strongest Basic)5.29ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area174.64 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity235.47 m3·mol-1ChemAxon
Polarizability97.49 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
Humans
Pharmacological action
No
Actions
Substrate
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
References
  1. NHIVC [Link]
  2. Harvoni FDA label [File]
Kind
Protein
Organism
Humans
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 11, 2019 07:01