Ledipasvir

Identification

Summary

Ledipasvir is a direct-acting antiviral agent used to treat specific hepatitis C virus (HCV) infections in combination with other antiviral agents.

Brand Names

Harvoni

Generic Name

Ledipasvir

DrugBank Accession Number

DB09027

Background

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.

Type

Small Molecule

Groups

Approved

Structure

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MOLSDFPDBSMILESInChI

Similar Structures

Structure for Ledipasvir (DB09027)

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Weight

Average: 888.9999
Monoisotopic: 888.41343791

Chemical Formula

C₄₉H₅₄F₂N₈O₆

Synonyms

• Ledipasvir
• Lédipasvir
• Ledipasvirum

External IDs

• GS 5885
• GS-5885
• GS5885
• WHO 9796

Pharmacology

Indication

When used in combination with the antiviral medication sofosbuvir, ledipasvir is indicated for the treatment of treatment of chronic hepatitis C virus (HCV) in adults and pediatric patients 3 years of age and older with the following conditions:¹⁰

• Genotype 1, 4, 5, or 6 infection without cirrhosis or with compensated cirrhosis.
• Genotype 1 infection with decompensated cirrhosis, in combination with ribavirin.
• Genotype 1 or 4 infection who are liver transplant recipients without cirrhosis or with compensated cirrhosis, in combination with ribavirin.

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

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Associated Conditions

• Chronic Hepatitis C Genotype 1
• Chronic hepatitis C genotype 5
• Genotype 4 Chronic Hepatitis C
• Genotype 6 chronic hepatitis C infection

Contraindications & Blackbox Warnings

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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.

Target	Actions	Organism
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 ^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

Adverse Effects

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Toxicity

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

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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abacavir	Abacavir may decrease the excretion rate of Ledipasvir which could result in a higher serum level.
Abemaciclib	The serum concentration of Abemaciclib can be increased when it is combined with Ledipasvir.
Abrocitinib	The serum concentration of Ledipasvir can be increased when it is combined with Abrocitinib.
Aceclofenac	Aceclofenac may decrease the excretion rate of Ledipasvir which could result in a higher serum level.
Acemetacin	Acemetacin may decrease the excretion rate of Ledipasvir which could result in a higher serum level.
Acetaminophen	Acetaminophen may decrease the excretion rate of Ledipasvir which could result in a higher serum level.
Acetazolamide	Acetazolamide may increase the excretion rate of Ledipasvir which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acid	Acetylsalicylic acid may decrease the excretion rate of Ledipasvir which could result in a higher serum level.
Aclidinium	Aclidinium may decrease the excretion rate of Ledipasvir which could result in a higher serum level.
Acrivastine	Ledipasvir may decrease the excretion rate of Acrivastine which could result in a higher serum level.

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Food Interactions

• Avoid St. John's Wort. This herb induces PGP and may reduce the serum concentration of ledipasvir.
• Take separate from antacids. Take at least 4 hours before or after antacids.
• Take with or without food.

Products

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Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Harvoni	Ledipasvir (90 mg) + Sofosbuvir (400 mg)	Tablet, film coated	Oral	Gilead Sciences Ireland Uc	2016-09-08	Not applicable
Harvoni	Ledipasvir (33.75 mg/1) + Sofosbuvir (150 mg/1)	Pellet	Oral	Gilead Sciences, Inc	2019-08-28	Not applicable
Harvoni	Ledipasvir (90 mg) + Sofosbuvir (400 mg)	Tablet	Oral	Gilead Sciences	2014-10-16	Not applicable
Harvoni	Ledipasvir (45 mg/1) + Sofosbuvir (200 mg/1)	Tablet, film coated	Oral	Gilead Sciences, Inc	2019-08-28	Not applicable
Harvoni	Ledipasvir (45 mg) + Sofosbuvir (200 mg)	Tablet, film coated	Oral	Gilead Sciences Ireland Uc	2020-12-22	Not applicable
Harvoni	Ledipasvir (45 mg) + Sofosbuvir (200 mg)	Tablet	Oral	Gilead Sciences Ireland Uc	2020-12-22	Not applicable
Harvoni	Ledipasvir (90 mg/1) + Sofosbuvir (400 mg/1)	Tablet, film coated	Oral	Gilead Sciences, Inc	2014-10-10	Not applicable
Harvoni	Ledipasvir (45 mg/1) + Sofosbuvir (200 mg/1)	Pellet	Oral	Gilead Sciences, Inc	2019-08-28	Not applicable
Harvoni	Ledipasvir (90 mg) + Sofosbuvir (400 mg)	Tablet, film coated	Oral	Gilead Sciences Ireland Uc	2016-09-08	Not applicable
Harvoni	Ledipasvir (33.75 mg) + Sofosbuvir (150 mg)	Pellet	Oral	Gilead Sciences Ireland Uc	2020-12-22	Not applicable

Categories

ATC Codes

J05AP51 — Sofosbuvir and ledipasvir

• J05AP — Antivirals for treatment of HCV infections
• J05A — DIRECT ACTING ANTIVIRALS
• J05 — ANTIVIRALS FOR SYSTEMIC USE
• J — ANTIINFECTIVES FOR SYSTEMIC USE

Drug Categories

• Anti-Infective Agents
• Antiinfectives for Systemic Use
• Antiviral Agents
• Antivirals for Systemic Use
• Antivirals for treatment of HCV infections
• BCRP/ABCG2 Inhibitors
• Direct Acting Antivirals
• Drugs that are Mainly Renally Excreted
• Hepatitis C Virus NS5A Inhibitor
• Heterocyclic Compounds, Fused-Ring
• P-glycoprotein inhibitors
• P-glycoprotein substrates
• Treatments for Hepatitis C

Chemical TaxonomyProvided by Classyfire

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 / Azacyclic compounds / Hydrocarbon derivatives / Organic oxides / Carbonyl compounds / Organofluorides / Organonitrogen compounds / Organopnictogen compounds / Alkyl fluorides

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Substituents

Alkyl fluoride / Alkyl halide / Alpha-amino acid amide / Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzimidazole / Carbamic acid ester / Carbonic acid derivative / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Fluorene / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / Methylcarbamate / N-acyl-piperidine / N-acylpyrrolidine / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organofluoride / Organohalogen compound / Organoheterocyclic compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Piperidine / Pyrrolidine / Tertiary carboxylic acid amide / Valine or derivatives

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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)

Affected organisms

• Hepatitis C Virus

Chemical Identifiers

UNII

013TE6E4WV

CAS number

1256388-51-8

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

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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
7. Dusheiko G: Side effects of alpha interferon in chronic hepatitis C. Hepatology. 1997 Sep;26(3 Suppl 1):112S-121S. [Article]
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. [Article]
9. American Association for the Study of Liver Diseases; Infectious Diseases Society of America. HCV guidance. http://hcvguidelines.org. Accessed June 12, 2017. [Link]
10. FDA Approved Drug Products: Harvoni (Ledipasvir and Sofosbuvir) tablets or pellets for oral use [Link]

External Links

KEGG Drug

D10442

PubChem Compound

67505836

PubChem Substance

310264981

ChemSpider

29271894

RxNav

1591922

ChEBI

85089

ChEMBL

CHEMBL2374220

ZINC

ZINC000150338819

PharmGKB

PA166128166

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

Wikipedia

Ledipasvir

FDA label

Download (486 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Completed	Basic Science	Cardiovascular Disease (CVD) / Hepatitis C Virus (HCV) Infection / Human Immunodeficiency Virus (HIV) Infections	1
4	Completed	Other	Coinfection, HIV / Hepatitis C Virus (HCV) Infection	1
4	Completed	Treatment	Beta-Thalassemia / Hepatitis C Virus (HCV) Infection	1
4	Completed	Treatment	Chronic Hepatitis C Virus (HCV) Infection	3
4	Completed	Treatment	Chronic Hepatitis C Virus (HCV) Infection / Chronic Obstructive Pulmonary Disease (COPD) / Heart Failure / Interstitial Lung Disease	1
4	Completed	Treatment	Cirrhosis of the Liver / Hepatitis C Virus (HCV) Infection / Human Immunodeficiency Virus (HIV) Infections	1
4	Completed	Treatment	Coronavirus Disease 2019 (COVID‑19) / COVID	1
4	Completed	Treatment	Genotype 1 Hepatitis C Virus	1
4	Completed	Treatment	Hepatitis C Infection With HIV Co-Infection	1
4	Completed	Treatment	Hepatitis C Virus (HCV) Infection	4

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Granule	Oral
Pellet	Oral
Tablet	Oral
Tablet, coated	Oral
Tablet, film coated	Oral
Tablet, film coated	Oral	90 mg

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US8841278	Yes	2014-09-23	2030-11-12
US7964580	Yes	2011-06-21	2029-09-26
US8334270	Yes	2012-12-18	2028-09-21
US8822430	Yes	2014-09-02	2030-11-12
US8633309	Yes	2014-01-21	2029-09-26
US8273341	Yes	2012-09-25	2030-11-12
US8618076	Yes	2013-12-31	2031-06-11
US8735372	Yes	2014-05-27	2028-09-21
US8580765	Yes	2013-11-12	2028-09-21
US8889159	Yes	2014-11-18	2029-09-26
US9085573	Yes	2015-07-21	2028-09-21
US9284342	Yes	2016-03-15	2031-03-13
US8088368	Yes	2012-01-03	2030-11-12
US9393256	Yes	2016-07-19	2033-03-14
US9511056	Yes	2016-12-06	2030-11-12
US10039779	Yes	2018-08-07	2034-07-30
US10456414	No	2019-10-29	2032-09-14

Properties

State

Solid

Experimental Properties

Property	Value	Source
logP	3.8	FDA Label
pKa	pka1 = 4.0, pka2 = 5.0	FDA Label

Predicted Properties

Property	Value	Source
Water Solubility	0.00388 mg/mL	ALOGPS
logP	5.98	ALOGPS
logP	7.18	Chemaxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	11.33	Chemaxon
pKa (Strongest Basic)	5.29	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	6	Chemaxon
Hydrogen Donor Count	4	Chemaxon
Polar Surface Area	174.64 Å2	Chemaxon
Rotatable Bond Count	12	Chemaxon
Refractivity	235.47 m3·mol-1	Chemaxon
Polarizability	97.49 Å3	Chemaxon
Number of Rings	10	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Targets

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Details1. Nonstructural protein 5A

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

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Drug created at November 26, 2014 23:19 / Updated at April 01, 2022 19:23