Daclatasvir

Identification

Summary

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

Generic Name

Daclatasvir

DrugBank Accession Number

DB09102

Background

Daclatasvir is a direct-acting antiviral agent against Hepatitis C Virus (HCV) used for the treatment of chronic HCV genotype 1 and 3 infection. It is marketed under the name DAKLINZA and is contained in daily oral tablets as the hydrochloride salt form . Hepatitis C is 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 ⁸. Daclatasvir was the first drug with demonstrated safety and therapeutic efficacy in treating HCV genotype 3 without the need for co-administration of interferon or Ribavirin. It exerts its antiviral action by preventing RNA replication and virion assembly via binding to NS5A, a nonstructural phosphoprotein encoded by HCV. Binding to the N-terminus of the D1 domain of NS5A prevents its interaction with host cell proteins and membranes required for virion replication complex assembly. Daclatasvir is shown to target both the cis- and trans-acting functions of NS5A and disrupts the function of new HCV replication complexes by modulating the NS5A phosphorylation status ³. The most common critical NS5A amino acid substitutions that led to reduced susceptibility to daclatasvir therapy occured at position Q30 (Q30H/K/R) and M28 in genotype 1a patients and Y93H in genotype 3 patients.

According to 2017 American Association for the Study of Liver Diseases (AASLD), 60mg of daclatasvir is recommended with 400mg Sofosbuvir for genotype 1a/b patients with or without cirrhosis as second-line therapy. The same dosing regimen can be used as first-line therapy in patients with genotype 3 without cirrhosis and second-line therapy in genotype 3 patients with compensated cirrhosis. Combination therapies that include daclatasir can be used for challenging-to-treat patients who have HIV-1 coinfection, advanced cirrhosis, or post-liver transplant recurrence of HCV ⁹. The therapy is intended to cure or achieve a sustained virologic response (SVR12), 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.

Daclatasvir was FDA-approved in July 2015 for use with Sofosbuvir (Sovaldi) with or without Ribavirin to treat HCV genotype 1 and 3 infections. The SVR12 in HCV genotype 1a-infected treatment-naïve subjects without and with cirrhosis undergoing daclatasvir and Sofosbuvir therapy were 88% and 99%, respectively ^Label. The same dosing regimen in treatment-naïve patients with HCV genotype 3 infection with or without cirrhosis achieved SVR12 rates of 71% and 98%, respectively ^Label.

Type

Small Molecule

Groups

Approved, Investigational

Structure

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Similar Structures

Structure for Daclatasvir (DB09102)

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Weight

Average: 738.89
Monoisotopic: 738.385331362

Chemical Formula

C₄₀H₅₀N₈O₆

Synonyms

• BMS-790052
• Daclatasvir

External IDs

• BMS 790052
• BMS 790052-05
• BMS-790052-05
• EBP 883
• EBP-883

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Pharmacology

Indication

Indicated for use with sofosbuvir, with or without ribavirin, for the treatment of chronic HCV genotype 1a/b or 3 infection. The dosing regimen of 60mg daclatasvir 60 mg with 400mg sofosbuvir once a day is recommended for both genontypes.

Resistance: Reduced susceptibility to daclatasvir was associated with the polymorphisms at NS5A amino acid positions M28, Q30, L31, and Y93 in genotypes 1a, 1b, and 3a patients. NS5A Resistance Testing is recommended for HCV genotype 1a-infected patients with cirrhosis prior to the initiaition of the treatment, as the risk of resistance development is higher in genotype 1a patients.

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Used in combination to treat	Chronic hepatitis c	Regimen in combination with: Sofosbuvir (DB08934)	••• •••••		••• ••••••••
Used in combination to treat	Chronic hepatitis c genotype 1	Regimen in combination with: Sofosbuvir (DB08934), Ribavirin (DB00811)	••••••••••••
Used in combination to treat	Chronic hepatitis c genotype 1	Regimen in combination with: Sofosbuvir (DB08934)	••••••••••••
Used in combination to treat	Chronic hepatitis c genotype 2	Regimen in combination with: Sofosbuvir (DB08934)	••• •••••
Used in combination to treat	Chronic hepatitis c genotype 3	Regimen in combination with: Ribavirin (DB00811), Sofosbuvir (DB08934)	••••••••••••

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Pharmacodynamics

Daclatasvir is a direct-acting antiviral agent that targets the NS5A and causes a decrease in serum HCV RNA levels. It disrupts HCV replication by specifically inhibiting the critical functions of an NS5A protein in the replication complex ³. It is shown to cause downregulation of the hyperphosphorylation of NS5A. It does not appear to prolong the QT interval even when given at 3 times the maximum recommended dose.

Mechanism of action

NS5A is a viral nonstructural phospoprotein that is part of a functional replication complex in charge of viral RNA genome amplification on endoplasmic reticulum membranes. It has the ability to bind to HCV RNA. It is shown to have two distinct functions in HCV RNA replication based on phosphorylated states. Maintaining the HCV replication complex is mediated by the cis-acting function of basally phosphorylated NS5A and the trans-acting function of hyperphosphorylated NS5A modulates HCV assembly and infectious particle formation ³. Daclatasvir is shown to disrupt hyperphosphorylated NS5A proteins thus interfere with the function of new HCV replication complexes. It is also reported that daclatasvir also blocks both intracellular viral RNA synthesis and virion assembly/secretion in vivo ².

Target	Actions	Organism
ANonstructural protein 5A	inhibitor	Hepatitis C Virus

Absorption

Studies demonstrated that peak plasma concentrations typically occurred within 2 hours after administration of multiple oral doses ranging from 1 - 100 mg once daily. Steady state is reached after approximately 4 days of once-daily daclatasvir administration. The absolute bioavailability of the tablet formulation is 67%.

Volume of distribution

The approximate volume of distribution of daclatasvir is 47 L in patients who was orally administered 60 mg tablet followed by 100 µg [13C,15N]-daclatasvir intravenously.

Protein binding

Daclatasvir is highly protein bound (99%).

Metabolism

Daclastavir is a substrate of CYP3A enzymes where its metabolism is predominantly mediated by CYP3A4 isoform. Oxidative pathways included δ-oxidation of the pyrrolidine moiety, resulting in ring opening to an aminoaldehyde intermediate followed by an intramolecular reaction between the aldehyde and the proximal imidazole nitrogen atom ⁷. High proportion of the drug in the plasma (greater than 97%) is in the unchanged form.

Route of elimination

Approximately 88% of total dose of daclatasvir is eliminated into bile and feces in which 53% remains as unchanged form, while 6.6% of the total dose is eliminated primarily unchanged in the urine.

Half-life

Following multiple dose administration of daclatasvir in HCV-infected subjects, with doses ranging from 1 mg to 100 mg once daily, the terminal elimination half-life of daclatasvir ranged from approximately 12 to 15 hours.

Clearance

In subjects who received daclatasvir 60 mg tablet orally followed by 100 µg radiolabeled daclatasvir intravenously, the total clearance was 4.2 L/h.

Adverse Effects

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Toxicity

The most common adverse effects experienced in patients undergoing daclatasvir and sofosbuvir therapy include headache, fatigue, nausea and diarrhea. Similar side effects are seen when ribavirin is added, in addition to rash, insomnia, anemia, dizziness and somnolence. There are postmarketing cases that link serious symptomatic bradycardia with Daklinza when used in conjunction with sofosbuvir and amiodarone. Coadministration of these three drugs is not recommended unless there are no other alternatives.

Pathways

Not Available

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Interactions

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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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Abametapir	The serum concentration of Daclatasvir can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Daclatasvir can be increased when combined with Abatacept.
Abemaciclib	The serum concentration of Abemaciclib can be increased when it is combined with Daclatasvir.
Acalabrutinib	The metabolism of Daclatasvir can be decreased when combined with Acalabrutinib.
Adalimumab	The metabolism of Daclatasvir can be increased when combined with Adalimumab.

Food Interactions

• Avoid grapefruit products. Grapefruit inhibits the CYP3A metabolism of daclatasvir, which may increase its serum concentration. Dose changes may be necessary.
• Avoid St. John's Wort. This herb induces the CYP3A metabolism of daclatasvir and may reduce its serum concentration. Co-administration of daclatasvir with St. John's Wort is contraindicated.
• Take with or without food. Daclatasvir AUC and Cmax are slightly reduced when administered with food.

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Daclatasvir dihydrochloride	50ZO25C11D	1009119-65-6	BVZLLUDATICXCI-JMSCDMLISA-N

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Daclatasvir	Tablet	30 mg/1	Oral	Bristol-Myers Squibb Company	2014-11-24	2015-07-24
Daclatasvir	Tablet	60 mg/1	Oral	Bristol-Myers Squibb Company	2014-11-24	2015-07-24
Daklinza	Tablet	30 mg	Oral	Bristol Myers Squibb	2015-09-08	2019-08-01
Daklinza	Tablet	90 mg/1	Oral	E.R. Squibb & Sons, L.L.C.	2016-05-18	2019-04-30
Daklinza	Tablet	30 mg/1	Oral	E.R. Squibb & Sons, L.L.C.	2015-07-27	2020-06-30

Categories

ATC Codes

J05AP58 — Daclatasvir, asunaprevir and beclabuvir

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

J05AP07 — Daclatasvir

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

Drug Categories

• Acids, Acyclic
• Amino Acids
• Amino Acids, Branched-Chain
• Amino Acids, Essential
• Amino Acids, Peptides, and Proteins
• Antiinfectives for Systemic Use
• Antiviral Agents
• Antivirals for Systemic Use
• Antivirals for treatment of HCV infections
• BCRP/ABCG2 Inhibitors
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 CYP3A5 Substrates
• Cytochrome P-450 CYP3A7 Substrates
• Cytochrome P-450 Substrates
• Direct Acting Antivirals
• HCV Replication Complex Inhibitors
• Hepatitis C Virus NS5A Inhibitor
• OATP1B1/SLCO1B1 Inhibitors
• OATP1B3 inhibitors
• Organic Anion Transporting Polypeptide 1B1 Inhibitors
• Organic Anion Transporting Polypeptide 1B3 Inhibitors
• P-glycoprotein inhibitors
• P-glycoprotein substrates

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as valine and derivatives. These are compounds containing valine or a derivative thereof resulting from reaction of valine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Valine and derivatives

Alternative Parents

Biphenyls and derivatives / Alpha amino acid amides / Phenylimidazoles / N-acylpyrrolidines / Tertiary carboxylic acid amides / Methylcarbamates / Heteroaromatic compounds / Organic carbonic acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds

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Substituents

4-phenylimidazole / 5-phenylimidazole / Alpha-amino acid amide / Aromatic heteromonocyclic compound / Azacycle / Azole / Benzenoid / Biphenyl / Carbamic acid ester / Carbonic acid derivative / Carbonyl group / Carboxamide group / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / Methylcarbamate / Monocyclic benzene moiety / N-acylpyrrolidine / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organoheterocyclic compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Pyrrolidine / Tertiary carboxylic acid amide / Valine or derivatives

show 18 more

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

carbamate ester, imidazoles, biphenyls, carboxamide, valine derivative (CHEBI:82977)

Affected organisms

• Hepatitis C Virus

Chemical Identifiers

UNII

LI2427F9CI

CAS number

1009119-64-5

InChI Key

FKRSSPOQAMALKA-CUPIEXAXSA-N

InChI

InChI=1S/C40H50N8O6/c1-23(2)33(45-39(51)53-5)37(49)47-19-7-9-31(47)35-41-21-29(43-35)27-15-11-25(12-16-27)26-13-17-28(18-14-26)30-22-42-36(44-30)32-10-8-20-48(32)38(50)34(24(3)4)46-40(52)54-6/h11-18,21-24,31-34H,7-10,19-20H2,1-6H3,(H,41,43)(H,42,44)(H,45,51)(H,46,52)/t31-,32-,33-,34-/m0/s1

IUPAC Name

methyl N-[(2S)-1-[(2S)-2-[5-(4'-{2-[(2S)-1-[(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl]pyrrolidin-2-yl]-1H-imidazol-5-yl}-[1,1'-biphenyl]-4-yl)-1H-imidazol-2-yl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate

SMILES

COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C1=NC=C(N1)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=CN=C(N1)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)OC)C(C)C

References

General References

1. Belema M, Nguyen VN, Bachand C, Deon DH, Goodrich JT, James CA, Lavoie R, Lopez OD, Martel A, Romine JL, Ruediger EH, Snyder LB, St Laurent DR, Yang F, Zhu J, Wong HS, Langley DR, Adams SP, Cantor GH, Chimalakonda A, Fura A, Johnson BM, Knipe JO, Parker DD, Santone KS, Fridell RA, Lemm JA, O'Boyle DR 2nd, Colonno RJ, Gao M, Meanwell NA, Hamann LG: Hepatitis C virus NS5A replication complex inhibitors: the discovery of daclatasvir. J Med Chem. 2014 Mar 13;57(5):2013-32. doi: 10.1021/jm401836p. Epub 2014 Feb 12. [Article]
2. Guedj J, Dahari H, Rong L, Sansone ND, Nettles RE, Cotler SJ, Layden TJ, Uprichard SL, Perelson AS: Modeling shows that the NS5A inhibitor daclatasvir has two modes of action and yields a shorter estimate of the hepatitis C virus half-life. Proc Natl Acad Sci U S A. 2013 Mar 5;110(10):3991-6. doi: 10.1073/pnas.1203110110. Epub 2013 Feb 19. [Article]
3. Lee C: Daclatasvir: potential role in hepatitis C. Drug Des Devel Ther. 2013 Oct 16;7:1223-33. doi: 10.2147/DDDT.S40310. eCollection 2013. [Article]
4. Smith MA, Regal RE, Mohammad RA: Daclatasvir: A NS5A Replication Complex Inhibitor for Hepatitis C Infection. Ann Pharmacother. 2016 Jan;50(1):39-46. doi: 10.1177/1060028015610342. Epub 2015 Oct 20. [Article]
5. Berger C, Romero-Brey I, Radujkovic D, Terreux R, Zayas M, Paul D, Harak C, Hoppe S, Gao M, Penin F, Lohmann V, Bartenschlager R: Daclatasvir-like inhibitors of NS5A block early biogenesis of hepatitis C virus-induced membranous replication factories, independent of RNA replication. Gastroenterology. 2014 Nov;147(5):1094-105.e25. doi: 10.1053/j.gastro.2014.07.019. Epub 2014 Jul 18. [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. Li W, Zhao W, Liu X, Huang X, Lopez OD, Leet JE, Fancher RM, Nguyen V, Goodrich J, Easter J, Hong Y, Caceres-Cortes J, Chang SY, Ma L, Belema M, Hamann LG, Gao M, Zhu M, Shu YZ, Humphreys WG, Johnson BM: Biotransformation of Daclatasvir In Vitro and in Nonclinical Species: Formation of the Main Metabolite by Pyrrolidine delta-Oxidation and Rearrangement. Drug Metab Dispos. 2016 Jun;44(6):809-20. doi: 10.1124/dmd.115.068866. Epub 2016 Mar 30. [Article]
8. American Association for the Study of Liver Diseases; Infectious Diseases Society of America. HCV guidance. http://hcvguidelines.org. Accessed June 12, 2017. [Link]
9. American Liver Foundation: Advances in Medications to Treat Hepatitis C [Link]
10. FDA Approved Drug Products: DAKLINZA (daclatasvir) tablets, for oral use [Link]
11. NPRA: Dasvir (Daclatasvir) Oral Tablet [Link]

External Links

KEGG Drug

D10105

PubChem Compound

25154714

PubChem Substance

310265027

ChemSpider

24609522

BindingDB

50387084

RxNav

1606218

ChEBI

82977

ChEMBL

CHEMBL2023898

ZINC

ZINC000068204830

PharmGKB

PA166128167

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

Wikipedia

Daclatasvir

FDA label

Download (794 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Treatment	Chronic Hepatitis C Virus (HCV) Infection	2
4	Completed	Treatment	Chronic Hepatitis C Virus (HCV) Infection / Renal Failure, Chronic Renal Failure	1
4	Completed	Treatment	Cirrhosis of the Liver / Hepatitis C Virus (HCV) Infection	1
4	Completed	Treatment	Coronavirus Disease 2019 (COVID‑19)	1
4	Completed	Treatment	Drug Use / Hepatitis C Virus (HCV) Infection	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Tablet	Oral	30 mg/1
Tablet	Oral	60 mg/1
Tablet	Oral	30 mg
Tablet	Oral	60 mg
Tablet	Oral	90 mg/1
Tablet, film coated	Oral	30 MG
Tablet, film coated	Oral	60 MG
Tablet, film coated	Oral	90 MG
Tablet, film coated	Oral	30.00 mg
Tablet, film coated	Oral	60.00 mg
Tablet, film coated	Oral

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US8900566	No	2014-12-02	2027-08-08
US8642025	No	2014-02-04	2027-08-11
US8629171	No	2014-01-14	2031-06-13
US8329159	No	2012-12-11	2028-04-13
US9421192	No	2016-08-23	2027-08-08

Properties

State

Solid

Experimental Properties

Property	Value	Source
water solubility	Freely soluble (>700 mg/mL)	FDA Label

Predicted Properties

Property	Value	Source
Water Solubility	0.00852 mg/mL	ALOGPS
logP	4.67	ALOGPS
logP	4.18	Chemaxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	11.15	Chemaxon
pKa (Strongest Basic)	6.09	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	13	Chemaxon
Refractivity	201.82 m3·mol-1	Chemaxon
Polarizability	83.91 Å3	Chemaxon
Number of Rings	6	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, Negative (Annotated)	Predicted LC-MS/MS	splash10-004i-3100009000-1a7bc99ba064bbcc3002
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-05d0-0000049500-28ad661428e4728d1a46
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-001i-0000098200-9de979be007c78d42ff6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-004j-3000029100-ee8759c1af79a1c09f53
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0kar-9300001200-5dbd0cd79e660900e7a8
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-004s-7200922800-254b1582f2a2ff4f193c

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	255.02672	predicted	DeepCCS 1.0 (2019)
[M+H]+	256.92215	predicted	DeepCCS 1.0 (2019)
[M+Na]+	262.7039	predicted	DeepCCS 1.0 (2019)

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

References

1. Gao M: Antiviral activity and resistance of HCV NS5A replication complex inhibitors. Curr Opin Virol. 2013 Oct;3(5):514-20. doi: 10.1016/j.coviro.2013.06.014. Epub 2013 Jul 27. [Article]

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Drug created at September 16, 2015 21:59 / Updated at February 20, 2024 23:54