BALAPIRAVIR

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H30N6O8
Molecular Weight	494.4983
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)C(=O)OC[C@]1(O[C@H]([C@H](OC(=O)C(C)C)[C@@H]1OC(=O)C(C)C)N2C=CC(N)=NC2=O)N=[N+]=[N-]

InChI

InChIKey=VKXWOLCNTHXCLF-DXEZIKHYSA-N

InChI=1S/C21H30N6O8/c1-10(2)17(28)32-9-21(25-26-23)15(34-19(30)12(5)6)14(33-18(29)11(3)4)16(35-21)27-8-7-13(22)24-20(27)31/h7-8,10-12,14-16H,9H2,1-6H3,(H2,22,24,31)/t14-,15+,16-,21-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C21H30N6O8
Molecular Weight	494.4983
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18828074 | https://www.ncbi.nlm.nih.gov/pubmed/16316989 | https://www.ncbi.nlm.nih.gov/pubmed/22166557 | https://www.ncbi.nlm.nih.gov/pubmed/22807519 | https://www.ncbi.nlm.nih.gov/pubmed/26596942 | https://www.ncbi.nlm.nih.gov/pubmed/22166557https://www.ncbi.nlm.nih.gov/pubmed/16316989 | https://www.ncbi.nlm.nih.gov/pubmed/19778160

R1479 (4′-azidocytidine) is a specific inhibitor of hepatitis C virus (HCV) replication. 4′-azidocytidine triphosphate is an inhibitor of native HCV replicase and recombinant HCV polymerase (NS5B). Balapiravir (R1626) is the tri-isobutyrate ester prodrug of R1479 under clinical development to improve exposure of R1479 upon oral administration.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Hepatitis C virus NS5B RNA-dependent RNA polymerase 14 Target ID: CHEMBL5375 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18828074 \| https://www.ncbi.nlm.nih.gov/pubmed/16316989	Inhibitor 8504		40.0 nM [Ki]
Hepatitis C virus NS5B RNA-dependent RNA polymerase 14 Target ID: CHEMBL5375 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16316989	Inhibitor 8504		40.0 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Hepatitis C 42 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18828074	Primary	Phase II 1147	Unknown Approved Use Unknown
Dengue virus infection 12 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22807519	Primary	Phase I 438	Unknown Approved Use Unknown
Hepatitis C 42 Sources: http://adisinsight.springer.com/drugs/800018944	Primary	Phase I 438	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
16.54 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22807519/	1500 mg single, oral dose: 1500 mg route of administration: Oral experiment type: SINGLE co-administered:	R-1479 serum	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
23.86 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22807519/	3000 mg single, oral dose: 3000 mg route of administration: Oral experiment type: SINGLE co-administered:	R-1479 serum	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
9.9 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18570306/	1500 mg 2 times / day steady-state, oral dose: 1500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	R-1479 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
4 μg/mL CLINICAL TRIAL https://aasldpubs.onlinelibrary.wiley.com/doi/epdf/10.1002/hep.22321	500 mg 2 times / day multiple, oral dose: 500 mg route of administration: Oral experiment type: MULTIPLE co-administered:	R-1479 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
10 μg/mL CLINICAL TRIAL https://aasldpubs.onlinelibrary.wiley.com/doi/epdf/10.1002/hep.22321	1500 mg 2 times / day multiple, oral dose: 1500 mg route of administration: Oral experiment type: MULTIPLE co-administered:	R-1479 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
15 μg/mL CLINICAL TRIAL https://aasldpubs.onlinelibrary.wiley.com/doi/epdf/10.1002/hep.22321	3000 mg 2 times / day multiple, oral dose: 3000 mg route of administration: Oral experiment type: MULTIPLE co-administered:	R-1479 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
24 μg/mL CLINICAL TRIAL https://aasldpubs.onlinelibrary.wiley.com/doi/epdf/10.1002/hep.22321	4500 mg 2 times / day multiple, oral dose: 4500 mg route of administration: Oral experiment type: MULTIPLE co-administered:	R-1479 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
16.54 μg/mL CLINICAL TRIAL https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3610419/	1500 mg 2 times / day multiple, oral dose: 1500 mg route of administration: Oral experiment type: MULTIPLE co-administered:	R-1479 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
23.86 μg/mL CLINICAL TRIAL https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3610419/	3000 mg 2 times / day multiple, oral dose: 3000 mg route of administration: Oral experiment type: MULTIPLE co-administered:	R-1479 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
110.56 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22807519/	1500 mg single, oral dose: 1500 mg route of administration: Oral experiment type: SINGLE co-administered:	R-1479 serum	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
167.04 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22807519/	3000 mg single, oral dose: 3000 mg route of administration: Oral experiment type: SINGLE co-administered:	R-1479 serum	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
63.3 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18570306/	1500 mg 2 times / day steady-state, oral dose: 1500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	R-1479 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
110.56 μg × h/mL CLINICAL TRIAL https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3610419/	1500 mg 2 times / day multiple, oral dose: 1500 mg route of administration: Oral experiment type: MULTIPLE co-administered:	R-1479 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
167.04 μg × h/mL CLINICAL TRIAL https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3610419/	3000 mg 2 times / day multiple, oral dose: 3000 mg route of administration: Oral experiment type: MULTIPLE co-administered:	R-1479 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
4.62 h CLINICAL TRIAL https://aasldpubs.onlinelibrary.wiley.com/doi/epdf/10.1002/hep.22321	500 mg 2 times / day multiple, oral dose: 500 mg route of administration: Oral experiment type: MULTIPLE co-administered:		R-1479 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
5.87 h CLINICAL TRIAL https://aasldpubs.onlinelibrary.wiley.com/doi/epdf/10.1002/hep.22321	4500 mg 2 times / day multiple, oral dose: 4500 mg route of administration: Oral experiment type: MULTIPLE co-administered:		R-1479 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
4500 mg 2 times / day multiple, oral Highest studied dose Dose: 4500 mg, 2 times / day Route: oral Route: multiple Dose: 4500 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/18553458/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/18553458/	Disc. AE: Nausea, Vomiting... AEs leading to discontinuation/dose reduction: Nausea (grade 3, 11.1%) Vomiting (11.1%) Sources: https://pubmed.ncbi.nlm.nih.gov/18553458/
1500 mg 2 times / week multiple, oral Studied dose Dose: 1500 mg, 2 times / week Route: oral Route: multiple Dose: 1500 mg, 2 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/22166557/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/22166557/	Disc. AE: Eye disorders... AEs leading to discontinuation/dose reduction: Eye disorders (grade 3, 7%) Sources: https://pubmed.ncbi.nlm.nih.gov/22166557/

AEs

AE	Significance	Dose	Population
Vomiting	11.1% Disc. AE	4500 mg 2 times / day multiple, oral Highest studied dose Dose: 4500 mg, 2 times / day Route: oral Route: multiple Dose: 4500 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/18553458/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/18553458/
Nausea	grade 3, 11.1% Disc. AE	4500 mg 2 times / day multiple, oral Highest studied dose Dose: 4500 mg, 2 times / day Route: oral Route: multiple Dose: 4500 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/18553458/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/18553458/
Eye disorders	grade 3, 7% Disc. AE	1500 mg 2 times / week multiple, oral Studied dose Dose: 1500 mg, 2 times / week Route: oral Route: multiple Dose: 1500 mg, 2 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/22166557/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/22166557/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYPs 29	P-gp 2052 CYPs 33 UCK1 3	CYPs 17

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYPs 35	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/18553458/	no
CYPs 35	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/18553458/	no

Drug as victim

Target	Modality	Activity
CYPs 33	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18553458/	no
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/11691726#section=BioAssay-Results Page: 3 \| 4	no
UCK1 3	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19055482/	yes

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00DEJW	https://www.1pchem.com/search?query=1P00DEJW
Achemo Scientific Limited	AC-75364	http://www.achemo.com/search/?Keyword=AC-75364
AK Scientific	3995AH	https://aksci.com/item_detail.php?cat=3995AH
eMolecules	44811737	https://orderbb.emolecules.com/search/#?query=44811737
KeyOrganics	AS-56761	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-56761
Lab Network	LN01342751	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01342751
Lab Seeker	SC-94848	http://www.labseeker.com/search.php?keywords=SC-94848&category=0
LabSeeker	SC-94848	http://www.labseeker.com/search.php?keywords=SC-94848&category=0
mcule	MCULE-2702719304	https://mcule.com/MCULE-2702719304/
mcule	MCULE-4346372188	https://mcule.com/MCULE-4346372188/
MedChem Express	HY-10444	https://www.medchemexpress.com/search.html?q=HY-10444&ft=&fa=&fp=
Molnova	M14594	https://www.molnova.com/en/serch-list.html?keywords=M14594
MolPort	MolPort-028-720-591	https://www.molport.com/shop/molecule-link/MolPort-028-720-591

PubMed

Title	Date	PubMed
Activation of peripheral blood mononuclear cells by dengue virus infection depotentiates balapiravir.	2014-02	24257621
Inhibition of hepatitis C virus replication by GS-6620, a potent C-nucleoside monophosphate prodrug.	2014	24419349
Balapiravir plus peginterferon alfa-2a (40KD)/ribavirin in a randomized trial of hepatitis C genotype 1 patients.	2011-12-15	22166557
2'-Deoxy-2'-spirocyclopropylcytidine revisited: a new and selective inhibitor of the hepatitis C virus NS5B polymerase.	2010-11-25	21033671
PSI-7851, a pronucleotide of beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine monophosphate, is a potent and pan-genotype inhibitor of hepatitis C virus replication.	2010-08	20516278
Synthesis of new acridone derivatives, inhibitors of NS3 helicase, which efficiently and specifically inhibit subgenomic HCV replication.	2010-04-22	20337460
The design, synthesis, and antiviral activity of monofluoro and difluoro analogues of 4'-azidocytidine against hepatitis C virus replication: the discovery of 4'-azido-2'-deoxy-2'-fluorocytidine and 4'-azido-2'-dideoxy-2',2'-difluorocytidine.	2009-05-14	19341305
Substituted imidazopyridines as potent inhibitors of HCV replication.	2009-05	19303654
Amidinoanthracyclines - a new group of potential anti-hepatitis C virus compounds.	2009-04	19199832
The design, synthesis, and antiviral activity of 4'-azidocytidine analogues against hepatitis C virus replication: the discovery of 4'-azidoarabinocytidine.	2009-01-08	19055482
R-1626, a specific oral NS5B polymerase inhibitor of hepatitis C virus.	2008-10	18828074
Robust antiviral activity of R1626, a novel nucleoside analog: a randomized, placebo-controlled study in patients with chronic hepatitis C.	2008-08	18553458
Existence of hepatitis C virus NS5B variants naturally resistant to non-nucleoside, but not to nucleoside, polymerase inhibitors among untreated patients.	2008-06	18343801
The hepatitis C virus replicon presents a higher barrier to resistance to nucleoside analogs than to nonnucleoside polymerase or protease inhibitors.	2008-05	18285474
2'-deoxy-4'-azido nucleoside analogs are highly potent inhibitors of hepatitis C virus replication despite the lack of 2'-alpha-hydroxyl groups.	2008-01-25	18003608
Design, synthesis, and antiviral properties of 4'-substituted ribonucleosides as inhibitors of hepatitis C virus replication: the discovery of R1479.	2007-05-01	17317178
The novel nucleoside analog R1479 (4'-azidocytidine) is a potent inhibitor of NS5B-dependent RNA synthesis and hepatitis C virus replication in cell culture.	2006-02-17	16316989
Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.	1992-04-17	1573638

Patents

Sample Use Guides

In Vivo Use Guide

The phase 2, double-blind international trial evaluated the optimal treatment regimen of balapiravir plus peginterferon alfa-2a (40KD)/ribavirin in hepatitis C genotype 1 patients. Treatment-naive genotype 1 patients were randomized to one of seven treatment groups in which they received balapiravir 500, 1,000, or 1,500 mg twice daily, peginterferon alfa-2a (40KD) 180 or 90 µg/week and ribavirin 1,000/1,200 mg/day or peginterferon alfa-2a (40KD)/ribavirin. The planned treatment duration with balapiravir was reduced from 24 to 12 weeks due to safety concerns.

Route of Administration: Oral

In Vitro Use Guide

R1479 (4'-azidocytidine) is a specific inhibitor of HCV replication in the HCV subgenomic replicon system (IC(50) = 1.28 microM). R1479 showed no effect on cell viability or proliferation of HCV replicon or Huh-7 cells at concentrations up to 2 mM.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:22:42 GMT 2025` Edited by `admin` on `Mon Mar 31 18:22:42 GMT 2025`
Record UNII	VOT0LP7I9K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

R-1626

Preferred Name

English

BALAPIRAVIR

Official Name

English

R1626

Code

English

Balapiravir [WHO-DD]

Common Name

English

RO-4588161

Code

English

RO4588161

Code

English

CYTIDINE, 4'-C-AZIDO-, 2',3',5'-TRIS(2-METHYLPROPANOATE)

Common Name

English

balapiravir [INN]

Common Name

English

4-AMINO-1-(4-C-AZIDO-2',3',5'-TRI-O-(2-METHYLPROPANOYL)-.BETA.-D-RIBOFURANOSYL)PYRIMIDIN- 2(1H)-ONE

Common Name

English

BALAPIRAVIR [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C281