ZANAMIVIR

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C12H20N4O7
Molecular Weight	332.3098
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)N[C@@H]1[C@@H](NC(N)=N)C=C(O[C@H]1[C@H](O)[C@H](O)CO)C(O)=O

InChI

InChIKey=ARAIBEBZBOPLMB-UFGQHTETSA-N

InChI=1S/C12H20N4O7/c1-4(18)15-8-5(16-12(13)14)2-7(11(21)22)23-10(8)9(20)6(19)3-17/h2,5-6,8-10,17,19-20H,3H2,1H3,(H,15,18)(H,21,22)(H4,13,14,16)/t5-,6+,8+,9+,10+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C12H20N4O7
Molecular Weight	332.3098
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.drugbank.ca/drugs/DB00558 | https://www.ncbi.nlm.nih.gov/pubmed/16100701
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021036s027lbl.pdf

Zanamivir, an antiviral agent, is a neuraminidase inhibitor indicated for treatment of uncomplicated acute illness due to influenza A and B virus in adults and pediatric patients 7 years and older who have been symptomatic for no more than 2 days. Zanamivir has also been shown to significantly inhibit the human sialidases NEU3 and NEU2 in the micromolar range (Ki 3.7 +/-0.48 and 12.9+/-0.07 uM, respectively), which could account for some of the rare side effects of zanamivir. The proposed mechanism of action of zanamivir is via inhibition of influenza virus neuraminidase with the possibility of alteration of virus particle aggregation and release. By binding and inhibiting the neuraminidase protein, the drug renders the influenza virus unable to escape its host cell and infect others. Zanamivir was the first neuraminidase inhibitor commercially developed. It is currently marketed by GlaxoSmithKline under the trade name Relenza as a powder for oral inhalation.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Neuraminidase 21 Target ID: CHEMBL2051 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021036s027lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/27487569 \| https://www.ncbi.nlm.nih.gov/pubmed/24613627	Inhibitor 8504		0.21 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Influenza virus infections 34 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021036s027lbl.pdf	Primary		Approved 8583	RELENZA Approved Use RELENZA, an influenza neuraminidase inhibitor, is indicated for: Treatment of influenza in patients aged 7 years and older who have been symptomatic for no more than 2 days. (1.1) Prophylaxis of influenza in patients aged 5 years and older. (1.2) Launch Date 1999

C_max

Value	Dose	Analyte	Population
12.75 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10429835/	16 mg single, intravenous dose: 16 mg route of administration: Intravenous experiment type: SINGLE co-administered:	ZANAMIVIR serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
42 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10429835/	16 mg single, nasal dose: 16 mg route of administration: Nasal experiment type: SINGLE co-administered:	ZANAMIVIR serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
86 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10429835/	16 mg 6 times / day multiple, nasal dose: 16 mg route of administration: Nasal experiment type: MULTIPLE co-administered:	ZANAMIVIR serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
63 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10429835/	16 mg single, respiratory dose: 16 mg route of administration: Respiratory experiment type: SINGLE co-administered:	ZANAMIVIR serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
139 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10429835/	16 mg 4 times / day multiple, respiratory dose: 16 mg route of administration: Respiratory experiment type: MULTIPLE co-administered:	ZANAMIVIR serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
39 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10429835/	10 mg single, respiratory dose: 10 mg route of administration: Respiratory experiment type: SINGLE co-administered:	ZANAMIVIR serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
54 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10429835/	10 mg 4 times / day multiple, respiratory dose: 10 mg route of administration: Respiratory experiment type: MULTIPLE co-administered:	ZANAMIVIR serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
2400 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10429835/	16 mg single, intravenous dose: 16 mg route of administration: Intravenous experiment type: SINGLE co-administered:	ZANAMIVIR serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
266 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10429835/	16 mg single, nasal dose: 16 mg route of administration: Nasal experiment type: SINGLE co-administered:	ZANAMIVIR serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
212 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10429835/	16 mg 6 times / day multiple, nasal dose: 16 mg route of administration: Nasal experiment type: MULTIPLE co-administered:	ZANAMIVIR serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
294 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10429835/	16 mg single, respiratory dose: 16 mg route of administration: Respiratory experiment type: SINGLE co-administered:	ZANAMIVIR serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
425 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10429835/	16 mg 4 times / day multiple, respiratory dose: 16 mg route of administration: Respiratory experiment type: MULTIPLE co-administered:	ZANAMIVIR serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
247 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10429835/	10 mg single, respiratory dose: 10 mg route of administration: Respiratory experiment type: SINGLE co-administered:	ZANAMIVIR serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
160 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10429835/	10 mg 4 times / day multiple, respiratory dose: 10 mg route of administration: Respiratory experiment type: MULTIPLE co-administered:	ZANAMIVIR serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
1.67 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10429835/	16 mg single, intravenous dose: 16 mg route of administration: Intravenous experiment type: SINGLE co-administered:	ZANAMIVIR serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.43 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10429835/	16 mg single, nasal dose: 16 mg route of administration: Nasal experiment type: SINGLE co-administered:	ZANAMIVIR serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2.21 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10429835/	16 mg single, respiratory dose: 16 mg route of administration: Respiratory experiment type: SINGLE co-administered:	ZANAMIVIR serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.56 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10429835/	10 mg single, respiratory dose: 10 mg route of administration: Respiratory experiment type: SINGLE co-administered:	ZANAMIVIR serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
100 mg single, intravenous Dose: 100 mg Route: intravenous Route: single Dose: 100 mg Sources: https://pubmed.ncbi.nlm.nih.gov/23587959	unhealthy, 18-79 years Health Status: unhealthy Age Group: 18-79 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/23587959	Other AEs: Abdominal pain, Headache... Other AEs: Abdominal pain (mild, 1 patient) Headache (moderate, 1 patient) Diarrhea (mild, 1 patient) Weakness (1 patient) Lightheadedness (1 patient) Heart pounding (1 patient) Rash (mild, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/23587959
5 mg 1 times / day multiple, respiratory Recommended Dose: 5 mg, 1 times / day Route: respiratory Route: multiple Dose: 5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20095840/	pregnant, 25 years Health Status: pregnant Age Group: 25 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/20095840/	Other AEs: Respiratory obstruction unspecified, Hypoxemia... Other AEs: Respiratory obstruction unspecified (grade 5, 1 patient) Hypoxemia (severe, 1 patient) Pneumothorax (grade 5, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/20095840/
600 mg 2 times / day multiple, intravenous Highest studied dose Dose: 600 mg, 2 times / day Route: intravenous Route: multiple Dose: 600 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/23983212	unhealthy, 47.5 years (range: 18–94 years) Health Status: unhealthy Age Group: 47.5 years (range: 18–94 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/23983212	Other AEs: Liver injury, Rash... Other AEs: Liver injury (acute, 10%) Rash (3%) Venous thrombophlebitis (3%) Ventricular arrhythmia (grade 3-4, 2 patients) Liver injury (grade 3-4, 2 patients) Encephalopathy (grade 3-4, 2 patients) Renal failure (grade 3-4, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/23983212
12 mg/kg 1 times / day multiple, intravenous Dose: 12 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 12 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/29051331	unhealthy, 6 month - 18 years Health Status: unhealthy Age Group: 6 month - 18 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/29051331	Other AEs: Neutropenia, Aspartate aminotransferase increased... Other AEs: Neutropenia (3%) Aspartate aminotransferase increased (1%) Delirium (1%) Eosinophilia (1%) Insomnia (1%) Left ventricular hypertrophy (1%) Troponin I increased (1%) Vomiting (1%) Sources: https://pubmed.ncbi.nlm.nih.gov/29051331

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP 303 UGT 219

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 303	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021036s025lbl.pdf#page=13 Page: 13.0	no
UGT 219	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021036s025lbl.pdf#page=13 Page: 13.0	no

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:50663	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:50663
ChemicalBook	CB0292498	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0292498
eMolecules	31590542	https://www.emolecules.com/cgi-bin/more?vid=31590542
MolPort	MolPort-006-167-580	https://www.molport.com/shop/molecule-link/MolPort-006-167-580
MolPort	MolPort-020-313-391	https://www.molport.com/shop/molecule-link/MolPort-020-313-391
Selleck Chemicals	zanamivir-relenza	http://www.selleckchem.com/products/zanamivir-relenza.html
ZINC	ZINC000003918138	http://zinc15.docking.org/substances/ZINC000003918138

PubMed

Title	Date	PubMed
Characterization of 2 influenza A(H3N2) clinical isolates with reduced susceptibility to neuraminidase inhibitors due to mutations in the hemagglutinin gene.	2002-10-15	12355356
Comparison of colorimetric, fluorometric, and visual methods for determining anti-influenza (H1N1 and H3N2) virus activities and toxicities of compounds.	2002-10	12367731
Current strategies for management of influenza in the elderly population.	2002-09-15	12203171
Influenza prevention 2002-2003.	2002-09-02	12205427
Cost-effectiveness of newer treatment strategies for influenza.	2002-09	12361816
Summaries for patients. Influenza vaccination or antiviral treatment for healthy working adults: an economic analysis.	2002-08-20	12186536
Economic analysis of influenza vaccination and antiviral treatment for healthy working adults.	2002-08-20	12186512
Synthesis and anti-influenza evaluation of polyvalent sialidase inhibitors bearing 4-guanidino-Neu5Ac2en derivatives.	2002-08-05	12113811
Synthesis and anti-influenza virus activity of 7-O-alkylated derivatives related to zanamivir.	2002-08-05	12113810
Synthesis and anti-influenza virus activity of 4-guanidino-7-substituted Neu5Ac2en derivatives.	2002-08-05	12113809
The management of influenza in people of working age.	2002-08	12181374
Development of a novel influenza A antiviral assay.	2002-08	12176147
Analysis of the desialidation process of the haemagglutinin protein of influenza B virus: the host-dependent desialidation step.	2002-07	12075092
Influenza.	2002-06	12230692
[A revolutionary change in the diagnosis and treatment of influenza].	2002-06	12227179
Gateways to Clinical Trials. June 2002.	2002-06	12168506
Susceptibility of recent Canadian influenza A and B virus isolates to different neuraminidase inhibitors.	2002-06	12062387
Peramivir (BCX-1812, RWJ-270201): potential new therapy for influenza.	2002-06	12036429
Structural studies of the resistance of influenza virus neuramindase to inhibitors.	2002-05-23	12014958
Role of phosphatidylserine exposure and sugar chain desialylation at the surface of influenza virus-infected cells in efficient phagocytosis by macrophages.	2002-05-17	11884410
Neuraminidase inhibitors as antivirals.	2002-05-15	12110259
Exploitation of the Herpes simplex virus translocating protein VP22 to carry influenza virus proteins into cells for studies of apoptosis: direct confirmation that neuraminidase induces apoptosis and indications that other proteins may have a role.	2002-05	12021867
Evidence-based emergency medicine/systematic review abstract. Use of the neuraminidase inhibitor class of antiviral drugs for treatment of healthy adults with an acute influenza-like illness.	2002-05	11973564
Prevention and control of influenza. Recommendations of the Advisory Committee on Immunization Practices (ACIP).	2002-04-12	12002171
Antiviral therapy of influenza.	2002-04	12122950
Challenges and options in the management of viral infections after stem cell transplantation.	2002-04	11904784
In vitro characterization of A-315675, a highly potent inhibitor of A and B strain influenza virus neuraminidases and influenza virus replication.	2002-04	11897583
Syncytium formation and HIV-1 replication are both accentuated by purified influenza and virus-associated neuraminidase.	2002-03-22	11781317
[Pneumonia diagnosis in the practice on the test-bench: how much diagnosis is necessary?].	2002-03-15	11894183
Accumulation of defective neuraminidase (NA) genes by influenza A viruses in the presence of NA inhibitors as a marker of reduced dependence on NA.	2002-03-01	11865415
Influenza in the acute hospital setting.	2002-03	11944184
Patient perspective on zanamivir in the treatment of influenza.	2002-02-08	11831842
Neuraminidase inhibitors for the treatment and prevention of influenza.	2002-02	11829724
Dry powder inhaler: influence of humidity on topology and adhesion studied by AFM.	2002-01-31	11790505
Influenza in the nursing home.	2002-01-01	11804444
Antiviral therapy for influenza virus infections.	2002-01	12118841
The use of zanamivir to treat influenza A and B infection after allogeneic stem cell transplantation.	2002-01	11850704
Zanamivir is an effective treatment for influenza in children undergoing therapy for acute lymphoblastic leukemia.	2002	12238587
Zanamivir for the treatment of influenza in adults: a systematic review and economic evaluation.	2002	12065066
Zanamivir: an update of its use in influenza.	2002	11790157
Zanamivir: an alternative translation.	2001-12-29	11779395
Clinical effectiveness and cost effectiveness of zanamivir (Relenza): translating the evidence into clinical practice, a National Institute for Clinical Excellence view.	2001-12-29	11779390
Treatment of influenza with neuraminidase inhibitors: virological implications.	2001-12-29	11779389
Zanamivir: from drug design to the clinic.	2001-12-29	11779388
Perspectives on antiviral use during pandemic influenza.	2001-12-29	11779387
Are we ready for the next flu pandemic?	2001-12	11871800
Zanamivir: a second look. Still no tangible impact on influenza.	2001-12	11824440
Management of influenza in patients with asthma or chronic obstructive pulmonary disease.	2001-12	11770690
Synthesis of influenza neuraminidase inhibitors.	2001-11	11899618
Zanamivir: a review of clinical safety in individuals at high risk of developing influenza-related complications.	2001	11772145

Patents

Sample Use Guides

In Vivo Use Guide

Usual Adult Dose for Influenza 10 mg (2 inhalations) inhaled orally twice a day (12 hours apart) for 5 days If possible, 2 doses should be taken on the first day, provided there are at least 2 hours between the doses. Usual Adult Dose for Influenza Prophylaxis 10 mg (2 inhalations) inhaled orally once a day Duration: Household setting: 10 days Community outbreak: 28 days

Route of Administration: Oral

In Vitro Use Guide

An MDCK cell-grown P2 isolate of influenza A(H3N2) virus, A/Mississippi/05/2011, exhibited highly reduced inhibition by zanamivir with IC50 1.19 nM

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:12:46 GMT 2025` Edited by `admin` on `Mon Mar 31 18:12:46 GMT 2025`
Record UNII	L6O3XI777I
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ZANAMIVIR

Official Name

English

RELENZA

Preferred Name

English

ZANAMIVIR [MI]

Common Name

English

ZANAMIVIR [ORANGE BOOK]

Common Name

English

D-GLYCERO-D-GALACTO-NON-2-ENONIC ACID, 5-(ACETYLAMINO)-4-((AMINOIMINOMETHYL)AMINO)-2,6-ANHYDRO-3,4,5-TRIDEOXY-

Common Name

English

ZANAMIVIR [VANDF]

Common Name

English

zanamivir [INN]

Common Name

English

Zanamivir [WHO-DD]

Common Name

English

GR-121167X

Code

English

5-(ACETYLAMINO)-4-((AMINOIMINOMETHYL)-AMINO)-2,6-ANHYDRO-3,4,5-TRIDEOXY-D-GLYCERO-D-GALACTO-NON-2-ENONIC ACID

Common Name

English

GR-121167

Code

English

ZANAMIVIR [MART.]

Common Name

English

ZANAMIVIR [USAN]

Common Name

English

ZANAMIVIR [HSDB]

Common Name

English

GG167

Code

English

ZANAMIVIR [USP MONOGRAPH]

Common Name

English

ZANAMIVIR [USP-RS]

Common Name

English

GR 121167X

Code

English

GG-167

Code

English

Classification Tree Code System Code

LIVERTOX

NBK548527