ZANAMIVIR HYDRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C12H20N4O7.H2O
Molecular Weight	350.3251
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=OELRRAURPSTFEX-VCFRRRQNSA-N

InChI=1S/C12H20N4O7.H2O/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);1H2/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

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 8297		0.21 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Influenza virus infections 33 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021036s027lbl.pdf	Primary		Approved 8429	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
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
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
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
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
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
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

AUC

Value	Dose	Analyte	Population
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
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
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
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
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
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

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
3.56 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
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

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 n = 4 Health Status: unhealthy Age Group: 18-79 years Sex: M+F Population Size: 4 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 n = 1 Health Status: pregnant Age Group: 25 years Sex: F Population Size: 1 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) n = 130 Health Status: unhealthy Condition: influenza Age Group: 47.5 years (range: 18–94 years) Sex: M+F Population Size: 130 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 (starting) 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 n = 71 Health Status: unhealthy Condition: influenza Age Group: 6 month - 18 years Sex: M+F Population Size: 71 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 270 UGT 192

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 270	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021036s025lbl.pdf#page=13 Page: 13.0	no
UGT 192	substrate 3367 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
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
eMolecules	31590542	https://www.emolecules.com/cgi-bin/more?vid=31590542

PubMed

Title	Date	PubMed
In vitro and in vivo assay systems for study of influenza virus inhibitors.	2000 Oct	11080536
Zanamivir: a review of clinical safety in individuals at high risk of developing influenza-related complications.	2001	11772145
Zanamivir: a rational approach to influenza B.	2001	11234975
Comparison of the anti-influenza virus activity of RWJ-270201 with those of oseltamivir and zanamivir.	2001 Apr	11257030
Unprepared for an influenza pandemic.	2001 Aug 25	11545086
Zanamivir: a second look. Still no tangible impact on influenza.	2001 Dec	11824440
Management of influenza in patients with asthma or chronic obstructive pulmonary disease.	2001 Dec	11770690
Characterization of an influenza A (H3N2) virus resistant to the cyclopentane neuraminidase inhibitor RWJ-270201.	2001 Dec	11675142
Zanamivir: an alternative translation.	2001 Dec 29	11779395
Clinical effectiveness and cost effectiveness of zanamivir (Relenza): translating the evidence into clinical practice, a National Institute for Clinical Excellence view.	2001 Dec 29	11779390
Treatment of influenza with neuraminidase inhibitors: virological implications.	2001 Dec 29	11779389
Zanamivir: from drug design to the clinic.	2001 Dec 29	11779388
Perspectives on antiviral use during pandemic influenza.	2001 Dec 29	11779387
Utility of zanamivir for chemoprophylaxis of concomitant influenza A and B in a complex continuing-care population.	2001 Feb 1	11227819
Does the availability of a neuraminidase inhibitor impair influenza vaccination? A report from Austria.	2001 Feb 28	11345055
[What is current opinion of antiviral therapy for the flu in 2001?].	2001 Jan	11218299
Prophylactic and symptomatic treatment of influenza. Current and developing options.	2001 Jan	11198262
Neuraminidase inhibitors: zanamivir and oseltamivir.	2001 Jan	11197587
Zanamivir for the treatment of influenza A and B infection in high-risk patients: a pooled analysis of randomized controlled trials.	2001 Jan 22	11176734
Adverse cutaneous reactions to influenza vaccinations and chemotherapy.	2001 Jul	11678994
Advances in pharmacology. New treatments for influenza: neuraminidase inhibitors.	2001 Jun	11434154
Position statement: global neuraminidase inhibitor susceptibility network.	2001 Mar	11428241
Cyclopentane neuraminidase inhibitors with potent in vitro anti-influenza virus activities.	2001 Mar	11181354
Rapid pharmacotherapeutic intervention for an influenza A outbreak in the Canadian Arctic: lessons from the Sanikiluaq experience.	2001 Nov	11768446
The effect of zanamivir treatment on the early immune response to influenza vaccination.	2001 Sep 14	11535325
Virology. The origin and control of pandemic influenza.	2001 Sep 7	11546857
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
Prevention and control of influenza. Recommendations of the Advisory Committee on Immunization Practices (ACIP).	2002 Apr 12	12002171
Development of a novel influenza A antiviral assay.	2002 Aug	12176147
Neuraminidase inhibitors for the treatment and prevention of influenza.	2002 Feb	11829724
Influenza in the nursing home.	2002 Jan 1	11804444
Dry powder inhaler: influence of humidity on topology and adhesion studied by AFM.	2002 Jan 31	11790505
Analysis of the desialidation process of the haemagglutinin protein of influenza B virus: the host-dependent desialidation step.	2002 Jul	12075092
Influenza.	2002 Jun	12230692
[A revolutionary change in the diagnosis and treatment of influenza].	2002 Jun	12227179
Gateways to Clinical Trials. June 2002.	2002 Jun	12168506
Influenza in the acute hospital setting.	2002 Mar	11944184
Syncytium formation and HIV-1 replication are both accentuated by purified influenza and virus-associated neuraminidase.	2002 Mar 22	11781317
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 May	11973564
Role of phosphatidylserine exposure and sugar chain desialylation at the surface of influenza virus-infected cells in efficient phagocytosis by macrophages.	2002 May 17	11884410
Structural studies of the resistance of influenza virus neuramindase to inhibitors.	2002 May 23	12014958
Comparison of colorimetric, fluorometric, and visual methods for determining anti-influenza (H1N1 and H3N2) virus activities and toxicities of compounds.	2002 Oct	12367731
Characterization of 2 influenza A(H3N2) clinical isolates with reduced susceptibility to neuraminidase inhibitors due to mutations in the hemagglutinin gene.	2002 Oct 15	12355356
Cost-effectiveness of newer treatment strategies for influenza.	2002 Sep	12361816

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 `Sat Dec 16 08:45:09 GMT 2023` Edited by `admin` on `Sat Dec 16 08:45:09 GMT 2023`
Record UNII	9E25RDB1Q0
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ZANAMIVIR HYDRATE

Common Name

English

(+)-(4S,5R,6R)-5-ACETYLAMINO-4-GUANIDINO-6-((1R,2R)-1,2,3- TRIHYDROXYPROPYL)-5,6-DIHYDRO-4H-PYRAN-2-CARBOXYLIC ACID HYDRATE

Systematic Name

English

J1.917.534K

Code

English

(4S)-6.ALPHA.-((1R,2R)-1,2,3-TRIHYDROXYPROPYL)-5.BETA.-(ACETYLAMINO)-4.ALPHA.-GUANIDINO-5,6-DIHYDRO-4H-PYRAN-2-CARBOXYLIC ACID HYDRATE

Systematic Name

English

ZANAMIVIR HYDRATE [JAN]

Common Name

English

Zanamivir hydrate [WHO-DD]

Common Name

English

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

Systematic Name

English

D01937

Code

English

ZANAMIVIR HYDRATE [EP MONOGRAPH]

Common Name

English

Code System Code Type Description

CAS

551942-41-7

Created by admin on Sat Dec 16 08:45:09 GMT 2023 , Edited by admin on Sat Dec 16 08:45:09 GMT 2023

NON-SPECIFIC STOICHIOMETRY

EVMPD

SUB22616

Created by admin on Sat Dec 16 08:45:09 GMT 2023 , Edited by admin on Sat Dec 16 08:45:09 GMT 2023

PRIMARY

PUBCHEM

636424

Created by admin on Sat Dec 16 08:45:09 GMT 2023 , Edited by admin on Sat Dec 16 08:45:09 GMT 2023

PRIMARY

FDA UNII

9E25RDB1Q0

Created by admin on Sat Dec 16 08:45:09 GMT 2023 , Edited by admin on Sat Dec 16 08:45:09 GMT 2023

PRIMARY

SMS_ID

100000086521

Created by admin on Sat Dec 16 08:45:09 GMT 2023 , Edited by admin on Sat Dec 16 08:45:09 GMT 2023

PRIMARY

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ACTIVE MOIETY

AE	Significance	Dose	Population
Heart pounding	1 patient	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 n = 4 Health Status: unhealthy Age Group: 18-79 years Sex: M+F Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/23587959
Lightheadedness	1 patient	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 n = 4 Health Status: unhealthy Age Group: 18-79 years Sex: M+F Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/23587959
Weakness	1 patient	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 n = 4 Health Status: unhealthy Age Group: 18-79 years Sex: M+F Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/23587959
Abdominal pain	mild, 1 patient	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 n = 4 Health Status: unhealthy Age Group: 18-79 years Sex: M+F Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/23587959
Diarrhea	mild, 1 patient	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 n = 4 Health Status: unhealthy Age Group: 18-79 years Sex: M+F Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/23587959
Rash	mild, 1 patient	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 n = 4 Health Status: unhealthy Age Group: 18-79 years Sex: M+F Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/23587959
Headache	moderate, 1 patient	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 n = 4 Health Status: unhealthy Age Group: 18-79 years Sex: M+F Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/23587959
Pneumothorax	grade 5, 1 patient	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 n = 1 Health Status: pregnant Age Group: 25 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/20095840/
Respiratory obstruction unspecified	grade 5, 1 patient	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 n = 1 Health Status: pregnant Age Group: 25 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/20095840/
Hypoxemia	severe, 1 patient	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 n = 1 Health Status: pregnant Age Group: 25 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/20095840/
Rash	3%	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) n = 130 Health Status: unhealthy Condition: influenza Age Group: 47.5 years (range: 18–94 years) Sex: M+F Population Size: 130 Sources: https://pubmed.ncbi.nlm.nih.gov/23983212
Venous thrombophlebitis	3%	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) n = 130 Health Status: unhealthy Condition: influenza Age Group: 47.5 years (range: 18–94 years) Sex: M+F Population Size: 130 Sources: https://pubmed.ncbi.nlm.nih.gov/23983212
Liver injury	acute, 10%	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) n = 130 Health Status: unhealthy Condition: influenza Age Group: 47.5 years (range: 18–94 years) Sex: M+F Population Size: 130 Sources: https://pubmed.ncbi.nlm.nih.gov/23983212
Renal failure	grade 3-4, 1 patient	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) n = 130 Health Status: unhealthy Condition: influenza Age Group: 47.5 years (range: 18–94 years) Sex: M+F Population Size: 130 Sources: https://pubmed.ncbi.nlm.nih.gov/23983212
Encephalopathy	grade 3-4, 2 patients	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) n = 130 Health Status: unhealthy Condition: influenza Age Group: 47.5 years (range: 18–94 years) Sex: M+F Population Size: 130 Sources: https://pubmed.ncbi.nlm.nih.gov/23983212
Liver injury	grade 3-4, 2 patients	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) n = 130 Health Status: unhealthy Condition: influenza Age Group: 47.5 years (range: 18–94 years) Sex: M+F Population Size: 130 Sources: https://pubmed.ncbi.nlm.nih.gov/23983212
Ventricular arrhythmia	grade 3-4, 2 patients	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) n = 130 Health Status: unhealthy Condition: influenza Age Group: 47.5 years (range: 18–94 years) Sex: M+F Population Size: 130 Sources: https://pubmed.ncbi.nlm.nih.gov/23983212
Aspartate aminotransferase increased	1%	12 mg/kg 1 times / day multiple, intravenous (starting) 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 n = 71 Health Status: unhealthy Condition: influenza Age Group: 6 month - 18 years Sex: M+F Population Size: 71 Sources: https://pubmed.ncbi.nlm.nih.gov/29051331
Delirium	1%	12 mg/kg 1 times / day multiple, intravenous (starting) 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 n = 71 Health Status: unhealthy Condition: influenza Age Group: 6 month - 18 years Sex: M+F Population Size: 71 Sources: https://pubmed.ncbi.nlm.nih.gov/29051331
Eosinophilia	1%	12 mg/kg 1 times / day multiple, intravenous (starting) 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 n = 71 Health Status: unhealthy Condition: influenza Age Group: 6 month - 18 years Sex: M+F Population Size: 71 Sources: https://pubmed.ncbi.nlm.nih.gov/29051331
Insomnia	1%	12 mg/kg 1 times / day multiple, intravenous (starting) 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 n = 71 Health Status: unhealthy Condition: influenza Age Group: 6 month - 18 years Sex: M+F Population Size: 71 Sources: https://pubmed.ncbi.nlm.nih.gov/29051331
Left ventricular hypertrophy	1%	12 mg/kg 1 times / day multiple, intravenous (starting) 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 n = 71 Health Status: unhealthy Condition: influenza Age Group: 6 month - 18 years Sex: M+F Population Size: 71 Sources: https://pubmed.ncbi.nlm.nih.gov/29051331
Troponin I increased	1%	12 mg/kg 1 times / day multiple, intravenous (starting) 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 n = 71 Health Status: unhealthy Condition: influenza Age Group: 6 month - 18 years Sex: M+F Population Size: 71 Sources: https://pubmed.ncbi.nlm.nih.gov/29051331
Vomiting	1%	12 mg/kg 1 times / day multiple, intravenous (starting) 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 n = 71 Health Status: unhealthy Condition: influenza Age Group: 6 month - 18 years Sex: M+F Population Size: 71 Sources: https://pubmed.ncbi.nlm.nih.gov/29051331
Neutropenia	3%	12 mg/kg 1 times / day multiple, intravenous (starting) 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 n = 71 Health Status: unhealthy Condition: influenza Age Group: 6 month - 18 years Sex: M+F Population Size: 71 Sources: https://pubmed.ncbi.nlm.nih.gov/29051331

Details

SMILES

InChI

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

Originator

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Conditions

Approved Use

Launch Date

Cmax

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

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

C_max

T_1/2