Details of the Drug

General Information of Drug (ID: DMFMBZ4)

Drug Name

Zanamivir

Synonyms

zanamivir; 139110-80-8; Relenza; 4-Guanidino-Neu5Ac2en; GANA; Zanamavir; MODIFIED SIALIC ACID; GG167; UNII-L6O3XI777I; GG 167; GR-121167X; Zanamivir (Relenza); Relenza (TN); 4-Guanidino-2,4-dideoxy-2,3-dehydro-N-acetylneuraminic acid; GR 121167X; CHEMBL222813; L6O3XI777I; ZMR; CHEBI:50663; GANA (inhibitor); 5-Acetamido-2,6-anhydro-3,4,5-trideoxy-4-guanidino-D-glycero-D-galacto-non-2-enonic acid; GNA; AK163166; GG-167; DSSTox_CID_3749; DSSTox_RID_77184; DSSTox_GSID_23749; Zanamivir [USAN:INN:BAN]; HSDB 7437; C12H20N4O7; GANA; Zanamivir hydrate; GR121167X; Zanamivir (USAN/INN); (2R,3R,4S)-3-acetamido-4-(diaminomethylideneamino)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid; 4-Guanidino-NeueAc2en; 5-(acetylamino)-4-{[amino(imino)methyl]amino}-2,6-anhydro-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid; ZNV; 4-guanidino-Neu5Ac2en; BAC-zanamivir

Indication

Disease Entry	ICD 11	Status	REF
Influenza virus infection	1E30-1E32	Approved	[1], [2]

Therapeutic Class

Antiviral Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 2

Molecular Weight (mw)

332.31

Topological Polar Surface Area (xlogp)

-3.2

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [3]
Bioavailability: The bioavailability of drug is 4-17% [4]
Clearance: The drug present in the plasma can be removed from the body at the rate of 1.6 mL/min/kg [5]
Elimination: 100% of drug is excreted from urine in the unchanged form [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 2.5 - 5.1 hours [5]
Metabolism: The drug is not metabolised [4]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.85976 micromolar/kg/day [6]
Unbound Fraction: The unbound fraction of drug in plasma is 0.86% [5]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.23 L/kg [5]
Water Solubility: The ability of drug to dissolve in water is measured as 18 mg/mL [3]

Chemical Identifiers

Formula: C12H20N4O7
IUPAC Name: (2R,3R,4S)-3-acetamido-4-(diaminomethylideneamino)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
Canonical SMILES: CC(=O)N[C@@H]1[C@H](C=C(O[C@H]1[C@@H]([C@@H](CO)O)O)C(=O)O)N=C(N)N
InChI: 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
InChIKey: ARAIBEBZBOPLMB-UFGQHTETSA-N

Cross-matching ID

PubChem CID: 60855
ChEBI ID: CHEBI:50663
CAS Number: 139110-80-8
DrugBank ID: DB00558
TTD ID: D00NPP
VARIDT ID: DR00960

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Influenza Neuraminidase (Influ NA)	TT50QJ3	NRAM_I33A0	Inhibitor	[7], [8]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
2	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
3	BDDCS applied to over 900 drugs
4	FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
5	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
7	Current and future antiviral therapy of severe seasonal and avian influenza. Antiviral Res. 2008 Apr;78(1):91-102.
8	Antiviral agents for influenza, hepatitis C and herpesvirus, enterovirus and rhinovirus infections. Med J Aust. 2001 Jul 16;175(2):112-6.
9	Developing new antiviral agents for influenza treatment: what does the future hold Clin Infect Dis. 2009 Jan 1;48 Suppl 1:S3-13.
10	How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
11	Inhibition of neuraminidase inhibitor-resistant influenza virus by DAS181, a novel sialidase fusion protein. PLoS One. 2009 Nov 6;4(11):e7838.
12	US patent application no. 2010,0081,713, Compositions and methods for treating viral infections.
13	CN patent application no. 104447481, Benzoic acid thiourea anti-influenza virus compounds as well as preparation method and use thereof.
14	Neuraminidase inhibitory activities of flavonols isolated from Rhodiola rosea roots and their in vitro anti-influenza viral activities. Bioorg Med Chem. 2009 Oct 1;17(19):6816-23.