CAS 139110-80-8|GANA|ZMR|Zanamavir|Modified sialic acid|zanamivir|Zanamivir|Relenza|GNA|(2R,3R,4S)-4-[(diaminomethylidene)amino]-3-acetamido-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6...

General Information

Structure

Molecular Formula

C₁₂H₂₀N₄O₇

Molecular Mass

332.3098

Exact Mass

332.133199

Charge

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

Canonic Smiles

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

Isomeric Smiles

O1[C@H]([C@H](NC(=O)C)[C@@H](N=C(N)N)C=C1C(=O)O)[C@H](O)[C@H](O)CO

Calculated Properties

JChem

Acid pKa

3.2536163

H Acceptors

H Donor

LogD (pH = 5.5)

-5.8297024

LogD (pH = 7.4)

-5.827702

Log P

-5.8277187

Molar Refractivity

76.19

Polarizability

29.490557

Polar Surface Area

200.72

Rotatable Bonds

Lipinski's Rule of Five

false

ALOGPS 2.1

Log P

-2.3

LOG S

-1.66

Solubility (Water)

7.31e+00 g/l

Data Source

Academic Data

Data Source

Names and Identifiers

Synonyms

GANAZMRZanamavirModified sialic acidZanamivirGNA

IUPAC Traditional name

zanamivir

Brand Name

Relenza

IUPAC name

(2R,3R,4S)-4-[(diaminomethylidene)amino]-3-acetamido-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid

Names and Identifiers

Registration numbers

PubChem SID

16096390346508581

PubChem CID

60855

CAS Number

139110-80-8

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

-3

Solubility

7.31 mg/mL [Predicted by ALOGPS]

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00558

Drug Groups

approved; investigational

Description

A guanido-neuraminic acid that is used to inhibit neuraminidase. [PubChem]

Indication

For the prevention and treatment of influenza A and B.

Pharmacology

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 microM, respectively), which could account for some of the rare side effects of zanamivir.

Affected Organisms

Influenza A virus

Influenza B virus

Biotransformation

Not metabolized

Absorption

Absolute bioavailability is very low following oral administration (2%). Following oral inhalation, bioavailability is 4% to 17%.

Half Life

2.5-5.1 hours

Protein Binding

Zanamivir has limited plasma protein binding (<10%).

Elimination

It is excreted unchanged in the urine with excretion of a single dose completed within 24 hours.
Unabsorbed drug is excreted in the feces.Zanamivir is renally excreted as unchanged drug.

Clearance

* 2.5 - 10.9 L/h [Following oral inhalation 10 mg]
* 5.3 L/h [Normal renal function receiving IV single dose of 4 mg or 2 mg]
* 2.7 L/h [Patients with mild and moderate renal impairement receiving IV single dose of 4 mg or 2 mg]
* 0.8 L/h [Patients with severe renal impairement receiving IV single dose of 4 mg or 2 mg]

References

• Meindl P, Bodo G, Palese P, Schulman J, Tuppy H: Inhibition of neuraminidase activity by derivatives of 2-deoxy-2,3-dehydro-N-acetylneuraminic acid. Virology. 1974 Apr;58(2):457-63. [Pubmed]

• von Itzstein M, Wu WY, Kok GB, Pegg MS, Dyason JC, Jin B, Van Phan T, Smythe ML, White HF, Oliver SW, et al.: Rational design of potent sialidase-based inhibitors of influenza virus replication. Nature. 1993 Jun 3;363(6428):418-23. [Pubmed]

• Hata K, Koseki K, Yamaguchi K, Moriya S, Suzuki Y, Yingsakmongkon S, Hirai G, Sodeoka M, von Itzstein M, Miyagi T: Limited Inhibitory Effects of Oseltamivir and Zanamivir on Human Sialidases. Antimicrob Agents Chemother. 2008 Aug 11. [Pubmed]

• Sugaya N, Tamura D, Yamazaki M, Ichikawa M, Kawakami C, Kawaoka Y, Mitamura K: Comparison of the clinical effectiveness of oseltamivir and zanamivir against influenza virus infection in children. Clin Infect Dis. 2008 Aug 1;47(3):339-45. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Molecule Details

References

PubChem Literature

From Data Sources

• Meindl P, Bodo G, Palese P, Schulman J, Tuppy H: Inhibition of neuraminidase activity by derivatives of 2-deoxy-2,3-dehydro-N-acetylneuraminic acid. Virology. 1974 Apr;58(2):457-63. Pubmed

References

Bioactivity

PubChem BioAssay

Bioactivity

Navigation

General Information

Calculated Properties

• RDKit

• JChem

• ALOGPS 2.1

Data Source

• Academic Data

Names and Identifiers

• Synonyms

• IUPAC Traditional name

• Brand Name

• IUPAC name

Registration numbers

• PubChem SID

• PubChem CID

• CAS Number

• Physical Property

• DrugBank

• PubChem Literature

• From Data Sources

Bioactivity

• PubChem BioAssay

Synonyms

GANAZMRZanamavirModified sialic acidZanamivirGNA

IUPAC Traditional name

zanamivir

IUPAC name

(2R,3R,4S)-4-[(diaminomethylidene)amino]-3-acetamido-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid

PubChem SID

16096390346508581

CAS Number

139110-80-8

Physical Property

Hydrophobicity(logP)

-3

Solubility

7.31 mg/mL [Predicted by ALOGPS]

From Data Sources

• Meindl P, Bodo G, Palese P, Schulman J, Tuppy H: Inhibition of neuraminidase activity by derivatives of 2-deoxy-2,3-dehydro-N-acetylneuraminic acid. Virology. 1974 Apr;58(2):457-63. Pubmed

DrugBank

DB00558

Drug Groups

approved; investigational

Description

A guanido-neuraminic acid that is used to inhibit neuraminidase. [PubChem]

Indication

For the prevention and treatment of influenza A and B.

Pharmacology

Affected Organisms

Influenza A virus

Influenza B virus

Biotransformation

Not metabolized

Absorption

Absolute bioavailability is very low following oral administration (2%). Following oral inhalation, bioavailability is 4% to 17%.

Half Life

2.5-5.1 hours

Protein Binding

Zanamivir has limited plasma protein binding (<10%).

Elimination

It is excreted unchanged in the urine with excretion of a single dose completed within 24 hours.
Unabsorbed drug is excreted in the feces.Zanamivir is renally excreted as unchanged drug.

Clearance

References

• Meindl P, Bodo G, Palese P, Schulman J, Tuppy H: Inhibition of neuraminidase activity by derivatives of 2-deoxy-2,3-dehydro-N-acetylneuraminic acid. Virology. 1974 Apr;58(2):457-63. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Molecule

ID:440