Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:50 UTC |
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Update Date | 2020-02-26 21:40:10 UTC |
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HMDB ID | HMDB0014698 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Zanamivir |
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Description | Zanamivir is only found in individuals that have used or taken this drug. It is a guanido-neuraminic acid that is used to inhibit neuraminidase. [PubChem]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. |
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Structure | |
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Synonyms | Value | Source |
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(2R,3R,4S)-3-(Acetylamino)-4-carbamimidamido-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid | ChEBI | 4-Guanidino-2,4-dideoxy-2,3-dehydro-N-acetylneuraminic acid | ChEBI | 4-Guanidino-neu5ac2En | ChEBI | 5-(Acetylamino)-2,6-anhydro-4-carbamimidamido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid | ChEBI | 5-Acetamido-2,6-anhydro-3,4,5-trideoxy-4-guanidino-D-glycero-D-galacto-non-2-enonic acid | ChEBI | GANA | ChEBI | Relenza | ChEBI | (2R,3R,4S)-3-(Acetylamino)-4-carbamimidamido-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylate | Generator | 4-Guanidino-2,4-dideoxy-2,3-dehydro-N-acetylneuraminate | Generator | 5-(Acetylamino)-2,6-anhydro-4-carbamimidamido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate | Generator | 5-Acetamido-2,6-anhydro-3,4,5-trideoxy-4-guanidino-D-glycero-D-galacto-non-2-enonate | Generator | GNA | HMDB | Modified sialic acid | HMDB | Zanamavir | HMDB | ZMR | HMDB | Biota brand OF zanamivir | HMDB | Zanamivir glaxosmithkline brand | HMDB | 2,3-Didehydro-2,4-dideoxy-4-guanidinyl-N-acetylneuraminic acid | HMDB | 4 Guanidino neu5ac2En | HMDB | 4-Guanidino-2,4-dideoxy-2,3-didehydro-N-acetylneuraminic acid | HMDB | 4-Guanidino-2-deoxy-2,3-didehydro-N-acetylneuraminic acid | HMDB | 5-Acetylamino-2,6-anhydro-4-guanidino-3,4,5-trideoxy-D-galacto-non-enoic acid | HMDB | Glaxo wellcome brand OF zanamivir | HMDB | 4 Guanidino 2 deoxy 2,3 didehydro N acetylneuraminic acid | HMDB | Acid, 4-guanidino-2-deoxy-2,3-didehydro-N-acetylneuraminic | HMDB | Zanamivir biota brand | HMDB | 2,3-Didehydro-2,4-dideoxy-4-guanidino-N-acetyl-D-neuraminic acid | HMDB | GlaxoSmithKline brand OF zanamivir | HMDB |
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Chemical Formula | C12H20N4O7 |
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Average Molecular Weight | 332.3098 |
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Monoisotopic Molecular Weight | 332.133199014 |
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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 |
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Traditional Name | zanamivir |
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CAS Registry Number | 139110-80-8 |
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SMILES | [H][C@]1(OC(=C[C@H](N=C(N)N)[C@H]1NC(C)=O)C(O)=O)[C@H](O)[C@H](O)CO |
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InChI Identifier | 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 |
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InChI Key | ARAIBEBZBOPLMB-UFGQHTETSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as acetamides. These are organic compounds with the general formula RNHC(=O)CH3, where R= organyl group. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Carboxylic acid derivatives |
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Direct Parent | Acetamides |
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Alternative Parents | |
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Substituents | - Acetamide
- Guanidine
- Secondary alcohol
- Secondary carboxylic acid amide
- Carboxylic acid
- Oxacycle
- Monocarboxylic acid or derivatives
- Organoheterocyclic compound
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Carboximidamide
- Polyol
- Organic oxygen compound
- Primary alcohol
- Carbonyl group
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Biological location: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 7.31 g/L | Not Available | LogP | -3 | Not Available |
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Predicted Properties | |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-08gi-9333000000-192a3fb0a765cc76272a | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive | splash10-0a4i-9120247000-a1f231eacdbcd584b683 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01c9-2089000000-4b363928c7080b58eaf9 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-8091000000-e955bc5727f97f64f636 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03di-9310000000-1499e6041e5831b4268f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-02pr-4092000000-e0a953096602bf725d43 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-08fv-7190000000-e7e50811b55c4d55c4d9 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9110000000-23c8a48c94cc1cdcc136 | Spectrum |
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General 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:4362431 ]
- 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:8502295 ]
- 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. doi: 10.1086/589748. [PubMed:18582202 ]
- 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 Oct;52(10):3484-91. doi: 10.1128/AAC.00344-08. Epub 2008 Aug 11. [PubMed:18694948 ]
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