Basic information
- CAS
187227-45-8- Standard SMILES
CCC(CC)O[C@@H]1C=C(C(=O)O)C[C@H](N)[C@H]1NC(C)=O- InChIKey
NENPYTRHICXVCS-YNEHKIRRSA-N- Molecular formula
- C14H24N2O4
- Average molar mass
- 284.35 g/mol
- Monoisotopic mass
- 284.17360725
Overview
Oseltamivir acid is a cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid which is substituted at positions 3, 4, and 5 by pentan-3-yloxy, acetamido, and amino groups, respectively (the 3R,4R,5S enantiomer). An antiviral drug, it is used as the corresponding ethyl ester prodrug, oseltamivir, to slow the spread of influenza. It has a role as an antiviral drug, an EC 3.2.1.18 (exo-alpha-sialidase) inhibitor and a marine xenobiotic metabolite. It is a cyclohexenecarboxylic acid, an amino acid, an acetate ester and a primary amino compound.
Names & identifiers
- Preferred name
- Ro 64-0802
- IUPAC
- (3R,4R,5S)-4-acetamido-5-amino-3-pentan-3-yloxycyclohexene-1-carboxylic acid
- English name
- Oseltamivir acid
- Molecular formula
- C14H24N2O4
- Molecular weight
- 284.35
Names & synonyms
Oseltamivir acid187227-45-8Ro 64-0802Oseltamivir free acidRo-64-0802Oseltamivir acid, (-)-K6106LV5Q81-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, (3R,4R,5S)-RO-640802CHEBI:73139DTXSID50171996(3R,4R,5S)-4-acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylic acid
Show more names
Oseltamivir impurity CAids095377Aids-095377Oseltamiviracid/GS4071Oseltamivir acid, >=98%
RefChem:56723DTXCID6094487Oseltamivir carboxylateGS4071GS 4071GS-4071Oseltamivir-carboxylateCHEMBL674
Database identifiers
- CAS
187227-45-8- PubChem CID
- 449381
- DTXSID
DTXSID50171996- ChEMBL
CHEMBL2296412- ChEBI
Properties
Computed structural properties
- XLogP
- -1.9
- Topological polar surface area
- 102 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 6
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 391
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 183 · 183-185°C
- Boiling point
- 508.7 · 508.7±50.0 °C(Predicted)
- Density
- 1.15 · 1.15±0.1 g/cm3(Predicted)
- storage temp.
- 2 · Keep in dark place,Sealed in dry,2-8°C
- solubility
- 14.2 mg/mL · ≥14.2 mg/mL in DMSO; ≥46.1 mg/mL in H2O with gentle warming; ≥97 mg/mL in EtOH with gentle warming
- form
- Solid
- pka
- 4.13 · 4.13±0.60(Predicted)
- color
- White to off-white
- Major Application
- pharmaceutical (small molecule)
- InChI
- InChI=1S/C14H24N2O4/c1-4-10(5-2)20-12-7-9(14(18)19)6-11(15)13(12)16-8(3)17/h7,10-13H,4-6,15H2,1-3H3,(H,16,17)(H,18,19)/t11-,12+,13+/m0/s1
- InChIKey
- NENPYTRHICXVCS-YNEHKIRRSA-N
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- WGK 3
- hs_code
- 9999999999
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
ATC CodeJ05AH02
FDA Pharmacological Classification
K6106LV5Q8
OSELTAMIVIR ACID
Established Pharmacologic Class [EPC] - Neuraminidase Inhibitor
Mechanisms of Action [MoA] - Neuraminidase Inhibitors
Oseltamivir acid is a Neuraminidase Inhibitor. The mechanism of action of oseltamivir acid is as a Neuraminidase Inhibitor.
OSELTAMIVIR ACID
Uses & manufacturing
Use ClassificationPharmaceuticals -> Transformation products
Applications
DescriptionOseltamivir (GS-4104) is an antiviral prodrug targeted against the influenza viruses. Oseltamivir acid is the active metabolite of oseltamivir. It acts as an inhibitor of influenza neuraminidases A and B (IC50 = 0.1 to 4.9 nM for both enzymes), in this way preventing virus budding and release.
UsesOseltamivir Acid is a metabolite of Oseltamivir (O701000).
UsesOseltamivir Acid (Oseltamivir EP Impurity C) is a metabolite of Oseltamivir (O701000). It is a COVID19-related research product.
Suppliers100 total
苏州道澜生物医药科技有限公司15952404857 · [email protected]
天津始加生物医药科技有限公司15022261580 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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