Oseltamivir

HCID 65028CAS 196618-13-0

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Basic information

Standard SMILES: CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1
InChIKey: VSZGPKBBMSAYNT-RRFJBIMHSA-N
Molecular formula: C16H28N2O4
Average molar mass: 312.4 g/mol
Monoisotopic mass: 312.20490738

Names & identifiers

Preferred name: Oseltamivir
IUPAC: ethyl (3R,4R,5S)-4-acetamido-5-amino-3-pentan-3-yloxycyclohexene-1-carboxylate
English name: Oseltamivir
Molecular formula: C16H28N2O4
Molecular weight: 312.4

Names & synonyms

oseltamivir196618-13-0Tamvir(-)-oseltamivirGS-4104ebilfuminGS 4104oseltamivirumGS4104HSDB 7433ethyl (3R,4R,5S)-4-acetamido-5-amino-3-pentan-3-yloxycyclohexene-1-carboxylateRo-640796

Show more names

TAMIFLU(3R,4R,5S)-Ethyl 4-acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-enecarboxylateOstavirGOP-A-FluOseltamivrTaMiflu-FreeOSTELTAMIVIR

Ro-64-0796Ethyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylateRo 640796GS-4071 ETHYL ESTER20O93L6F9H1-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, ethyl ester, (3R-(3alpha,4beta,5alpha))-ethyl (3R,4R,5S)-5-amino-4-acetamido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylateRO64-0796

Database identifiers

CAS: 196618-13-0、204255-11-8
PubChem CID: 65028
DTXSID: DTXSID9044291
ChEMBL: CHEMBL1229
ChEBI: CHEBI:7798
UNII: 20O93L6F9H
Nikkaji: J871.765F

Properties

Computed structural properties

XLogP: 1.1
Topological polar surface area: 90.7 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 5
Rotatable bonds: 8
Heavy atoms: 22
Formal charge: 0
Complexity: 418

Physicochemical properties

Melting point: 107 · 107-108 °C
Boiling point: 473.3 · 473.3±45.0 °C(Predicted)
Density: 1.08 · 1.08±0.1 g/cm3(Predicted)
storage temp.: 2 · 2-8°C(protect from light)
solubility: Chloroform (Sparingly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
pka: 7.7 · 7.7 (25°); 6.6 (70°)
form: Solid
color: Off-White to Pale Beige
Henry's Law Constant: 3.4 · 3.4×1010 mol/(m3Pa) at 25℃, HSDB (2015)
Stability: Hygroscopic
InChI: InChI=1S/C16H28N2O4/c1-5-12(6-2)22-14-9-11(16(20)21-7-3)8-13(17)15(14)18-10(4)19/h9,12-15H,5-8,17H2,1-4H3,(H,18,19)/t13-,14+,15+/m0/s1
InChIKey: VSZGPKBBMSAYNT-RRFJBIMHSA-N
SMILES: C1(C(OCC)=O)C[C@H](N)[C@@H](NC(C)=O)[C@H](OC(CC)CC)C=1
CAS DataBase Reference: 196618 · 196618-13-0
NCI Dictionary of Cancer Terms: Tamiflu
FDA UNII: 20 O93L6F9H · 20O93L6F9H
NCI Drug Dictionary: Tamiflu
ATC code: 5 AH02 · J05AH02
EPA Substance Registry System: 1 · 1-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, ethyl ester, (3R,4R,5S)- (196618-13-0)
Protein binding: 42 · 42 (3 as carboxylate)
Excreted unchanged in urine: Negligible (99% excreted as carboxylate metabolite in urine)
Volume of distribution: 0.3 · 0.3-0.4(L/kg)
Biological half-life: 1 · 1-3, (6-10 as metabolite) / >20
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 261 · P261-P301+P312-P302+P352-P304+P340-P305+P351+P338
Hazardous Substances Data: 196618 · 196618-13-0(Hazardous Substances Data)

Safety & regulation

Safety data

Signal word: Warning
Symbol(GHS): GHS07
Hazard statements: H302-H315-H319-H335
Precautionary statements: P261-P301+P312-P302+P352-P304+P340-P305+P351+P338
Hazardous Substances Data: 196618-13-0(Hazardous Substances Data)

Chemistry & industry

Applications · 2 items

DescriptionOseltamivir is a drug that suppresses the action of influenza A, influenza B, and H1N1 influenza viruses in children and adults. Oseltamivir is administered for the treatment of influenza (flu) for people who are above the age of 2 weeks and have been experiencing flu-like symptoms for less than two days. Oseltamivir may also be prescribed for people who are above 1-year-old as a protective measure to prevent them from contracting influenza due to exposure to the virus without necessarily having indicated any symptoms of infection. The drug may not treat common cold. Oseltamivir goes by the brand name Tamiflu.

UsesOseltamivir is an orally active inhibitor of influenza virus neuraminidase; converted in vivo to the active acid metabolite. An antiviral drug. It is a COVID19-related research product.

Upstream & downstream products

Upstream raw materials

Downstream products

Oseltamivir phosphate ETHYL (3R,4R,5S)-4-ACETAMIDO-5-AZIDO-3-(1-ETHYLPROPOXY)CYCLOHEX-1-ENE-1-CARBOXYLATE

Suppliers50 total

北京华美互利生物化工010-56205725 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

合肥翰刚医药科技有限公司+8618062405514 · [email protected]

广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]

湖北金梭生物科技有限公司00123456789 · [email protected]

Additional notes

DefinitionChEBI: A cyclohexenecarboxylate ester that is the ethyl ester of oseltamivir acid. An antiviral prodrug (it is hydrolysed to the active free carboxylic acid in the liver), it is used to slow the spread of influenza.