| Identification | Back Directory | [Name]
OSELTAMIVIR ACID | [CAS]
187227-45-8 | [Synonyms]
Gs4071
Gs-4071
Gs 4071
Aids095377
Aids-095377
Oseltamivir impurity C
Oseltamivir acid, >=98%
Oseltamivir carboxylate
Oseltamivir EP Impurity C
OseltaMivir carboxylic acid
Oseltamivir carboxylate (OC)
204255-11-8 (Monophospate salt)
Oseltamivir Phosphate impurity C (EP)
Oseltamivir carboxylate (OC),Metabolite of oseltamivir
(3R,4R,5S)-4-acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-enecarboxylic acid
(3R,4R,5S)-4-Acetamido-5-amino-3-(1-ethylpropoxy)cyclohex-1-ene-1-carboxylic acid
(3R,4R,5S)-4-Acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohex-ene-1-carboxylic acid
1-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, (3R,4R,5S)-
OseltamivirCarboxylicAcid,4-(Acetylamino)-5-amino-3-(1-ethylpropoxy)-1-cyclohexence-1-carboxylicAcid | [Molecular Formula]
C14H24N2O4 | [MDL Number]
MFCD00953940 | [MOL File]
187227-45-8.mol | [Molecular Weight]
284.354 |
| Chemical Properties | Back Directory | [Melting point ]
183-185°C | [Boiling point ]
508.7±50.0 °C(Predicted) | [density ]
1.15±0.1 g/cm3(Predicted) | [storage temp. ]
-20?C Freezer, Under Inert Atmosphere | [solubility ]
≥14.2 mg/mL in DMSO; ≥46.1 mg/mL in H2O with gentle warming; ≥97 mg/mL in EtOH with gentle warming | [form ]
neat | [pka]
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 | [SMILES]
C1(C(O)=O)C[C@H](N)[C@@H](NC(C)=O)[C@H](OC(CC)CC)C=1 | [EPA Substance Registry System]
1-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, (3R,4R,5S)- (187227-45-8) |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Uses]
Oseltamivir Acid is a metabolite of Oseltamivir (O701000). | [Definition]
ChEBI: 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). A
antiviral drug, it is used as the corresponding ethyl ester prodrug, oseltamivir, to slow the spread of influenza. | [Description]
Oseltamivir (GS-4104) is an antiviral prodrug targeted against the influenza viruses.1,2 Oseltamivir acid is the active metabolite of oseltamivir.3,4 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.5,6,7 | [in vivo]
Oseltamivir acid (0.1, 1, or 10 mg/kg/day, twice daily by oral gavage) produces a dose-dependent antiviral effect against Vietnam/1203/04 (VN1203/04) virus. The 5-day regimen at 10 mg/kg/day protects 50% of mice; deaths in this treatment group are delayed and indicated the replication of residual virus after the completion of treatment. Dosages of 1 and 10 mg/kg/day significantly reduced virus titers in organs and provided 60% and 80% survival rates, respectively[5].
| [References]
[1] enguang feng, deju ye, jian li, dengyou zhang, jinfang wang, fei zhao, rolf hilgenfeld, mingyue zheng, hualiang jiang and hong liu. recent advances in neuraminidase inhibitor development as anti-influenza drugs. chem med chem 2012, 7: 1527 – 1536.
[2] tom jefferson reviewer, mark jones, peter doshi, elizabeth a spencer, igho onakpoya, carl j heneghan. oseltamivir for influenza in adults and children: systematic review of clinical study reports and summary of regulatory comment. bmj. 2014, 348: g2545.
[3] rashmi dixit, gulam khandaker, scott ilgoutz, harunor rashid and robert booy. emergence of oseltamivir resistance: control and management of influenza before, during and after the pandemic. infectious disorders – drug targets. 2013, 13 (1): 34-45. |
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