| Identification | Back Directory | [Name]
(4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid | [CAS]
203120-17-6 | [Synonyms]
CS-746
R 125489
Lanimivir
Laninamivir
Laninamivir-d3
Laninamivir (CS-8958)
(4S,5R,6R)-5-AcetaMido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-Methoxypropyl)-5,6-dihydro-4H-pyran-2-
(2R,3R,4S)-3-acetamido-2-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-4-guanidino-3,4-dihydro-2H-pyran-6-carboxylic acid
(4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid
D-glycero-D-galacto-Non-2-enonic acid, 5-(acetylamino)-4-[(aminoiminomethyl)amino]-2,6-anhydro-3,4,5-trideoxy-7-O-methyl- | [Molecular Formula]
C13H22N4O7 | [MDL Number]
MFCD18071611 | [MOL File]
203120-17-6.mol | [Molecular Weight]
346.34 |
| Chemical Properties | Back Directory | [Melting point ]
>300°C (dec.) | [density ]
1.61 | [storage temp. ]
-20°C Freezer | [solubility ]
Water (Slightly) | [form ]
Solid | [pka]
3.81±0.70(Predicted) | [color ]
White to Off-White | [Water Solubility ]
Water : 5 mg/mL (14.44 mM; Need ultrasonic) |
| Hazard Information | Back Directory | [Description]
Laninamivir octanoate (CS-8958), an ester prodrug form of the
neuraminidase (NA) inhibitor laninamivir (R-125489), was approved in
Japan in 2010 for treatment of influenza virus infections. Laninamivir
octanoate is given by intranasal administration at a 20 mg or 40 mg dose.
It has a long half-life in humans such that efficacy can be achieved after
only a single dose. In addition to vaccines for immunoprophylaxis, antiviral drugs play an
essential role in the treatment of influenza virus infections. Two
viral proteins have been targeted for therapeutic intervention: the M2
ion channel and NA. | [Originator]
Sankyo Co., Ltd. (Japan) | [Uses]
A new potent labelled neuraminidase | [Uses]
A new potent neuraminidase | [Definition]
ChEBI: Laninamivir is a member of acetamides. | [Brand name]
Inavir | [Synthesis]
Laninamivir octanoate is prepared starting from a neuraminic acid precursor. The route from 2,3-didehydroneuramic acid entails a multistep sequence to protect the acid and hydroxyl groups at the 4-, 20-, and 30-positions. Methylation of the remaining 10-hydroxyl by treatment with dimethylsulfate and NaH is followed by conversion of the 4-hydroxyl to an amine Cleavage of the 20,30-dihydroxy protecting group, conversion of the 4- NH2 to the guanidine, and acylation of the 30-OH group afford laninamivir octanoate. This three-step sequence can be reordered such that the guanidine is introduced first, followed by deprotection of the 20,30-diOH groups and acylation. An alternative sequence involves a Boc-protected guanidine intermediate, which is converted in a four-step sequence (deprotection of the acid and 20,30-hydroxyl groups, reprotection of the acid as its diphenylmethyl ether, acylation of the 30-OH and deprotection of the guanidine group) to laninamivir octanoate. Laninamivir can also be synthesized from the a-methyl glycoside of N-acetylneuramic acid methyl ester by an analogous route. |
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