(4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid
- CAS NO.:203120-17-6
- Empirical Formula: C13H22N4O7
- Molecular Weight: 346.34
- MDL number: MFCD18071611
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-19 15:53:33
What is (4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid?
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)
The Uses of (4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid
A new potent labelled neuraminidase
The Uses of (4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid
A new potent neuraminidase (NA) inhibitor, shows long-acting anti-influenza virus activity.
What are the applications of Application
Laninamivir-d3 is a potent labelled neuraminidase (NA) inhibitor
What are the applications of Application
Laninamivir is a new potent neuraminidase (NA) inhibitor, which shows long-acting anti-influenza virus activity
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.
Properties of (4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid
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) |
Safety information for (4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid
Computed Descriptors for (4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid
New Products
Tert-butyl bis(2-chloroethyl)carbamate 4-Methylphenylacetic acid N-Boc-D-alaninol N-BOC-D/L-ALANINOL 3-Morpholino-1-(4-nitrophenyl)-5,6-dihydropyridin- 2(1H)-one Furan-2,5-Dicarboxylic Acid Tropic acid DIETHYL AMINOMALONATE HYDROCHLORIDE 1,1’-CARBONYLDIIMIDAZOLE R-2-BENZYLOXY PROPIONIC ACID 1,1’-CARBONYLDI (1,2-4 TRIAZOLE) N-METHYL INDAZOLE-3-CARBOXYLIC ACID (2-Hydroxyphenyl)acetonitrile 4-Bromopyrazole 5-BROMO-2CYANO PYRIDINE 5,6-Dimethoxyindanone 5-broMo-2-chloro-N-cyclopentylpyriMidin-4-aMine 2-(Cyanocyclohexyl)acetic acid 4-methoxy-3,5-dinitropyridine 2-aminopropyl benzoate hydrochloride 1-(4-(aminomethyl)benzyl)urea hydrochloride diethyl 2-(2-((tertbutoxycarbonyl)amino) ethyl)malonate tert-butyl 4- (ureidomethyl)benzylcarbamate Ethyl-2-chloro((4-methoxyphenyl)hydrazono)acetateRelated products of tetrahydrofuran
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