ChemicalBook > CAS DataBase List > (4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-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
- Product 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 No.
- 203120-17-6
- Chemical Name
- (4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid
- Synonyms
- Laninamivir;CS-746;R 125489;Lanimivir;Laninamivir-d3;Laninamivir (CS-8958);Laninamivir Impurity 1 (Laninamivir);Laninamivir (Inavir, CS8958, R125489);R-125489,inhibit,Inhibitor,R125489,Influenza Virus,Laninamivir;(4S,5R,6R)-5-AcetaMido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-Methoxypropyl)-5,6-dihydro-4H-pyran-2-
- CBNumber
- CB72485059
- Molecular Formula
- C13H22N4O7
- Formula Weight
- 346.34
- MOL File
- 203120-17-6.mol
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(4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid Property
- Melting point:
- >300°C (dec.)
- Density
- 1.61
- storage temp.
- -20°C Freezer
- solubility
- Water (Slightly)
- pka
- 3.81±0.70(Predicted)
- form
- Solid
- color
- White to Off-White
- Water Solubility
- Water : 5 mg/mL (14.44 mM; Need ultrasonic)
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N-Bromosuccinimide Price
Usbiological
- Product number
- 015457
- Product name
- Laninamivir
- Packaging
- 500ug
- Price
- $496
- Updated
- 2021/12/16
TRC
- Product number
- L174000
- Product name
- Laninamivir
- Packaging
- 5mg
- Price
- $1695
- Updated
- 2021/12/16
Usbiological
- Product number
- 293873
- Product name
- Laninamivir
- Packaging
- 5mg
- Price
- $2903
- Updated
- 2021/12/16
AK Scientific
- Product number
- Y0284
- Product name
- Laninamivir
- Packaging
- 2mg
- Price
- $1535
- Updated
- 2021/12/16
Biosynth Carbosynth
- Product number
- ML58733
- Product name
- Laninamivir
- Packaging
- 5mg
- Price
- $2100
- Updated
- 2021/12/16
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(4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid Chemical Properties,Usage,Production
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 neuraminidase (NA) inhibitor, shows long-acting anti-influenza virus activity.
Uses
A new potent labelled 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.
(4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid Preparation Products And Raw materials
Raw materials
Preparation Products
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(4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid Suppliers
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