(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 (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-;(2R,3R,4S)-3-acetamido-2-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-4-guanidino-3,4-dihydro-2H-pyran-6-carboxylic acid
- CBNumber:
- CB72485059
- Molecular Formula:
- C13H22N4O7
- Molecular Weight:
- 346.34
- MDL Number:
- MFCD18071611
- MOL File:
- 203120-17-6.mol
(4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid Properties
| 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) |
| FDA UNII | B408IW3GL5 |
| ATC code | J05AH04 |
(4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid price
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Usbiological | 015457 | Laninamivir | 203120-17-6 | 500ug | $496 | 2021-12-16 | Buy |
| TRC | L174000 | Laninamivir | 203120-17-6 | 5mg | $1695 | 2021-12-16 | Buy |
| Usbiological | 293873 | Laninamivir | 203120-17-6 | 5mg | $2903 | 2021-12-16 | Buy |
| AK Scientific | Y0284 | Laninamivir | 203120-17-6 | 2mg | $1535 | 2021-12-16 | Buy |
| Biosynth Carbosynth | ML58733 | Laninamivir | 203120-17-6 | 5mg | $2100 | 2021-12-16 | Buy |
(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,Uses,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 labelled neuraminidase
Uses
A new potent neuraminidase (NA) inhibitor, 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.
(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
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| ATK CHEMICAL COMPANY LIMITED | +undefined-21-51877795 | ivan@atkchemical.com | China | 32480 | 60 |
| Biochempartner | 0086-13720134139 | candy@biochempartner.com | CHINA | 967 | 58 |
| BOC Sciences | +1-631-485-4226 | inquiry@bocsci.com | United States | 19553 | 58 |
| CONIER CHEM AND PHARMA LIMITED | +8618523575427 | sales@conier.com | China | 49390 | 58 |
| TargetMol Chemicals Inc. | +1-781-999-5354 +1-00000000000 | marketing@targetmol.com | United States | 19892 | 58 |
| Dayang Chem (Hangzhou) Co.,Ltd. | 571-88938639 +8617705817739 | info@dycnchem.com | CHINA | 52867 | 58 |
| InvivoChem | +1-708-310-1919 +1-13798911105 | sales@invivochem.cn | United States | 6393 | 58 |
| Nantong HI-FUTURE Biology Co., Ltd. | +undefined18051384581 | sales@chemhifuture.com | China | 3136 | 58 |
| PT CHEM GROUP LIMITED | +86-85511178 +86-85511178 | peter68@ptchemgroup.com | China | 35453 | 58 |
| GIHI CHEMICALS CO.,LIMITED | +8618058761490 | info@gihichemicals.com | China | 49999 | 58 |
| Supplier | Advantage |
|---|---|
| ATK CHEMICAL COMPANY LIMITED | 60 |
| Biochempartner | 58 |
| BOC Sciences | 58 |
| CONIER CHEM AND PHARMA LIMITED | 58 |
| TargetMol Chemicals Inc. | 58 |
| Dayang Chem (Hangzhou) Co.,Ltd. | 58 |
| InvivoChem | 58 |
| Nantong HI-FUTURE Biology Co., Ltd. | 58 |
| PT CHEM GROUP LIMITED | 58 |
| GIHI CHEMICALS CO.,LIMITED | 58 |