Back to ChemicalBook Home--->CAS DataBase List--->114870-03-0

114870-03-0

114870-03-0 Structure

114870-03-0 Structure
IdentificationBack Directory
[Name]

Fondaparinux sodium
[CAS]

114870-03-0
[Synonyms]

D01844
Arixtra
Arixtra (tn)
Fondaparin SodiuM
Fondaparinux sodium
Fondaparinux sodium N-4
Fondaparinux sodium, >=98%
Fondaparinux (sodium salt)
Fondaparinux sodiuM(D01844)
Fondaparinux sodium fandachem
Fondaparinux sodium USP/EP/BP
Fondaparinux and intermediates
Fondaparinux sodium (jan/usan/inn)
Fondaparinux SodiuM Identification
Natural heparin pentasaccharide Sodium
decasodium 6-[[6-[[2-carboxylato-4-hydroxy-6-[[4-hydroxy-6-methoxy-5-(sulfonatoamino)-2-(sulfonatooxymethyl)-3-oxanyl]oxy]-5-sulfonatooxy-3-oxanyl]oxy]-5-(sulfonatoamino)-4-sulfonatooxy-2-(sulfonatoox
Methyl O-2-Deoxy-6-O-sulfo-2-(sulfoamino)-α-D-glucopyranosyl-(14)-O-β- D-glucopyranuronosyl-(14)-O-2-deoxy-3,6-di-O-sulfo-2-(sulfoamino)-α-D-glucopyranosyl-(14)-O-2-O-sulfo-α-L-idopyranuronosyl-(14)-2-deoxy-2-(sulfoamino)-α-D-glucopyra
a-D-Glucopyranoside, methylO-2-deoxy-6-O-sulfo-2-(sulfoamino)-a-D-glucopyranosyl-(14)-O-b-D-glucopyranuronosyl-(14)-O-2-deoxy-3,6-di-O-sulfo-2-(sulfoamino)-a-D-glucopyranosyl-(14)-O-2-O-sulfo-a-L-idopyranuronosyl-(14)-2-deoxy-2-(sulfoamino)-,6-(hydrog
decasodiuM (2R,3S,4S,5R,6R)-3-{[(2R,3R,4R,5R,6R)-5-{[(2R,3R,4R,5S,6S)-6-carboxylato-5-{[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-(sulfonatoaMino)-6-[(sulfonatooxy)Methyl]oxan-2-yl]oxy}-3,4-dihydroxyoxan-2-yl]oxy}-3-(sulfonatoaMino)-4-(sulfonatooxy)-6-[(sulfonatoo
Methyl O-2-Deoxy-6-O-sulfo-2-(sulfoaMino)-α-D-glucopyranosyl-(14)-O-β- D-glucopyranuronosyl-(14)-O-2-deoxy-3,6-di-O-sulfo-2-(sulfoaMino)-α-D-glucopyranosyl-(14)-O-2-O-sulfo-α-L-idopyranuronosyl-(14)-2-deoxy-2-(sulfoaMino)-α-D-glucopyranoside 6-(Hydrogen Sulfate) DecasodiuM Salt
decasodium (2R,3S,4S,5R,6R)-3-[(2R,3R,4R,6R)-5-[(2R,3R,4S,5S,6S)-6-carboxylato-5-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-(sulfonatoamino)-6-(sulfonatooxymethyl)oxan-2-yl]oxy-3,4-dihydroxy-oxan-2-yl]oxy-3-(sulfonatoamino)-4-sulfonatooxy-6-(sulfonatooxymethyl)oxan-2-yl]oxy-4-hydroxy-6-[(2R,3S,4R,5R,6S)-4-hydroxy-6-methoxy-5-(sulfonatoamino)-2-(sulfonatooxymethyl)oxan-3-yl]oxy-5-sulfonatooxy-oxane-2-carboxylate
(2S,3S,4R,5R,6R)-6-(((2R,3R,4R,5R,6R)-6-(((2R,3S,4S,5R,6R)-2-Carboxy-4-hydroxy-6-(((2R,3S,4R,5R,6S)-4-hydroxy-6-methoxy-5-(sulfoamino)-2-((sulfooxy)methyl)tetrahydro-2H-pyran-3-yl)oxy)-5-(sulfooxy)tetrahydro-2H-pyran-3-yl)oxy)-5-(sulfoamino)-4-(sulfooxy)-2-((sulfooxy)methyl)tetrahydro-2H-pyran-3-yl)oxy)-3-(((2R,3R,4R,5S,6R)-4,5-dihydroxy-3-(sulfoamino)-6-((sulfooxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-4,5-dihydroxytetrahydro-2H-pyran-2-carboxylic acid, decasodium salt
[EINECS(EC#)]

686-283-7
[Molecular Formula]

C31H43N3O49S8.10Na
[Molecular Weight]

1728.08
[MOL File]

114870-03-0.mol
Chemical PropertiesBack Directory
[alpha ]

D23 +48° (c = 0.61 in water)
[storage temp. ]

-70°C
[CAS DataBase Reference]

114870-03-0
Safety DataBack Directory
[HS Code ]

3822000002
Hazard InformationBack Directory
[Description]

Fondaparinux sodium was first introduced in the US for prophylaxis of deep vein thrombosis which may lead to pulmonary embolism following major orthopaedic surgery. Fondaparinux is the first of a new class of antithrombic agents distinct from low molecular weight heparin (LMWH) and heparin. This entirely synthetic molecule is a copy of the heparin pentasaccharide sequence, the shortest fragment able to catalyze antithrombin lllmediated inhibition of factor Xa thereby inhibiting thrombin generation without antithrombin action. Fondaparinux does not display significant effects on coagulation tests (such as activated partial thromboplastin time and prothrombin time), does not bind to platelet factor 4 or promote heparin-induced thrombocytopenia. In phase III studies, fondaparinux significantly reduced the incidence of thromboembolism following orthopedic surgery, with an overall risk reduction of 50% in comparison to the LMWH, enoxaparin. Following subcutaneous administration, fondaparinux has a nearly complete bioavailability, a rapid onset of action, a prolonged half-life (17.2 h) enabling once daily dosing and is not metabolized preceeding renal excretion. The drug appears to be generally safe, with haemoragic complications either comparable to or higher than those for LMWH.
[Chemical Properties]

White Powder (after lyophilisation)
[Originator]

Sanofi-Synthelabo (France)
[Uses]

Synthetic pentasaccharide corresponding to the anti-thrombin binding site of heparin. Anti-thrombotic.
[Definition]

ChEBI: An organic sodium salt, being the decasodium salt of fondaparinux.
[Brand name]

Arixtra (GlaxoSmithKline).
[Biochem/physiol Actions]

Fondaparinux sodium is an antithrombotic anticoagulant, a Factor Xa inhibitor. Fondaparinux sodium is chemically related to low molecular weight heparins. Its pentasaccharide structure corresponds to the antithrombin III (ATIII) binding site of heparin. Fondaparinux sodium binding at this site potentiates the natural inhibitory effect of ATIII against factor Xa by a factor of approximately 300, which results in inhibition of thrombin generation.
[Chemical Synthesis]

Starting from Dglucose, D-cellobiose, and D-glucosamine, the production process for the synthesis of the pentasaccharide involves about 55 steps. The synthesis was accomplished by preparing a fully-protected pentasaccharide, and then converting it into the final product. The choice of protecting groups was dictated by two factors: the need to introduce sulfate substituents (O- as well as N-linked), carboxylate groups and hydroxyl groups, in the proper positions on the target molecule, and the constraints of current methods for oligosaccharide synthesis, particularly the use of 2-azido glucose derivatives to achieve stereoselective introduction of α-D-linked glucosamine units. All the monosaccharide synthons were obtained from glucose or from glucosamine, and the synthesis is outlined in the scheme. Trisaccharide 108 and disaccharide 109 are the two key building blocks in the synthesis. Coupling 108 and 109 was carried out at -20°C in DCE. Fully protected pentasaccharide 110 was then converted into the target compound 10 using traditional methods: saponification, O-sulfation, cleavage of benzyl ethers with simultaneous reduction of azido into amino functions and finally N-sulfation. Preparation of trisaccharide building block 108 started from 1,6-anhydrocellobiose (111). Selective protection at 4’,6’ position was achieved through benzylidenation to provide crude 112 which was converted into epoxide 113 by treatment with sodium methoxide and benzylation. Compound 113 was isolated after filtration on silica gel and crystallization (m.p. 184-5°C). Trans-diaxial opening of the epoxide yielded the 2-azido derivative (66%) which was acetylated to give 114 (99%). The benzylidene was cleaved (92%) and the diol was then converted into 115 by successive tritylation, levulinoylation, detritylation, oxidation, methylation and hydrazinolysis (60% over the 6 steps). Imidate 116 was prepared in the usual way from its hydroxyl precursor and coupled with 115 to give O-linked trisaccharide 117 in 78% yield. Compound 117 was acetolysed (91%), the anomeric acetate was cleaved by benzylamine in ether (100%) and imidate 108 was obtained by reaction with potassium carbonate and trichloroacetonitrile at room temperature (α, β- mixture with α as the predominant isomer, 76%). The preparation of the other building block 109 is described as following. Selective 6-acetylation of 118 by N - acetylimidazole in DCE gave 119 in 60% yield. Treatment of 119 with 120 using DCE/pyridinium perchlorate and followed dechloroacetylation using hydrazinedithiocarbonate afforded the crystalline disaccharide 109.

114870-03-0 suppliers list
Company Name: ENBRIDGE PHARMTECH CO., LTD.
Tel: ; , +8613812269233;+8613812269233
Fax: 0510-83591909
Website: www.chemicalbook.com/ShowSupplierProductsList1053464/0.htm
Company Name: Shanghai Minbiotech Co., Ltd.
Tel: +86 17315815539
Fax:
Website:
Company Name: AFINE CHEMICALS LIMITED
Tel: 008657185134551
Fax: 008657185134895
Website: www.afinechem.com/index.html
Company Name: Henan DaKen Chemical CO.,LTD.
Tel: +86-371-66670886
Fax:
Website: https://www.dakenchem.com/
Company Name: Henan Tianfu Chemical Co.,Ltd.
Tel: 0371-55170693
Fax: 0371-55170693
Website: http://www.tianfuchem.net/
Company Name: Hangzhou FandaChem Co.,Ltd.
Tel: 008615858145714
Fax: +86-571-56059825
Website: www.fandachem.com
Company Name: Shanghai Yingrui Biopharma Co., Ltd.
Tel: +86-21-33585366 E-mail:sales03@shyrchem.com
Fax: +86-21-34979012
Website: www.shyrchem.com
Company Name: ATK CHEMICAL COMPANY LIMITED
Tel: +86 21 5161 9050/ 5187 7795
Fax: +86 21 5161 9052/ 5187 7796
Website: www.atkchemical.com
Company Name: Hefei TNJ Chemical Industry Co.,Ltd.
Tel: +86-0551-65418679
Fax: 86-0551-65418697
Website: www.tnjchem.com
Company Name: career henan chemical co
Tel: +86-0371-55982848
Fax:
Website: www.coreychem.com/index.html
Company Name: Shaanxi Yikanglong Biotechnology Co., Ltd.
Tel: 17791478691
Fax:
Website: www.chemicalbook.com/ShowSupplierProductsList30927/0.htm
Company Name: TianYuan Pharmaceutical CO.,LTD
Tel: +86-755-23284190 13684996853
Fax: +86-755-23284190
Website: www.tianpharm.com
Company Name: Nanjing Dolon Biotechnology Co.,Ltd.
Tel: 18905173768
Fax:
Website: www.chemicalbook.com/ShowSupplierProductsList31215/0.htm
Company Name: Hubei Jusheng Technology Co.,Ltd.
Tel: 86-18871470254
Fax: 027-59599243
Website: www.hubeijusheng.com
Company Name: Xiamen AmoyChem Co., Ltd
Tel: +86 592-605 1114
Fax:
Website: www.amoychem.com
Company Name: BOC Sciences
Tel: 1-631-485-4226
Fax: 1-631-614-7828
Website: https://www.chemicalbook.com/ShowSupplierProductsList518419/0.htm
Company Name: Chongqing Chemdad Co., Ltd
Tel: +86-13650506873
Fax:
Website: http://www.chemdad.com/
Company Name: CONIER CHEM AND PHARMA LIMITED
Tel: 86-18523575427
Fax:
Website: http://www.conier.com/
Tags:114870-03-0 Related Product Information
7758-19-2 532-32-1 7647-14-5 15307-79-6 144-55-8 7757-82-6 127-09-3 1310-73-2 51460-26-5 28002-18-8