ChemicalBook >> CAS DataBase List >>Fondaparinux sodium

Fondaparinux sodium

CAS No.
114870-03-0
Chemical Name:
Fondaparinux sodium
Synonyms
Fondaparin SodiuM;Arixtra;Fondaparinux and intermediates;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;(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)-;D01844;Arixtra (tn)
CBNumber:
CB41456602
Molecular Formula:
C31H43N3O49S8.10Na
Molecular Weight:
1728.08
MDL Number:
MFCD06794972
MOL File:
114870-03-0.mol
MSDS File:
SDS
Last updated:2024-11-19 23:02:33

Fondaparinux sodium Properties

Melting point >209°C (dec.)
alpha D23 +48° (c = 0.61 in water)
storage temp. 2-8°C
solubility Water
form Solid
color White to Off-White
InChIKey XEKSTYNIJLDDAZ-UWCYYFDCNA-D
NCI Dictionary of Cancer Terms Arixtra; fondaparinux sodium
FDA UNII X0Q6N9USOZ
NCI Drug Dictionary Arixtra

Pharmacokinetic data

Protein binding 97-98.6 (to anti-thrombin)
Excreted unchanged in urine 64-77%
Volume of distribution 0.1-0.12(L/kg)
Biological half-life 17-21 / 72

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H332
Precautionary statements  P261-P271-P304+P340-P312
HS Code  3822000002
NFPA 704
0
3 0

Fondaparinux sodium price More Price(31)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 1282718 Fondaparinux sodium identification United States Pharmacopeia (USP) Reference Standard 114870-03-0 30MG $760 2024-03-01 Buy
Sigma-Aldrich 1282707 Fondaparinux sodium for Assay United States Pharmacopeia (USP) Reference Standard 114870-03-0 0.6ML $601 2024-03-01 Buy
Cayman Chemical 24033 Fondaparinux (sodium salt) ≥95% 114870-03-0 1mg $33 2024-03-01 Buy
Cayman Chemical 24033 Fondaparinux (sodium salt) ≥95% 114870-03-0 5mg $106 2024-03-01 Buy
Cayman Chemical 24033 Fondaparinux (sodium salt) ≥95% 114870-03-0 10mg $190 2024-03-01 Buy
Product number Packaging Price Buy
1282718 30MG $760 Buy
1282707 0.6ML $601 Buy
24033 1mg $33 Buy
24033 5mg $106 Buy
24033 10mg $190 Buy

Fondaparinux sodium Chemical Properties,Uses,Production

Contraindications

Fondaparinux sodium injection is contraindicated in the following conditions:
Severe renal impairment (creatinine clearance <30 mL/min) in prophylaxis or treatment of venous thromboembolism.
Active major bleeding.
Bacterial endocarditis.
Thrombocytopenia associated with a positive in vitro test for anti-platelet antibody in the presence of fondaparinux sodium.
Body weight <50 kg (venous thromboembolism prophylaxis only).
History of serious hypersensitivity reaction (e.g., angioedema, anaphylactoid/anaphylactic reactions) to fondaparinux sodium.

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

Fondaparinux sodium has been used to test its neutralizing effect towards enterovirus D68-947 infection. It may be used in ultraviolet photodissociation (UVPD) measurements.

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.

Indications

Fondaparinux sodium injection is a Factor Xa inhibitor (anticoagulant) indicated for:
Prophylaxis of deep vein thrombosis (DVT) in patients undergoing hip fracture surgery (including extended prophylaxis), hip replacement surgery, knee replacement surgery, or abdominal surgery.
Treatment of DVT or acute pulmonary embolism (PE) when administered in conjunction with warfarin.

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.

Clinical Use

Prophylaxis of deep vein thrombosis
Treatment of deep vein thrombosis, pulmonary embolism, unstable angina and after a myocardial infarction

Side effects

Fondaparinux sodium is a prescription medication and as such, most people do not have serious side effects. However, pain, bruising, redness, and swelling at the injection site may occur, as well as headache, nausea, vomiting, swelling of the hands and feet, or fever. A few serious side effects may occur: easy bleeding or bruising; dark urine, yellowing of the eyes or skin; shortness of breath, coughing up blood, chest pain, unusual dizziness, fainting, fast or irregular heartbeat; joint or muscle pain; confusion. Very few patients may experience allergic reactions (e.g. rash, itching or swelling (especially on face/tongue/throat); severe dizziness, difficulty breathing).

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 |á-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?ˉ,6?ˉ 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 (|á, |?- mixture with |á 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.

Synthesis_114870-03-0

Drug interactions

Potentially hazardous interactions with other drugs
Increased risk of bleeding in combination with any other drugs that affect coagulation.

Metabolism

Although not fully evaluated, there is no evidence of fondaparinux metabolism and in particular no evidence for the formation of active metabolites. Fondaparinux is excreted to 64-77% by the kidney as unchanged compound.

Fondaparinux sodium Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 317)Suppliers
Supplier Tel Email Country ProdList Advantage
Chengdu Aupone Pharmaceutical Co.Ltd.
+86-28-+86-28-87843998-6060-6060 +8618631098571 lijiaqi@aupone.com China 54 58
ENBRIDGE PHARMTECH CO., LTD.
+8613812269233 tinayang@enbridgepharm.com China 322 58
Shanghai Minbiotech Co., Ltd.
+8617315815539 sales@minbiotech.com CHINA 129 58
AFINE CHEMICALS LIMITED
+86-0571-85134551 sales@afinechem.com China 15352 58
Biopole Pharmatech Co., Ltd.
+8615151475053 biopole@163.com China 37 58
Hebei Weibang Biotechnology Co., Ltd
+8615531157085 abby@weibangbio.com China 8807 58
Hebei Mojin Biotechnology Co., Ltd
+86 13288715578 +8613288715578 sales@hbmojin.com China 12834 58
Hebei Yanxi Chemical Co., Ltd.
+8617531190177 peter@yan-xi.com China 5857 58
Sinoway Industrial co., ltd.
0592-5800732; +8613806035118 xie@china-sinoway.com China 988 58
Henan Bao Enluo International TradeCo.,LTD
+86-17331933971 +86-17331933971 deasea125996@gmail.com China 2472 58

Related articles

View Lastest Price from Fondaparinux sodium manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Fondaparinux Sodium pictures 2024-12-25 Fondaparinux Sodium
114870-03-0
US $0.00-0.00 / Kg/Bag 1Kg/Bag 99% up, High Density 20 tons Sinoway Industrial co., ltd.
Fondaparinux sodium pictures 2024-11-19 Fondaparinux sodium
114870-03-0
US $33.00-71.00 / mg ≥98% 10g TargetMol Chemicals Inc.
Fondaparinux sodium pictures 2024-11-18 Fondaparinux sodium
114870-03-0
US $10.00 / KG 1KG 99% 10 mt Hebei Weibang Biotechnology Co., Ltd
  • Fondaparinux Sodium pictures
  • Fondaparinux Sodium
    114870-03-0
  • US $0.00-0.00 / Kg/Bag
  • 99% up, High Density
  • Sinoway Industrial co., ltd.
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 Fondaparinux SodiuM Identification Fondaparinux sodium N-4 Fondaparinux sodium, >=98% 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 Fondaparinux sodium Arixtra (tn) D01844 Fondaparinux sodium (jan/usan/inn) Fondaparinux sodiuM(D01844) Fondaparinux (sodium salt) Natural heparin pentasaccharide Sodium (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 Fondaparinux sodium USP/EP/BP US-DMF No. : 030767 Fondaparinux Sodium (Fondaparinux Sodium) Fondaparinux Sodium Identification(Secondary Standards traceble to USP) Fondaparinux Sodium for Assay (COLD SHIPMENT REQUIRED) (1282707) Fondaparinux Sodium Identification (1282718) Fondaparin SodiuM 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 Arixtra 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 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 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 Fondaparinux and intermediates (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)- Sodium daparinux Fondaparinux Sodiun (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, sodium salt decasodium 6-[[6-[[2-carboxylato-4-hydroxy-6-[[4-hydroxy-6-methoxy-5-(sulfonatoamino)-2-(sulfonatooxymethyl)-3-oxanyl]oxy 114870-03-0 14870-03-0 C31H43N3O49S810Na C31H43N3Na10O49S8 Intermediates & Fine Chemicals Oligosaccharides Pharmaceuticals Sulfur & Selenium Compounds 114870-03-0