Fondaparinux sodium

ChemicalBook > CAS DataBase List > Fondaparinux sodium

Contraindications

Product Name: 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
Formula Weight: 1728.08
MOL File: 114870-03-0.mol

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Fondaparinux sodium Property

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

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Safety

HS Code: 3822000002

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H332Harmful if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 1282718
Product name: Fondaparinux sodium identification
Purity: United States Pharmacopeia (USP) Reference Standard
Packaging: 30MG
Price: $760
Updated: 2024/03/01

Sigma-Aldrich

Product number: 1282707
Product name: Fondaparinux sodium for Assay
Purity: United States Pharmacopeia (USP) Reference Standard
Packaging: 0.6ML
Price: $601
Updated: 2024/03/01

Cayman Chemical

Product number: 24033
Product name: Fondaparinux (sodium salt)
Purity: ≥95%
Packaging: 1mg
Price: $33
Updated: 2024/03/01

Cayman Chemical

Product number: 24033
Product name: Fondaparinux (sodium salt)
Purity: ≥95%
Packaging: 5mg
Price: $106
Updated: 2024/03/01

Cayman Chemical

Product number: 24033
Product name: Fondaparinux (sodium salt)
Purity: ≥95%
Packaging: 10mg
Price: $190
Updated: 2024/03/01

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Fondaparinux sodium Chemical Properties,Usage,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.

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

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View Lastest Price from Fondaparinux sodium manufacturers

Sinoway Industrial co., ltd.

Product: Fondaparinux Sodium 114870-03-0
Price: US $0.00-0.00/Kg/Bag
Min. Order: 1Kg/Bag
Purity: 99% up, High Density
Supply Ability: 20 tons
Release date: 2023-09-13

Chengdu Aupone Pharmaceutical Co.Ltd.

Product: Fondaparinux sodium 114870-03-0
Price: US $0.00/gram
Min. Order: 1gram
Purity: 99%
Supply Ability: 1tons
Release date: 2024-03-14

Biopole Pharmatech Co., Ltd.

Product: Fondaparinux Sodium 114870-03-0
Price: US $0.00/g
Min. Order: 1g
Purity: 99.99%HPLC
Supply Ability: 200kg
Release date: 2024-01-22

114870-03-0, Fondaparinux sodiumRelated Search:

Sodium acetate Sodium benzoate Sodium hydroxide Sodium chlorite Sodium sulfosalicylate Sodium sulfate Carbazochrome sodium sulfonate Sodium bicarbonate Diclofenac sodium Sulbenicillin sodium Sodium chloride Fondaparinux D-GLUCOSAMINE-2,3,6-TRISULFATE, TRISODIUM SALT D-GLUCOSAMINE-3,6-DI-O-SULPHATE (2NA) Fondaparinux Sodiun sodium sodium 2-(hexyloxy)ethyl sulphate IC 831423

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-glucopyranoside 6-(Hydrogen Sulfate) DecasodiuM Salt

Fondaparinux SodiuM Identification

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

Fondaparinux sodium N-4

Fondaparinux sodium, >=98%

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

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

Arixtra (tn)

D01844

Fondaparinux sodium (jan/usan/inn)

Fondaparinux sodiuM(D01844)

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

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

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)

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