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Identification
NameFondaparinux sodium
Accession NumberDB00569  (APRD00500)
TypeSmall Molecule
GroupsApproved, Investigational
Description

Fondaparinux (Arixtra) is a synthetic pentasaccharide anticoagulant. Apart from the O-methyl group at the reducing end of the molecule, the identity and sequence of the five monomeric sugar units contained in fondaparinux is identical to a sequence of five monomeric sugar units that can be isolated after either chemical or enzymatic cleavage of the polymeric glycosaminoglycan heparin and heparan sulfate (HS). This monomeric sequence in heparin and HS is thought to form the high affinity binding site for the natural anti-coagulant factor, antithrombin III (ATIII). Binding of heparin/HS to ATIII has been shown to increase the anti-coagulant activity of antithrombin III 1000-fold. Fondaparinux potentiates the neutralizing action of ATIII on activated Factor X 300-fold. Fondaparinux may be used: to prevent venous thromboembolism in patients who have undergone orthopedic surgery of the lower limbs (e.g. hip fracture, hip replacement and knee surgery); to prevent VTE in patients undergoing abdominal surgery who are are at high risk of thromboembolic complications; in the treatment of deep vein thrombosis (DVT) and pumonary embolism (PE); in the management of unstable angina (UA) and non-ST segment elevation myocardial infarction (NSTEMI); and in the management of ST segment elevation myocardial infarction (STEMI).

Structure
Thumb
Synonyms
SynonymLanguageCode
ArixtraNot AvailableNot Available
Methyl O-2-deoxy-6-O-sulfo-2-(sulfoamino)-alpha-D-glucopyranosyl-(1-4)-O-beta-D-glucopyranuronosyl-(1-4)-O-2-deoxy-3,6-di-O-sulfo-2-(sulfoamino)-alpha-D-glucopyranosyl-(1-4)-O-2-O-sulfo-alpha-L-idopyranuronosyl-(1-4)-2-deoxy-6-O-sulfo-2-(sulfoamino)-alpha-D-glucopyranoside, decasodium saltNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Arixtrainjection, solution2.5 mg/.5mLsubcutaneousGlaxo Smith Kline Llc2005-03-302016-10-31Us 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Arixtrainjection, solution5 mg/.4mLsubcutaneousGlaxo Smith Kline Llc2004-11-172016-11-30Us 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Arixtrainjection, solution7.5 mg/.6mLsubcutaneousGlaxo Smith Kline Llc2004-11-172016-11-30Us 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Arixtrainjection, solution10 mg/.8mLsubcutaneousGlaxo Smith Kline Llc2004-11-172016-09-30Us 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Arixtrainjection, solution7.5 mg/.6mLsubcutaneousPhysicians Total Care, Inc.2004-11-17Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fondaparinux Sodiuminjection, solution2.5 mg/.5mLsubcutaneousApotex Corp.2011-07-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fondaparinux Sodiuminjection, solution5 mg/.4mLsubcutaneousApotex Corp.2011-07-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fondaparinux Sodiuminjection, solution7.5 mg/.6mLsubcutaneousApotex Corp.2011-07-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fondaparinux Sodiuminjection, solution10 mg/.8mLsubcutaneousApotex Corp.2011-07-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fondaparinux Sodiuminjection, solution2.5 mg/.5mLsubcutaneousMylan Institutional LLC2015-01-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fondaparinux Sodiuminjection, solution5 mg/.4mLsubcutaneousMylan Institutional LLC2015-01-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fondaparinux Sodiuminjection, solution7.5 mg/.6mLsubcutaneousMylan Institutional LLC2015-01-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fondaparinux Sodiuminjection, solution10 mg/.8mLsubcutaneousMylan Institutional LLC2015-01-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Arixtrainjection, solution2.5 mg/.5mLsubcutaneousMylan Institutional LLC2014-05-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Arixtrainjection, solution5 mg/.4mLsubcutaneousMylan Institutional LLC2014-05-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Arixtrainjection, solution7.5 mg/.6mLsubcutaneousMylan Institutional LLC2014-05-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Arixtrainjection, solution10 mg/.8mLsubcutaneousMylan Institutional LLC2014-05-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Arixtrasolution2.5 mgintravenousGlaxosmithkline IncNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Arixtrasolution12.5 mgsubcutaneousGlaxosmithkline IncNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Fondaparinux Sodiuminjection2.5 mg/.5mLsubcutaneousDr. Reddy's Laboratories Limited2011-07-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fondaparinux Sodiuminjection5 mg/.4mLsubcutaneousDr. Reddy's Laboratories Limited2011-07-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fondaparinux Sodiuminjection7.5 mg/.6mLsubcutaneousDr. Reddy's Laboratories Limited2011-07-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fondaparinux Sodiuminjection10 mg/.8mLsubcutaneousDr. Reddy's Laboratories Limited2011-07-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number114870-03-0
WeightAverage: 1730.097
Monoisotopic: 1728.786427203
Chemical FormulaC31H45N3Na10O49S8
InChI KeyXEKSTYNIJLDDAZ-JASSWCPGSA-F
InChI
InChI=1S/C31H53N3O49S8.10Na/c1-69-27-9(33-85(48,49)50)13(37)17(6(74-27)3-71-88(57,58)59)76-31-22(83-91(66,67)68)16(40)21(24(81-31)26(43)44)79-29-10(34-86(51,52)53)19(82-90(63,64)65)18(7(75-29)4-72-89(60,61)62)77-30-15(39)14(38)20(23(80-30)25(41)42)78-28-8(32-84(45,46)47)12(36)11(35)5(73-28)2-70-87(54,55)56;;;;;;;;;;/h5-24,27-40H,2-4H2,1H3,(H,41,42)(H,43,44)(H,45,46,47)(H,48,49,50)(H,51,52,53)(H,54,55,56)(H,57,58,59)(H,60,61,62)(H,63,64,65)(H,66,67,68);;;;;;;;;;/q;10*+1/p-8/t5-,6-,7-,8-,9-,10-,11-,12-,13-,14-,15-,16+,17-,18-,19-,20+,21+,22-,23+,24-,27+,28-,29-,30-,31-;;;;;;;;;;/m1........../s1
IUPAC Name
decasodium N-[(2S,3R,4R,5S,6R)-5-{[(2R,3R,4S,5S,6R)-6-carboxy-5-{[(2R,3R,4R,5R,6R)-5-{[(2R,3R,4R,5S,6S)-6-carboxy-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-[(sulfonatooxy)methyl]oxan-2-yl]oxy}-4-hydroxy-3-(sulfonatooxy)oxan-2-yl]oxy}-4-hydroxy-2-methoxy-6-[(sulfonatooxy)methyl]oxan-3-yl]sulfamate
SMILES
[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].CO[C@H]1O[C@H](COS([O-])(=O)=O)[C@@H](O[C@@H]2O[C@H]([C@@H](O[C@H]3O[C@H](COS([O-])(=O)=O)[C@@H](O[C@@H]4O[C@@H]([C@@H](O[C@H]5O[C@H](COS([O-])(=O)=O)[C@@H](O)[C@H](O)[C@H]5NS([O-])(=O)=O)[C@H](O)[C@H]4O)C(O)=O)[C@H](OS([O-])(=O)=O)[C@H]3NS([O-])(=O)=O)[C@H](O)[C@H]2OS([O-])(=O)=O)C(O)=O)[C@H](O)[C@H]1NS([O-])(=O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as oligosaccharide sulfates. These are carbohydrates containing between 3 and 9 sugar units, one of which bear one or more sulfate groups.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassOligosaccharides
Direct ParentOligosaccharide sulfates
Alternative Parents
Substituents
  • Oligosaccharide sulfate
  • Fatty acyl glycoside
  • O-glucuronide
  • 1-o-glucuronide
  • Glucuronic acid or derivatives
  • Glucosamine
  • O-glycosyl compound
  • Glycosyl compound
  • Pyran carboxylic acid
  • Pyran carboxylic acid or derivatives
  • Amino saccharide
  • Sulfuric acid monoester
  • Fatty acyl
  • Sulfuric acid ester
  • Alkyl sulfate
  • Sulfate-ester
  • Pyran
  • Oxane
  • Sulfuric acid monoamide
  • Dicarboxylic acid or derivatives
  • Organic sulfuric acid or derivatives
  • Secondary alcohol
  • Carboxylic acid salt
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organic alkali metal salt
  • Organic sodium salt
  • Organic salt
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Organic cation
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationApproved for: (1) prophylaxis of VTE for up to one month post surgery in patients undergoing orthopedic surgery of the lower limbs such as hip fracture, hip replacement and knee surgery; (2) prophylaxis of VTE patients undergoing abdominal surgery who are at high risk of thromboembolic complications (e.g. patients undergoing abdominal cancer surgery); (3) treatment of acute DVT and PE; (4) management of UA and NSTEMI for the prevention of death and subsequent myocardial infarction (MI); and (5) management of STEMI for the prevention of death and myocardial reinfarction in patients who are managed with thrombolytics or who are initially to receive no form of reperfusion therapy. Fondaparinux should not be used as the sole anticoagulant during percutaneous coronary intervention (PCI) due to an increased risk of guiding catheter thrombosis.
PharmacodynamicsFondaparinux binds specifically to the natural anticoagulant factor, ATIII. Binding to ATIII potentiates the neutralizing action of ATIII on Factor Xa 300-times. Neutralization of Factor Xa decreases the conversion of prothrombin to thrombin, which subsequently decreases the conversion of fibrinogen to fibrin (loose meshwork). The decrease in thrombin also decreases the activation of Factor XIII, which decreases the conversion of fibrin in its loose meshwork form to its stabilized meshwork form. Disruption of the coagulation cascade effectively decreases the formation of blood clots. Fondaparinux does not inactivate thrombin (activated Factor II). According to the manufacturer, fondaparinux has no known effect on platelet function. In studies comparing fondaparinux to enoxaparin, decreases in platelet levels were observed in similar numbers of patients from both groups (2-5%) (PMID 11794148, 12049860). At the recommended dose, Fondaparinux does not affect fibrinolytic activity or bleeding time. There is no antidote for fondaparinux. Monitoring of the anticoagulant activity of fondaparinux is not generally required. The anti-factor Xa assay may be used to monitor therapy in special populations such as those with renal impairment or who are pregnant. Complete blood count (CBC) and kidney function should be monitored during treatment.
Mechanism of actionThe antithrombotic activity of fondaparinux is the result of ATIII-mediated selective inhibition of Factor Xa. By selectively binding to ATIII, Fondaparinux potentiates (about 300 times) the neutralization of Factor Xa by ATIII. Neutralization of Factor Xa interrupts the blood coagulation cascade and thus inhibits thrombin formation and thrombus development. It is thought that fondaparinux is unlikely to induce thrombocytopenia via a heparin-induced thrombocytopenia (HIT)-like mechanism given its chemical structure (PMID 19825921). As a result, fondaparinux has been used as an alternative anticoagulant in heparin-induced thrombocytopenia (HIT) patients (PMID 19737996, 19432027, 18217156). However, it is important to note that rare cases of HIT have been reported in patients treated with fondaparinux (PMID 20351685, 20351686).
Absorption100% bioavailability when administered subcutaneously
Volume of distribution
  • 7 – 11 L (healthy adults), distributed primarily in blood
Protein binding94% in vitro protein binding specifically to ATIII
Metabolism

Not metabolized

Route of eliminationIn individuals with normal kidney function, fondaparinux is eliminated in urine mainly as unchanged drug.
Half life17-21 hours
ClearanceNot Available
ToxicityAs with other anticoagulants, the main concern is increased bleed risk. The risk of hemorrhage may increase with decreased renal function, body mass less than 50 kg, and moderate to severe hepatic function.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Fondaparinux Action PathwayDrug actionSMP00273
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9857
Blood Brain Barrier-0.8953
Caco-2 permeable-0.6312
P-glycoprotein substrateNon-substrate0.6876
P-glycoprotein inhibitor INon-inhibitor0.6169
P-glycoprotein inhibitor IINon-inhibitor0.9493
Renal organic cation transporterNon-inhibitor0.9327
CYP450 2C9 substrateNon-substrate0.8037
CYP450 2D6 substrateNon-substrate0.8179
CYP450 3A4 substrateNon-substrate0.5537
CYP450 1A2 substrateNon-inhibitor0.7505
CYP450 2C9 substrateNon-inhibitor0.7664
CYP450 2D6 substrateNon-inhibitor0.8799
CYP450 2C19 substrateNon-inhibitor0.757
CYP450 3A4 substrateNon-inhibitor0.9208
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9172
Ames testNon AMES toxic0.5944
CarcinogenicityNon-carcinogens0.763
BiodegradationNot ready biodegradable0.8922
Rat acute toxicity2.4465 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8431
hERG inhibition (predictor II)Non-inhibitor0.6468
Pharmacoeconomics
Manufacturers
  • Glaxosmithkline
Packagers
Dosage forms
FormRouteStrength
Injectionsubcutaneous10 mg/.8mL
Injectionsubcutaneous2.5 mg/.5mL
Injectionsubcutaneous5 mg/.4mL
Injectionsubcutaneous7.5 mg/.6mL
Injection, solutionsubcutaneous10 mg/.8mL
Injection, solutionsubcutaneous2.5 mg/.5mL
Injection, solutionsubcutaneous5 mg/.4mL
Injection, solutionsubcutaneous7.5 mg/.6mL
Solutionintravenous2.5 mg
Solutionsubcutaneous12.5 mg
Prices
Unit descriptionCostUnit
Arixtra 7.5 mg/0.6ml Solution 0.6ml Syringe148.62USD syringe
Arixtra 2.5 mg/0.5ml Solution 0.5ml Syringe63.15USD syringe
Arixtra (0.5 Ml Syringe) 2.5 mg/syr Syringe17.38USD syringe
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP0.4Not Available
Predicted Properties
PropertyValueSource
logP-10ChemAxon
pKa (Strongest Acidic)-3ChemAxon
Physiological Charge-10ChemAxon
Hydrogen Acceptor Count44ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area828.12 Å2ChemAxon
Rotatable Bond Count27ChemAxon
Refractivity246.87 m3·mol-1ChemAxon
Polarizability119.2 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Jean-Francois Branellec, Christian Morello, Pierre Potier, Patrick Trouilleux, Petrus Marcus Bastiaansen, Henricus Cornelis Claassen, “Highly pure fondaparinux sodium composition, process for preparing said composition and pharmaceutical compositions containing it as active principle.” U.S. Patent US20050020536, issued January 27, 2005.

US20050020536
General Reference
  1. GlaxoSmithKline. Arixtra® (fondaparinux sodium) injection prescribing information. Mississauga, ON. 2010 May.
  2. Eriksson BI, Bauer KA, Lassen MR, Turpie AG: Fondaparinux compared with enoxaparin for the prevention of venous thromboembolism after hip-fracture surgery. N Engl J Med. 2001 Nov 1;345(18):1298-304. Pubmed
  3. Turpie AG, Bauer KA, Eriksson BI, Lassen MR: Postoperative fondaparinux versus postoperative enoxaparin for prevention of venous thromboembolism after elective hip-replacement surgery: a randomised double-blind trial. Lancet. 2002 May 18;359(9319):1721-6. Pubmed
  4. Lassen MR, Bauer KA, Eriksson BI, Turpie AG: Postoperative fondaparinux versus preoperative enoxaparin for prevention of venous thromboembolism in elective hip-replacement surgery: a randomised double-blind comparison. Lancet. 2002 May 18;359(9319):1715-20. Pubmed
  5. Bauer KA, Eriksson BI, Lassen MR, Turpie AG: Fondaparinux compared with enoxaparin for the prevention of venous thromboembolism after elective major knee surgery. N Engl J Med. 2001 Nov 1;345(18):1305-10. Pubmed
  6. Bauer KA, Eriksson BI, Lassen MR, Turpie AG: Fondaparinux compared with enoxaparin for the prevention of venous thromboembolism after elective major knee surgery. N Engl J Med. 2001 Nov 1;345(18):1305-10. Pubmed
  7. Agnelli G, Bergqvist D, Cohen AT, Gallus AS, Gent M: Randomized clinical trial of postoperative fondaparinux versus perioperative dalteparin for prevention of venous thromboembolism in high-risk abdominal surgery. Br J Surg. 2005 Oct;92(10):1212-20. Pubmed
  8. Buller HR, Davidson BL, Decousus H, Gallus A, Gent M, Piovella F, Prins MH, Raskob G, Segers AE, Cariou R, Leeuwenkamp O, Lensing AW: Fondaparinux or enoxaparin for the initial treatment of symptomatic deep venous thrombosis: a randomized trial. Ann Intern Med. 2004 Jun 1;140(11):867-73. Pubmed
  9. Buller HR, Davidson BL, Decousus H, Gallus A, Gent M, Piovella F, Prins MH, Raskob G, van den Berg-Segers AE, Cariou R, Leeuwenkamp O, Lensing AW: Subcutaneous fondaparinux versus intravenous unfractionated heparin in the initial treatment of pulmonary embolism. N Engl J Med. 2003 Oct 30;349(18):1695-702. Pubmed
  10. Yusuf S, Mehta SR, Chrolavicius S, Afzal R, Pogue J, Granger CB, Budaj A, Peters RJ, Bassand JP, Wallentin L, Joyner C, Fox KA: Comparison of fondaparinux and enoxaparin in acute coronary syndromes. N Engl J Med. 2006 Apr 6;354(14):1464-76. Epub 2006 Mar 14. Pubmed
  11. Bassand JP, Richard-Lordereau I, Cadroy Y: Efficacy and safety of fondaparinux in patients with acute coronary syndromes. Expert Rev Cardiovasc Ther. 2007 Nov;5(6):1013-26. Pubmed
  12. Steg PG, Jolly SS, Mehta SR, Afzal R, Xavier D, Rupprecht HJ, Lopez-Sendon JL, Budaj A, Diaz R, Avezum A, Widimsky P, Rao SV, Chrolavicius S, Meeks B, Joyner C, Pogue J, Yusuf S: Low-dose vs standard-dose unfractionated heparin for percutaneous coronary intervention in acute coronary syndromes treated with fondaparinux: the FUTURA/OASIS-8 randomized trial. JAMA. 2010 Sep 22;304(12):1339-49. Epub 2010 Aug 31. Pubmed
  13. Yusuf S, Mehta SR, Chrolavicius S, Afzal R, Pogue J, Granger CB, Budaj A, Peters RJ, Bassand JP, Wallentin L, Joyner C, Fox KA: Effects of fondaparinux on mortality and reinfarction in patients with acute ST-segment elevation myocardial infarction: the OASIS-6 randomized trial. JAMA. 2006 Apr 5;295(13):1519-30. Epub 2006 Mar 14. Pubmed
  14. Kovacs MJ: Successful treatment of heparin induced thrombocytopenia (HIT) with fondaparinux. Thromb Haemost. 2005 May;93(5):999-1000. Pubmed
  15. Ortel TL: Heparin-induced thrombocytopenia: when a low platelet count is a mandate for anticoagulation. Hematology Am Soc Hematol Educ Program. 2009:225-32. Pubmed
  16. Moser M, Bode C: New antithrombotic agents in acute coronary syndromes. Curr Opin Cardiol. 2009 Jul;24(4):313-7. Pubmed
  17. Hirsh J, Bauer KA, Donati MB, Gould M, Samama MM, Weitz JI: Parenteral anticoagulants: American College of Chest Physicians Evidence-Based Clinical Practice Guidelines (8th Edition). Chest. 2008 Jun;133(6 Suppl):141S-159S. Pubmed
  18. Geerts WH, Bergqvist D, Pineo GF, Heit JA, Samama CM, Lassen MR, Colwell CW: Prevention of venous thromboembolism: American College of Chest Physicians Evidence-Based Clinical Practice Guidelines (8th Edition). Chest. 2008 Jun;133(6 Suppl):381S-453S. Pubmed
  19. Kearon C, Kahn SR, Agnelli G, Goldhaber S, Raskob GE, Comerota AJ: Antithrombotic therapy for venous thromboembolic disease: American College of Chest Physicians Evidence-Based Clinical Practice Guidelines (8th Edition). Chest. 2008 Jun;133(6 Suppl):454S-545S. Pubmed
  20. Anderson JL, Adams CD, Antman EM, Bridges CR, Califf RM, Casey DE Jr, Chavey WE 2nd, Fesmire FM, Hochman JS, Levin TN, Lincoff AM, Peterson ED, Theroux P, Wenger NK, Wright RS, Smith SC Jr, Jacobs AK, Adams CD, Anderson JL, Antman EM, Halperin JL, Hunt SA, Krumholz HM, Kushner FG, Lytle BW, Nishimura R, Ornato JP, Page RL, Riegel B: ACC/AHA 2007 guidelines for the management of patients with unstable angina/non-ST-Elevation myocardial infarction: a report of the American College of Cardiology/American Heart Association Task Force on Practice Guidelines (Writing Committee to Revise the 2002 Guidelines for the Management of Patients With Unstable Angina/Non-ST-Elevation Myocardial Infarction) developed in collaboration with the American College of Emergency Physicians, the Society for Cardiovascular Angiography and Interventions, and the Society of Thoracic Surgeons endorsed by the American Association of Cardiovascular and Pulmonary Rehabilitation and the Society for Academic Emergency Medicine. J Am Coll Cardiol. 2007 Aug 14;50(7):e1-e157. Pubmed
  21. Goodman SG, Menon V, Cannon CP, Steg G, Ohman EM, Harrington RA: Acute ST-segment elevation myocardial infarction: American College of Chest Physicians Evidence-Based Clinical Practice Guidelines (8th Edition). Chest. 2008 Jun;133(6 Suppl):708S-775S. Pubmed
  22. Warkentin TE, Greinacher A, Koster A, Lincoff AM: Treatment and prevention of heparin-induced thrombocytopenia: American College of Chest Physicians Evidence-Based Clinical Practice Guidelines (8th Edition). Chest. 2008 Jun;133(6 Suppl):340S-380S. Pubmed
  23. Harrington RA, Becker RC, Cannon CP, Gutterman D, Lincoff AM, Popma JJ, Steg G, Guyatt GH, Goodman SG: Antithrombotic therapy for non-ST-segment elevation acute coronary syndromes: American College of Chest Physicians Evidence-Based Clinical Practice Guidelines (8th Edition). Chest. 2008 Jun;133(6 Suppl):670S-707S. Pubmed
External Links
ATC CodesNot Available
AHFS Codes
  • 20:12.04.92
PDB Entries
FDA labelDownload (289 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AbciximabAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
AcenocoumarolMay enhance the anticoagulant effect of other Anticoagulants.
Acetylsalicylic acidMay enhance the anticoagulant effect of Anticoagulants.
AlteplaseThrombolytic Agents may enhance the anticoagulant effect of Anticoagulants.
Aminosalicylic AcidSalicylates may enhance the anticoagulant effect of Anticoagulants.
AnagrelideAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
AnistreplaseMay enhance the anticoagulant effect of Anticoagulants.
ApixabanMay enhance the anticoagulant effect of Anticoagulants.
ArgatrobanMay enhance the anticoagulant effect of other Anticoagulants.
Bismuth SubsalicylateSalicylates may enhance the anticoagulant effect of Anticoagulants.
BivalirudinMay enhance the anticoagulant effect of other Anticoagulants.
CelecoxibNonsteroidal Anti-Inflammatory Agents may enhance the anticoagulant effect of Anticoagulants.
CilostazolAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
CitalopramAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
Citric AcidMay enhance the anticoagulant effect of other Anticoagulants.
ClopidogrelAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
Cyproterone acetateProgestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
Dabigatran etexilateMay enhance the anticoagulant effect of Anticoagulants.
DalteparinMay enhance the anticoagulant effect of other Anticoagulants.
DanaparoidMay enhance the anticoagulant effect of other Anticoagulants.
DasatinibMay enhance the anticoagulant effect of Anticoagulants.
DeferasiroxAnticoagulants may enhance the adverse/toxic effect of Deferasirox. Specifically, the risk for GI ulceration/irritation or GI bleeding may be increased.
Deoxycholic AcidAnticoagulants may enhance the adverse/toxic effect of Deoxycholic Acid. Specifically, the risk for bleeding or bruising in the treatment area may be increased.
DesogestrelEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
DesvenlafaxineAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
DicoumarolMay enhance the anticoagulant effect of other Anticoagulants.
DiflunisalAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
DipyridamoleAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
DrospirenoneEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
DuloxetineAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
DydrogesteroneMay diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
Edetic AcidMay enhance the anticoagulant effect of other Anticoagulants.
EnoxaparinMay enhance the anticoagulant effect of other Anticoagulants.
EpoprostenolProstacyclin Analogues may enhance the adverse/toxic effect of Anticoagulants. Specifically, the antiplatelet effects of these agents may lead to an increased risk of bleeding with the combination.
EptifibatideAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
EscitalopramAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
EstropipateEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
Ethinyl EstradiolEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
Ethyl biscoumacetateMay enhance the anticoagulant effect of other Anticoagulants.
EthynodiolEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
EtodolacAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
EtonogestrelProgestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
FenoprofenAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
FloctafenineAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
FluoxetineAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
FluvoxamineAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
GestodeneMay diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
HeparinMay enhance the anticoagulant effect of other Anticoagulants.
HomoharringtonineMay enhance the adverse/toxic effect of Omacetaxine. Specifically, the risk for bleeding-related events may be increased.
IbritumomabMay enhance the adverse/toxic effect of Ibritumomab. Both agents may contribute to an increased risk of bleeding.
IbuprofenAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
IcosapentOmega-3 Fatty Acids may enhance the anticoagulant effect of Anticoagulants.
Icosapent ethylOmega-3 Fatty Acids may enhance the anticoagulant effect of Anticoagulants.
IloprostProstacyclin Analogues may enhance the adverse/toxic effect of Anticoagulants. Specifically, the antiplatelet effects of these agents may lead to an increased risk of bleeding with the combination.
IndomethacinAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
KetoprofenAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
KetorolacAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
LevomilnacipranAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
LevonorgestrelProgestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
Magnesium salicylateSalicylates may enhance the anticoagulant effect of Anticoagulants.
Medroxyprogesterone AcetateProgestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
Mefenamic acidAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
Megestrol acetateProgestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
MeloxicamAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
MestranolEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
MilnacipranAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
NabumetoneAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
NadroparinMay enhance the anticoagulant effect of other Anticoagulants.
NaproxenAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
NorelgestrominEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
NorethindroneProgestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
NorgestimateEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
ObinutuzumabAnticoagulants may enhance the adverse/toxic effect of Obinutuzumab. Specifically, the risk of serious bleeding-related events may be increased.
OxaprozinAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
ParoxetineAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
Pentosan PolysulfatePentosan Polysulfate Sodium may enhance the anticoagulant effect of Anticoagulants.
PhenindioneMay enhance the anticoagulant effect of other Anticoagulants.
PhenprocoumonMay enhance the anticoagulant effect of other Anticoagulants.
PiperazineEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
PiroxicamAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
PrasugrelAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
ProgesteroneProgestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
ReteplaseThrombolytic Agents may enhance the anticoagulant effect of Anticoagulants.
RidogrelMay enhance the anticoagulant effect of Anticoagulants.
RivaroxabanAnticoagulants may enhance the anticoagulant effect of Rivaroxaban.
Salicylate-sodiumMay enhance the anticoagulant effect of Anticoagulants.
SalsalateSalicylates may enhance the anticoagulant effect of Anticoagulants.
SertralineAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
StreptokinaseMay enhance the anticoagulant effect of Anticoagulants.
SugammadexMay enhance the anticoagulant effect of Anticoagulants.
SulindacAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
SulodexideMay enhance the anticoagulant effect of other Anticoagulants.
TenecteplaseThrombolytic Agents may enhance the anticoagulant effect of Anticoagulants.
Tiaprofenic acidAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
TicagrelorAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
TiclopidineAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
TinzaparinMay enhance the anticoagulant effect of other Anticoagulants.
TipranavirMay enhance the anticoagulant effect of Anticoagulants.
TirofibanAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
TolmetinAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
TositumomabMay enhance the adverse/toxic effect of Tositumomab and Iodine I 131 Tositumomab. Specifically, the risk of bleeding-related adverse effects may be increased.
TreprostinilProstacyclin Analogues may enhance the adverse/toxic effect of Anticoagulants. Specifically, the antiplatelet effects of these agents may lead to an increased risk of bleeding with the combination.
UrokinaseMay enhance the anticoagulant effect of Anticoagulants.
VenlafaxineAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
VilazodoneAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
Vitamin EVitamin E may enhance the anticoagulant effect of Anticoagulants. Vitamin E may also increase the overall risk for bleeding.
VorapaxarMay enhance the adverse/toxic effect of Anticoagulants. More specifically, this combination is expected to increase the risk of bleeding.
WarfarinMay enhance the anticoagulant effect of other Anticoagulants.
Food InteractionsNot Available

Targets

1. Antithrombin-III

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: potentiator

Components

Name UniProt ID Details
Antithrombin-III P01008 Details

References:

  1. Paolucci F, Clavies MC, Donat F, Necciari J: Fondaparinux sodium mechanism of action: identification of specific binding to purified and human plasma-derived proteins. Clin Pharmacokinet. 2002;41 Suppl 2:11-8. Pubmed
  2. Cheng JW: Fondaparinux: a new antithrombotic agent. Clin Ther. 2002 Nov;24(11):1757-69; discussion 1719. Pubmed
  3. Dager WE, Andersen J, Nutescu E: Special considerations with fondaparinux therapy: heparin-induced thrombocytopenia and wound healing. Pharmacotherapy. 2004 Jul;24(7 Pt 2):88S-94S. Pubmed
  4. Donat F, Duret JP, Santoni A, Cariou R, Necciari J, Magnani H, de Greef R: The pharmacokinetics of fondaparinux sodium in healthy volunteers. Clin Pharmacokinet. 2002;41 Suppl 2:1-9. Pubmed

2. Coagulation factor X

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Coagulation factor X P00742 Details

References:

  1. Grouzi E, Kyriakou E, Panagou I, Spiliotopoulou I: Fondaparinux for the treatment of acute heparin-induced thrombocytopenia: a single-center experience. Clin Appl Thromb Hemost. 2010 Dec;16(6):663-7. Epub 2009 Oct 13. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:11