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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
Arixtra
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 salt
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Arixtrainjection, solution10 mg/.8mLsubcutaneousMylan Institutional LLC2015-05-06Not applicableUs
Arixtrainjection, solution2.5 mg/.5mLsubcutaneousGlaxo Smith Kline Llc2005-03-30Not applicableUs
Arixtrasolution12.5 mgsubcutaneousAspen Pharma Trading Limited2008-04-17Not applicableCanada
Arixtrainjection, solution7.5 mg/.6mLsubcutaneousMylan Institutional LLC2015-05-06Not applicableUs
Arixtrasolution12.5 mgsubcutaneousAspen Pharma Trading Limited2008-04-17Not applicableCanada
Arixtrainjection, solution5 mg/.4mLsubcutaneousMylan Institutional LLC2015-08-07Not applicableUs
Arixtrainjection, solution2.5 mg/.5mLsubcutaneousMylan Institutional LLC2015-05-06Not applicableUs
Arixtrasolution12.5 mgsubcutaneousAspen Pharma Trading Limited2008-04-17Not applicableCanada
Arixtrainjection, solution7.5 mg/.6mLsubcutaneousPhysicians Total Care, Inc.2004-11-17Not applicableUs
Arixtrasolution2.5 mgintravenous; subcutaneousAspen Pharma Trading Limited2002-07-19Not applicableCanada
Arixtrainjection, solution10 mg/.8mLsubcutaneousGlaxo Smith Kline Llc2004-11-17Not applicableUs
Arixtrainjection, solution7.5 mg/.6mLsubcutaneousGlaxo Smith Kline Llc2004-11-17Not applicableUs
Arixtrainjection, solution5 mg/.4mLsubcutaneousGlaxo Smith Kline Llc2004-11-17Not applicableUs
Fondaparinux Sodiuminjection, solution10 mg/.8mLsubcutaneousApotex Corp.2011-07-18Not applicableUs
Fondaparinux Sodiuminjection, solution7.5 mg/.6mLsubcutaneousApotex Corp.2011-07-18Not applicableUs
Fondaparinux Sodiuminjection, solution5 mg/.4mLsubcutaneousApotex Corp.2011-07-18Not applicableUs
Fondaparinux Sodiuminjection, solution2.5 mg/.5mLsubcutaneousApotex Corp.2011-07-18Not applicableUs
Fondaparinux Sodiuminjection, solution10 mg/.8mLsubcutaneousMylan Institutional LLC2015-01-05Not applicableUs
Fondaparinux Sodiuminjection, solution7.5 mg/.6mLsubcutaneousMylan Institutional LLC2015-01-05Not applicableUs
Fondaparinux Sodiuminjection, solution5 mg/.4mLsubcutaneousMylan Institutional LLC2015-01-05Not applicableUs
Fondaparinux Sodiuminjection, solution2.5 mg/.5mLsubcutaneousMylan Institutional LLC2015-01-05Not applicableUs
Fondaparinux Sodium Injectionsolution2.5 mgintravenous; subcutaneousDr Reddys Laboratories Ltd2014-03-21Not applicableCanada
Fondaparinux Sodium Injectionsolution10 mgsubcutaneousDr Reddys Laboratories LtdNot applicableNot applicableCanada
Fondaparinux Sodium Injectionsolution5 mgsubcutaneousDr Reddys Laboratories LtdNot applicableNot applicableCanada
Fondaparinux Sodium Injectionsolution7.5 mgsubcutaneousDr Reddys Laboratories Ltd2014-03-21Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Fondaparinux Sodiuminjection2.5 mg/.5mLsubcutaneousDr. Reddy's Laboratories Limited2011-07-14Not applicableUs
Fondaparinux Sodiuminjection10 mg/.8mLsubcutaneousDr. Reddy's Laboratories Limited2011-07-14Not applicableUs
Fondaparinux Sodiuminjection7.5 mg/.6mLsubcutaneousDr. Reddy's Laboratories Limited2011-07-14Not applicableUs
Fondaparinux Sodiuminjection5 mg/.4mLsubcutaneousDr. Reddy's Laboratories Limited2011-07-14Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIX0Q6N9USOZ
CAS number114870-03-0
WeightAverage: 1730.097
Monoisotopic: 1728.786427203
Chemical FormulaC31H45N3Na10O49S8
InChI KeyInChIKey=XEKSTYNIJLDDAZ-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[[email protected]]1O[[email protected]](COS([O-])(=O)=O)[C@@H](O[C@@H]2O[[email protected]]([C@@H](O[[email protected]]3O[[email protected]](COS([O-])(=O)=O)[C@@H](O[C@@H]4O[C@@H]([C@@H](O[[email protected]]5O[[email protected]](COS([O-])(=O)=O)[C@@H](O)[[email protected]](O)[[email protected]]5NS([O-])(=O)=O)[[email protected]](O)[[email protected]]4O)C(O)=O)[[email protected]](OS([O-])(=O)=O)[[email protected]]3NS([O-])(=O)=O)[[email protected]](O)[[email protected]]2OS([O-])(=O)=O)C(O)=O)[[email protected]](O)[[email protected]]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).
Related Articles
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 inhibitorNon-inhibitor0.7664
CYP450 2D6 inhibitorNon-inhibitor0.8799
CYP450 2C19 inhibitorNon-inhibitor0.757
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Glaxosmithkline
Packagers
Dosage forms
FormRouteStrength
Injection, solutionsubcutaneous10 mg/.8mL
Injection, solutionsubcutaneous2.5 mg/.5mL
Injection, solutionsubcutaneous5 mg/.4mL
Injection, solutionsubcutaneous7.5 mg/.6mL
Solutionsubcutaneous12.5 mg
Injectionsubcutaneous10 mg/.8mL
Injectionsubcutaneous2.5 mg/.5mL
Injectionsubcutaneous5 mg/.4mL
Injectionsubcutaneous7.5 mg/.6mL
Solutionintravenous; subcutaneous2.5 mg
Solutionsubcutaneous10 mg
Solutionsubcutaneous5 mg
Solutionsubcutaneous7.5 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 References
  1. 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:11794148 ]
  2. 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:12049860 ]
  3. 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:12049858 ]
  4. 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:11794149 ]
  5. 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:16175516 ]
  6. 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:15172900 ]
  7. 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:14585937 ]
  8. 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:16537663 ]
  9. 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:18035917 ]
  10. 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. doi: 10.1001/jama.2010.1320. Epub 2010 Aug 31. [PubMed:20805623 ]
  11. 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:16537725 ]
  12. Kuo KH, Kovacs MJ: Successful treatment of heparin induced thrombocytopenia (HIT) with fondaparinux. Thromb Haemost. 2005 May;93(5):999-1000. [PubMed:15886823 ]
  13. Ortel TL: Heparin-induced thrombocytopenia: when a low platelet count is a mandate for anticoagulation. Hematology Am Soc Hematol Educ Program. 2009:225-32. doi: 10.1182/asheducation-2009.1.225. [PubMed:20008202 ]
  14. Moser M, Bode C: New antithrombotic agents in acute coronary syndromes. Curr Opin Cardiol. 2009 Jul;24(4):313-7. doi: 10.1097/HCO.0b013e32832bd350. [PubMed:19395952 ]
  15. 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. doi: 10.1378/chest.08-0689. [PubMed:18574264 ]
  16. 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. doi: 10.1378/chest.08-0656. [PubMed:18574271 ]
  17. 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. doi: 10.1378/chest.08-0658. [PubMed:18574272 ]
  18. 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:17692738 ]
  19. 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. doi: 10.1378/chest.08-0665. [PubMed:18574277 ]
  20. 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. doi: 10.1378/chest.08-0677. [PubMed:18574270 ]
  21. 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. doi: 10.1378/chest.08-0691. [PubMed:18574276 ]
External Links
ATC CodesNot Available
AHFS Codes
  • 20:12.04.92
PDB Entries
FDA labelDownload (289 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AbciximabAbciximab may increase the anticoagulant activities of Fondaparinux sodium.
AcenocoumarolAcenocoumarol may increase the anticoagulant activities of Fondaparinux sodium.
Acetylsalicylic acidAcetylsalicylic acid may increase the anticoagulant activities of Fondaparinux sodium.
AlteplaseAlteplase may increase the anticoagulant activities of Fondaparinux sodium.
Aminosalicylic AcidAminosalicylic Acid may increase the anticoagulant activities of Fondaparinux sodium.
AnagrelideAnagrelide may increase the anticoagulant activities of Fondaparinux sodium.
AnistreplaseAnistreplase may increase the anticoagulant activities of Fondaparinux sodium.
ApixabanApixaban may increase the anticoagulant activities of Fondaparinux sodium.
ArgatrobanFondaparinux sodium may increase the anticoagulant activities of Argatroban.
Bismuth SubsalicylateBismuth Subsalicylate may increase the anticoagulant activities of Fondaparinux sodium.
BivalirudinFondaparinux sodium may increase the anticoagulant activities of Bivalirudin.
CaffeineCaffeine may increase the anticoagulant activities of Fondaparinux sodium.
CangrelorCangrelor may increase the anticoagulant activities of Fondaparinux sodium.
CelecoxibCelecoxib may increase the anticoagulant activities of Fondaparinux sodium.
ChlorotrianiseneChlorotrianisene may decrease the anticoagulant activities of Fondaparinux sodium.
CilostazolCilostazol may increase the anticoagulant activities of Fondaparinux sodium.
CitalopramCitalopram may increase the anticoagulant activities of Fondaparinux sodium.
Citric AcidCitric Acid may increase the anticoagulant activities of Fondaparinux sodium.
ClopidogrelClopidogrel may increase the anticoagulant activities of Fondaparinux sodium.
CollagenaseThe risk or severity of adverse effects can be increased when Fondaparinux sodium is combined with Collagenase.
Collagenase clostridium histolyticumThe risk or severity of adverse effects can be increased when Fondaparinux sodium is combined with Collagenase clostridium histolyticum.
Cyproterone acetateThe therapeutic efficacy of Fondaparinux sodium can be decreased when used in combination with Cyproterone acetate.
Dabigatran etexilateDabigatran etexilate may increase the anticoagulant activities of Fondaparinux sodium.
DalteparinDalteparin may increase the anticoagulant activities of Fondaparinux sodium.
DanaparoidFondaparinux sodium may increase the anticoagulant activities of Danaparoid.
DasatinibDasatinib may increase the anticoagulant activities of Fondaparinux sodium.
DeferasiroxThe risk or severity of adverse effects can be increased when Fondaparinux sodium is combined with Deferasirox.
Deoxycholic AcidThe risk or severity of adverse effects can be increased when Fondaparinux sodium is combined with Deoxycholic Acid.
DesirudinFondaparinux sodium may increase the anticoagulant activities of Desirudin.
DesogestrelThe therapeutic efficacy of Fondaparinux sodium can be decreased when used in combination with Desogestrel.
DesvenlafaxineDesvenlafaxine may increase the anticoagulant activities of Fondaparinux sodium.
DiclofenacDiclofenac may increase the anticoagulant activities of Fondaparinux sodium.
DicoumarolDicoumarol may increase the anticoagulant activities of Fondaparinux sodium.
DienogestThe therapeutic efficacy of Fondaparinux sodium can be decreased when used in combination with Dienogest.
DiflunisalDiflunisal may increase the anticoagulant activities of Fondaparinux sodium.
DihydrocodeineDihydrocodeine may increase the anticoagulant activities of Fondaparinux sodium.
DipyridamoleDipyridamole may increase the anticoagulant activities of Fondaparinux sodium.
DrospirenoneDrospirenone may decrease the anticoagulant activities of Fondaparinux sodium.
DuloxetineDuloxetine may increase the anticoagulant activities of Fondaparinux sodium.
DydrogesteroneThe therapeutic efficacy of Fondaparinux sodium can be decreased when used in combination with Dydrogesterone.
Edetic AcidEdetic Acid may increase the anticoagulant activities of Fondaparinux sodium.
EdoxabanEdoxaban may increase the anticoagulant activities of Fondaparinux sodium.
EnoxaparinEnoxaparin may increase the anticoagulant activities of Fondaparinux sodium.
EpoprostenolThe risk or severity of adverse effects can be increased when Epoprostenol is combined with Fondaparinux sodium.
EptifibatideEptifibatide may increase the anticoagulant activities of Fondaparinux sodium.
EscitalopramEscitalopram may increase the anticoagulant activities of Fondaparinux sodium.
EstradiolEstradiol may decrease the anticoagulant activities of Fondaparinux sodium.
Estrone sulfateEstropipate may decrease the anticoagulant activities of Fondaparinux sodium.
Ethinyl EstradiolEthinyl Estradiol may decrease the anticoagulant activities of Fondaparinux sodium.
Ethyl biscoumacetateEthyl biscoumacetate may increase the anticoagulant activities of Fondaparinux sodium.
Ethynodiol diacetateEthynodiol may decrease the anticoagulant activities of Fondaparinux sodium.
EtodolacEtodolac may increase the anticoagulant activities of Fondaparinux sodium.
EtonogestrelThe therapeutic efficacy of Fondaparinux sodium can be decreased when used in combination with Etonogestrel.
FenoprofenFenoprofen may increase the anticoagulant activities of Fondaparinux sodium.
FloctafenineFloctafenine may increase the anticoagulant activities of Fondaparinux sodium.
FluoxetineFluoxetine may increase the anticoagulant activities of Fondaparinux sodium.
FlurbiprofenFlurbiprofen may increase the anticoagulant activities of Fondaparinux sodium.
FluvoxamineFluvoxamine may increase the anticoagulant activities of Fondaparinux sodium.
GestodeneThe therapeutic efficacy of Fondaparinux sodium can be decreased when used in combination with Gestodene.
HeparinHeparin may increase the anticoagulant activities of Fondaparinux sodium.
HomoharringtonineThe risk or severity of adverse effects can be increased when Fondaparinux sodium is combined with Homoharringtonine.
Hydroxyprogesterone caproateThe therapeutic efficacy of Fondaparinux sodium can be decreased when used in combination with Hydroxyprogesterone caproate.
Ibritumomab tiuxetanThe risk or severity of adverse effects can be increased when Fondaparinux sodium is combined with Ibritumomab.
IbrutinibThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Fondaparinux sodium.
IbuprofenIbuprofen may increase the anticoagulant activities of Fondaparinux sodium.
IcosapentIcosapent may increase the anticoagulant activities of Fondaparinux sodium.
Icosapent ethylIcosapent ethyl may increase the anticoagulant activities of Fondaparinux sodium.
IloprostThe risk or severity of adverse effects can be increased when Iloprost is combined with Fondaparinux sodium.
IndomethacinIndomethacin may increase the anticoagulant activities of Fondaparinux sodium.
InfliximabInfliximab may increase the anticoagulant activities of Fondaparinux sodium.
KetoprofenKetoprofen may increase the anticoagulant activities of Fondaparinux sodium.
KetorolacKetorolac may increase the anticoagulant activities of Fondaparinux sodium.
LevomilnacipranLevomilnacipran may increase the anticoagulant activities of Fondaparinux sodium.
LevonorgestrelThe therapeutic efficacy of Fondaparinux sodium can be decreased when used in combination with Levonorgestrel.
LimaprostThe risk or severity of adverse effects can be increased when Limaprost is combined with Fondaparinux sodium.
Magnesium salicylateMagnesium salicylate may increase the anticoagulant activities of Fondaparinux sodium.
Medroxyprogesterone acetateThe therapeutic efficacy of Fondaparinux sodium can be decreased when used in combination with Medroxyprogesterone Acetate.
Mefenamic acidMefenamic acid may increase the anticoagulant activities of Fondaparinux sodium.
Megestrol acetateThe therapeutic efficacy of Fondaparinux sodium can be decreased when used in combination with Megestrol acetate.
MeloxicamMeloxicam may increase the anticoagulant activities of Fondaparinux sodium.
MestranolMestranol may decrease the anticoagulant activities of Fondaparinux sodium.
MilnacipranMilnacipran may increase the anticoagulant activities of Fondaparinux sodium.
NabumetoneNabumetone may increase the anticoagulant activities of Fondaparinux sodium.
NadroparinFondaparinux sodium may increase the anticoagulant activities of Nadroparin.
NaproxenNaproxen may increase the anticoagulant activities of Fondaparinux sodium.
NintedanibThe risk or severity of adverse effects can be increased when Fondaparinux sodium is combined with Nintedanib.
NorethisteroneThe therapeutic efficacy of Fondaparinux sodium can be decreased when used in combination with Norethindrone.
NorgestimateNorgestimate may decrease the anticoagulant activities of Fondaparinux sodium.
ObinutuzumabThe risk or severity of adverse effects can be increased when Fondaparinux sodium is combined with Obinutuzumab.
Omega-3 fatty acidsOmega-3 fatty acids may increase the anticoagulant activities of Fondaparinux sodium.
Omega-3-acid ethyl estersOmega-3-acid ethyl esters may increase the anticoagulant activities of Fondaparinux sodium.
OxaprozinOxaprozin may increase the anticoagulant activities of Fondaparinux sodium.
ParoxetineParoxetine may increase the anticoagulant activities of Fondaparinux sodium.
Pentosan PolysulfatePentosan Polysulfate may increase the anticoagulant activities of Fondaparinux sodium.
PhenindionePhenindione may increase the anticoagulant activities of Fondaparinux sodium.
PhenprocoumonPhenprocoumon may increase the anticoagulant activities of Fondaparinux sodium.
PiroxicamPiroxicam may increase the anticoagulant activities of Fondaparinux sodium.
PrasugrelPrasugrel may increase the anticoagulant activities of Fondaparinux sodium.
ProgesteroneThe therapeutic efficacy of Fondaparinux sodium can be decreased when used in combination with Progesterone.
ReteplaseReteplase may increase the anticoagulant activities of Fondaparinux sodium.
RidogrelRidogrel may increase the anticoagulant activities of Fondaparinux sodium.
RivaroxabanFondaparinux sodium may increase the anticoagulant activities of Rivaroxaban.
SalsalateSalsalate may increase the anticoagulant activities of Fondaparinux sodium.
SertralineSertraline may increase the anticoagulant activities of Fondaparinux sodium.
StreptokinaseStreptokinase may increase the anticoagulant activities of Fondaparinux sodium.
SugammadexSugammadex may increase the anticoagulant activities of Fondaparinux sodium.
SulindacSulindac may increase the anticoagulant activities of Fondaparinux sodium.
SulodexideSulodexide may increase the anticoagulant activities of Fondaparinux sodium.
TenecteplaseTenecteplase may increase the anticoagulant activities of Fondaparinux sodium.
Tiaprofenic acidTiaprofenic acid may increase the anticoagulant activities of Fondaparinux sodium.
TiboloneTibolone may increase the anticoagulant activities of Fondaparinux sodium.
TicagrelorTicagrelor may increase the anticoagulant activities of Fondaparinux sodium.
TiclopidineTiclopidine may increase the anticoagulant activities of Fondaparinux sodium.
TinzaparinFondaparinux sodium may increase the anticoagulant activities of Tinzaparin.
TipranavirTipranavir may increase the anticoagulant activities of Fondaparinux sodium.
TirofibanTirofiban may increase the anticoagulant activities of Fondaparinux sodium.
TolmetinTolmetin may increase the anticoagulant activities of Fondaparinux sodium.
TositumomabThe risk or severity of adverse effects can be increased when Fondaparinux sodium is combined with Tositumomab.
TreprostinilThe risk or severity of adverse effects can be increased when Treprostinil is combined with Fondaparinux sodium.
UrokinaseUrokinase may increase the anticoagulant activities of Fondaparinux sodium.
VenlafaxineVenlafaxine may increase the anticoagulant activities of Fondaparinux sodium.
VilazodoneVilazodone may increase the anticoagulant activities of Fondaparinux sodium.
Vitamin EVitamin E may increase the anticoagulant activities of Fondaparinux sodium.
VorapaxarThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Fondaparinux sodium.
VortioxetineVortioxetine may increase the anticoagulant activities of Fondaparinux sodium.
WarfarinWarfarin may increase the anticoagulant activities of Fondaparinux sodium.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
potentiator
General Function:
Serine-type endopeptidase inhibitor activity
Specific Function:
Most important serine protease inhibitor in plasma that regulates the blood coagulation cascade. AT-III inhibits thrombin, matriptase-3/TMPRSS7, as well as factors IXa, Xa and XIa. Its inhibitory activity is greatly enhanced in the presence of heparin.
Gene Name:
SERPINC1
Uniprot ID:
P01008
Molecular Weight:
52601.935 Da
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:12383040 ]
  2. Cheng JW: Fondaparinux: a new antithrombotic agent. Clin Ther. 2002 Nov;24(11):1757-69; discussion 1719. [PubMed:12501872 ]
  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:15317404 ]
  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:12383039 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Serine-type endopeptidase activity
Specific Function:
Factor Xa is a vitamin K-dependent glycoprotein that converts prothrombin to thrombin in the presence of factor Va, calcium and phospholipid during blood clotting.
Gene Name:
F10
Uniprot ID:
P00742
Molecular Weight:
54731.255 Da
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. doi: 10.1177/1076029609347900. Epub 2009 Oct 13. [PubMed:19825921 ]
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:11