Please Wait
Applying Filters...
Menu
Xls
2D Structure
Also known as: 114870-03-0, Arixtra, Quixidar, Fondaparin sodium, Sr-90107a, Org 31540
Molecular Formula
C31H43N3Na10O49S8
Molecular Weight
1728.1  g/mol
InChI Key
XEKSTYNIJLDDAZ-JASSWCPGSA-D
FDA UNII
X0Q6N9USOZ

Synthetic pentasaccharide that mediates the interaction of HEPARIN with ANTITHROMBINS and inhibits FACTOR Xa; it is used for prevention of VENOUS THROMBOEMBOLISM after surgery.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
decasodium;(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5R,6R)-6-[(2R,3S,4S,5R,6R)-2-carboxylato-4-hydroxy-6-[(2R,3S,4R,5R,6S)-4-hydroxy-6-methoxy-5-(sulfonatoamino)-2-(sulfonatooxymethyl)oxan-3-yl]oxy-5-sulfonatooxyoxan-3-yl]oxy-5-(sulfonatoamino)-4-sulfonatooxy-2-(sulfonatooxymethyl)oxan-3-yl]oxy-3-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-(sulfonatoamino)-6-(sulfonatooxymethyl)oxan-2-yl]oxy-4,5-dihydroxyoxane-2-carboxylate
2.1.2 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-10/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
2.1.3 InChI Key
XEKSTYNIJLDDAZ-JASSWCPGSA-D
2.1.4 Canonical SMILES
COC1C(C(C(C(O1)COS(=O)(=O)[O-])OC2C(C(C(C(O2)C(=O)[O-])OC3C(C(C(C(O3)COS(=O)(=O)[O-])OC4C(C(C(C(O4)C(=O)[O-])OC5C(C(C(C(O5)COS(=O)(=O)[O-])O)O)NS(=O)(=O)[O-])O)O)OS(=O)(=O)[O-])NS(=O)(=O)[O-])O)OS(=O)(=O)[O-])O)NS(=O)(=O)[O-].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+]
2.1.5 Isomeric SMILES
CO[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)COS(=O)(=O)[O-])O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](O2)C(=O)[O-])O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)COS(=O)(=O)[O-])O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C(=O)[O-])O[C@@H]5[C@@H]([C@H]([C@@H]([C@H](O5)COS(=O)(=O)[O-])O)O)NS(=O)(=O)[O-])O)O)OS(=O)(=O)[O-])NS(=O)(=O)[O-])O)OS(=O)(=O)[O-])O)NS(=O)(=O)[O-].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+]
2.2 Other Identifiers
2.2.1 UNII
X0Q6N9USOZ
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Arixtra

2. Fondaparinux

3. Quixidar

2.3.2 Depositor-Supplied Synonyms

1. 114870-03-0

2. Arixtra

3. Quixidar

4. Fondaparin Sodium

5. Sr-90107a

6. Org 31540

7. Sr 90107a

8. Fondaparinux Sodium For Assay

9. Org-31540

10. Fondaparinux Sodium Identification

11. X0q6n9usoz

12. Ic-851589

13. Xantidar

14. Arixtra (tn)

15. Unii-x0q6n9usoz

16. Fondaparinux Sodium [usan]

17. Fondaparinux Sodium [usan:inn:ban]

18. Gsk-576428

19. Ic 85158

20. Sr-90107

21. Chembl1200644

22. Fondaparinux Sodium [mi]

23. Fondaparinux Sodium [inn]

24. Fondaparinux Sodium [jan]

25. Dtxsid501027612

26. Fondaparinux Sodium [mart.]

27. Fondaparinux Sodium (jan/usp/inn)

28. Fondaparinux Sodium [usp-rs]

29. Fondaparinux Sodium [who-dd]

30. Natural Heparin Pentasaccharide Sodium

31. Akos005146286

32. Fondaparinux Sodium [ema Epar]

33. Ccg-270693

34. Fondaparinux Sodium [orange Book]

35. As-80003

36. Fondaparinux Sodium [usp Monograph]

37. C71476

38. D01844

39. A803253

40. Q421218

41. Alpha-d-glucopyranoside, 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-2-(sulfoamino)-, 6-(hydrogen Sulfate), Decasodium Salt

42. Decasodium 6-[6-[2-carboxylato-4-hydroxy-6-[4-hydroxy-6-methoxy-5-(sulfonatoamino)-2-(sulfonatooxymethyl)tetrahydropyran-3-yl]oxy-5-sulfonatooxy-tetrahydropyran-3-yl]oxy-5-(sulfonatoamino)-4-sulfonatooxy-2-(sulfonatooxymethyl)tetrahydropyran-3-yl]oxy-3-[4;fondaparinux Sodium

43. Methly 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

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 1728.1 g/mol
Molecular Formula C31H43N3Na10O49S8
Hydrogen Bond Donor Count9
Hydrogen Bond Acceptor Count52
Rotatable Bond Count20
Exact Mass1726.7707769 g/mol
Monoisotopic Mass1726.7707769 g/mol
Topological Polar Surface Area901 Ų
Heavy Atom Count101
Formal Charge0
Complexity3330
Isotope Atom Count0
Defined Atom Stereocenter Count25
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count11
4 Drug and Medication Information
4.1 Drug Indication

* 1. 5-mg/0. 3-ml and 2. 5-mg/0. 5-ml solution for injection:

Prevention of venous thromboembolic events (VTE) in adults undergoing major orthopaedic surgery of the lower limbs such as hip fracture, major knee surgery or hip-replacement surgery.

Prevention of VTE in adults undergoing abdominal surgery who are judged to be at high risk of thromboembolic complications, such as patients undergoing abdominal cancer surgery.

Prevention of VTE in adult medical patients who are judged to be at high risk for VTE and who are immobilised due to acute illness such as cardiac insufficiency and / or acute respiratory disorders, and / or acute infectious or inflammatory disease.

Treatment of adults with acute symptomatic spontaneous superficial-vein thrombosis of the lower limbs without concomitant deep-vein thrombosis.

* 2. 5-mg/0. 5-ml solution for injection:

Treatment of unstable angina or non-ST-segment-elevation myocardial infarction (UA/NSTEMI) in adult patients for whom urgent (< 120 mins) invasive management (PCI) is not indicated.

infarction (STEMI) in adult patients who are managed with thrombolytics or who initially are to receive no other form of reperfusion therapy.

* 5-mg/0. 4-ml, 7. 5-mg/0. 6-ml and 10-mg/0. 8-ml solution for injection:

Treatment of adults with acute deep-vein thrombosis (DVT) and treatment of acute pulmonary embolism (PE), except in haemodynamically unstable patients or patients who require thrombolysis or pulmonary embolectomy.


1. 5 mg/0. 3 ml and 2. 5 mg/0. 5 ml, solution for injection:

Prevention of Venous Thromboembolic Events (VTE) in patients undergoing major orthopaedic surgery of the lower limbs such as hip fracture, major knee surgery or hip replacement surgery.

Prevention of Venous Thromboembolic Events (VTE) in patients undergoing abdominal surgery who are judged to be at high risk of thromboembolic complications, such as patients undergoing abdominal cancer surgery (see section 5. 1).

Prevention of Venous Thromboembolic Events (VTE) in medical patients who are judged to be at high risk for VTE and who are immobilised due to acute illness such as cardiac insufficiency and/or acute respiratory disorders, and/or acute infectious or inflammatory disease.

2. 5 mg/0. 5 ml, solution for injection:

Treatment of unstable angina or non-ST segment elevation myocardial infarction (UA/NSTEMI) in patients for whom urgent (< 120 mins) invasive management (PCI) is not indicated (see sections 4. 4 and 5. 1).

Treatment of ST segment elevation myocardial infarction (STEMI) in patients who are managed with thrombolytics or who initially are to receive no other form of reperfusion therapy.

5 mg/0. 4 ml, 7. 5 mg/0. 6 ml and 10 mg/0. 8 ml solution for injection:

Treatment of acute Deep Vein Thrombosis (DVT) and treatment of acute Pulmonary Embolism (PE), except in haemodynamically unstable patients or patients who require thrombolysis or pulmonary embolectomy.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Factor Xa Inhibitors

Endogenous factors and drugs that inhibit or block the activity of FACTOR XA. (See all compounds classified as Factor Xa Inhibitors.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Factor Xa Inhibitors [MoA]; Factor Xa Inhibitor [EPC]
5.3 ATC Code

B01AX05


B01AX05