PRD_900028

fondaparinux

PRD_900028 is described in the Biologically Interesting Molecule Reference Dictionary (BIRD).

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Chemical Component Summary

Namefondaparinux
Identifiers(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-(sulfooxymethyl)oxan-3-yl]oxy-5-sulfooxy-oxan-3-yl]oxy-5-(sulfoamino)-4-sulfooxy-2-(sulfooxymethyl)oxan-3 -yl]oxy-3-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-(sulfoamino)-6-(sulfooxymethyl)oxan-2-yl]oxy-4,5-dihydroxy-oxane-2-carboxyli c acid
FormulaC31 H53 N3 O49 S8
Molecular Weight1,508.263
TypeSACCHARIDE
Isomeric SMILESCO[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
InChIInChI=1S/C31H53N3O49S8/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)/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
InChIKeyKANJSNBRCNMZMV-ABRZTLGGSA-N
CompositionPolymer Sequences: ZDO-IDS-SUS-BDP-SGN
BIRD classANTICOAGULANT
Represented AsBRANCHED
Compound Detailsn/a
Descriptionn/a

Chemical Details

Formal Charge0
Atom Count144
Chiral Atom Count25
Bond Count148
Aromatic Bond Count0

Drug Info: DrugBank

DrugBank IDDB00569 
NameFondaparinux
Groups
  • investigational
  • approved
DescriptionFondaparinux (Arixtra) is a synthetic anticoagulant agent consisting of five monomeric sugar units and a O-methyl group at the reducing end of the molecule. It is structurally similar to polymeric glycosaminoglycan heparin and heparan sulfate (HS) when they are cleaved into monomeric units. The monomeric sequence in heparin and HS is thought to form the high affinity binding site for the natural anti-coagulant factor, antithrombin III (ATIII). Once bound to heparin or HS, the anticoagulant activity of ATIII is potentiated by 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).
Synonyms
  • Fondaparinux sodium
  • Natural heparin pentasaccharide
  • Fondaparinux
Brand Names
  • Fondaparinux Sodium Injection
  • Fondaparinux Sodium
  • Arixtra
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.
Categories
  • Anticoagulants
  • Antithrombins
  • Blood and Blood Forming Organs
  • Carbohydrates
  • Cardiovascular Agents
ATC-CodeB01AX05
CAS number104993-28-4

Drug Targets

NameTarget SequencePharmacological ActionActions
Coagulation factor XMGRPLHLVLLSASLAGLLLLGESLFIRREQANNILARVTRANSFLEEMKK...unknowninhibitor
Antithrombin-IIIMYSNVIGTVTSGKRKVYLLSLLLIGFWDCVTCHGSPVDICTAKPRDIPMN...unknownpotentiator
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL1201202
PubChem 5282448
ChEMBL CHEMBL1201202
ChEBI CHEBI:61033