Structure via PubChem · Public domain (PubChem)
fondaparinux
Sign in to saveAlso known as natural heparin pentasaccharide, Arixtra
Fondaparinux (trade name Arixtra) is an anticoagulant medication chemically related to low molecular weight heparins. It is marketed by Viatris. A generic version developed by Alchemia is marketed within the US by Dr. Reddy's Laboratories.
Chemical data
- Formula
- C31H53N3O49S8
- Molecular weight
- 1508.3 g/mol
- IUPAC name
- (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-sulfooxyoxan-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-dihydroxyoxane-2-carboxylic acid
- 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
- InChIKey
- KANJSNBRCNMZMV-ABRZTLGGSA-N
- XLogP
- -14.7
- Polar surface area
- 873 Ų
- H-bond donors
- 19
- H-bond acceptors
- 52
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Oligosaccharide
- First approval
- 2001
- Admin. routes
- parenteral
- Indications
- atrial fibrillation, morbid obesity, ovarian carcinoma, venous thromboembolism
via ChEMBL · EBI
Research
2,357 papers- Fondaparinux Sodium: Recent Advances in the Management of Thrombosis.Journal of cardiovascular pharmacology and therapeutics · 2023
- Fondaparinux.Current pharmaceutical design · 2005
- Fondaparinux-associated heparin-induced thrombocytopenia.European journal of haematology · 2013
- Fondaparinux sodium.Drugs of today (Barcelona, Spain : 1998) · 2002
- Fondaparinux sodium.Drugs · 2002
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 1506.951
- Has use
- medication
Show 9 more facts
- 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
- chemical formula
- C₃₁H₅₃N₃O₄₉S₈
- isomeric SMILES
- 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
- NCI Thesaurus ID
- C73142
- subject has role
- direct Xa inhibitor
- medical condition treated
- pulmonary embolism
- significant drug interaction
- abciximab
- defined daily dose
- 2.5
- physically interacts with
- Serpin family C member 1
Sources (7)
via Wikidata · CC0
~3 min read
Encyclopedic overview
8 sectionsContents
- Medical uses
- Comparison to other agents
- Pharmacology
- Mechanism of action
- Chemistry
- Abbreviations
- References
- External links
Fondaparinux (trade name Arixtra) is an anticoagulant medication chemically related to low molecular weight heparins. It is marketed by Viatris. A generic version developed by Alchemia is marketed within the US by Dr. Reddy's Laboratories.
==Medical uses== Clinically, it is used for the prevention of deep vein thrombosis in patients who have had orthopedic surgery as well as for the treatment of deep vein thrombosis and pulmonary embolism.
Excerpted from Wikipedia’s “fondaparinux” article, available under the CC BY-SA 4.0 licence.