Fondaparinux sodiumProduct ingredient for Fondaparinux

Name

Fondaparinux sodium

Drug Entry

Fondaparinux

Fondaparinux (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).

See full entry for Fondaparinux

Accession Number

DBSALT002741

Structure

Similar Structures

Synonyms

Not Available

UNII

X0Q6N9USOZ

CAS Number

114870-03-0

Weight

Average: 1728.03
Monoisotopic: 1726.77077697

Chemical Formula

C₃₁H₄₃N₃Na₁₀O₄₉S₈

InChI Key

XEKSTYNIJLDDAZ-JASSWCPGSA-D

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

IUPAC Name

decasodium (2R,3S,4S,5R,6R)-3-{[(2R,3R,4R,5R,6R)-5-{[(2R,3R,4R,5S,6S)-6-carboxy-5-{[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-(sulfoamino)-6-[(sulfooxy)methyl]oxan-2-yl]oxy}-3,4-dihydroxyoxan-2-yl]oxy}-3-(sulfoamino)-4-(sulfooxy)-6-[(sulfooxy)methyl]oxan-2-yl]oxy}-4-hydroxy-6-{[(2R,3S,4R,5R,6S)-4-hydroxy-6-methoxy-5-(sulfoamino)-2-[(sulfooxy)methyl]oxan-3-yl]oxy}-5-(sulfooxy)oxane-2-carboxylate

SMILES

[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[H][C@@]1(O[C@@H]2[C@@H](COS([O-])(=O)=O)O[C@]([H])(O[C@H]3[C@H](O)[C@@H](OS([O-])(=O)=O)[C@]([H])(O[C@H]4[C@H](O)[C@@H](NS([O-])(=O)=O)[C@@H](OC)O[C@@H]4COS([O-])(=O)=O)O[C@H]3C([O-])=O)[C@H](NS([O-])(=O)=O)[C@H]2OS([O-])(=O)=O)O[C@@H]([C@@H](O[C@@]2([H])O[C@H](COS([O-])(=O)=O)[C@@H](O)[C@H](O)[C@H]2NS([O-])(=O)=O)[C@H](O)[C@H]1O)C([O-])=O

External Links

KEGG Drug: D01844
ChemSpider: 552174
ChEMBL: CHEMBL1200644
PharmGKB: PA164746297
Wikipedia: Fondaparinux

Predicted Properties

Property	Value	Source
Water Solubility	17.4 mg/mL	ALOGPS
logP	0.72	ALOGPS
logP	-10	Chemaxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	-3	Chemaxon
Physiological Charge	-10	Chemaxon
Hydrogen Acceptor Count	44	Chemaxon
Hydrogen Donor Count	9	Chemaxon
Polar Surface Area	833.78 Å²	Chemaxon
Rotatable Bond Count	27	Chemaxon
Refractivity	268.55 m³·mol^-1	Chemaxon
Polarizability	119.9 Å³	Chemaxon
Number of Rings	5	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Fondaparinux sodiumProduct ingredient for Fondaparinux

Structure for Fondaparinux sodium (DBSALT002741)