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Details

Stereochemistry ABSOLUTE
Molecular Formula C31H53N3O49S8
Molecular Weight 1508.263
Optical Activity UNSPECIFIED
Defined Stereocenters 25 / 25
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FONDAPARINUX

SMILES

[H][C@@]4(O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@]([H])(O[C@H]2[C@H](O)[C@@H](OS(O)(=O)=O)[C@]([H])(O[C@H]3[C@H](O)[C@@H](NS(O)(=O)=O)[C@@H](OC)O[C@@H]3COS(O)(=O)=O)O[C@H]2C(O)=O)[C@H](NS(O)(=O)=O)[C@H]1OS(O)(=O)=O)O[C@@H]([C@@H](O[C@@]5([H])O[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

InChI

InChIKey=KANJSNBRCNMZMV-ABRZTLGGSA-N
InChI=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

HIDE SMILES / InChI

Molecular Formula C31H53N3O49S8
Molecular Weight 1508.263
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 25 / 25
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Fondaparinux is a synthetic and specific inhibitor of activated Factor X (Xa). By selectively binding to antithrombin III (ATIII), fondaparinux sodium potentiates (about 300 times) the innate neutralization of Factor Xa by ATIII. Neutralization of Factor Xa interrupts the blood coagulation cascade and thus inhibits thrombin formation and thrombus development. Fondaparinux is indicated for the prophylaxis of deep vein thrombosis (DVT), which may lead to pulmonary embolism (PE): in patients undergoing hip fracture surgery, including extended prophylaxis; in patients undergoing hip replacement surgery; in patients undergoing knee replacement surgery; in patients undergoing abdominal surgery who are at risk for thromboembolic complications. The most serious adverse reactions reported with Fondaparinux are bleeding complications and thrombocytopenia. Agents that may enhance the risk of hemorrhage should be discontinued prior to initiation of therapy with Fondaparinux unless these agents are essential.

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ARIXTRA

Cmax

ValueDoseCo-administeredAnalytePopulation
1.46 mg/L
10 mg single, subcutaneous
FONDAPARINUX plasma
Homo sapiens
1.52 mg/L
10 mg 1 times / day steady-state, subcutaneous
FONDAPARINUX plasma
Homo sapiens
0.34 mg/L
2.5 mg single, subcutaneous
FONDAPARINUX plasma
Homo sapiens
0.445 mg/L
2.5 mg 1 times / day steady-state, subcutaneous
FONDAPARINUX plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
19.6 mg × h/L
10 mg single, subcutaneous
FONDAPARINUX plasma
Homo sapiens
20.66 mg × h/L
10 mg 1 times / day steady-state, subcutaneous
FONDAPARINUX plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
19 h
2.5 mg single, subcutaneous
FONDAPARINUX plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
6%
2.5 mg single, subcutaneous
FONDAPARINUX plasma
Homo sapiens

Doses

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
In patients undergoing hip fracture, hip replacement, or knee replacement surgery, the recommended dose of ARIXTRA is 2.5 mg administered by subcutaneous injection once daily after hemostasis has been established. Administer the initial dose no earlier than 6 to 8 hours after surgery. Administration of ARIXTRA earlier than 6 hours after surgery increases the risk of major bleeding. The usual duration of therapy is 5 to 9 days; up to 11 days of therapy was administered in clinical trials. In patients undergoing hip fracture surgery, an extended prophylaxis course of up to 24 additional days is recommended. In patients undergoing hip fracture surgery, a total of 32 days (peri-operative and extended prophylaxis) was administered in clinical trials. In patients undergoing abdominal surgery, the recommended dose of ARIXTRA is 2.5 mg administered by subcutaneous injection once daily after hemostasis has been established. Administer the initial dose no earlier than 6 to 8 hours after surgery. Administration of ARIXTRA earlier than 6 hours after surgery increases the risk of major bleeding. The usual duration of administration is 5 to 9 days, and up to 10 days of ARIXTRA was administered in clinical trials. In patients with acute symptomatic DVT and in patients with acute symptomatic PE, the recommended dose of ARIXTRA is 5 mg (body weight <50 kg), 7.5 mg (body weight 50 to 100 kg), or 10 mg (body weight >100 kg) by subcutaneous injection once daily (ARIXTRA treatment regimen). Initiate concomitant treatment with warfarin sodium as soon as possible, usually within 72 hours. Continue treatment with ARIXTRA for at least 5 days and until a therapeutic oral anticoagulant effect is established (INR 2 to 3). The usual duration of administration of ARIXTRA is 5 to 9 days; up to 26 days of ARIXTRA injection was administered in clinical trials.
Route of Administration: Other
Substance Class Chemical
Record UNII
J177FOW5JL
Record Status Validated (UNII)
Record Version