Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C31H53N3O49S8 |
Molecular Weight | 1508.2733 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 25 / 25 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CO[C@]1([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(COS(=O)(=O)O)O1)O[C@@]2([H])[C@@]([H])([C@]([H])([C@@]([H])([C@]([H])(C(=O)O)O2)O[C@]3([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(COS(=O)(=O)O)O3)O[C@@]4([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(C(=O)O)O4)O[C@]5([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(COS(=O)(=O)O)O5)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
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
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 Target | Pharmacology | Condition | Potency |
---|---|---|---|
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ARIXTRA Approved UseARIXTRA is a Factor Xa inhibitor (anticoagulant) indicated for: •Prophylaxis of deep vein thrombosis (DVT) in patients undergoing hip fracture surgery (including extended prophylaxis), hip replacement surgery, knee replacement surgery, or abdominal surgery. (1.1) •Treatment of DVT or acute pulmonary embolism (PE) when administered in conjunction with warfarin. (1.2, 1.3) Launch Date1.00768317E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.46 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12383043 |
10 mg single, subcutaneous dose: 10 mg route of administration: Subcutaneous experiment type: SINGLE co-administered: |
FONDAPARINUX plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1.52 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12383043 |
10 mg 1 times / day steady-state, subcutaneous dose: 10 mg route of administration: Subcutaneous experiment type: STEADY-STATE co-administered: |
FONDAPARINUX plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
0.34 mg/L |
2.5 mg single, subcutaneous dose: 2.5 mg route of administration: Subcutaneous experiment type: SINGLE co-administered: |
FONDAPARINUX plasma | Homo sapiens population: UNKNOWN age: ADULT sex: MALE food status: UNKNOWN |
|
0.445 mg/L |
2.5 mg 1 times / day steady-state, subcutaneous dose: 2.5 mg route of administration: Subcutaneous experiment type: STEADY-STATE co-administered: |
FONDAPARINUX plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
19.6 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12383043 |
10 mg single, subcutaneous dose: 10 mg route of administration: Subcutaneous experiment type: SINGLE co-administered: |
FONDAPARINUX plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
20.66 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12383043 |
10 mg 1 times / day steady-state, subcutaneous dose: 10 mg route of administration: Subcutaneous experiment type: STEADY-STATE co-administered: |
FONDAPARINUX plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
19 h |
2.5 mg single, subcutaneous dose: 2.5 mg route of administration: Subcutaneous experiment type: SINGLE co-administered: |
FONDAPARINUX plasma | Homo sapiens population: UNKNOWN age: ADULT sex: MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6% |
2.5 mg single, subcutaneous dose: 2.5 mg route of administration: Subcutaneous experiment type: SINGLE co-administered: |
FONDAPARINUX plasma | Homo sapiens population: UNKNOWN age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
2.5 mg 1 times / day steady, subcutaneous Recommended Dose: 2.5 mg, 1 times / day Route: subcutaneous Route: steady Dose: 2.5 mg, 1 times / day Sources: |
unhealthy, 53.6–77.7 years n = 38 Health Status: unhealthy Condition: COVID-19 Age Group: 53.6–77.7 years Sex: M+F Population Size: 38 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: (Label) 10, (PMDA_A100) 29, (PMDA_K101) 10 |
unlikely | |||
Page: (Label) 10, (PMDA_A100) 29, (PMDA_K101) 10 |
unlikely | |||
Page: (Label) 10, (PMDA_A100) 29, (PMDA_K101) 10 |
unlikely | |||
Page: (Label) 10, (PMDA_A100) 29, (PMDA_K101) 10 |
unlikely | |||
Page: (Label) 10, (PMDA_A100) 29, (PMDA_K101) 10 |
unlikely | |||
Page: (Label) 10, (PMDA_A100) 29, (PMDA_K101) 10 |
unlikely | |||
Page: (Label) 10, (PMDA_A100) 29, (PMDA_K101) 10 |
weak |
PubMed
Title | Date | PubMed |
---|---|---|
Current anticoagulation options in percutaneous intervention: designing patient-specific strategies. | 2002 Fall |
|
Reversing anticoagulants both old and new. | 2002 Jun-Jul |
|
Two new antithrombotic agents (fondaparinux and ximelagatran) and their implications in anesthesia. | 2002 Jun-Jul |
|
Fondaparinux sodium. | 2002 Mar |
|
Fondaparinux: a new antithrombotic agent. | 2002 Nov |
|
Use of neuraxial anesthesia with selective factor Xa inhibitors. | 2002 Nov |
|
Thromboprophylaxis dosing: the relationship between timing of first administration, efficacy, and safety. | 2002 Nov |
|
Use of selective factor Xa inhibitors in special populations. | 2002 Nov |
|
Fondaparinux: basic properties and efficacy and safety in venous thromboembolism prophylaxis. | 2002 Nov |
|
Selective factor Xa inhibitors: practical guidelines for use. | 2002 Nov |
|
Ability of recombinant factor VIIa to reverse the anticoagulant effect of the pentasaccharide fondaparinux in healthy volunteers. | 2002 Nov 12 |
|
Fondaparinux versus enoxaparin for prevention of venous. | 2002 Nov 16 |
|
Fondaparinux versus enoxaparin for prevention of venous. | 2002 Nov 16 |
|
Fondaparinux versus enoxaparin for prevention of venous thromboembolism. | 2002 Nov 16 |
|
Enoxaparin or fondaparinux for thrombosis prevention after orthopaedic surgery. | 2002 Nov 23 |
|
Enoxaparin or fondaparinux for thrombosis prevention after orthopaedic surgery. | 2002 Nov 23 |
|
[Management of heparin-induced thrombocytopenia]. | 2002 Nov-Dec |
|
Fondaparinux (Arixtra): a new anticoagulant. | 2002 Oct |
|
In vitro comparison of the effect of heparin, enoxaparin and fondaparinux on tests of coagulation. | 2002 Sep 1 |
|
A new antithrombotic strategy, the selective inhibition of coagulation factors, and its importance to the orthopedic specialist. | 2002 Winter |
|
A meta-analysis of fondaparinux versus enoxaparin in the prevention of venous thromboembolism after major orthopaedic surgery. | 2002 Winter |
|
Management of thrombotic and cardiovascular disorders in the new millenium. | 2003 Apr |
|
Cost analysis: fondaparinux versus preoperative and postoperative enoxaparin as venous thromboembolic event prophylaxis in elective hip arthroplasty. | 2003 Apr |
|
Low-molecular-weight heparins and heparinoids. | 2003 Apr 21 |
|
Efficacy and safety of fondaparinux in major orthopedic surgery according to the timing of its first administration. | 2003 Aug |
|
Fondaparinux and enoxaparin in comparison to unfractionated heparin in preventing thrombus formation on mechanical heart valves in an ex vivo rabbit model. | 2003 Aug |
|
Prevention of venous thromboembolism after major orthopaedic surgery: is fondaparinux an advance? | 2003 Aug 16 |
|
Influence of the duration of fondaparinux (Arixtra) prophylaxis in preventing venous thromboembolism following major orthopedic surgery. | 2003 Feb |
|
Heparin, low-molecular-weight heparins, and heparin pentasaccharide: basic and clinical differentiation. | 2003 Feb |
|
Fondaparinux: new preparation. No better than LMWH in preventing pulmonary embolism. | 2003 Feb |
|
Fondaparinux requires further study before firm recommendation. | 2003 Feb 24 |
|
[New anticoagulants -- their clinical significance]. | 2003 Jan |
|
[The best of vascular medicine in 2002]. | 2003 Jan |
|
Evaluation of the pharmacological properties and clinical results of the synthetic pentasaccharide (fondaparinux). | 2003 Jan 1 |
|
[New and future antithrombotic agents in thrombo-embolic venous disease]. | 2003 Jan 1 |
|
Gateways to clinical trials. | 2003 Jan-Feb |
|
New drugs 2003, part II. | 2003 Jul |
|
Fondaparinux: a synthetic selective factor-Xa inhibitor. | 2003 Jul-Aug |
|
Factor Xa is highly protected from antithrombin-fondaparinux and antithrombin-enoxaparin when incorporated into the prothrombinase complex. | 2003 Jun |
|
Gateways to clinical trials. | 2003 Jun |
|
Selective factor Xa inhibition improves efficacy of venous thromboembolism prophylaxis in orthopedic surgery. | 2003 Jun |
|
Duration of prophylaxis against venous thromboembolism with fondaparinux after hip fracture surgery: a multicenter, randomized, placebo-controlled, double-blind study. | 2003 Jun 9 |
|
The design of venous thromboembolism prophylaxis trials: is enoxaparin more effective than fondaparinux? | 2003 May |
|
Factor X inhibitors. | 2003 May |
|
[New anticoagulants]. | 2003 May 10 |
|
[New antithrombotic agents. Towards a new therapeutic plan]. | 2003 May 15 |
|
[Fondaparinux for thrombosis prevention after orthopaedic surgery: a revolution?]. | 2003 May 31 |
|
Effects of fondaparinux compared with dalteparin, enoxaparin and unfractionated heparin on human osteoblasts. | 2003 Oct |
|
Fondaparinux, the first selective factor Xa inhibitor. | 2003 Sep |
|
Mechanism of catalysis of inhibition of factor IXa by antithrombin in the presence of heparin or pentasaccharide. | 2003 Sep 12 |
Patents
Sample Use Guides
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
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Common Name | English | ||
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Common Name | English | ||
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Common Name | English |
Classification Tree | Code System | Code | ||
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LIVERTOX |
434
Created by
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WHO-ATC |
B01AX05
Created by
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LOINC |
74217-1
Created by
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NCI_THESAURUS |
C263
Created by
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NDF-RT |
N0000175635
Created by
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NDF-RT |
N0000175637
Created by
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WHO-VATC |
QB01AX05
Created by
admin on Sat Jun 26 09:56:09 UTC 2021 , Edited by admin on Sat Jun 26 09:56:09 UTC 2021
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Code System | Code | Type | Description | ||
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C73142
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104993-28-4
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321208
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PRIMARY | RxNorm | ||
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DB00569
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PRIMARY | |||
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5282448
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PRIMARY | |||
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104993-28-4
Created by
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PRIMARY | |||
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1236
Created by
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PRIMARY | |||
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SUB25907
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PRIMARY | |||
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7845
Created by
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PRIMARY | |||
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Fondaparinux
Created by
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PRIMARY | |||
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J177FOW5JL
Created by
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PRIMARY | |||
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FONDAPARINUX
Created by
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PRIMARY | |||
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6819
Created by
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PRIMARY | |||
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C438268
Created by
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PRIMARY |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)