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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
Structure of FONDAPARINUX

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

HIDE SMILES / InChI
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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ARIXTRA

Approved Use

ARIXTRA 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 Date

1.00768317E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.46 mg/L
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
19.6 mg × h/L
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
unlikely
unlikely
unlikely
unlikely
unlikely
unlikely
weak
PubMed

PubMed

TitleDatePubMed
Fondaparinux sodium does not cross the placental barrier: study using the in-vitro human dually perfused cotyledon model.
2002
Absence of interaction of fondaparinux sodium with digoxin in healthy volunteers.
2002
The synthetic pentasaccharide fondaparinux sodium does not interact with oral warfarin.
2002
Fondaparinux sodium mechanism of action: identification of specific binding to purified and human plasma-derived proteins.
2002
The pharmacokinetics of fondaparinux sodium in healthy volunteers.
2002
Current anticoagulation options in percutaneous intervention: designing patient-specific strategies.
2002 Fall
[A new synthetic coagulation inhibitor. Only half as many thromboembolisms].
2002 Jul 11
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
Gateways to clinical trials.
2002 May
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 versus enoxaparin for prevention of venous.
2002 Nov 16
Enoxaparin or fondaparinux for thrombosis prevention after orthopaedic surgery.
2002 Nov 23
[Management of heparin-induced thrombocytopenia].
2002 Nov-Dec
Traditional versus modern anticoagulant strategies: summary of the literature.
2002 Oct 15
In vitro comparison of the effect of heparin, enoxaparin and fondaparinux on tests of coagulation.
2002 Sep 1
The potential role of fondaparinux as venous thromboembolism prophylaxis after total hip or knee replacement or hip fracture surgery.
2002 Sep 9
Therapeutic considerations in the management of patients with heparin-induced thrombocytopenia.
2002 Summer
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
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
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
[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

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
Name Type Language
FONDAPARINUX
HSDB   VANDF   WHO-DD  
Common Name English
FONDAPARINUX [WHO-DD]
Common Name English
FONDAPARINUX [VANDF]
Common Name English
FONDAPARINUX [HSDB]
Common Name English
Classification Tree Code System Code
LIVERTOX 434
Created by admin on Sat Jun 26 09:56:09 UTC 2021 , Edited by admin on Sat Jun 26 09:56:09 UTC 2021
WHO-ATC B01AX05
Created by admin on Sat Jun 26 09:56:09 UTC 2021 , Edited by admin on Sat Jun 26 09:56:09 UTC 2021
LOINC 74217-1
Created by admin on Sat Jun 26 09:56:09 UTC 2021 , Edited by admin on Sat Jun 26 09:56:09 UTC 2021
NCI_THESAURUS C263
Created by admin on Sat Jun 26 09:56:09 UTC 2021 , Edited by admin on Sat Jun 26 09:56:09 UTC 2021
NDF-RT N0000175635
Created by admin on Sat Jun 26 09:56:09 UTC 2021 , Edited by admin on Sat Jun 26 09:56:09 UTC 2021
NDF-RT N0000175637
Created by admin on Sat Jun 26 09:56:09 UTC 2021 , Edited by admin on Sat Jun 26 09:56:09 UTC 2021
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
Code System Code Type Description
NCI_THESAURUS
C73142
Created by admin on Sat Jun 26 09:56:09 UTC 2021 , Edited by admin on Sat Jun 26 09:56:09 UTC 2021
PRIMARY
CAS
104993-28-4
Created by admin on Sat Jun 26 09:56:09 UTC 2021 , Edited by admin on Sat Jun 26 09:56:09 UTC 2021
PRIMARY
RXCUI
321208
Created by admin on Sat Jun 26 09:56:09 UTC 2021 , Edited by admin on Sat Jun 26 09:56:09 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB00569
Created by admin on Sat Jun 26 09:56:09 UTC 2021 , Edited by admin on Sat Jun 26 09:56:09 UTC 2021
PRIMARY
PUBCHEM
5282448
Created by admin on Sat Jun 26 09:56:09 UTC 2021 , Edited by admin on Sat Jun 26 09:56:09 UTC 2021
PRIMARY
EPA CompTox
104993-28-4
Created by admin on Sat Jun 26 09:56:09 UTC 2021 , Edited by admin on Sat Jun 26 09:56:09 UTC 2021
PRIMARY
DRUG CENTRAL
1236
Created by admin on Sat Jun 26 09:56:09 UTC 2021 , Edited by admin on Sat Jun 26 09:56:09 UTC 2021
PRIMARY
EVMPD
SUB25907
Created by admin on Sat Jun 26 09:56:09 UTC 2021 , Edited by admin on Sat Jun 26 09:56:09 UTC 2021
PRIMARY
HSDB
7845
Created by admin on Sat Jun 26 09:56:09 UTC 2021 , Edited by admin on Sat Jun 26 09:56:09 UTC 2021
PRIMARY
LACTMED
Fondaparinux
Created by admin on Sat Jun 26 09:56:09 UTC 2021 , Edited by admin on Sat Jun 26 09:56:09 UTC 2021
PRIMARY
FDA UNII
J177FOW5JL
Created by admin on Sat Jun 26 09:56:09 UTC 2021 , Edited by admin on Sat Jun 26 09:56:09 UTC 2021
PRIMARY
WIKIPEDIA
FONDAPARINUX
Created by admin on Sat Jun 26 09:56:09 UTC 2021 , Edited by admin on Sat Jun 26 09:56:09 UTC 2021
PRIMARY
IUPHAR
6819
Created by admin on Sat Jun 26 09:56:09 UTC 2021 , Edited by admin on Sat Jun 26 09:56:09 UTC 2021
PRIMARY
MESH
C438268
Created by admin on Sat Jun 26 09:56:09 UTC 2021 , Edited by admin on Sat Jun 26 09:56:09 UTC 2021
PRIMARY