U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C31H43N3O49S8.10Na
Molecular Weight 1728.082
Optical Activity UNSPECIFIED
Defined Stereocenters 25 / 25
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FONDAPARINUX SODIUM

SMILES

[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[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=XEKSTYNIJLDDAZ-JASSWCPGSA-D
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

HIDE SMILES / InChI

Molecular Formula C31H43N3O49S8
Molecular Weight 1498.184
Charge -10
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 25 / 25
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Absence of interaction of fondaparinux sodium with digoxin in healthy volunteers.
2002
Absence of interaction of fondaparinux sodium with aspirin and piroxicam in healthy male volunteers.
2002
The synthetic pentasaccharide fondaparinux sodium does not interact with oral warfarin.
2002
Fondaparinux sodium is not metabolised in mammalian liver fractions and does not inhibit cytochrome P450-mediated metabolism of concomitant drugs.
2002
Gateways to Clinical Trials.
2002 Apr
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
Benefit of selective factor inhibition.
2002 Jun
Treatment of symptomatic venous thromboembolism: improving outcomes.
2002 Jun
Unresolved issues in the prevention and treatment of venous thromboembolism.
2002 Jun
Selective inhibition of coagulation factors: advances in antithrombotic therapy.
2002 Jun
The role of thrombin inhibition during percutaneous coronary intervention.
2002 Jun
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
Absence of placental transfer of pentasaccharide (Fondaparinux, Arixtra) in the dually perfused human cotyledon in vitro.
2002 May
Postoperative fondaparinux versus preoperative enoxaparin for prevention of venous thromboembolism in elective hip-replacement surgery: a randomised double-blind comparison.
2002 May 18
Fondaparinux: a new antithrombotic agent.
2002 Nov
Use of neuraxial anesthesia with selective factor Xa inhibitors.
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
[Recent therapeutic strategies and new drugs].
2002 Sep
Absence of an interaction between the synthetic pentasaccharide fondaparinux and oral warfarin.
2002 Sep
A new antithrombotic strategy, the selective inhibition of coagulation factors, and its importance to the orthopedic specialist.
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
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
Fondaparinux: new preparation. No better than LMWH in preventing pulmonary embolism.
2003 Feb
Fondaparinux requires further study before firm recommendation.
2003 Feb 24
Evaluation of the pharmacological properties and clinical results of the synthetic pentasaccharide (fondaparinux).
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
Selective factor Xa inhibition improves efficacy of venous thromboembolism prophylaxis in orthopedic surgery.
2003 Jun
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
[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
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
Substance Class Chemical
Created
by admin
on Thu Jul 06 21:55:21 UTC 2023
Edited
by admin
on Thu Jul 06 21:55:21 UTC 2023
Record UNII
X0Q6N9USOZ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FONDAPARINUX SODIUM
EMA EPAR   INN   JAN   MART.   MI   ORANGE BOOK   USAN   WHO-DD  
INN   USAN  
Official Name English
FONDAPARINUX SODIUM [USP MONOGRAPH]
Common Name English
FONDAPARINUX SODIUM [USAN]
Common Name English
FONDAPARIN SODIUM
Common Name English
FONDAPARINUX SODIUM [JAN]
Common Name English
SR-90107A
Code English
fondaparinux sodium [INN]
Common Name English
QUIXIDAR
Brand Name English
FONDAPARINUX SODIUM [ORANGE BOOK]
Common Name English
FONDAPARINUX SODIUM [EMA EPAR]
Common Name English
FONDAPARINUX SODIUM [MI]
Common Name English
IC-851589
Code English
FONDAPARINUX SODIUM [MART.]
Common Name English
SR 90107A
Code English
FONDAPARINUX SODIUM IDENTIFICATION
USP-RS  
Common Name English
ORG 31540
Code English
ORG-31540
Code English
ARIXTRA
Brand Name English
FONDAPARINUX SODIUM FOR ASSAY
USP-RS  
Common Name English
FONDAPARINUX SODIUM [USP-RS]
Common Name English
Fondaparinux sodium [WHO-DD]
Common Name English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS QUIXIDAR (WITHDRAWN: PULMONARY EMBOLISM)
Created by admin on Thu Jul 06 21:55:21 UTC 2023 , Edited by admin on Thu Jul 06 21:55:21 UTC 2023
EMA ASSESSMENT REPORTS QUIXIDAR (WITHDRAWN: MYOCARDIAL INFARCTION)
Created by admin on Thu Jul 06 21:55:21 UTC 2023 , Edited by admin on Thu Jul 06 21:55:21 UTC 2023
NCI_THESAURUS C263
Created by admin on Thu Jul 06 21:55:21 UTC 2023 , Edited by admin on Thu Jul 06 21:55:21 UTC 2023
EMA ASSESSMENT REPORTS ARIXTRA (AUTHORIZED: MYOCARDIAL INFARCTION)
Created by admin on Thu Jul 06 21:55:21 UTC 2023 , Edited by admin on Thu Jul 06 21:55:21 UTC 2023
EMA ASSESSMENT REPORTS ARIXTRA (AUTHORIZED: PULMONARY EMBOLISM)
Created by admin on Thu Jul 06 21:55:21 UTC 2023 , Edited by admin on Thu Jul 06 21:55:21 UTC 2023
EMA ASSESSMENT REPORTS QUIXIDAR (WITHDRAWN: ANGINA, UNSTABLE)
Created by admin on Thu Jul 06 21:55:21 UTC 2023 , Edited by admin on Thu Jul 06 21:55:21 UTC 2023
EMA ASSESSMENT REPORTS QUIXIDAR (WITHDRAWN: VENOUS THROMBOSIS)
Created by admin on Thu Jul 06 21:55:21 UTC 2023 , Edited by admin on Thu Jul 06 21:55:21 UTC 2023
EMA ASSESSMENT REPORTS ARIXTRA (AUTHORIZED: ANGINA, UNSTABLE)
Created by admin on Thu Jul 06 21:55:21 UTC 2023 , Edited by admin on Thu Jul 06 21:55:21 UTC 2023
EMA ASSESSMENT REPORTS ARIXTRA (AUTHORIZED: VENOUS THROMBOSIS)
Created by admin on Thu Jul 06 21:55:21 UTC 2023 , Edited by admin on Thu Jul 06 21:55:21 UTC 2023
Code System Code Type Description
PUBCHEM
636380
Created by admin on Thu Jul 06 21:55:21 UTC 2023 , Edited by admin on Thu Jul 06 21:55:21 UTC 2023
PRIMARY
DRUG BANK
DB00569
Created by admin on Thu Jul 06 21:55:21 UTC 2023 , Edited by admin on Thu Jul 06 21:55:21 UTC 2023
PRIMARY
RS_ITEM_NUM
1282718
Created by admin on Thu Jul 06 21:55:21 UTC 2023 , Edited by admin on Thu Jul 06 21:55:21 UTC 2023
PRIMARY
DAILYMED
X0Q6N9USOZ
Created by admin on Thu Jul 06 21:55:21 UTC 2023 , Edited by admin on Thu Jul 06 21:55:21 UTC 2023
PRIMARY
RXCUI
322154
Created by admin on Thu Jul 06 21:55:21 UTC 2023 , Edited by admin on Thu Jul 06 21:55:21 UTC 2023
PRIMARY RxNorm
SMS_ID
100000089289
Created by admin on Thu Jul 06 21:55:21 UTC 2023 , Edited by admin on Thu Jul 06 21:55:21 UTC 2023
PRIMARY
CHEBI
31632
Created by admin on Thu Jul 06 21:55:21 UTC 2023 , Edited by admin on Thu Jul 06 21:55:21 UTC 2023
PRIMARY
MERCK INDEX
M5529
Created by admin on Thu Jul 06 21:55:21 UTC 2023 , Edited by admin on Thu Jul 06 21:55:21 UTC 2023
PRIMARY Merck Index
EVMPD
SUB12504MIG
Created by admin on Thu Jul 06 21:55:21 UTC 2023 , Edited by admin on Thu Jul 06 21:55:21 UTC 2023
PRIMARY
FDA UNII
X0Q6N9USOZ
Created by admin on Thu Jul 06 21:55:21 UTC 2023 , Edited by admin on Thu Jul 06 21:55:21 UTC 2023
PRIMARY
INN
7653
Created by admin on Thu Jul 06 21:55:21 UTC 2023 , Edited by admin on Thu Jul 06 21:55:21 UTC 2023
PRIMARY
NCI_THESAURUS
C47539
Created by admin on Thu Jul 06 21:55:21 UTC 2023 , Edited by admin on Thu Jul 06 21:55:21 UTC 2023
PRIMARY
USAN
NN-42
Created by admin on Thu Jul 06 21:55:21 UTC 2023 , Edited by admin on Thu Jul 06 21:55:21 UTC 2023
PRIMARY
RS_ITEM_NUM
1282707
Created by admin on Thu Jul 06 21:55:21 UTC 2023 , Edited by admin on Thu Jul 06 21:55:21 UTC 2023
ALTERNATIVE
ChEMBL
CHEMBL1201202
Created by admin on Thu Jul 06 21:55:21 UTC 2023 , Edited by admin on Thu Jul 06 21:55:21 UTC 2023
PRIMARY
CAS
114870-03-0
Created by admin on Thu Jul 06 21:55:21 UTC 2023 , Edited by admin on Thu Jul 06 21:55:21 UTC 2023
PRIMARY
EPA CompTox
DTXSID501027612
Created by admin on Thu Jul 06 21:55:21 UTC 2023 , Edited by admin on Thu Jul 06 21:55:21 UTC 2023
PRIMARY
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