FONDAPARINUX SODIUM

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 Search

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

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=49e0d7bc-3f49-849b-c77c-98682d1c0d19 | https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=ec235119-cb58-4939-942c-11d3923d289f | https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/021345s010lbl.pdf | https://www.ema.europa.eu/en/documents/product-information/arixtra-epar-product-information_en-1.pdf

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
Coagulation factor X 20 Target ID: CHEMBL244 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/021345s010lbl.pdf \| https://www.ema.europa.eu/en/documents/product-information/arixtra-epar-product-information_en-1.pdf	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Deep Vein Thrombosis 3 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021345s019lbl.pdf	Primary		Approved 8429	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 2001

C_max

Value	Dose	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021345s019lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021345s019lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
19 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021345s019lbl.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
6% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021345s019lbl.pdf	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: https://pubmed.ncbi.nlm.nih.gov/33027192/	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: https://pubmed.ncbi.nlm.nih.gov/33027192/	Sources: https://pubmed.ncbi.nlm.nih.gov/33027192/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2A6 707 CYP2C19 1478 CYP2E1 882

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21345lbl.pdf#page=10, https://www.pmda.go.jp/drugs/2007/P200700021/34027800_21900AMX00909_A100_2.pdf#page=29, https://www.pmda.go.jp/drugs/2007/P200700021/34027800_21900AMX00909_K101_1.pdf#page=10 Page: (Label) 10, (PMDA_A100) 29, (PMDA_K101) 10	unlikely
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21345lbl.pdf#page=10, https://www.pmda.go.jp/drugs/2007/P200700021/34027800_21900AMX00909_A100_2.pdf#page=29, https://www.pmda.go.jp/drugs/2007/P200700021/34027800_21900AMX00909_K101_1.pdf#page=10 Page: (Label) 10, (PMDA_A100) 29, (PMDA_K101) 10	unlikely
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21345lbl.pdf#page=10, https://www.pmda.go.jp/drugs/2007/P200700021/34027800_21900AMX00909_A100_2.pdf#page=29, https://www.pmda.go.jp/drugs/2007/P200700021/34027800_21900AMX00909_K101_1.pdf#page=10 Page: (Label) 10, (PMDA_A100) 29, (PMDA_K101) 10	unlikely
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21345lbl.pdf#page=10, https://www.pmda.go.jp/drugs/2007/P200700021/34027800_21900AMX00909_A100_2.pdf#page=29, https://www.pmda.go.jp/drugs/2007/P200700021/34027800_21900AMX00909_K101_1.pdf#page=10 Page: (Label) 10, (PMDA_A100) 29, (PMDA_K101) 10	unlikely
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21345lbl.pdf#page=10, https://www.pmda.go.jp/drugs/2007/P200700021/34027800_21900AMX00909_A100_2.pdf#page=29, https://www.pmda.go.jp/drugs/2007/P200700021/34027800_21900AMX00909_K101_1.pdf#page=10 Page: (Label) 10, (PMDA_A100) 29, (PMDA_K101) 10	unlikely
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21345lbl.pdf#page=10, https://www.pmda.go.jp/drugs/2007/P200700021/34027800_21900AMX00909_A100_2.pdf#page=29, https://www.pmda.go.jp/drugs/2007/P200700021/34027800_21900AMX00909_K101_1.pdf#page=10 Page: (Label) 10, (PMDA_A100) 29, (PMDA_K101) 10	unlikely
CYP2A6 739	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21345lbl.pdf#page=10, https://www.pmda.go.jp/drugs/2007/P200700021/34027800_21900AMX00909_A100_2.pdf#page=29, https://www.pmda.go.jp/drugs/2007/P200700021/34027800_21900AMX00909_K101_1.pdf#page=10 Page: (Label) 10, (PMDA_A100) 29, (PMDA_K101) 10	weak

Sourcing

Vendor/Aggregator	ID	URL
ABI Chem	AC1NR037
AK Scientific, Inc. (AKSCI)	Y1945	http://www.aksci.com/item_detail.php?cat=Y1945
Ambinter	Amb19893464	http://www.ambinter.com/reference/19893464
BLD Pharm	BD01281397	http://www.bldpharm.com/products/104993-28-4.html
PubChem	5282448	https://pubchem.ncbi.nlm.nih.gov/compound/5282448
iChemical	EBD4034244	http://www.ichemical.com/products/104993-28-4.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Absence of interaction of fondaparinux sodium with digoxin in healthy volunteers.	2002	12383044
Fondaparinux sodium is not metabolised in mammalian liver fractions and does not inhibit cytochrome P450-mediated metabolism of concomitant drugs.	2002	12383041
Fondaparinux sodium mechanism of action: identification of specific binding to purified and human plasma-derived proteins.	2002	12383040
The pharmacokinetics of fondaparinux sodium in healthy volunteers.	2002	12383039
Current anticoagulation options in percutaneous intervention: designing patient-specific strategies.	2002 Fall	12556751
Reversing anticoagulants both old and new.	2002 Jun-Jul	12557411
Two new antithrombotic agents (fondaparinux and ximelagatran) and their implications in anesthesia.	2002 Jun-Jul	12557410
Fondaparinux sodium.	2002 Mar	12532174
Fondaparinux: a new antithrombotic agent.	2002 Nov	12501872
Ability of recombinant factor VIIa to reverse the anticoagulant effect of the pentasaccharide fondaparinux in healthy volunteers.	2002 Nov 12	12427650
Fondaparinux versus enoxaparin for prevention of venous.	2002 Nov 16	12443628
Fondaparinux versus enoxaparin for prevention of venous.	2002 Nov 16	12443627
Fondaparinux versus enoxaparin for prevention of venous thromboembolism.	2002 Nov 16	12443626
Enoxaparin or fondaparinux for thrombosis prevention after orthopaedic surgery.	2002 Nov 23	12457832
[Management of heparin-induced thrombocytopenia].	2002 Nov-Dec	12666266
Fondaparinux (Arixtra): a new anticoagulant.	2002 Oct	12425373
Traditional versus modern anticoagulant strategies: summary of the literature.	2002 Oct 15	12400244
[Recent therapeutic strategies and new drugs].	2002 Sep	12422466
Venous thromboembolic disease prophylaxis in patients undergoing orthopedic surgery of the lower extremity.	2002 Sep	12349891
A new antithrombotic strategy, the selective inhibition of coagulation factors, and its importance to the orthopedic specialist.	2002 Winter	12597063
A meta-analysis of fondaparinux versus enoxaparin in the prevention of venous thromboembolism after major orthopaedic surgery.	2002 Winter	12597061
Management of thrombotic and cardiovascular disorders in the new millenium.	2003 Apr	12812377
Cost analysis: fondaparinux versus preoperative and postoperative enoxaparin as venous thromboembolic event prophylaxis in elective hip arthroplasty.	2003 Apr	12723772
Low-molecular-weight heparins and heparinoids.	2003 Apr 21	12776722
Efficacy and safety of fondaparinux in major orthopedic surgery according to the timing of its first administration.	2003 Aug	12888887
Fondaparinux and enoxaparin in comparison to unfractionated heparin in preventing thrombus formation on mechanical heart valves in an ex vivo rabbit model.	2003 Aug	12888871
Prevention of venous thromboembolism after major orthopaedic surgery: is fondaparinux an advance?	2003 Aug 16	12932379
Influence of the duration of fondaparinux (Arixtra) prophylaxis in preventing venous thromboembolism following major orthopedic surgery.	2003 Feb	12871516
Heparin, low-molecular-weight heparins, and heparin pentasaccharide: basic and clinical differentiation.	2003 Feb	12627673
Fondaparinux: new preparation. No better than LMWH in preventing pulmonary embolism.	2003 Feb	12602371
Fondaparinux requires further study before firm recommendation.	2003 Feb 24	12588215
[New anticoagulants -- their clinical significance].	2003 Jan	12638473
[The best of vascular medicine in 2002].	2003 Jan	12613366
Evaluation of the pharmacological properties and clinical results of the synthetic pentasaccharide (fondaparinux).	2003 Jan 1	12679126
[New and future antithrombotic agents in thrombo-embolic venous disease].	2003 Jan 1	12673926
Gateways to clinical trials.	2003 Jan-Feb	12690708
New drugs 2003, part II.	2003 Jul	12851504
Fondaparinux: a synthetic selective factor-Xa inhibitor.	2003 Jul-Aug	12877762
Factor Xa is highly protected from antithrombin-fondaparinux and antithrombin-enoxaparin when incorporated into the prothrombinase complex.	2003 Jun	12871328
Gateways to clinical trials.	2003 Jun	12851663
Selective factor Xa inhibition improves efficacy of venous thromboembolism prophylaxis in orthopedic surgery.	2003 Jun	12820819
Duration of prophylaxis against venous thromboembolism with fondaparinux after hip fracture surgery: a multicenter, randomized, placebo-controlled, double-blind study.	2003 Jun 9	12796070
The design of venous thromboembolism prophylaxis trials: is enoxaparin more effective than fondaparinux?	2003 May	12800460
Factor X inhibitors.	2003 May	12720491
[New anticoagulants].	2003 May 10	12768805
[New antithrombotic agents. Towards a new therapeutic plan].	2003 May 15	12846024
[Fondaparinux for thrombosis prevention after orthopaedic surgery: a revolution?].	2003 May 31	12797930
Effects of fondaparinux compared with dalteparin, enoxaparin and unfractionated heparin on human osteoblasts.	2003 Oct	12874702
Fondaparinux, the first selective factor Xa inhibitor.	2003 Sep	12913785
Mechanism of catalysis of inhibition of factor IXa by antithrombin in the presence of heparin or pentasaccharide.	2003 Sep 12	12832413

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

Name

Type

Language

FONDAPARINUX SODIUM

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

Common Name

English

ORG 31540

Code

English

ORG-31540

Code

English

ARIXTRA

Brand Name

English

FONDAPARINUX SODIUM FOR ASSAY

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)