FONDAPARINUX

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 Search

SMILES

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

Molecular Formula	C31H53N3O49S8
Molecular Weight	1508.263
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	25 / 25
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 21 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 8504

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 8583	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 Health Status: unhealthy Age Group: 53.6–77.7 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/33027192/	Sources: https://pubmed.ncbi.nlm.nih.gov/33027192/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2A6 879 CYP2C19 2057 CYP2E1 1060

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 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 2141	inhibitor 4027 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 2497	inhibitor 4027 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 2546	inhibitor 4027 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 1146	inhibitor 4027 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 2633	inhibitor 4027 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 911	inhibitor 4027 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
iChemical	EBD4034244	http://www.ichemical.com/products/104993-28-4.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
PubChem	5282448	https://pubchem.ncbi.nlm.nih.gov/compound/5282448

PubMed

Title	Date	PubMed
Effects of fondaparinux compared with dalteparin, enoxaparin and unfractionated heparin on human osteoblasts.	2003-10	12874702
Mechanism of catalysis of inhibition of factor IXa by antithrombin in the presence of heparin or pentasaccharide.	2003-09-12	12832413
Fondaparinux, the first selective factor Xa inhibitor.	2003-09	12913785
Prevention of venous thromboembolism after major orthopaedic surgery: is fondaparinux an advance?	2003-08-16	12932379
Efficacy and safety of fondaparinux in major orthopedic surgery according to the timing of its first administration.	2003-08	12888887
Fondaparinux and enoxaparin in comparison to unfractionated heparin in preventing thrombus formation on mechanical heart valves in an ex vivo rabbit model.	2003-08	12888871
Fondaparinux: a synthetic selective factor-Xa inhibitor.	2003-07-25	12877762
New drugs 2003, part II.	2003-07	12851504
Duration of prophylaxis against venous thromboembolism with fondaparinux after hip fracture surgery: a multicenter, randomized, placebo-controlled, double-blind study.	2003-06-09	12796070
Factor Xa is highly protected from antithrombin-fondaparinux and antithrombin-enoxaparin when incorporated into the prothrombinase complex.	2003-06	12871328
Gateways to clinical trials.	2003-06	12851663
Selective factor Xa inhibition improves efficacy of venous thromboembolism prophylaxis in orthopedic surgery.	2003-06	12820819
[Fondaparinux for thrombosis prevention after orthopaedic surgery: a revolution?].	2003-05-31	12797930
[New antithrombotic agents. Towards a new therapeutic plan].	2003-05-15	12846024
[New anticoagulants].	2003-05-10	12768805
The design of venous thromboembolism prophylaxis trials: is enoxaparin more effective than fondaparinux?	2003-05	12800460
Factor X inhibitors.	2003-05	12720491
Low-molecular-weight heparins and heparinoids.	2003-04-21	12776722
Gateways to clinical trials.	2003-04-15	12690708
[Management of heparin-induced thrombocytopenia].	2003-04-02	12666266
Management of thrombotic and cardiovascular disorders in the new millenium.	2003-04	12812377
Cost analysis: fondaparinux versus preoperative and postoperative enoxaparin as venous thromboembolic event prophylaxis in elective hip arthroplasty.	2003-04	12723772
Fondaparinux requires further study before firm recommendation.	2003-02-24	12588215
Reversing anticoagulants both old and new.	2003-02-01	12557411
Two new antithrombotic agents (fondaparinux and ximelagatran) and their implications in anesthesia.	2003-02-01	12557410
Influence of the duration of fondaparinux (Arixtra) prophylaxis in preventing venous thromboembolism following major orthopedic surgery.	2003-02	12871516
Heparin, low-molecular-weight heparins, and heparin pentasaccharide: basic and clinical differentiation.	2003-02	12627673
Fondaparinux: new preparation. No better than LMWH in preventing pulmonary embolism.	2003-02	12602371
Evaluation of the pharmacological properties and clinical results of the synthetic pentasaccharide (fondaparinux).	2003-01-01	12679126
[New and future antithrombotic agents in thrombo-embolic venous disease].	2003-01-01	12673926
[New anticoagulants -- their clinical significance].	2003-01	12638473
[The best of vascular medicine in 2002].	2003-01	12613366
Enoxaparin or fondaparinux for thrombosis prevention after orthopaedic surgery.	2002-11-23	12457832
Enoxaparin or fondaparinux for thrombosis prevention after orthopaedic surgery.	2002-11-23	12457831
Fondaparinux versus enoxaparin for prevention of venous.	2002-11-16	12443628
Fondaparinux versus enoxaparin for prevention of venous.	2002-11-16	12443627
Fondaparinux versus enoxaparin for prevention of venous thromboembolism.	2002-11-16	12443626
Ability of recombinant factor VIIa to reverse the anticoagulant effect of the pentasaccharide fondaparinux in healthy volunteers.	2002-11-12	12427650
Fondaparinux: a new antithrombotic agent.	2002-11	12501872
Use of neuraxial anesthesia with selective factor Xa inhibitors.	2002-11	12463580
Thromboprophylaxis dosing: the relationship between timing of first administration, efficacy, and safety.	2002-11	12463579
Use of selective factor Xa inhibitors in special populations.	2002-11	12463578
Fondaparinux: basic properties and efficacy and safety in venous thromboembolism prophylaxis.	2002-11	12463577
Selective factor Xa inhibitors: practical guidelines for use.	2002-11	12463576
Fondaparinux (Arixtra): a new anticoagulant.	2002-10	12425373
In vitro comparison of the effect of heparin, enoxaparin and fondaparinux on tests of coagulation.	2002-09-01	12479885
Fondaparinux sodium.	2002-03	12532174
A new antithrombotic strategy, the selective inhibition of coagulation factors, and its importance to the orthopedic specialist.	2002	12597063
A meta-analysis of fondaparinux versus enoxaparin in the prevention of venous thromboembolism after major orthopaedic surgery.	2002	12597061
Current anticoagulation options in percutaneous intervention: designing patient-specific strategies.	2002	12556751

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 Created by `admin` on `Mon Mar 31 18:07:14 GMT 2025` Edited by `admin` on `Mon Mar 31 18:07:14 GMT 2025`
Record UNII	J177FOW5JL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FONDAPARINUX

Common Name

English

ORG-31540 free acid

Preferred Name

English

SR-901107A

Code

English

FONDAPARINUX [VANDF]

Common Name

English

SR 901107A

Code

English

FONDAPARINUX [HSDB]

Common Name

English

Fondaparinux [WHO-DD]

Common Name

English

ORG31540 free acid

Code

English

Classification Tree Code System Code

LIVERTOX

NBK548551