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+].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=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	22.98976928
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Fondaparinux compared with enoxaparin for the prevention of venous thromboembolism after elective major knee surgery.	2001 Nov 1	11794149
Fondaparinux sodium does not cross the placental barrier: study using the in-vitro human dually perfused cotyledon model.	2002	12383045
Absence of interaction of fondaparinux sodium with digoxin in healthy volunteers.	2002	12383044
Absence of interaction of fondaparinux sodium with aspirin and piroxicam in healthy male volunteers.	2002	12383043
The synthetic pentasaccharide fondaparinux sodium does not interact with oral warfarin.	2002	12383042
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
Fondaparinux sodium.	2002	12109927
Gateways to Clinical Trials.	2002 Apr	12087878
Fondaparinux versus enoxaparin for the prevention of venous thromboembolism.	2002 Apr	11934350
The synthetic pentasaccharide fondaparinux: first in the class of antithrombotic agents that selectively inhibit coagulation factor Xa.	2002 Aug	12244487
Fondaparinux for post-operative venous thrombosis prophylaxis.	2002 Aug	12195605
[Two new very promising antithrombotic agents: pentasaccharide and ximelagatran].	2002 Jan	11887562
Pentasaccharides.	2002 Jul	12124678
[A new synthetic coagulation inhibitor. Only half as many thromboembolisms].	2002 Jul 11	12198888
Benefit of selective factor inhibition.	2002 Jun	12073180
Treatment of symptomatic venous thromboembolism: improving outcomes.	2002 Jun	12073179
Unresolved issues in the prevention and treatment of venous thromboembolism.	2002 Jun	12073178
Optimizing prophylaxis of venous thromboembolism.	2002 Jun	12073177
Selective inhibition of coagulation factors: advances in antithrombotic therapy.	2002 Jun	12073176
Fondaparinux sodium.	2002 Mar	12532174
Arixtra injection. FDA approves synthetic anticlotting drug.	2002 Mar	11902038
Prevention of venous thromboembolism with fondaparinux.	2002 Mar 21	11911133
FDA approves synthetic blood thinner.	2002 Mar-Apr	11989471
Gateways to clinical trials.	2002 May	12092009
Absence of placental transfer of pentasaccharide (Fondaparinux, Arixtra) in the dually perfused human cotyledon in vitro.	2002 May	12038785
Fondaparinux (Arixtra), a new anticoagulant.	2002 May 13	12011755
Use of neuraxial anesthesia with selective factor Xa inhibitors.	2002 Nov	12463580
Use of selective factor Xa inhibitors in special populations.	2002 Nov	12463578
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
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
Absence of an interaction between the synthetic pentasaccharide fondaparinux and oral warfarin.	2002 Sep	12236851
Heparin pentasaccharide.	2002 Sep	12172461
Factor Xa inhibition in the prevention of venous thromboembolism and treatment of patients with venous thromboembolism.	2002 Sep	12172443
Fondaparinux vs enoxaparin for the prevention of venous thromboembolism in major orthopedic surgery: a meta-analysis of 4 randomized double-blind studies.	2002 Sep 9	12196081
The potential role of fondaparinux as venous thromboembolism prophylaxis after total hip or knee replacement or hip fracture surgery.	2002 Sep 9	12196077
Therapeutic considerations in the management of patients with heparin-induced thrombocytopenia.	2002 Summer	12091763
A meta-analysis of fondaparinux versus enoxaparin in the prevention of venous thromboembolism after major orthopaedic surgery.	2002 Winter	12597061
Prevention of venous thromboembolism after major orthopaedic surgery: is fondaparinux an advance?	2003 Aug 16	12932379
[New anticoagulants -- their clinical significance].	2003 Jan	12638473
Gateways to clinical trials.	2003 Jun	12851663
[New antithrombotic agents. Towards a new therapeutic plan].	2003 May 15	12846024

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 `Wed Apr 02 07:50:12 GMT 2025` Edited by `admin` on `Wed Apr 02 07:50:12 GMT 2025`
Record UNII	X0Q6N9USOZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FONDAPARINUX SODIUM FOR ASSAY

Preferred Name

English

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

SR 90107A DECASODIUM SALT

Code

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

SR-90107A DECASODIUM SALT

Code

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)