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

[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=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 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
Fondaparinux compared with enoxaparin for the prevention of venous thromboembolism after elective major knee surgery.	2001 Nov 1	11794149
Setting a standard for venous thromboembolism prophylaxis.	2001 Nov 1	11715835
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 aspirin and piroxicam in healthy male volunteers.	2002	12383043
The pharmacokinetics of fondaparinux sodium in healthy volunteers.	2002	12383039
Fondaparinux sodium.	2002	12109927
Fondaparinux for post-operative venous thrombosis prophylaxis.	2002 Aug	12195605
[Two new very promising antithrombotic agents: pentasaccharide and ximelagatran].	2002 Jan	11887562
Selective inhibition of coagulation factors: advances in antithrombotic therapy.	2002 Jun	12073176
Arixtra injection. FDA approves synthetic anticlotting drug.	2002 Mar	11902038
Gateways to clinical trials.	2002 May	12092009
Postoperative fondaparinux versus preoperative enoxaparin for prevention of venous thromboembolism in elective hip-replacement surgery: a randomised double-blind comparison.	2002 May 18	12049858
Fondaparinux: a new synthetic pentasaccharide for thrombosis prevention.	2002 May 18	12049854
Use of neuraxial anesthesia with selective factor Xa inhibitors.	2002 Nov	12463580
Thromboprophylaxis dosing: the relationship between timing of first administration, efficacy, and safety.	2002 Nov	12463579
Use of selective factor Xa inhibitors in special populations.	2002 Nov	12463578
Fondaparinux: basic properties and efficacy and safety in venous thromboembolism prophylaxis.	2002 Nov	12463577
Ability of recombinant factor VIIa to reverse the anticoagulant effect of the pentasaccharide fondaparinux in healthy volunteers.	2002 Nov 12	12427650
[Management of heparin-induced thrombocytopenia].	2002 Nov-Dec	12666266
Factor Xa inhibition in the prevention of venous thromboembolism and treatment of patients with venous thromboembolism.	2002 Sep	12172443
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
Cost analysis: fondaparinux versus preoperative and postoperative enoxaparin as venous thromboembolic event prophylaxis in elective hip arthroplasty.	2003 Apr	12723772
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
Heparin, low-molecular-weight heparins, and heparin pentasaccharide: basic and clinical differentiation.	2003 Feb	12627673
Fondaparinux requires further study before firm recommendation.	2003 Feb 24	12588215
Gateways to clinical trials.	2003 Jan-Feb	12690708
Selective factor Xa inhibition improves efficacy of venous thromboembolism prophylaxis in orthopedic surgery.	2003 Jun	12820819
[New antithrombotic agents. Towards a new therapeutic plan].	2003 May 15	12846024
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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:44:28 GMT 2023` Edited by `admin` on `Fri Dec 15 15:44:28 GMT 2023`
Record UNII	J177FOW5JL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FONDAPARINUX

Common Name

English

FONDAPARINUX [VANDF]

Common Name

English

FONDAPARINUX [HSDB]

Common Name

English

Fondaparinux [WHO-DD]

Common Name

English

Classification Tree Code System Code

LIVERTOX

NBK548551