fondaparinux Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
synthetic heparinoids 1236 104993-28-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • fondaparinux
  • fondaparin
  • heparin pentasaccharide
  • fondaparinux sodium
  • arixtra
  • fondaparin sodium
Synthetic pentasaccharide that mediates the interaction of HEPARIN with ANTITHROMBINS and inhibits FACTOR Xa; it is used for prevention of VENOUS THROMBOEMBOLISM after surgery.
  • Molecular weight: 1508.22
  • Formula: C31H53N3O49S8
  • CLOGP: -10.96
  • LIPINSKI: 3
  • HAC: 52
  • HDO: 19
  • TPSA: 805.48
  • ALOGS: -2.28
  • ROTB: 27

Drug dosage:

DoseUnitRoute
2.50 mg P

ADMET properties:

PropertyValueReference
CL (Clearance) 0.07 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.21 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 19.30 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Dec. 7, 2001 FDA MYLAN IRELAND LTD

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Haematoma 605.71 18.56 228 8738 31644 46645452
Muscle haemorrhage 342.16 18.56 87 8879 3217 46673879
Pulmonary embolism 258.98 18.56 193 8773 108392 46568704
Anaemia 188.69 18.56 238 8728 255541 46421555
Shock haemorrhagic 179.11 18.56 66 8900 8558 46668538
Incorrect product administration duration 165.23 18.56 64 8902 9513 46667583
Heparin-induced thrombocytopenia 160.15 18.56 51 8915 4258 46672838
Deep vein thrombosis 149.18 18.56 123 8843 79650 46597446
Cerebral haemorrhage 143.39 18.56 81 8885 28290 46648806
Haemorrhage 124.84 18.56 95 8871 54774 46622322
Post procedural haemorrhage 122.33 18.56 48 8918 7378 46669718
Haemoglobin decreased 114.30 18.56 132 8834 128817 46548279
Melaena 113.21 18.56 69 8897 27703 46649393
Post procedural haematoma 112.82 18.56 30 8936 1321 46675775
Retroperitoneal haematoma 101.20 18.56 32 8934 2608 46674488
Intra-abdominal haematoma 93.68 18.56 27 8939 1604 46675492
Subcutaneous haematoma 85.30 18.56 25 8941 1576 46675520
Incision site haematoma 82.34 18.56 14 8952 61 46677035
Subdural haematoma 81.99 18.56 43 8923 12954 46664142
Compartment syndrome 75.67 18.56 24 8942 1975 46675121
Thrombocytopenia 71.83 18.56 104 8862 126477 46550619
Abdominal wall haematoma 70.86 18.56 25 8941 2856 46674240
Haematemesis 67.93 18.56 51 8915 28755 46648341
Thrombosis 62.79 18.56 65 8901 56004 46621092
Blood loss anaemia 61.75 18.56 31 8935 8526 46668570
Haemorrhage subcutaneous 59.42 18.56 22 8944 2884 46674212
Extradural haematoma 53.51 18.56 17 8949 1406 46675690
Tooth erosion 51.46 18.56 13 8953 466 46676630
Incision site haemorrhage 45.35 18.56 12 8954 518 46676578
Intra-abdominal haemorrhage 45.30 18.56 17 8949 2313 46674783
Pulpitis dental 40.50 18.56 12 8954 785 46676311
Fatigue 40.07 18.56 35 8931 608662 46068434
Skin necrosis 39.24 18.56 23 8943 8581 46668515
Thrombocytosis 38.69 18.56 19 8947 4983 46672113
Rectal haemorrhage 35.19 18.56 40 8926 38215 46638881
Haemoperitoneum 33.81 18.56 14 8952 2468 46674628
Cerebral haematoma 32.94 18.56 15 8951 3324 46673772
Abdominal wall haemorrhage 31.87 18.56 7 8959 135 46676961
Red blood cell count decreased 31.52 18.56 35 8931 32588 46644508
Gastrointestinal haemorrhage 30.62 18.56 54 8912 77319 46599777
Splenic rupture 27.88 18.56 10 8956 1197 46675899
Hemiplegia 27.63 18.56 17 8949 6921 46670175
Shock 27.50 18.56 27 8939 21818 46655278
Gastric haemorrhage 27.42 18.56 16 8950 5918 46671178
Toxic skin eruption 27.13 18.56 21 8945 12366 46664730
Injection site haematoma 26.98 18.56 16 8950 6096 46671000
Hypovolaemic shock 26.70 18.56 15 8951 5168 46671928
Off label use 26.48 18.56 143 8823 379698 46297398
Headache 26.32 18.56 32 8934 478320 46198776
Periodontitis 26.27 18.56 13 8953 3463 46673633
Wound haemorrhage 25.64 18.56 11 8955 2116 46674980
Venous thrombosis limb 25.55 18.56 12 8954 2851 46674245
Haematocrit decreased 24.65 18.56 32 8934 35025 46642071
Intraventricular haemorrhage 23.45 18.56 10 8956 1895 46675201
Retroperitoneal haemorrhage 23.01 18.56 11 8955 2719 46674377
Hypoperfusion 22.89 18.56 9 8957 1388 46675708
Spinal cord compression 22.69 18.56 12 8954 3672 46673424
Postoperative wound complication 22.56 18.56 8 8958 927 46676169
Post procedural swelling 21.93 18.56 6 8960 294 46676802
Platelet count increased 21.80 18.56 20 8946 14854 46662242
Prothrombin level decreased 21.75 18.56 7 8959 603 46676493
Insomnia 21.65 18.56 3 8963 164921 46512175
Drug hypersensitivity 21.46 18.56 10 8956 243815 46433281
Toxicity to various agents 21.42 18.56 7 8959 211759 46465337
Pallor 20.92 18.56 24 8942 23142 46653954
Spontaneous haematoma 20.59 18.56 7 8959 715 46676381
Renal failure 19.63 18.56 57 8909 113537 46563559
Traumatic haematoma 19.20 18.56 8 8958 1432 46675664
Hepatic function abnormal 19.06 18.56 28 8938 34393 46642703
Brain herniation 19.05 18.56 10 8956 3013 46674083

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Incorrect product administration duration 203.11 19.75 61 6188 3861 29942368
Haematoma 202.34 19.75 99 6150 23854 29922375
Muscle haemorrhage 130.74 19.75 43 6206 3660 29942569
Heparin-induced thrombocytopenia 122.36 19.75 45 6204 5338 29940891
Pulmonary embolism 101.93 19.75 102 6147 78033 29868196
Haemorrhage 99.52 19.75 80 6169 45999 29900230
Anaemia 91.95 19.75 159 6090 207833 29738396
Cerebral haemorrhage 88.29 19.75 65 6184 32822 29913407
Post procedural haemorrhage 73.64 19.75 35 6214 7875 29938354
Shock haemorrhagic 72.05 19.75 37 6212 9828 29936401
Post procedural haematoma 58.78 19.75 19 6230 1528 29944701
Deep vein thrombosis 57.70 19.75 67 6182 60434 29885795
Melaena 50.99 19.75 47 6202 32390 29913839
Haematuria 48.44 19.75 53 6196 44781 29901448
Subdural haematoma 47.52 19.75 36 6213 18936 29927293
Thrombosis 47.50 19.75 51 6198 42180 29904049
Thrombocytosis 44.14 19.75 19 6230 3394 29942835
Extradural haematoma 42.73 19.75 14 6235 1175 29945054
Haematemesis 41.23 19.75 38 6211 26165 29920064
Retroperitoneal haematoma 39.12 19.75 16 6233 2516 29943713
Retroperitoneal haemorrhage 34.73 19.75 15 6234 2700 29943529
Adrenal haemorrhage 34.34 19.75 8 6241 186 29946043
Thrombocytopenia 34.29 19.75 83 6166 136961 29809268
Intra-abdominal haematoma 33.46 19.75 12 6237 1322 29944907
Haemoglobin decreased 31.68 19.75 72 6177 114026 29832203
Abdominal wall haematoma 30.89 19.75 12 6237 1649 29944580
Spinal cord haemorrhage 29.97 19.75 8 6241 328 29945901
Gastrointestinal haemorrhage 28.14 19.75 57 6192 83389 29862840
Off label use 25.44 19.75 111 6138 249179 29697050
Subacute cutaneous lupus erythematosus 24.42 19.75 8 6241 671 29945558
Venous thrombosis 23.23 19.75 12 6237 3222 29943007
Haemorrhagic stroke 23.19 19.75 15 6234 6132 29940097
Lumbosacral plexus injury 22.12 19.75 4 6245 24 29946205
Haemorrhage intracranial 22.09 19.75 21 6228 15011 29931218
Intra-abdominal haemorrhage 21.72 19.75 10 6239 2092 29944137
Gastric haemorrhage 21.59 19.75 17 6232 9450 29936779
Haemarthrosis 21.31 19.75 11 6238 2948 29943281
Altered state of consciousness 20.54 19.75 23 6226 19896 29926333

Pharmacologic Action:

SourceCodeDescription
ATC B01AX05 BLOOD AND BLOOD FORMING ORGANS
ANTITHROMBOTIC AGENTS
ANTITHROMBOTIC AGENTS
Other antithrombotic agents
FDA MoA N0000175635 Factor Xa Inhibitors
FDA EPC N0000175637 Factor Xa Inhibitor
MeSH PA D000925 Anticoagulants
MeSH PA D000991 Antithrombins
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D065427 Factor Xa Inhibitors
MeSH PA D006401 Hematologic Agents
MeSH PA D011480 Protease Inhibitors
MeSH PA D015842 Serine Proteinase Inhibitors
CHEBI has role CHEBI:50249 anticoagulante

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Deep venous thrombosis indication 128053003
Pulmonary thromboembolism indication 233935004
Prevention of deep vein thrombosis indication 439993001
Myocardial infarction off-label use 22298006 DOID:5844
Acute coronary syndrome off-label use 394659003
Diabetic retinopathy contraindication 4855003 DOID:8947
Gastrointestinal ulcer contraindication 40845000
Acute nephropathy contraindication 58574008
Blood coagulation disorder contraindication 64779008 DOID:1247
Operation on brain contraindication 70586009
Heparin-induced thrombocytopenia contraindication 73397007
Kidney disease contraindication 90708001 DOID:557
Autoimmune thrombocytopenia contraindication 128091003
Hemorrhagic cerebral infarction contraindication 230706003
Local anesthetic intrathecal block contraindication 231249005
Procedure on spine contraindication 238181003
Anemia contraindication 271737000 DOID:2355
Lumbar puncture contraindication 277762005
Bacterial endocarditis contraindication 301183007
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Surgical procedure on eye proper contraindication 373353005
Hypertensive urgency contraindication 443482000
Significant Bleeding contraindication
Platelet Aggregation Inhibition contraindication
Placement of Epidural Catheter contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 0.23 acidic
pKa2 0.94 acidic
pKa3 2.46 acidic
pKa4 3.08 acidic
pKa5 11.49 acidic
pKa6 11.98 acidic
pKa7 12.26 acidic
pKa8 12.43 acidic
pKa9 12.91 acidic
pKa10 13.69 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Antithrombin-III Secreted ACTIVATOR Kd 7.49 IUPHAR CHEMBL

External reference:

IDSource
4021296 VUID
N0000148733 NUI
D01844 KEGG_DRUG
114870-03-0 SECONDARY_CAS_RN
4021296 VANDF
C1099665 UMLSCUI
CHEBI:31632 CHEBI
NTO PDB_CHEM_ID
CHEMBL1200644 ChEMBL_ID
CHEMBL1201202 ChEMBL_ID
CHEMBL1276258 ChEMBL_ID
DB00569 DRUGBANK_ID
D000077425 MESH_DESCRIPTOR_UI
636380 PUBCHEM_CID
C049714 MESH_SUPPLEMENTAL_RECORD_UI
6819 IUPHAR_LIGAND_ID
7653 INN_ID
J177FOW5JL UNII
321208 RXNORM
16268 MMSL
184641 MMSL
18938 MMSL
42652 MMSL
d04786 MMSL
009549 NDDF
009550 NDDF
385517000 SNOMEDCT_US
395236007 SNOMEDCT_US
708189008 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 0781-3443 INJECTION 2.50 mg SUBCUTANEOUS ANDA 27 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 0781-3454 INJECTION 5 mg SUBCUTANEOUS ANDA 27 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 0781-3465 INJECTION 7.50 mg SUBCUTANEOUS ANDA 27 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 0781-3476 INJECTION 10 mg SUBCUTANEOUS ANDA 27 sections
fondaparinux sodium HUMAN PRESCRIPTION DRUG LABEL 1 11797-154 INJECTION, SOLUTION 2.50 mg SUBCUTANEOUS ANDA 28 sections
fondaparinux sodium HUMAN PRESCRIPTION DRUG LABEL 1 11797-155 INJECTION, SOLUTION 5 mg SUBCUTANEOUS ANDA 28 sections
fondaparinux sodium HUMAN PRESCRIPTION DRUG LABEL 1 11797-156 INJECTION, SOLUTION 7.50 mg SUBCUTANEOUS ANDA 28 sections
fondaparinux sodium HUMAN PRESCRIPTION DRUG LABEL 1 11797-157 INJECTION, SOLUTION 10 mg SUBCUTANEOUS ANDA 28 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 43598-606 INJECTION 10 mg SUBCUTANEOUS ANDA 26 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 43598-607 INJECTION 2.50 mg SUBCUTANEOUS ANDA 26 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 43598-608 INJECTION 5 mg SUBCUTANEOUS ANDA 26 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 43598-609 INJECTION 7.50 mg SUBCUTANEOUS ANDA 26 sections
ARIXTRA HUMAN PRESCRIPTION DRUG LABEL 1 54868-5501 INJECTION, SOLUTION 7.50 mg SUBCUTANEOUS NDA 27 sections
ARIXTRA HUMAN PRESCRIPTION DRUG LABEL 1 54868-5652 INJECTION, SOLUTION 5 mg SUBCUTANEOUS NDA 27 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 55111-678 INJECTION 2.50 mg SUBCUTANEOUS ANDA 27 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 55111-679 INJECTION 5 mg SUBCUTANEOUS ANDA 27 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 55111-680 INJECTION 7.50 mg SUBCUTANEOUS ANDA 27 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 55111-681 INJECTION 10 mg SUBCUTANEOUS ANDA 27 sections
FONDAPARINUX SODIUM Human Prescription Drug Label 1 55150-230 INJECTION, SOLUTION 2.50 mg SUBCUTANEOUS ANDA 28 sections
FONDAPARINUX SODIUM Human Prescription Drug Label 1 55150-231 INJECTION, SOLUTION 5 mg SUBCUTANEOUS ANDA 28 sections
FONDAPARINUX SODIUM Human Prescription Drug Label 1 55150-232 INJECTION, SOLUTION 7.50 mg SUBCUTANEOUS ANDA 28 sections
FONDAPARINUX SODIUM Human Prescription Drug Label 1 55150-233 INJECTION, SOLUTION 10 mg SUBCUTANEOUS ANDA 28 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 67457-582 INJECTION, SOLUTION 2.50 mg SUBCUTANEOUS NDA authorized generic 28 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 67457-583 INJECTION, SOLUTION 5 mg SUBCUTANEOUS NDA authorized generic 28 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 67457-584 INJECTION, SOLUTION 7.50 mg SUBCUTANEOUS NDA authorized generic 28 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 67457-585 INJECTION, SOLUTION 10 mg SUBCUTANEOUS NDA authorized generic 28 sections
Arixtra HUMAN PRESCRIPTION DRUG LABEL 1 67457-592 INJECTION, SOLUTION 2.50 mg SUBCUTANEOUS NDA 28 sections
Arixtra HUMAN PRESCRIPTION DRUG LABEL 1 67457-593 INJECTION, SOLUTION 5 mg SUBCUTANEOUS NDA 28 sections
Arixtra HUMAN PRESCRIPTION DRUG LABEL 1 67457-594 INJECTION, SOLUTION 7.50 mg SUBCUTANEOUS NDA 28 sections
Arixtra HUMAN PRESCRIPTION DRUG LABEL 1 67457-595 INJECTION, SOLUTION 10 mg SUBCUTANEOUS NDA 28 sections