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Identification
NameArdeparin
Accession NumberDB00407  (APRD00803)
TypeSmall Molecule
GroupsApproved, Withdrawn
Description

Ardeparin, marketed under the US trade name Normiflo, is a low molecular weight heparin (LMWH) anticoagulant used for the prevention of postoperative venous thrombosis. Ardeparin is derived via peroxide degradation of heparin extracted from porcine intestinal mucosa. Its molecular weight ranges from 2000 to 15,000 with an average molecular weight of 5500 to 6500. Normiflo was withdrawn from the US market in March 2000.

Structure
Thumb
Synonyms
Ardeparin sodium
External Identifiers Not Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
NormifloWyeth-Ayerst (United States)
Brand mixturesNot Available
SaltsNot Available
Categories
UNII12M44VTJ7B
CAS number9041-08-1
WeightNot Available
Chemical FormulaNot Available
InChI KeyNot Available
InChINot Available
IUPAC NameNot Available
SMILESNot Available
Taxonomy
ClassificationNot classified
Pharmacology
IndicationFor prevention of deep vein thrombosis, which may result in pulmonary embolism, following knee surgery.
PharmacodynamicsArdeparin, an anticoagulant, is a fractionated heparin. It acts at multiple sites in the normal coagulation system to inhibit reactions that lead to the clotting of blood and the formation of fibrin clots both in vitro and in vivo.
Mechanism of actionArdeparin binds to antithrombin III, accelerating its activity in inactivating factor Xa and thrombin, thereby inhibiting thrombosis. Ardeparin also binds to heparin cofactor II, inhibiting thrombin. Ardeparin does not effect prothrombin time (PT) assays and may prolong activated partial thromboplastin time (APTT). Ardeparin has double the anti-factor Xa activity versus anti-factor IIa activity, compared to unfractionated heparin which has approximately equal anti-factor Xa activity and anti-factor IIa activity.
Related Articles
AbsorptionWell absorbed following subcutaneous administration, with a mean bioavailability of 92% (based on anti-factor Xa activity).
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Liver and the reticulo-endothelial system are the sites of biotransformation.

Route of eliminationNot Available
Half lifeElimination half-life for anti-factor Xa activity averages 3.3 hours following a single intravenous dose, while elimination half-life for anti-factor IIa activity averages 1.2 hours following a single intravenous dose.
ClearanceNot Available
ToxicitySymptoms of overdose may include excessive bleeding and bruising.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Enoxaparin Action PathwayDrug actionSMP00272
Ardeparin Action PathwayDrug actionSMP00275
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal AbsorptionNot AvailableNot Available
Blood Brain BarrierNot AvailableNot Available
Caco-2 permeableNot AvailableNot Available
P-glycoprotein substrateNot AvailableNot Available
P-glycoprotein inhibitor INot AvailableNot Available
P-glycoprotein inhibitor IINot AvailableNot Available
Renal organic cation transporterNot AvailableNot Available
CYP450 2C9 substrateNot AvailableNot Available
CYP450 2D6 substrateNot AvailableNot Available
CYP450 3A4 substrateNot AvailableNot Available
CYP450 1A2 substrateNot AvailableNot Available
CYP450 2C9 inhibitorNot AvailableNot Available
CYP450 2D6 inhibitorNot AvailableNot Available
CYP450 2C19 inhibitorNot AvailableNot Available
CYP450 3A4 inhibitorNot AvailableNot Available
CYP450 inhibitory promiscuityNot AvailableNot Available
Ames testNot AvailableNot Available
CarcinogenicityNot AvailableNot Available
BiodegradationNot AvailableNot Available
Rat acute toxicityNot AvailableNot applicable
hERG inhibition (predictor I)Not AvailableNot Available
hERG inhibition (predictor II)Not AvailableNot Available
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Wyeth ayerst laboratories
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubilitySolubleNot Available
Predicted PropertiesNot Available
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS Codes
  • 20:12.04.16
  • 92:00.00
PDB Entries
FDA labelNot Available
MSDSDownload (65.5 KB)
Interactions
Drug Interactions
Drug
AliskirenArdeparin may increase the hyperkalemic activities of Aliskiren.
AmilorideArdeparin may increase the hyperkalemic activities of Amiloride.
Azilsartan medoxomilArdeparin may increase the hyperkalemic activities of Azilsartan medoxomil.
BalsalazideThe risk or severity of adverse effects can be increased when Balsalazide is combined with Ardeparin.
BenazeprilArdeparin may increase the hyperkalemic activities of Benazepril.
CanagliflozinArdeparin may increase the hyperkalemic activities of Canagliflozin.
CandesartanArdeparin may increase the hyperkalemic activities of Candesartan.
CaptoprilArdeparin may increase the hyperkalemic activities of Captopril.
CilazaprilArdeparin may increase the hyperkalemic activities of Cilazapril.
EnalaprilArdeparin may increase the hyperkalemic activities of Enalapril.
EnalaprilatArdeparin may increase the hyperkalemic activities of Enalaprilat.
EplerenoneArdeparin may increase the hyperkalemic activities of Eplerenone.
EprosartanArdeparin may increase the hyperkalemic activities of Eprosartan.
FosinoprilArdeparin may increase the hyperkalemic activities of Fosinopril.
IrbesartanArdeparin may increase the hyperkalemic activities of Irbesartan.
LisinoprilArdeparin may increase the hyperkalemic activities of Lisinopril.
LosartanArdeparin may increase the hyperkalemic activities of Losartan.
MesalazineThe risk or severity of adverse effects can be increased when Mesalazine is combined with Ardeparin.
MetforminArdeparin may increase the hyperkalemic activities of Metformin.
MoexiprilArdeparin may increase the hyperkalemic activities of Moexipril.
OlmesartanArdeparin may increase the hyperkalemic activities of Olmesartan.
OlsalazineThe risk or severity of adverse effects can be increased when Olsalazine is combined with Ardeparin.
PaliferminThe serum concentration of Palifermin can be increased when it is combined with Ardeparin.
PentoxifyllinePentoxifylline may increase the anticoagulant activities of Ardeparin.
PerindoprilArdeparin may increase the hyperkalemic activities of Perindopril.
Potassium ChlorideArdeparin may increase the hyperkalemic activities of Potassium Chloride.
Potassium CitrateArdeparin may increase the hyperkalemic activities of Potassium Citrate.
Potassium IodideArdeparin may increase the hyperkalemic activities of Potassium Iodide.
QuinaprilArdeparin may increase the hyperkalemic activities of Quinapril.
RamiprilArdeparin may increase the hyperkalemic activities of Ramipril.
SpironolactoneArdeparin may increase the hyperkalemic activities of Spironolactone.
TelmisartanArdeparin may increase the hyperkalemic activities of Telmisartan.
TrandolaprilArdeparin may increase the hyperkalemic activities of Trandolapril.
TriamtereneArdeparin may increase the hyperkalemic activities of Triamterene.
ValsartanArdeparin may increase the hyperkalemic activities of Valsartan.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
potentiator
General Function:
Serine-type endopeptidase inhibitor activity
Specific Function:
Most important serine protease inhibitor in plasma that regulates the blood coagulation cascade. AT-III inhibits thrombin, matriptase-3/TMPRSS7, as well as factors IXa, Xa and XIa. Its inhibitory activity is greatly enhanced in the presence of heparin.
Gene Name:
SERPINC1
Uniprot ID:
P01008
Molecular Weight:
52601.935 Da
References
  1. Mousa SA: The low molecular weight heparin, tinzaparin, in thrombosis and beyond. Cardiovasc Drug Rev. 2002 Fall;20(3):199-216. [PubMed:12397367 ]
  2. Lin P, Sinha U, Betz A: Antithrombin binding of low molecular weight heparins and inhibition of factor Xa. Biochim Biophys Acta. 2001 Apr 3;1526(1):105-13. [PubMed:11287128 ]
  3. Shaughnessy SG, Young E, Deschamps P, Hirsh J: The effects of low molecular weight and standard heparin on calcium loss from fetal rat calvaria. Blood. 1995 Aug 15;86(4):1368-73. [PubMed:7632944 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Serine-type endopeptidase inhibitor activity
Specific Function:
Thrombin inhibitor activated by the glycosaminoglycans, heparin or dermatan sulfate. In the presence of the latter, HC-II becomes the predominant thrombin inhibitor in place of antithrombin III (AT-III). Also inhibits chymotrypsin, but in a glycosaminoglycan-independent manner.Peptides at the N-terminal of HC-II have chemotactic activity for both monocytes and neutrophils.
Gene Name:
SERPIND1
Uniprot ID:
P05546
Molecular Weight:
57070.16 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Mousa SA: The low molecular weight heparin, tinzaparin, in thrombosis and beyond. Cardiovasc Drug Rev. 2002 Fall;20(3):199-216. [PubMed:12397367 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
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Drug created on June 13, 2005 07:24 / Updated on October 26, 2015 11:36