Banner
targets (2)
for drugs
Identification
Name Ardeparin
Accession Number DB00407 (APRD00803)
Type small molecule
Groups approved, withdrawn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 Normiflo was withdrawn from the US market in March 2000.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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Normiflo Wyeth-Ayerst (United States)
Brand mixtures Not Available
Categories
  • Anticoagulants
  • Antithrombotic Agents
  • Heparins
CAS number Not Available
Weight Average: 1134.928
Monoisotopic: 1134.006993818
Chemical Formula C26H42N2O37S5
InChI Key InChIKey=HTTJABKRGRZYRN-UHFFFAOYSA-N
InChI
InChI=1S/C26H42N2O37S5/c1-4(30)27-7-9(31)13(6(56-23(7)39)3-55-67(43,44)45)58-26-19(65-70(52,53)54)12(34)16(20(62-26)22(37)38)60-24-8(28-66(40,41)42)15(63-68(46,47)48)14(5(2-29)57-24)59-25-18(64-69(49,50)51)11(33)10(32)17(61-25)21(35)36/h5-20,23-26,28-29,31-34,39H,2-3H2,1H3,(H,27,30)(H,35,36)(H,37,38)(H,40,41,42)(H,43,44,45)(H,46,47,48)(H,49,50,51)(H,52,53,54)
Plain Text
IUPAC Name
3-[(5-{[6-carboxy-4,5-dihydroxy-3-(sulfooxy)oxan-2-yl]oxy}-6-(hydroxymethyl)-3-(sulfoamino)-4-(sulfooxy)oxan-2-yl)oxy]-6-({5-acetamido-4,6-dihydroxy-2-[(sulfooxy)methyl]oxan-3-yl}oxy)-4-hydroxy-5-(sulfooxy)oxane-2-carboxylic acid
SMILES
CC(=O)NC1C(O)OC(COS(O)(=O)=O)C(OC2OC(C(OC3OC(CO)C(OC4OC(C(O)C(O)C4OS(O)(=O)=O)C(O)=O)C(OS(O)(=O)=O)C3NS(O)(=O)=O)C(O)C2OS(O)(=O)=O)C(O)=O)C1O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Carbohydrates
Substructures
  • Carbohydrates
  • Aminoglycosides
  • Glycerol and Derivatives
  • Hydroxy Compounds
  • Pyrans
  • Acetates
  • Acetals and Derivatives
  • Glucuronides
  • Amino Ketones
  • Sulfuric Acids and Derivatives
  • Sulfonyls
  • Ethers
  • Sulfate Esters
  • Carboxylic Acids and Derivatives
  • Alcohols and Polyols
  • Heterocyclic compounds
  • Carboxamides and Derivatives
Pharmacology
Indication For prevention of deep vein thrombosis, which may result in pulmonary embolism, following knee surgery.
Pharmacodynamics Ardeparin, 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 action Ardeparin 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.
Absorption Well absorbed following subcutaneous administration, with a mean bioavailability of 92% (based on anti-factor Xa activity).
Volume of distribution Not Available
Protein binding Not Available
Metabolism Liver and the reticulo-endothelial system are the sites of biotransformation.
Route of elimination Not Available
Half life Elimination 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.
Clearance Not Available
Toxicity Symptoms of overdose may include excessive bleeding and bruising.
Affected organisms
  • Humans and other mammals
Pathways
Pathway Name SMPDB ID
Smp00275 Ardeparin Pathway SMP00275
Pharmacoeconomics
Manufacturers
  • Wyeth ayerst laboratories
Packagers Not Available
Dosage forms
Form Route Strength
Injection Subcutaneous
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
water solubility Soluble Not Available
Predicted Properties
Property Value Source
water solubility 1.08e+01 g/l ALOGPS
logP -1.7 ALOGPS
logP -8.3 ChemAxon
logS -2 ALOGPS
pKa (strongest acidic) -2.8 ChemAxon
physiological charge -7 ChemAxon
hydrogen acceptor count 33 ChemAxon
hydrogen donor count 15 ChemAxon
polar surface area 610.49 ChemAxon
rotatable bond count 20 ChemAxon
refractivity 195.91 ChemAxon
polarizability 93.37 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
PubChem Compound 772 Link_out
PubChem Substance 46505194 Link_out
ChemSpider 751 Link_out
Therapeutic Targets Database DAP000428 Link_out
PharmGKB PA164754878 Link_out
Drugs.com http://www.drugs.com/mtm/ardeparin.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Ardeparin Link_out
ATC Codes
  • B01AB05
  • B01AB01
AHFS Codes
  • 20:12.04.16
  • 92:00.00
PDB Entries
FDA label Not Available
MSDS show (65.5 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Antithrombin-III

Pharmacological action: yes
Actions: potentiator

Most important serine protease inhibitor in plasma that regulates the blood coagulation cascade. AT-III inhibits thrombin as well as factors IXa, Xa and XIa. Its inhibitory activity is greatly enhanced in the presence of heparin

Organism class: human
UniProt ID: P01008 Link_out
Gene: SERPINC1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Mousa SA: The low molecular weight heparin, tinzaparin, in thrombosis and beyond. Cardiovasc Drug Rev. 2002 Fall;20(3):199-216. Pubmed
  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
  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

2. Heparin cofactor 2

Pharmacological action: yes
Actions: agonist

Peptides at the N-terminal of HC-II have chemotactic activity for both monocytes and neutrophils

Organism class: human
UniProt ID: P05546 Link_out
Gene: SERPIND1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  3. Mousa SA: The low molecular weight heparin, tinzaparin, in thrombosis and beyond. Cardiovasc Drug Rev. 2002 Fall;20(3):199-216. Pubmed
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19