enoxaparin   Click here for help

GtoPdb Ligand ID: 6811

Synonyms: Clexane® | enoxaparin sodium | Lovenox® | PK-10169 | RP-54563
Approved drug
enoxaparin is an approved drug (FDA (1993), FDA (2016))
Compound class: Synthetic organic
Comment: A Low-Molecular-Weight Heparin antithrombin-III activator. It consists of fractionated material from pig mucosa but the PubChem structure represents the major form.

Biosimilar drugs: The EMA approved enoxaparin biosimilars named Inhixa and Thorinane in 2016.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 39
Hydrogen bond donors 15
Rotatable bonds 22
Topological polar surface area 652.39
Molecular weight 1134.01
XLogP -13.27
No. Lipinski's rules broken 3
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Canonical SMILES OCC1OC(OC2C(OC(C(C2O)OS(=O)(=O)O)OC2C(COS(=O)(=O)O)OC(C(C2O)NC(=O)C)O)C(=O)O)C(C(C1OC1OC(C(=O)O)C(C(C1OS(=O)(=O)O)O)O)OS(=O)(=O)O)NS(=O)(=O)O
Isomeric SMILES OCC1OC(OC2C(OC(C(C2O)OS(=O)(=O)O)OC2C(COS(=O)(=O)O)OC(C(C2O)NC(=O)C)O)C(=O)O)C(C(C1OC1OC(C(=O)O)C(C(C1OS(=O)(=O)O)O)O)OS(=O)(=O)O)NS(=O)(=O)O
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)
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
serpin family C member 1 Primary target of this compound Hs Activator Activation - - - 2
Description: Catalyses the inactivation of coagulation proteases by activated antithrombin-III