heparin   Click here for help

GtoPdb Ligand ID: 4214

Synonyms: HepFlush®
Approved drug
heparin is an approved drug (FDA (1939))
Comment: Heparin is an endogenous secretory glycosaminoglycan (GAG) that is released predominantly from connective tissue mast cells. Isolated heparin is used clinically as an anti-coagulant. Structurally, heparins (generally known as unfractionated heparin) are a heterogeneous group of anionic, sulfated GAGs. Commercial preparations usually vary in size from 12-15 kDa, while a low molecular weight (fractionated) versions are also available. Database entries may specify the sodium salt forms.

SARS-CoV-2: There is strong experimental evidence which shows that heparin interacts directly with GAG-binding motifs on the Spike glycoprotein of SARS-CoV-2 [3], and that inhibiting this interaction can reduce SARS-CoV-2 infection of host cells [6,8]. These findings suggest that heparin may offer repurposing potential as a prophylactic COVID-19 therapeutic [2], in addition to its benefit as a treatment for COVID-19-related thrombotic complications.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 35
Hydrogen bond donors 14
Rotatable bonds 19
Topological polar surface area 588.61
Molecular weight 1039.04
XLogP -11.46
No. Lipinski's rules broken 3
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Canonical SMILES CC(=O)NC1C(OC2C(OC(C(C2O)O)OC2C(O)OC(C(C2CS(=O)(=O)O)OS(=O)(=O)O)OC2C(OC(C(C2O)OS(=O)(=O)O)O)C(=O)O)C(=O)O)OC(C(C1O)O)COS(=O)(=O)O
Isomeric SMILES CC(=O)N[C@H]1[C@@H](O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)O)O[C@@H]2[C@@H](O)O[C@@H]([C@@H]([C@H]2CS(=O)(=O)O)OS(=O)(=O)O)O[C@@H]2[C@@H](OC([C@@H]([C@H]2O)OS(=O)(=O)O)O)C(=O)O)C(=O)O)O[C@@H]([C@H]([C@@H]1O)O)COS(=O)(=O)O
InChI InChI=1S/C26H41NO34S4/c1-4(28)27-7-9(30)8(29)6(2-52-63(43,44)45)53-24(7)56-15-10(31)11(32)25(58-19(15)21(36)37)55-13-5(3-62(40,41)42)14(60-64(46,47)48)26(59-22(13)38)57-16-12(33)17(61-65(49,50)51)23(39)54-18(16)20(34)35/h5-19,22-26,29-33,38-39H,2-3H2,1H3,(H,27,28)(H,34,35)(H,36,37)(H,40,41,42)(H,43,44,45)(H,46,47,48)(H,49,50,51)/t5-,6+,7+,8+,9+,10+,11+,12-,13-,14+,15-,16-,17+,18+,19-,22-,23?,24+,25+,26-/m0/s1
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Summary of Clinical Use Click here for help
Heparin is used clinically as an anti-coagulant.

In response to the SARS-CoV-2 pandemic plans are underway to evaluate haparin in COVID-19 patients, as part of the UK's Accelerating COVID-19 Research and Development (ACCORD) initiative (June 2020). ACCORD aims to fast-track potential treatments for COVID-19 through early-stage clinical trials [9]. In this setting heparin will primarily be acting classically as an anti-coagulant to reduce mortality caused by COVID-associated thromboembolic events [5,7]. It may also have non-anticoagulant activities that are beneficial in this disease [4].
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Heparin binds reversibly to antithrombin III (ATIII) and leads to almost instantaneous inactivation of coagulation factors IIa and Xa, thereby reducing clotting function.