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
1. Gotti R, Parma B, Spelta F, Liverani L. (2013)
Affinity capillary electrophoresis in binding study of antithrombin to heparin from different sources.
Talanta, 105: 366-71. [PMID:23598032]
2. Gupta Y, Maciorowski D, Zak SE, Kulkarni CV, Herbert AS, Durvasula R, Fareed J, Dye JM, Kempaiah P. (2021)
Heparin: A simplistic repurposing to prevent SARS-CoV-2 transmission in light of its in-vitro nanomolar efficacy.
Int J Biol Macromol, 183: 203-212. [PMID:33915212]
3. Kim SY, Jin W, Sood A, Montgomery DW, Grant OC, Fuster MM, Fu L, Dordick JS, Woods RJ, Zhang F et al.. (2020)
Characterization of heparin and severe acute respiratory syndrome-related coronavirus 2 (SARS-CoV-2) spike glycoprotein binding interactions.
Antiviral Res, 181: 104873. [PMID:32653452]
4. Lindahl U, Li JP. (2020)
Heparin - An old drug with multiple potential targets in Covid-19 therapy.
J Thromb Haemost, 18 (9): 2422-2424. [PMID:32426897]
5. Poggiali E, Bastoni D, Ioannilli E, Vercelli A, Magnacavallo A. (2020)
Deep Vein Thrombosis and Pulmonary Embolism: Two Complications of COVID-19 Pneumonia?.
Eur J Case Rep Intern Med, 7 (5): 001646. [PMID:32399449]
6. Tandon R, Sharp JS, Zhang F, Pomin VH, Ashpole NM, Mitra D, McCandless MG, Jin W, Liu H, Sharma P et al.. (2021)
Effective Inhibition of SARS-CoV-2 Entry by Heparin and Enoxaparin Derivatives.
J Virol, 95 (3). DOI: 10.1128/JVI.01987-20 [PMID:33173010]
7. Tang N, Bai H, Chen X, Gong J, Li D, Sun Z. (2020)
Anticoagulant treatment is associated with decreased mortality in severe coronavirus disease 2019 patients with coagulopathy.
J Thromb Haemost, 18 (5): 1094-1099. [PMID:32220112]
8. Tree JA, Turnbull JE, Buttigieg KR, Elmore MJ, Coombes N, Hogwood J, Mycroft-West CJ, Lima MA, Skidmore MA, Karlsson R et al.. (2021)
Unfractionated heparin inhibits live wild type SARS-CoV-2 cell infectivity at therapeutically relevant concentrations.
Br J Pharmacol, 178 (3): 626-635. [PMID:33125711]
9. UK Department of Health and Social Care. 
COVID-19 treatments could be fast-tracked through new national clinical trial initiative.
Accessed on 01/06/2020. Modified on 01/06/2020. gov.uk, https://www.gov.uk/government/news/covid-19-treatments-could-be-fast-tracked-through-new-national-clinical-trial-initiative