Discovery of glycyrrhetinic acid as an orally active, direct inhibitor of blood coagulation factor xa

Thrombosis Research

Volumn 133, Issue 3, 2014, Pages 501-506

  Jiang, Lilong ^a,b   Wang, Qiong ^a   Shen, Shu ^a   Xiao, Tongshu ^c   Li, Youbin ^b,c  

^a NANJING UNIVERSITY OF CHINESE MEDICINE   (China)

^b HAINAN MEDICAL UNIVERSITY   (China)

^c Jiangsu Provincial Institute of Traditional Chinese Medicine   (China)

Author keywords

Anticoagulation; Blood Coagulation Factor Xa; Glycyrrhiza glabra; Prothrombin Time (PT); Thrombosis

Indexed keywords

ANTICOAGULANT AGENT; BLOOD CLOTTING FACTOR 10A; GLYCYRRHETINIC ACID;

ANIMAL; BLOOD; DISEASE MODEL; HEMORRHAGE; MALE; METABOLISM; ORAL DRUG ADMINISTRATION; PROTHROMBIN TIME; RAT; TAIL; VASCULARIZATION; VENOUS THROMBOSIS; WISTAR RAT;

ADMINISTRATION, ORAL; ANIMALS; ANTICOAGULANTS; DISEASE MODELS, ANIMAL; FACTOR XA; GLYCYRRHETINIC ACID; HEMORRHAGE; MALE; PROTHROMBIN TIME; RATS; RATS, WISTAR; TAIL; VENOUS THROMBOSIS;

EID: 84893953993     PISSN: 00493848     EISSN: 18792472     Source Type: Journal    
DOI: 10.1016/j.thromres.2013.12.025     Document Type: Article

References (31)

1. E.G. Nabel, and E. Braunwald A tale of coronary artery disease and myocardial infarction N Engl J Med 366 2012 54 63
2. J.J. Ferguson, R.M. Califf, E.M. Antman, M. Cohen, C.L. Grines, and S. Goodman et al. Enoxaparin vs unfractionated heparin in high-risk patients with non-ST-segment elevation acute coronary syndromes managed with an intended early invasive strategy: primary results of the SYNERGY randomized trial JAMA 292 2004 45 54
3. R. Holzheimer G. Low-molecular-weight heparin (LMWH) in the treatment of thrombosis Eur J Med Res 9 2004 225 239
4. M.H. Ebell Evidence-based initiation of warfarin (Coumadin) Am Fam Physician 71 2005 763 765
5. E. Perzborn, S. Roehrig, A. Straub, D. Kubitza, and F. Misselwitz et al. The discovery and development of rivaroxaban, an oral, direct factor Xa inhibitor Nat Rev Drug Discov 10 2011 61 75
6. M.T. Lee, and T.E. Klein Pharmacogenetics of warfarin: challenges and opportunities J Hum Genet 58 2013 334 338
7. R.J. Leadley Coagulation factor Xa inhibition: biological background and rationale Curr Top Med Chem 1 2001 151 159
8. V. Laux, E. Perzborn, and S. Heitmeier Direct inhibitors of coagulation proteins - the end of the heparin and low-molecular-weight heparin era for anticoagulant therapy? Thromb Haemost 102 2009 892 899
9. C.H. Yeh, J.C. Fredenburgh, and J.I. Weitz Oral Direct Factor Xa Inhibitors Circ Res 111 2012 7069 7078
10. G.P. Tuszynski, T.B. Gasic, and G.J. Gasic Isolation and characterization of antistasin. An inhibitor of metastasis and coagulation J Biol Chem 262 1987 9718 9723
11. L. Waxman, D.E. Smith, K.E. Arecuri, and G.P. Vlasuk et al. Tick anticoagulant peptide (TAP) is a novel inhibitor of blood coagulation factor Xa Science 248 1990 593 596
12. V. Chu, K. Brown, D. Colussi, Y.M. Choi, D. Green, and H.W. Pauls et al. In vitro characterization of a novel Factor Xa inhibitor, RPR 130737 Thromb Res 99 2000 71 82
13. K.R. Stark, and A.A. James Isolation and characterization of the gene encoding a novel factor Xa-directed anticoagulant from the yellow fever mosquito, Aedes aegypti J Biol Chem 273 33 1998 20802 20809
14. J.B. King, M.B. West, P.F. Cook, and M.H. Hanigan et al. A Novel, Species-specific Class of Uncompetitive Inhibitors of γ-Glutamyl Transpeptidase J Biol Chem 284 14 2009 9059 9065
15. P.N. Walsh, E. Camp, and D. Dende Different requirements for intrinsic factor-Xa forming activity and platelet factor 3 activity and their relationship to platelet aggregation and secretion Br J Haematol 40 2 1978 Oct 311 331
16. Y. Imaeda, T. Miyawaki, H. Sakamoto, F. Itoh, N. Konishi, and K. Hiroe et al. Discovery of sulfonylalkylamides: A new class of orally active factor Xa inhibitors Bioorg Med Chem 2008 2257 2258
17. E. Perzborn, J. Strassburger, A. Wilmen, J. Pohlmann, S. Roehrig, and K.H. Schlemmer et al. In vitro and in vivo studies of the novel antithrombotic agent BAY 59-7939 - an oral, direct Factor Xa inhibitor J Thromb Haemost 3 2005 514 521
18. F. Faria, E.M. Kelen, C.A. Sampaio, C. Bon, N. Duval, and A.M. Chudzinski-Tavassi et al. A new factor Xa inhibitor (lefaxin) from the Haementeria depressa leech Thromb Haemost 82 1999 1469 1473
19. V. Chopin, M. Salzet, J.I. Baert, F. Vandenbulcke, P.E. Sautiére, and J.P. Kerckaert et al. Therostasin, a novel cloting factor Xa inhibitor from the rhynchobdellid leech, Theromyzon tessulatum Biol Chem 275 2000 32701 32770
20. S.S. Mao, J. Huang, C. Welebob, M.P. Neeper, V.M. Garsky, and J.A. Shafer et al. Identification and characterization of variants of tick anticoagulant peptide with increased inhibitory potency toward human factor Xa Biochemistry 34 1995 5098 5103
21. P. Stanssens, P.W. Bergum, Y. Gansemans, L. Jespers, Y. Laroche, and S. Huang et al. Anticoagulant repertoire of the hookworm Ancylostoma caninum Proc Natl Acad Sci U S A 93 1996 2149 2154
22. L.M. Harison, A. Nerfinger, R.D. Bungiro, J.L. Córdova, P. Kuzmic, and M. Cappello et al. Molecular characterization of Ancylostoma inhibitors of coagulation factor Xa. Hookworm anticoagulant activity in vitro predicts parasite blood feeding in vivo Biol Chem 277 2002 6223 6229
23. R. Apitz-Castro, S. Béguin, A. Tablante, F. Bartoli, J.C. Holt, and H.C. Hemker et al. Purification and partial characterization of draculin, the anticoagulant factor present in the saliva of vampire bats(Desmodus rotundus) Thromb Haemost 73 1995 94 100
24. J.M. Ribeiro, M. Schneider, and J.A. Guimaraes Purification and characterization of Prolixin S(Nitrophorin2), the salivary anticoagulant of the blood sucking bug Rhodnius prolixus Biochemistry 308 1995 243 249
25. S. Saxena Glycyrrhiza glabra: Medicine over the millennium Nat Prod Radiance 4 5 2005 358 367
26. R.A. Al-Horani, A.Y. Mehta, and U.R. Desai Potent direct inhibitors of factor Xa based on the tetrahydroisoquinoline scaffold Eur J Med Chem 54 2012 771 783
27. K.P. Cabral Pharmacology of the new target-specific oral anticoagulants J Thromb Thrombolysis 36 2 2013 133 140
28. S. Vaiyapuri, C.I. Jones, and P. Sasikumar et al. Gap Junctions and Connexin Hemichannels Underpin Hemostasis and Thrombosis Circulation 125 20 2012 2479 2491
29. Cosmetic Ingredient Review Expert Panel Final report on the safety assessment of Glycyrrhetinic Acid, Potassium Glycyrrhetinate, Disodium Succinoyl Glycyrrhetinate, Glyceryl Glycyrrhetinate, Glycyrrhetinyl Stearate, Stearyl Glycyrrhetinate, Glycyrrhizic Acid, Ammonium Glycyrrhizate, Dipotassium Glycyrrhizate, Disodium Glycyrrhizate, Trisodium Glycyrrhizate, Methyl Glycyrrhizate, and Potassium Glycyrrhizinate Int J Toxicol 26 Suppl. 2 2007 79 112
30. X.J. Pan, H.Z. Liu, G.H. Jia, and Y.Y. Shu et al. Microwave-assisted extraction of glycyrrhizic acid from licorice root Biochem Eng J 5 2000 173 177
31. I.A. Murav'ev, and L.N. Savchenko Preparation of glycyrrhetinic acid from extracts of licorice root Pharm Chem J 13 1979 537 542