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Cidofovir

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520: 497: 1022: 40: 925:, non-steroid anti-inflammatory drugs, etc.) to increase their nephrotoxic potential. As it must be given concurrently with probenecid it is advised that drugs that are known to interact with probenecid (e.g. drugs that probenecid interferes with the renal tubular secretion of, such as paracetamol, aciclovir, aminosalicylic acid, etc.) are also withheld. 821:
which decreases side effects to the kidney. Probenecid mitigates nephrotoxicity by inhibiting organic anion transport of the proximal tubule epithelial cells of the kidney. In addition, hydration must be administered to patients receiving cidofovir. 1 liter of normal saline is recommended in
937:. It also inhibits human polymerases, but this action is 8–600 times weaker than its actions on viral DNA polymerases. It also incorporates itself into viral DNA, hence inhibiting viral DNA synthesis during reproduction. 165: 1655: 830:
The major dose-limiting side effect of cidofovir is nephrotoxicity (i.e., kidney damage). Other common side effects (occurring in >1% of people treated with the drug) include:
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Araya CE, Lew JF, Fennell RS, Neiberger RE, Dharnidharka VR (February 2006). "Intermediate-dose cidofovir without probenecid in the treatment of BK virus allograft nephropathy".
120: 755:, a cidofovir derivative with much higher activity against smallpox that can be taken orally has been developed. It has inhibitory effects on varicella-zoster virus replication 62: 1084: 592: 626: 1111:
Cundy, Kenneth C. "Clinical Pharmacokinetics of the Antiviral Nucleotide Analogues Cidofovir and Adefovir." Clinical Pharmacokinetics 36.2 (1999): 127–143.
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with successful case reports of its use. Despite this, the drug failed to demonstrate any efficacy in controlled studies. Cidofovir might have anti-
2101: 1666: 2635: 1947: 1894:"Effect of oral probenecid coadministration on the chronic toxicity and pharmacokinetics of intravenous cidofovir in cynomolgus monkeys" 2001: 1208: 889:(a uricosuric drug) and intravenous saline should always be administered with each cidofovir infusion to prevent this nephrotoxicity. 2161: 646: 1171: 767:
activity in a subgroup of transplant recipients. Cidofovir is being investigated as a complementary intralesional therapy against
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InChI=1S/C8H14N3O6P/c9-7-1-2-11(8(13)10-7)3-6(4-12)17-5-18(14,15)16/h1-2,6,12H,3-5H2,(H2,9,10,13)(H2,14,15,16)/t6-/m0/s1
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Hypersensitivity to cidofovir or probenecid (as probenecid needs to be given concurrently to avoid nephrotoxicity).
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although no clinical trials have been done to date, likely due to the abundance of safer alternatives such as
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Segarra-Newnham M, Vodolo KM (June 2001). "Use of cidofovir in progressive multifocal leukoencephalopathy".
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renal The above pharmacokinetic parameters are measured for cidofovir used in conjunction with probenecid.
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Its active metabolite, cidofovir diphosphate, inhibits viral replication by selectively inhibiting viral
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Brodfuehrer PR, Howell HG, Sapino Jr C, Vemishetti P (1994). "A practical synthesis of (S)-HPMPC".
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Cidofovir is only available as an intravenous formulation. Cidofovir is to be administered with
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Fernández-Morano T, del Boz J, González-Carrascosa M, Tortajada B, de Troya M (December 2011).
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Chilukuri S, Rosen T (April 2003). "Management of acyclovir-resistant herpes simplex virus".
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Cidofovir was discovered at the Institute of Organic Chemistry and Biochemistry, Prague, by
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Bradbury J (March 2002). "Orally available cidofovir derivative active against smallpox".
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Safrin S, Cherrington J, Jaffe HS (September 1997). "Clinical uses of cidofovir".
1131:"Vistide (cidofovir) dosing, indications, interactions, adverse effects, and more" 325: 1629: 1599: 72: 2612: 2504: 2470: 2456: 2451: 2246: 2207: 2203: 2194: 1304:"Human polyomavirus reactivation: disease pathogenesis and treatment approaches" 878: 841: 113: 2617: 2574: 2494: 2443: 2433: 2404: 2368: 2352: 2342: 2301: 2286: 2221: 1554: 959: 922: 918: 886: 818: 693: 568: 356: 2608: 2509: 2499: 2489: 2400: 2357: 2347: 2322: 2276: 2261: 2185: 2110: 910: 760: 748: 732: 704: 256: 66: 2009: 1910: 1893: 1834: 1775: 1718: 1607: 1572: 1515: 1480: 1423: 1388: 1339: 1280: 1245: 1021: 1919: 1320: 31: 2526: 2419: 2296: 2002:
10.1002/(SICI)1099-1654(199709)7:3<145::AID-RMV196>3.0.CO;2-0
1942:(2013 ed.). Adelaide: The Australian Medicines Handbook Unit Trust. 1013: 963: 764: 744: 336: 1586:
Soma MA, Albert DM (February 2008). "Cidofovir: to use or not to use?".
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It has been suggested as an antitumour agent, due to its suppression of
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Its only indication that has received regulatory approval worldwide is
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infections. Cidofovir has also been investigated as a treatment for
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Lacy SA, Hitchcock MJ, Lee WA, Tellier P, Cundy KC (August 1998).
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retinitis. Cidofovir has also shown efficacy in the treatment of
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efficacy and might be used on a limited basis in the event of a
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Journal of the European Academy of Dermatology and Venereology
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Current Opinion in Otolaryngology & Head and Neck Surgery
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and elevated liver enzymes and rare side effects include:
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Principles and Practice of Pediatric Infectious Disease
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It is known to interact with nephrotoxic agents (e.g.
1742:"In vitro activity of potential anti-poxvirus agents" 1977:. September 2010. Dosage and Administration: Dosage. 2596: 2573: 2552: 2545: 2469: 2442: 2418: 2387: 2335: 2315: 2231: 2170: 2160: 2151: 2142: 2133: 1355:"Cidofovir in the treatment of poxvirus infections" 612: 602: 580: 567: 531: 526: 507: 475: 455: 435: 415: 395: 375: 355: 335: 310: 290: 265: 255: 242: 232: 222: 214: 149: 144: 119: 105: 79: 61: 51: 46: 1799:"Cidofovir Activity against Poxvirus Infections" 1445:Magee WC, Hostetler KY, Evans DH (August 2005). 714:Cidofovir was approved for medical use in 1996. 324: 251:2.6 hours (active metabolites: 15–65 hours) 1693:"Topical cidofovir for viral warts in children" 1636:. American Society of Health-System Pharmacists 1004:Cidofovir can be synthesized from a pyrimidone 299: 2095: 1860: 1858: 699:medication primarily used as a treatment for 8: 464: 30: 1656:"Vistide : EPAR – Product Information" 1178:. Gilead Sciences Pty Ltd. 3 September 2013 2549: 2167: 2157: 2148: 2139: 2102: 2088: 2080: 1543:European Archives of Oto-Rhino-Laryngology 1203:. Elsevier Health Sciences. p. 1502. 741:progressive multifocal leukoencephalopathy 518: 495: 364: 1909: 1824: 1814: 1765: 1708: 1562: 1470: 1378: 1329: 1319: 822:conjunction with each dose of cidofovir. 384: 944:activity against the following viruses: 1630:"Cidofovir Monograph for Professionals" 1537:Broekema FI, Dikkers FG (August 2008). 1308:Clinical & Developmental Immunology 1047: 873:Whereas uncommon side effects include: 651: 631: 491: 344: 279: 1933: 1931: 1929: 1197:Long SS, Prober CG, Fischer M (2012). 509: 29: 1451:Antimicrobial Agents and Chemotherapy 1166: 1164: 1162: 1160: 1158: 1156: 1154: 1152: 1125: 1123: 1121: 1119: 1117: 444: 424: 71: 7: 1797:Andrei G, Snoeck R (December 2010). 988:and is marketed with the brand name 793:It has been used topically to treat 132: 751:incident involving smallpox cases. 404: 315: 634:O=C1/N=C(\C=C/N1C(OCP(=O)(O)O)CO)N 561: 25: 1710:10.1111/j.1468-3083.2010.03961.x 1508:10.1111/j.1399-3046.2005.00391.x 1020: 549: 543: 38: 1463:10.1128/AAC.49.8.3153-3162.2005 659:Key:VWFCHDSQECPREK-LURJTMIESA-N 18:Acyclic nucleoside phosphonates 1302:De Gascun CF, Carr MJ (2013). 1172:"Product Information VISTIDE®" 858:Decreased intraocular pressure 786:approval on 30 April 1998 and 555: 537: 1: 2070:10.1016/S0040-4039(00)76875-4 1940:Australian Medicines Handbook 1758:10.1016/s0166-3542(02)00198-5 1416:10.1016/S0140-6736(02)08115-1 1371:10.1016/S0166-3542(02)00008-6 1261:The Annals of Pharmacotherapy 1238:10.1016/S0733-8635(02)00093-1 1600:10.1097/MOO.0b013e3282f43408 992:by Gilead in the US, and by 282:({oxy}methyl)phosphonic acid 1990:Reviews in Medical Virology 790:approval on 23 April 1997. 2726: 782:approval on 26 June 1996, 527:Chemical and physical data 2630: 1663:European Medicines Agency 1555:10.1007/s00405-008-0658-0 1496:Pediatric Transplantation 1353:De Clercq E (July 2002). 667: 642: 622: 618:260 °C (500 °F) 270: 37: 2032:"Press Releases: Gilead" 1740:Kern ER (January 2003). 1037:, a prodrug of cidofovir 2685:Anti-herpes virus drugs 2553:Nucleic acid inhibitors 763:. Cidofovir shows anti- 1911:10.1006/toxs.1998.2481 1898:Toxicological Sciences 1176:TGA eBusiness Services 2588:Peginterferon alfa-2a 2537:Tenofovir alafenamide 1964:"Vistide (cidofovir)" 1938:Rossi S, ed. (2013). 2532:Tenofovir disoproxil 2518:Nucleotide analogues 2481:Nucleoside analogues 1226:Dermatologic Clinics 970:Human papillomavirus 2233:Pyrimidine analogue 2058:Tetrahedron Letters 1672:on 22 February 2014 1321:10.1155/2013/373579 984:, and developed by 949:Human herpesviruses 929:Mechanism of action 192:(Prescription only) 168:(Prescription only) 34: 2657:Never to phase III 2583:Interferon alfa 2b 1746:Antiviral Research 1359:Antiviral Research 1135:Medscape Reference 778:It first received 2667: 2666: 2626: 2625: 2465: 2464: 2383: 2382: 2331: 2330: 2311: 2310: 1949:978-0-9805790-9-3 1809:(12): 2803–2830. 1703:(12): 1487–1489. 1273:10.1345/aph.10338 1093:. 14 October 2020 893:Contraindications 679: 678: 604:Specific rotation 593:Interactive image 477:CompTox Dashboard 200: 187: 175: 163: 95: 16:(Redirected from 2717: 2710:Primary alcohols 2705:Phosphonic acids 2597:Multiple/unknown 2550: 2546:Multiple/general 2316:Not TK activated 2168: 2158: 2149: 2140: 2104: 2097: 2090: 2081: 2074: 2073: 2053: 2047: 2046: 2044: 2043: 2034:. 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738: 734: 730: 722: 717: 715: 712: 710: 706: 702: 698: 695: 691: 687: 684:, brand name 683: 673: 666: 657: 652: 648: 641: 632: 628: 621: 617: 615: 614:Melting point 611: 607: 605: 601: 594: 590: 589: 587: 584: 579: 572: 570: 566: 536: 534: 530: 525: 521: 517: 514: 512: 510:ECHA InfoCard 506: 498: 494: 493:DTXSID3043734 490: 489: 487: 478: 474: 467: 463: 462: 460: 458: 454: 447: 443: 442: 440: 438: 434: 427: 423: 422: 420: 418: 414: 407: 403: 402: 400: 398: 394: 387: 383: 382: 380: 378: 374: 367: 363: 362: 360: 358: 354: 347: 343: 342: 340: 338: 334: 327: 323: 322: 320: 313: 309: 302: 298: 297: 295: 293: 289: 280: 276: 269: 264: 260: 258: 254: 250: 248: 241: 237: 235: 231: 227: 225: 221: 217: 213: 206: 194: 191: 181: 179: 170: 167: 157: 156: 154: 152: 148: 143: 135: 130: 127: 126: 124: 122: 118: 115: 112: 110: 104: 98: 89: 88: 86: 84: 78: 74: 70: 68: 64: 60: 56: 54: 50: 47:Clinical data 45: 41: 36: 19: 2604:Filociclovir 2559: 2516: 2479: 2427: 2375:Tromantadine 2362: 2295: 2269: 2252:Trifluridine 2240: 2215: 2190:Valaciclovir 2179: 2064:(20): 3243. 2061: 2057: 2051: 2040:. Retrieved 2036:the original 2026: 1993: 1989: 1983: 1958: 1939: 1901: 1897: 1887: 1876:. Retrieved 1872: 1843: 1806: 1802: 1792: 1749: 1745: 1735: 1700: 1696: 1686: 1674:. Retrieved 1667:the original 1662: 1650: 1638:. Retrieved 1633: 1624: 1594:(1): 86–90. 1591: 1587: 1581: 1546: 1542: 1532: 1502:(1): 32–37. 1499: 1495: 1489: 1454: 1450: 1440: 1407: 1403: 1397: 1362: 1358: 1348: 1311: 1307: 1297: 1264: 1260: 1254: 1229: 1225: 1219: 1199: 1192: 1180:. Retrieved 1175: 1139:. Retrieved 1134: 1107: 1095:. Retrieved 1088: 1079: 1067:. Retrieved 1059: 1050: 1003: 989: 982:Antonín Holý 979: 954:Adenoviruses 941: 939: 932: 904: 901:Interactions 896: 872: 829: 826:Side effects 816: 804: 792: 777: 756: 726: 713: 685: 681: 680: 669:   457:NIAID ChemDB 244:Elimination 151:Legal status 145:Legal status 2690:Pyrimidones 2643:from market 2613:Taribavirin 2505:Telbivudine 2471:Hepatitis B 2457:Tecovirimat 2452:Methisazone 2247:Idoxuridine 2208:Famciclovir 2204:Penciclovir 2195:Ganciclovir 2144:Herpesvirus 2135:Baltimore I 2116:(primarily 1365:(1): 1–13. 996:elsewhere. 879:tachycardia 842:Neutropenia 735:-resistant 718:Medical use 576: g·mol 516:100.166.433 301:113852-37-2 266:Identifiers 114:Intravenous 53:Trade names 2674:Categories 2618:Moroxydine 2575:Interferon 2495:Lamivudine 2444:Poxviridae 2434:Rifampicin 2405:Resiquimod 2369:Fomivirsen 2353:Letermovir 2343:Amenamevir 2302:Cytarabine 2287:Sorivudine 2256:+tipiracil 2222:Vidarabine 2114:antivirals 2042:2007-12-05 1878:2019-06-05 1676:5 February 1640:5 February 1314:: 373579. 1182:5 February 1141:4 February 1042:References 1006:derivative 960:poxviruses 923:tacrolimus 919:vancomycin 887:Probenecid 819:probenecid 771:caused by 694:injectable 581:3D model ( 569:Molar mass 426:CHEBI:3696 386:768M1V522C 357:ChemSpider 292:CAS Number 275:IUPAC name 2653:Phase III 2641:Withdrawn 2609:Ribavirin 2560:Cidofovir 2510:Clevudine 2500:Lobucavir 2490:Entecavir 2401:Imiquimod 2358:Maribavir 2348:Docosanol 2323:Foscarnet 2277:Brivudine 2262:Edoxudine 2186:Aciclovir 2164:activated 2154:inhibitor 2111:DNA virus 1866:"Details" 1634:Drugs.com 1010:protected 1000:Synthesis 911:foscarnet 846:Hair loss 761:aciclovir 749:bioterror 733:aciclovir 723:DNA virus 705:retinitis 697:antiviral 682:Cidofovir 446:ChEMBL152 257:Excretion 246:half-life 107:Routes of 81:Pregnancy 73:Monograph 67:Drugs.com 32:Cidofovir 2527:Adefovir 2429:assembly 2420:Vaccinia 2297:cytosine 2018:32366514 2010:10398479 1835:21994641 1784:23136929 1776:12615301 1727:32295082 1719:21261749 1616:22895067 1608:18197029 1573:18458927 1524:24131709 1516:16499584 1481:16048917 1432:22903225 1424:11937193 1389:12076747 1340:23737811 1289:32026770 1281:11408993 1246:12757254 1097:17 April 1029:See also 1014:glycidol 964:smallpox 942:in vitro 852:Headache 849:Weakness 838:Vomiting 765:BK virus 757:in vitro 745:smallpox 672:(verify) 337:DrugBank 228:complete 121:ATC code 83:category 2271:thymine 2242:uridine 2217:adenine 2181:guanine 2120:, also 1920:9742650 1826:3185586 1803:Viruses 1767:9628899 1564:2441494 1472:1196213 1380:9533828 1331:3659475 1137:. WebMD 990:Vistide 976:History 875:anaemia 862:Uveitis 690:topical 688:, is a 686:Vistide 574:279.189 533:Formula 346:DB00369 312:PubChem 207:Rx-only 204:WARNING 176:: 137:) 131: ( 129:J05AB12 96: D 57:Vistide 2700:Ethers 2695:Amines 2636:WHO-EM 2522:NtRTIs 2485:NARTIs 2282:FV-100 2016:  2008:  1946:  1918:  1833:  1823:  1782:  1774:  1764:  1725:  1717:  1614:  1606:  1571:  1561:  1522:  1514:  1479:  1469:  1430:  1422:  1404:Lancet 1387:  1377:  1338:  1328:  1287:  1279:  1244:  1207:  1069:22 Oct 1008:and a 994:Pfizer 966:virus) 958:Human 867:Iritis 855:Chills 835:Nausea 703:(CMV) 627:SMILES 466:001049 437:ChEMBL 406:C06909 238:<6% 201: 188: 178:℞-only 164: 2473:(VII) 2336:Other 2126:D06BB 2122:S01AD 2014:S2CID 1967:(PDF) 1869:(PDF) 1780:S2CID 1723:S2CID 1670:(PDF) 1659:(PDF) 1612:S2CID 1520:S2CID 1428:S2CID 1285:S2CID 913:, IV 801:Other 795:warts 647:InChI 608:-97.3 583:JSmol 417:ChEBI 366:54636 326:60613 2124:and 2006:PMID 1944:ISBN 1916:PMID 1831:PMID 1772:PMID 1715:PMID 1678:2014 1642:2014 1604:PMID 1569:PMID 1512:PMID 1477:PMID 1420:PMID 1385:PMID 1336:PMID 1312:2013 1277:PMID 1242:PMID 1205:ISBN 1184:2014 1143:2014 1099:2024 1071:2023 881:and 807:FGF2 709:AIDS 397:KEGG 377:UNII 218:data 63:AHFS 2389:HPV 2118:J05 2066:doi 1998:doi 1973:). 1906:doi 1821:PMC 1811:doi 1762:PMC 1754:doi 1705:doi 1596:doi 1559:PMC 1551:doi 1547:265 1504:doi 1467:PMC 1459:doi 1412:doi 1408:359 1375:PMC 1367:doi 1326:PMC 1316:doi 1269:doi 1234:doi 1064:FDA 788:EMA 784:TGA 780:FDA 773:HPV 737:HSV 692:or 482:EPA 316:CID 190:POM 134:WHO 2676:: 2649:: 2393:MC 2162:TK 2062:35 2060:. 2012:. 2004:. 1992:. 1928:^ 1914:. 1902:44 1900:. 1896:. 1871:. 1857:^ 1829:. 1819:. 1805:. 1801:. 1778:. 1770:. 1760:. 1750:57 1748:. 1744:. 1721:. 1713:. 1701:25 1699:. 1695:. 1661:. 1632:. 1610:. 1602:. 1592:16 1590:. 1567:. 1557:. 1545:. 1541:. 1518:. 1510:. 1500:10 1498:. 1475:. 1465:. 1455:49 1453:. 1449:. 1426:. 1418:. 1406:. 1383:. 1373:. 1363:55 1361:. 1357:. 1334:. 1324:. 1310:. 1306:. 1283:. 1275:. 1265:35 1263:. 1240:. 1230:21 1228:. 1174:. 1151:^ 1133:. 1116:^ 1087:. 1062:. 1058:. 1016:. 921:, 909:, 885:. 809:. 797:. 775:. 711:. 547:14 197:US 184:UK 173:CA 166:S4 160:AU 92:AU 2611:/ 2524:: 2520:/ 2487:: 2483:/ 2431:: 2403:/ 2391:/ 2371:) 2367:( 2304:) 2300:( 2264:) 2258:) 2254:( 2245:( 2224:) 2220:( 2210:) 2206:/ 2197:/ 2188:/ 2184:( 2128:) 2103:e 2096:t 2089:v 2072:. 2068:: 2045:. 2020:. 2000:: 1994:7 1969:( 1952:. 1922:. 1908:: 1881:. 1837:. 1813:: 1807:2 1786:. 1756:: 1729:. 1707:: 1680:. 1644:. 1618:. 1598:: 1575:. 1553:: 1526:. 1506:: 1483:. 1461:: 1434:. 1414:: 1391:. 1369:: 1342:. 1318:: 1291:. 1271:: 1248:. 1236:: 1213:. 1186:. 1145:. 1101:. 1073:. 585:) 562:P 559:6 556:O 553:3 550:N 544:H 541:8 538:C 484:) 480:( 199:: 186:: 162:: 94:: 65:/ 20:)

Index

Acyclic nucleoside phosphonates

Trade names
AHFS
Drugs.com
Monograph
Pregnancy
category

Routes of
administration

Intravenous
ATC code
J05AB12
WHO
Legal status
S4
℞-only
POM
WARNING
Pharmacokinetic
Bioavailability
Protein binding
Elimination half-life
Excretion
IUPAC name
CAS Number
113852-37-2
PubChem
60613
DrugBank
DB00369
ChemSpider

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