496:
473:
445:
87:
562:
32:
78:
3881:
634:
InChI=1S/C33H47NO13/c1-18-10-8-6-4-3-5-7-9-11-21(45-32-30(39)28(34)29(38)19(2)44-32)15-25-27(31(40)41)22(36)17-33(42,47-25)16-20(35)14-24-23(46-24)12-13-26(37)43-18/h3-9,11-13,18-25,27-30,32,35-36,38-39,42H,10,14-17,34H2,1-2H3,(H,40,41)/b4-3+,7-5+,8-6+,11-9+,13-12+/t18-,19-,20+,21+,22+,23-,24-,25+,27-,28+,29-,30+,32+,33-/m1/s1
811:
While not currently approved for use on meats in the United States, some countries allow natamycin to be applied to the surface of dry and fermented sausages to prevent mold growth on the casing. Also, natamycin is approved for various dairy applications in the United States. More specifically,
913:
moulds. Natamycin is unique amongst related antifungals specifically because it does not directly cause membrane permeabilization. Structurally-related antibiotics with similar binding properties are thought to produce hydrophilic channels that allow leakage of potassium and sodium ions from the
900:
present in fungal cell membranes. Natamycin inhibits amino acid and glucose transport proteins leading to a loss of nutrient transport across the plasma membrane. While this binding is reversible, ergosterol binding acts as a universal mechanism of fungal inhibition, allowing natamycin to act on
827:
E235. Throughout the
European Union, it is approved only as a surface preservative for certain cheese and dried sausage products. It must not be detectable 5 mm below the rind. While natamycin is approved in different applications at different levels in the world, it is approved in over 150
791:
Natamycin has been used for decades in the food industry as a hurdle to fungal outgrowth in dairy products and other foods. Potential advantages for the usage of natamycin might include the replacement of traditional chemical preservatives, a neutral flavor impact, and less dependence on
779:. Natamycin shows negligible absorption into the body when administered in these ways. When taken orally, little or none is absorbed from the gastrointestinal tract, making it inappropriate for systemic infections. Natamycin lozenges are also prescribed to treat yeast infections and
812:
natamycin is commonly used in products such as cream cheeses, cottage cheese, sour cream, yogurt, shredded cheeses, cheese slices, and packaged salad mixes. One of the reasons for food producers to use natamycin is to replace the artificial preservative
2078:
1523:
Van
Leeuwen MR, Golovina EA, Dijksterhuis J (June 2009). "The polyene antimycotics nystatin and filipin disrupt the plasma membrane, whereas natamycin inhibits endocytosis in germinating conidia of Penicillium discolor".
2071:
2064:
3451:
1282:
3444:
961:
874:
than natamycin, but in all cases, the numbers are quite high. In humans, a dose of 500 mg/kg/day repeated over multiple days caused nausea, vomiting, and diarrhea.
1296:
Youssef AM, Assem FM, El-Sayed SM, Salama H, Abd El-Salam MH (2017). "Utilization of Edible Films and
Coatings as Packaging Materials for Preservation of Cheeses".
1751:
1739:
Natamycin was isolated for the first time in 1955 in the Gist-brocades research laboratories, from the fermentation broth of a culture of
Streptomyces natalensis.
839:
in 2002. In 2009, the EFSA considered the proposed use levels of natamycin are safe if it is used for the surface treatment for these cheese and sausage types.
3926:
3437:
1791:
816:. Natamycin is also known to diffuse slower and lesser into cheese when compared to sorbate, which could otherwise cause undesirable changes to the flavor.
141:
1253:
796:
for efficacy, as is common with chemical preservatives. It can be applied in a variety of ways: as an aqueous suspension (such as mixed into a
862:
is ≥2300 mg/kg, and doses of 500 mg/kg/day over two years caused no detectable differences in survival rate, growth, or incidence of
109:
1628:"Analysis of the mycosamine biosynthesis and attachment genes in the nystatin biosynthetic gene cluster of Streptomyces noursei ATCC 11455"
606:
1349:
1784:
1730:
1272:
2056:
3395:
2679:
2623:
1688:"Generation of the natamycin analogs by gene engineering of natamycin biosynthetic genes in Streptomyces chattanoogensis L10"
1237:
719:
1777:
870:
of natamycin also lack toxicity. The breakdown products of natamycin under various storage conditions may have a lower LD
877:
No evidence shows natamycin, at either pharmacological levels or levels encountered as a food additive, can harm normal
1759:
1132:
626:
3412:
2640:
918:
278:)-22--1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclooctacosa-8,14,16,18,20-pentaene-25-carboxylic acid
214:
884:
The EFSA has concluded that the use of natamycin as a food additive has no relevant risk for the development of
3162:
832:
2729:
1257:
955:
836:
491:
372:
1484:"Natamycin blocks fungal growth by binding specifically to ergosterol without permeabilizing the membrane"
1181:"Biotechnological production and application of the antibiotic pimaricin: biosynthesis and its regulation"
835:(EFSA) panel took over the responsibilities of providing scientific food safety advice to the EU from the
421:
3931:
718:
Natamycin was discovered in 1955 and approved for medical use in the United States in 1978. It is on the
452:
3871:
2488:
1839:
1482:
te
Welscher YM, ten Napel HH, Balagué MM, Souza CM, Riezman H, de Kruijff B, et al. (March 2008).
3429:
993:
modules, followed by additional enzymatic processes for oxidation and attachment of the substituents.
3230:
3200:
2672:
1373:
1148:
1029:
917:
Natamycin has very low solubility in water; however, natamycin is effective at very low levels. Its
3095:
2117:
1891:
1626:
Nedal A, Sletta H, Brautaset T, Borgos SE, Sekurova ON, Ellingsen TE, et al. (November 2007).
468:
3852:
3400:
3330:
2628:
2562:
2399:
1876:
1179:
Aparicio JF, Barreales EG, Payero TD, Vicente CM, de Pedro A, Santos-Aberturas J (January 2016).
943:
800:) sprayed on the product or into which the product is dipped, or in powdered form (along with an
127:
99:
2086:
881:, but definitive research may not be available. However, some people are allergic to natamycin.
3906:
3624:
3561:
3367:
3014:
2433:
2408:
2205:
1120:
361:
3642:
2584:
2320:
2216:
2211:
1464:
885:
658:
1446:
1357:
3901:
2665:
2336:
1871:
1639:
1580:
949:
934:
381:
296:
8:
3911:
3757:
3157:
2973:
2175:
1350:"Safety and regulation: the formal process for analyzing the test data on food additives"
990:
982:
704:
287:
1734:
1643:
1584:
495:
472:
45:
Please expand the article to include this information. Further details may exist on the
3586:
3320:
3290:
3285:
2284:
1660:
1627:
1603:
1568:
1549:
1424:
1374:
EFSA Panel on Food
Additives and Nutrient Sources added to Food (ANS) (December 2009).
1313:
1205:
1180:
852:
688:
444:
1567:
te
Welscher YM, van Leeuwen MR, de Kruijff B, Dijksterhuis J, Breukink E (July 2012).
3921:
3916:
3181:
2094:
1971:
1916:
1881:
1709:
1665:
1608:
1541:
1537:
1505:
1428:
1317:
1233:
1210:
1128:
922:
662:
1769:
1375:
3325:
3275:
2555:
2505:
1961:
1896:
1844:
1699:
1655:
1647:
1598:
1588:
1553:
1533:
1495:
1447:
Safety evaluation of certain food additives and contaminants: natamicin (pimaricin)
1416:
1387:
1305:
1200:
1192:
1156:
1021:
878:
801:
593:
508:
321:
194:
184:
174:
164:
154:
775:. It is applied topically as a cream, in eye drops, or (for oral infections) in a
3885:
3841:
3503:
3493:
2907:
2897:
2579:
2515:
1834:
1704:
1687:
1092:
974:
747:
119:
3796:
3775:
3581:
3571:
3463:
3406:
3337:
3280:
3250:
3235:
3003:
2892:
2634:
2451:
2356:
2290:
2221:
2140:
2098:
2087:
1986:
1981:
1866:
1800:
1573:
Proceedings of the
National Academy of Sciences of the United States of America
848:
776:
759:
670:
46:
1309:
1196:
3895:
3858:
3709:
3699:
3659:
3632:
3614:
3480:
3240:
3136:
3110:
2917:
2869:
2835:
2790:
2760:
2521:
2473:
2404:
2134:
2005:
1995:
1926:
1392:
903:
820:
712:
696:
583:
484:
440:
2657:
1686:
Liu SP, Yuan PH, Wang YY, Liu XF, Zhou ZX, Bu QT, et al. (April 2015).
1593:
1566:
3836:
3826:
3729:
3714:
3694:
3664:
3596:
3471:
3362:
3347:
3260:
3190:
3106:
2940:
2935:
2927:
2922:
2912:
2902:
2820:
2810:
2805:
2795:
2780:
2770:
2755:
2696:
2692:
2604:
2498:
2458:
2341:
2237:
2190:
2102:
1966:
1951:
1886:
1804:
1713:
1669:
1612:
1545:
1509:
1500:
1483:
1256:. Virginia-Maryland Regional College of Veterinary Medicine. Archived from
1214:
1153:
World Health
Organization model list of essential medicines: 21st list 2019
986:
728:
723:
682:
614:
OC(=O)3(O)C2(O)C(O)C4O4/C=C/C(=O)O(C)C\C=C\C=C\C=C\C=C\(O1O(C)(O)(N)1O)C3O2
189:
179:
169:
159:
149:
86:
69:
3747:
3724:
3719:
3704:
3689:
3684:
3609:
3604:
3576:
3518:
3513:
3508:
3460:
3381:
3342:
3300:
3270:
3171:
3115:
3051:
3039:
2887:
2879:
2874:
2845:
2840:
2830:
2825:
2800:
2775:
2536:
2424:
2346:
2180:
2150:
2041:
2036:
2031:
1956:
1936:
1921:
1901:
1816:
1651:
1053:
909:
867:
813:
780:
771:
753:
666:
20:
1161:
996:
Natamycin is produced on an industrial scale by fermentation of various
341:
3846:
3816:
3791:
3679:
3669:
3566:
3523:
3498:
3488:
3467:
3459:
3371:
3352:
3315:
3310:
3295:
3265:
3245:
3210:
3130:
3125:
3120:
3081:
3060:
3025:
2978:
2815:
2765:
2750:
2714:
2688:
2609:
2599:
2594:
2531:
2526:
2483:
2478:
2468:
2429:
2258:
2231:
2195:
2091:
2045:
1931:
1911:
1858:
1420:
1376:"Scientific Opinion on the use of natamycin (E 235) as a food additive"
1331:
978:
897:
708:
538:
352:
3831:
3674:
3651:
3552:
3542:
3357:
3305:
3034:
2959:
2785:
2741:
2414:
2389:
2331:
2303:
2274:
2268:
2252:
2242:
2185:
2155:
2021:
1854:
1824:
966:
805:
700:
692:
674:
307:
134:
113:
3765:
3739:
3255:
2998:
2950:
2860:
2463:
2384:
2373:
2369:
2311:
2170:
2165:
2145:
2000:
1946:
1277:
824:
765:
678:
432:
401:
332:
1012:
Natamycin was first isolated in 1955 from fermentation broth of a
896:
Natamycin inhibits the growth of fungi by specifically binding to
561:
3821:
3533:
3376:
2988:
2379:
2316:
2026:
1906:
1829:
970:
573:
1481:
31:
2360:
2326:
1813:
1522:
863:
412:
1569:"Polyene antibiotic that inhibits membrane transport proteins"
1178:
2725:
2589:
1123:. In Branen AL, Davidson PM, Salminen S, Thorngate J (eds.).
797:
552:
1453:(Report). International Programme on Chemical Safety (IPCS).
588:
Darkens at ±200 °C with vigorous decomposition at 280-300 °C
457:
77:
392:
1625:
1295:
1147:
1165:. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
745:
Natamycin is used to treat fungal infections, including
19:"E235" redirects here. For the Japanese train type, see
793:
720:
3869:
1799:
433:
1444:
1118:
1028:
was acquired. Pimaricin was later renamed after the
1619:
1095:. The American Society of Health-System Pharmacists
681:. Natamycin is also used in the food industry as a
1681:
1679:
3893:
665:around the eye. This includes infections of the
320:
1725:
1723:
1676:
1232:(38th ed.). London: Pharmaceutical press.
691:may occur. It is unclear if medical use during
295:
1685:
1273:"Kraft Singles Ditch Artificial Preservatives"
3927:World Health Organization essential medicines
3445:
2687:
2673:
2072:
1785:
1720:
1369:
1367:
1298:Journal of Packaging Technology and Research
1056:' "Unacceptable Ingredients for Food" list.
1032:(WHO) mandated that antibiotics produced by
858:found was 2.5-4.5 g/kg. In rats, the LD
3452:
3438:
2680:
2666:
2079:
2065:
1792:
1778:
1406:
1087:
1085:
1083:
1081:
1079:
1077:
1075:
1073:
1071:
1069:
808:) sprinkled on or mixed into the product.
494:
471:
443:
360:
85:
76:
1703:
1659:
1602:
1592:
1499:
1440:
1438:
1391:
1364:
1227:
1204:
1160:
1119:Davidson PM, Juneja VK, Branen J (2001).
1114:
1112:
1110:
380:
1174:
1172:
1230:Martindale: The Complete Drug Reference
1066:
707:families of medications. It results in
467:
340:
3894:
1632:Applied and Environmental Microbiology
1435:
1407:Oostendorp JG (1981). "Natamysin(R)".
1185:Applied Microbiology and Biotechnology
1141:
1107:
1047:
1016:cell culture. It was originally named
891:
485:
3433:
2661:
2060:
1773:
1332:"Regulatory and Approval Information"
1254:"Topical Antifungal Drugs: Natamycin"
1169:
1155:. Geneva: World Health Organization.
420:
118:
1445:Mattia A, Dr Cerniglia C, Baines J.
1285:from the original on 8 October 2022.
193:
183:
173:
163:
153:
25:
2444:Intestinal anti-inflammatory agents
1752:"Unacceptable Ingredients for Food"
1488:The Journal of Biological Chemistry
400:
311:
13:
726:of certain types of the bacterium
14:
3943:
2501:agents, excluding corticosteroids
3879:
1538:10.1111/j.1365-2672.2009.04165.x
919:minimum inhibitory concentration
851:. In animal studies, the lowest
525:
519:
30:
3163:thymidylate synthase inhibitors
1744:
1560:
1526:Journal of Applied Microbiology
1516:
1475:
1457:
1400:
1342:
1127:. CRC Press. pp. 599–600.
1040:was chosen in reference to the
981:groups attached. As with other
928:
640:Key:NCXMLFZGDNKEPB-FFPOYIOWSA-N
1354:understandingfoodadditives.org
1324:
1289:
1265:
1246:
1221:
965:. Structurally, its core is a
901:diverse fungal pathogens from
833:European Food Safety Authority
528:
513:
1:
2548:Antidiarrheal micro-organisms
1451:WHO Food Additives Series #48
1059:
1705:10.1016/j.micres.2015.01.013
837:Scientific Committee on Food
7:
933:Natamycin is produced as a
43:about biosynthesis pathway.
10:
3948:
2390:Camphorated opium tincture
2127:Intestinal anti-infectives
1840:Sodium monofluorophosphate
1756:Whole Foods Market IP. L.P
1731:"The origins of natamycin"
1007:
740:
503:Chemical and physical data
18:
3809:
3784:
3756:
3738:
3650:
3641:
3623:
3595:
3551:
3532:
3479:
3390:
3231:bromochlorosalicylanilide
3223:
3201:Aminoacyl tRNA synthetase
3199:
3180:
3156:
3149:
3094:
3073:
3050:
3024:
3013:
2972:
2949:
2859:
2740:
2724:
2713:
2704:
2618:
2572:
2547:
2443:
2355:
2301:
2126:
2110:
2014:
1980:
1853:
1812:
1310:10.1007/s41783-017-0012-3
1197:10.1007/s00253-015-7077-0
1149:World Health Organization
1030:World Health Organization
842:
622:
602:
592:
582:
572:
550:
537:
507:
502:
483:
451:
431:
411:
391:
371:
351:
331:
306:
286:
210:
205:
140:
126:
108:
98:
93:
84:
75:
2323:, known as Pepto-Bismol)
2118:Oral rehydration therapy
1892:Cetylpyridinium chloride
1692:Microbiological Research
1393:10.2903/j.efsa.2009.1412
1036:end in –mycin. The name
989:begins with a series of
847:Natamycin does not have
3853:Lactobacillus fermentum
2563:Saccharomyces boulardii
1594:10.1073/pnas.1203375109
1409:Antonie van Leeuwenhoek
1026:Streptomyces natalensis
1014:Streptomyces natalensis
786:
735:
3562:Diiodohydroxyquinoline
3015:Squalene monooxygenase
2852:Systemic: ketoconazole
1501:10.1074/jbc.M707821200
1121:"Antimicrobial Agents"
699:is safe. It is in the
41:is missing information
3043:Systemic: terbinafine
2585:Bismuth subsalicylate
2321:bismuth subsalicylate
2217:Succinylsulfathiazole
2212:Phthalylsulfathiazole
1052:Natamycin appears on
921:is less than 10
828:countries worldwide.
722:. It is produced by
659:antifungal medication
3331:Whitfield's ointment
3158:Pyrimidine analogues
2974:Polyene antimycotics
2573:Other antidiarrheals
2027:Acetylsalicylic acid
1872:Benzoxonium chloride
1652:10.1128/AEM.01122-07
1281:. 11 February 2014.
1228:Brayfield A (2014).
983:polyene antimycotics
935:secondary metabolite
2422:does not cross BBB:
1644:2007ApEnM..73.7400N
1585:2012PNAS..10911156T
1579:(28): 11156–11159.
1048:Society and culture
1000:strains, including
991:polyketide synthase
892:Mechanism of action
594:Solubility in water
578:1.35 g/ml g/cm
72:
3932:E-number additives
3417:Never to phase III
3321:tribromometacresol
3291:sodium thiosulfate
3286:selenium disulfide
3182:Mitotic inhibitors
2645:Never to phase III
1762:on 2 January 2018.
1421:10.1007/bf02342201
1360:on 7 January 2014.
1002:S. chattanoogensis
956:S. chattanoogensis
689:Allergic reactions
68:
3867:
3866:
3805:
3804:
3427:
3426:
3219:
3218:
3145:
3144:
3096:β-glucan synthase
3090:
3089:
3069:
3068:
2968:
2967:
2655:
2654:
2095:anti-inflammatory
2054:
2053:
1972:Tibezonium iodide
1917:Hydrogen peroxide
1882:Chlortetracycline
1845:Stannous fluoride
1737:on 16 July 2014.
1638:(22): 7400–7407.
1494:(10): 6393–6401.
1239:978-0-85711-139-5
663:fungal infections
648:
647:
563:Interactive image
453:CompTox Dashboard
64:
63:
3939:
3884:
3883:
3882:
3875:
3797:Methylrosaniline
3648:
3647:
3454:
3447:
3440:
3431:
3430:
3326:undecylenic acid
3276:potassium iodide
3154:
3153:
3022:
3021:
2738:
2737:
2722:
2721:
2711:
2710:
2682:
2675:
2668:
2659:
2658:
2556:Escherichia coli
2516:Aminosalicylates
2506:Cromoglicic acid
2081:
2074:
2067:
2058:
2057:
1962:Sodium perborate
1897:Domiphen bromide
1794:
1787:
1780:
1771:
1770:
1764:
1763:
1758:. Archived from
1748:
1742:
1741:
1733:. Archived from
1727:
1718:
1717:
1707:
1683:
1674:
1673:
1663:
1623:
1617:
1616:
1606:
1596:
1564:
1558:
1557:
1532:(6): 1908–1918.
1520:
1514:
1513:
1503:
1479:
1473:
1472:
1461:
1455:
1454:
1442:
1433:
1432:
1404:
1398:
1397:
1395:
1371:
1362:
1361:
1356:. Archived from
1346:
1340:
1339:
1328:
1322:
1321:
1293:
1287:
1286:
1269:
1263:
1261:
1260:on 7 April 2017.
1250:
1244:
1243:
1225:
1219:
1218:
1208:
1176:
1167:
1166:
1164:
1145:
1139:
1138:
1116:
1105:
1104:
1102:
1100:
1089:
1022:Pietermaritzburg
925:for most molds.
879:intestinal flora
802:anticaking agent
711:by altering the
677:. It is used as
653:, also known as
565:
545:
530:
527:
521:
515:
498:
487:
476:
475:
461:
459:
447:
435:
424:
404:
384:
364:
344:
324:
314:
313:
299:
197:
187:
177:
167:
157:
122:
89:
80:
73:
71:
67:
59:
56:
50:
34:
26:
3947:
3946:
3942:
3941:
3940:
3938:
3937:
3936:
3892:
3891:
3890:
3880:
3878:
3870:
3868:
3863:
3842:Povidone-iodine
3801:
3780:
3752:
3734:
3637:
3619:
3591:
3547:
3528:
3504:Oxytetracycline
3494:Chloramphenicol
3475:
3464:anti-infectives
3458:
3428:
3423:
3422:
3407:Clinical trials
3386:
3215:
3195:
3176:
3161:
3141:
3098:
3086:
3065:
3046:
3042:
3017:
3009:
3001:
2976:
2964:
2945:
2898:fosravuconazole
2855:
2731:
2730:lanosterol 14α-
2717:
2706:
2700:
2686:
2656:
2651:
2650:
2635:Clinical trials
2614:
2580:Albumin tannate
2568:
2543:
2452:corticosteroids
2439:
2357:Antipropulsives
2351:
2297:
2122:
2106:
2085:
2055:
2050:
2010:
1987:Glucocorticoids
1984:
1982:Corticosteroids
1976:
1849:
1835:Sodium fluoride
1808:
1798:
1768:
1767:
1750:
1749:
1745:
1729:
1728:
1721:
1684:
1677:
1624:
1620:
1565:
1561:
1521:
1517:
1480:
1476:
1463:
1462:
1458:
1443:
1436:
1405:
1401:
1372:
1365:
1348:
1347:
1343:
1330:
1329:
1325:
1294:
1290:
1271:
1270:
1266:
1252:
1251:
1247:
1240:
1226:
1222:
1177:
1170:
1146:
1142:
1135:
1117:
1108:
1098:
1096:
1091:
1090:
1067:
1062:
1050:
1010:
975:carboxylic acid
962:S. gilvosporeus
931:
894:
873:
861:
856:
845:
789:
743:
738:
644:
641:
636:
635:
630:
629:
618:
615:
610:
609:
568:
543:
533:
524:
518:
479:
455:
441:(preservatives)
427:
407:
387:
367:
347:
327:
310:
302:
282:
279:
218:
217:
201:
129:
104:Natacyn, others
60:
54:
51:
44:
35:
24:
17:
12:
11:
5:
3945:
3935:
3934:
3929:
3924:
3919:
3914:
3909:
3904:
3889:
3888:
3865:
3864:
3862:
3861:
3856:
3849:
3844:
3839:
3834:
3829:
3824:
3819:
3813:
3811:
3807:
3806:
3803:
3802:
3800:
3799:
3794:
3788:
3786:
3782:
3781:
3779:
3778:
3776:Amphotericin B
3773:
3768:
3762:
3760:
3754:
3753:
3751:
3750:
3744:
3742:
3736:
3735:
3733:
3732:
3727:
3722:
3717:
3712:
3707:
3702:
3697:
3692:
3687:
3682:
3677:
3672:
3667:
3662:
3656:
3654:
3645:
3639:
3638:
3636:
3635:
3629:
3627:
3621:
3620:
3618:
3617:
3612:
3607:
3601:
3599:
3593:
3592:
3590:
3589:
3584:
3582:Broxyquinoline
3579:
3574:
3572:Chlorquinaldol
3569:
3564:
3558:
3556:
3549:
3548:
3546:
3545:
3539:
3537:
3530:
3529:
3527:
3526:
3521:
3516:
3511:
3506:
3501:
3496:
3491:
3485:
3483:
3477:
3476:
3457:
3456:
3449:
3442:
3434:
3425:
3424:
3421:
3420:
3419:
3418:
3415:
3404:
3398:
3392:
3391:
3388:
3387:
3385:
3384:
3379:
3374:
3365:
3360:
3355:
3350:
3345:
3340:
3338:citronella oil
3334:
3333:
3328:
3323:
3318:
3313:
3308:
3303:
3298:
3293:
3288:
3283:
3281:salicylic acid
3278:
3273:
3268:
3263:
3258:
3253:
3251:crystal violet
3248:
3243:
3238:
3236:chlorophetanol
3233:
3227:
3225:
3221:
3220:
3217:
3216:
3214:
3213:
3206:
3204:
3197:
3196:
3194:
3193:
3186:
3184:
3178:
3177:
3175:
3174:
3167:
3165:
3151:
3147:
3146:
3143:
3142:
3140:
3139:
3134:
3128:
3123:
3118:
3113:
3102:
3100:
3092:
3091:
3088:
3087:
3085:
3084:
3077:
3075:
3071:
3070:
3067:
3066:
3064:
3063:
3056:
3054:
3048:
3047:
3045:
3044:
3037:
3030:
3028:
3019:
3011:
3010:
3008:
3007:
3004:amphotericin B
2996:
2991:
2984:
2982:
2970:
2969:
2966:
2965:
2963:
2962:
2955:
2953:
2947:
2946:
2944:
2943:
2938:
2931:
2930:
2925:
2920:
2915:
2910:
2905:
2900:
2895:
2893:fosfluconazole
2890:
2883:
2882:
2877:
2872:
2865:
2863:
2857:
2856:
2854:
2853:
2849:
2848:
2843:
2838:
2833:
2828:
2823:
2818:
2813:
2808:
2803:
2798:
2793:
2788:
2783:
2778:
2773:
2768:
2763:
2758:
2753:
2746:
2744:
2735:
2719:
2708:
2702:
2701:
2685:
2684:
2677:
2670:
2662:
2653:
2652:
2649:
2648:
2647:
2646:
2643:
2632:
2626:
2620:
2619:
2616:
2615:
2613:
2612:
2607:
2602:
2597:
2592:
2587:
2582:
2576:
2574:
2570:
2569:
2567:
2566:
2559:
2551:
2549:
2545:
2544:
2542:
2541:
2540:
2539:
2534:
2529:
2524:
2511:
2510:
2509:
2508:
2494:
2493:
2492:
2491:
2486:
2481:
2476:
2471:
2466:
2464:Hydrocortisone
2461:
2454:acting locally
2447:
2445:
2441:
2440:
2438:
2437:
2427:
2418:
2417:
2412:
2394:
2393:
2387:
2382:
2377:
2370:Opium tincture
2366:
2364:
2353:
2352:
2350:
2349:
2344:
2339:
2334:
2329:
2324:
2314:
2308:
2306:
2299:
2298:
2296:
2295:
2294:
2293:
2291:Broxyquinoline
2280:
2279:
2278:
2277:
2264:
2263:
2262:
2261:
2248:
2247:
2246:
2245:
2240:
2227:
2226:
2225:
2224:
2222:Sulfaguanidine
2219:
2214:
2201:
2200:
2199:
2198:
2193:
2188:
2183:
2178:
2173:
2168:
2163:
2158:
2153:
2148:
2143:
2141:Amphotericin B
2130:
2128:
2124:
2123:
2121:
2120:
2114:
2112:
2108:
2107:
2099:anti-infective
2088:Antidiarrheals
2084:
2083:
2076:
2069:
2061:
2052:
2051:
2049:
2048:
2039:
2034:
2029:
2024:
2018:
2016:
2012:
2011:
2009:
2008:
2003:
2001:Hydrocortisone
1998:
1992:
1990:
1978:
1977:
1975:
1974:
1969:
1964:
1959:
1954:
1949:
1944:
1939:
1934:
1929:
1924:
1919:
1914:
1909:
1904:
1899:
1894:
1889:
1884:
1879:
1874:
1869:
1867:Amphotericin B
1863:
1861:
1851:
1850:
1848:
1847:
1842:
1837:
1832:
1827:
1821:
1819:
1810:
1809:
1803:preparations (
1801:Stomatological
1797:
1796:
1789:
1782:
1774:
1766:
1765:
1743:
1719:
1675:
1618:
1559:
1515:
1474:
1456:
1434:
1415:(2): 170–171.
1399:
1363:
1341:
1323:
1288:
1264:
1245:
1238:
1220:
1168:
1140:
1133:
1125:Food Additives
1106:
1064:
1063:
1061:
1058:
1049:
1046:
1044:species name.
1009:
1006:
973:segment, with
930:
927:
893:
890:
871:
859:
854:
849:acute toxicity
844:
841:
788:
785:
760:Cephalosporium
742:
739:
737:
734:
661:used to treat
646:
645:
643:
642:
639:
637:
633:
625:
624:
623:
620:
619:
617:
616:
613:
605:
604:
603:
600:
599:
596:
590:
589:
586:
580:
579:
576:
570:
569:
567:
566:
558:
556:
548:
547:
541:
535:
534:
531:
522:
516:
511:
505:
504:
500:
499:
489:
481:
480:
478:
477:
464:
462:
449:
448:
437:
429:
428:
426:
425:
417:
415:
409:
408:
406:
405:
397:
395:
389:
388:
386:
385:
377:
375:
369:
368:
366:
365:
357:
355:
349:
348:
346:
345:
337:
335:
329:
328:
326:
325:
317:
315:
304:
303:
301:
300:
292:
290:
284:
283:
281:
280:
221:
213:
212:
211:
208:
207:
203:
202:
200:
199:
146:
144:
138:
137:
132:
130:administration
124:
123:
116:
106:
105:
102:
96:
95:
91:
90:
82:
81:
62:
61:
38:
36:
29:
15:
9:
6:
4:
3:
2:
3944:
3933:
3930:
3928:
3925:
3923:
3920:
3918:
3915:
3913:
3910:
3908:
3907:Preservatives
3905:
3903:
3900:
3899:
3897:
3887:
3877:
3876:
3873:
3860:
3859:Copper usnate
3857:
3855:
3854:
3850:
3848:
3845:
3843:
3840:
3838:
3835:
3833:
3830:
3828:
3825:
3823:
3820:
3818:
3815:
3814:
3812:
3808:
3798:
3795:
3793:
3790:
3789:
3787:
3783:
3777:
3774:
3772:
3769:
3767:
3764:
3763:
3761:
3759:
3755:
3749:
3746:
3745:
3743:
3741:
3737:
3731:
3728:
3726:
3723:
3721:
3718:
3716:
3713:
3711:
3710:Propenidazole
3708:
3706:
3703:
3701:
3700:Fenticonazole
3698:
3696:
3693:
3691:
3688:
3686:
3683:
3681:
3678:
3676:
3673:
3671:
3668:
3666:
3663:
3661:
3660:Metronidazole
3658:
3657:
3655:
3653:
3649:
3646:
3644:
3640:
3634:
3633:Sulfatolamide
3631:
3630:
3628:
3626:
3622:
3616:
3615:Ascorbic acid
3613:
3611:
3608:
3606:
3603:
3602:
3600:
3598:
3597:Organic acids
3594:
3588:
3585:
3583:
3580:
3578:
3575:
3573:
3570:
3568:
3565:
3563:
3560:
3559:
3557:
3554:
3550:
3544:
3541:
3540:
3538:
3535:
3531:
3525:
3522:
3520:
3517:
3515:
3512:
3510:
3507:
3505:
3502:
3500:
3497:
3495:
3492:
3490:
3487:
3486:
3484:
3482:
3478:
3473:
3469:
3465:
3462:
3461:Gynecological
3455:
3450:
3448:
3443:
3441:
3436:
3435:
3432:
3416:
3414:
3411:
3410:
3408:
3405:
3402:
3399:
3397:
3394:
3393:
3389:
3383:
3380:
3378:
3375:
3373:
3369:
3366:
3364:
3361:
3359:
3356:
3354:
3351:
3349:
3346:
3344:
3341:
3339:
3336:
3335:
3332:
3329:
3327:
3324:
3322:
3319:
3317:
3314:
3312:
3309:
3307:
3304:
3302:
3299:
3297:
3294:
3292:
3289:
3287:
3284:
3282:
3279:
3277:
3274:
3272:
3269:
3267:
3264:
3262:
3259:
3257:
3254:
3252:
3249:
3247:
3244:
3242:
3241:chlorphenesin
3239:
3237:
3234:
3232:
3229:
3228:
3226:
3222:
3212:
3208:
3207:
3205:
3202:
3198:
3192:
3188:
3187:
3185:
3183:
3179:
3173:
3169:
3168:
3166:
3164:
3159:
3155:
3152:
3150:Intracellular
3148:
3138:
3137:ibrexafungerp
3135:
3132:
3129:
3127:
3124:
3122:
3119:
3117:
3114:
3112:
3111:anidulafungin
3108:
3107:echinocandins
3104:
3103:
3101:
3097:
3093:
3083:
3079:
3078:
3076:
3072:
3062:
3058:
3057:
3055:
3053:
3049:
3041:
3038:
3036:
3032:
3031:
3029:
3027:
3023:
3020:
3016:
3012:
3005:
3000:
2997:
2995:
2992:
2990:
2986:
2985:
2983:
2980:
2975:
2971:
2961:
2957:
2956:
2954:
2952:
2948:
2942:
2939:
2937:
2933:
2932:
2929:
2926:
2924:
2921:
2919:
2918:oteseconazole
2916:
2914:
2911:
2909:
2908:isavuconazole
2906:
2904:
2901:
2899:
2896:
2894:
2891:
2889:
2885:
2884:
2881:
2878:
2876:
2873:
2871:
2870:efinaconazole
2867:
2866:
2864:
2862:
2858:
2851:
2850:
2847:
2844:
2842:
2839:
2837:
2836:sertaconazole
2834:
2832:
2829:
2827:
2824:
2822:
2819:
2817:
2814:
2812:
2809:
2807:
2804:
2802:
2799:
2797:
2794:
2792:
2791:fenticonazole
2789:
2787:
2784:
2782:
2779:
2777:
2774:
2772:
2769:
2767:
2764:
2762:
2761:chlormidazole
2759:
2757:
2754:
2752:
2748:
2747:
2745:
2743:
2739:
2736:
2733:
2727:
2723:
2720:
2716:
2712:
2709:
2703:
2698:
2694:
2690:
2683:
2678:
2676:
2671:
2669:
2664:
2663:
2660:
2644:
2642:
2639:
2638:
2636:
2633:
2630:
2627:
2625:
2622:
2621:
2617:
2611:
2608:
2606:
2603:
2601:
2598:
2596:
2593:
2591:
2588:
2586:
2583:
2581:
2578:
2577:
2575:
2571:
2565:
2564:
2560:
2558:
2557:
2553:
2552:
2550:
2546:
2538:
2535:
2533:
2530:
2528:
2525:
2523:
2522:Sulfasalazine
2520:
2519:
2518:
2517:
2513:
2512:
2507:
2504:
2503:
2502:
2500:
2496:
2495:
2490:
2489:Beclometasone
2487:
2485:
2482:
2480:
2477:
2475:
2474:Betamethasone
2472:
2470:
2467:
2465:
2462:
2460:
2457:
2456:
2455:
2453:
2449:
2448:
2446:
2442:
2435:
2431:
2428:
2426:
2423:
2420:
2419:
2416:
2413:
2410:
2406:
2405:Diphenoxylate
2403:
2401:
2396:
2395:
2391:
2388:
2386:
2383:
2381:
2378:
2375:
2371:
2368:
2367:
2365:
2362:
2358:
2354:
2348:
2345:
2343:
2340:
2338:
2335:
2333:
2330:
2328:
2325:
2322:
2318:
2315:
2313:
2310:
2309:
2307:
2305:
2300:
2292:
2289:
2288:
2287:
2286:
2282:
2281:
2276:
2273:
2272:
2271:
2270:
2266:
2265:
2260:
2257:
2256:
2255:
2254:
2250:
2249:
2244:
2241:
2239:
2236:
2235:
2234:
2233:
2229:
2228:
2223:
2220:
2218:
2215:
2213:
2210:
2209:
2208:
2207:
2203:
2202:
2197:
2194:
2192:
2189:
2187:
2184:
2182:
2179:
2177:
2174:
2172:
2169:
2167:
2164:
2162:
2159:
2157:
2154:
2152:
2149:
2147:
2144:
2142:
2139:
2138:
2137:
2136:
2132:
2131:
2129:
2125:
2119:
2116:
2115:
2113:
2109:
2104:
2100:
2096:
2093:
2089:
2082:
2077:
2075:
2070:
2068:
2063:
2062:
2059:
2047:
2043:
2040:
2038:
2035:
2033:
2030:
2028:
2025:
2023:
2020:
2019:
2017:
2013:
2007:
2006:Triamcinolone
2004:
2002:
1999:
1997:
1996:Dexamethasone
1994:
1993:
1991:
1988:
1983:
1979:
1973:
1970:
1968:
1965:
1963:
1960:
1958:
1955:
1953:
1950:
1948:
1945:
1943:
1940:
1938:
1935:
1933:
1930:
1928:
1927:Metronidazole
1925:
1923:
1920:
1918:
1915:
1913:
1910:
1908:
1905:
1903:
1900:
1898:
1895:
1893:
1890:
1888:
1885:
1883:
1880:
1878:
1877:Chlorhexidine
1875:
1873:
1870:
1868:
1865:
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1862:
1860:
1856:
1852:
1846:
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1418:
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1377:
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1336:Natamycin.com
1333:
1327:
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1303:
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1207:
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1134:9780824741709
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1027:
1023:
1019:
1015:
1005:
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988:
984:
980:
976:
972:
969:containing a
968:
964:
963:
958:
957:
952:
951:
946:
945:
944:S. natalensis
940:
936:
926:
924:
920:
915:
912:
911:
906:
905:
904:Saccharomyces
899:
889:
887:
882:
880:
875:
869:
865:
857:
850:
840:
838:
834:
829:
826:
822:
821:food additive
817:
815:
809:
807:
803:
799:
795:
784:
782:
778:
774:
773:
768:
767:
762:
761:
756:
755:
750:
749:
733:
731:
730:
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721:
716:
714:
713:cell membrane
710:
706:
702:
698:
697:breastfeeding
694:
690:
686:
684:
680:
676:
672:
668:
664:
660:
656:
652:
638:
632:
631:
628:
621:
612:
611:
608:
601:
597:
595:
591:
587:
585:
584:Melting point
581:
577:
575:
571:
564:
560:
559:
557:
554:
549:
542:
540:
536:
512:
510:
506:
501:
497:
493:
490:
488:
486:ECHA InfoCard
482:
474:
470:
469:DTXSID6021163
466:
465:
463:
454:
450:
446:
442:
438:
436:
430:
423:
422:ChEMBL1200656
419:
418:
416:
414:
410:
403:
399:
398:
396:
394:
390:
383:
379:
378:
376:
374:
370:
363:
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350:
343:
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338:
336:
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330:
323:
319:
318:
316:
309:
305:
298:
294:
293:
291:
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285:
277:
273:
269:
265:
261:
257:
253:
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245:
241:
237:
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225:
220:
219:
216:
209:
204:
196:
191:
186:
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176:
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166:
161:
156:
151:
148:
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145:
143:
139:
136:
133:
131:
125:
121:
117:
115:
111:
107:
103:
101:
97:
94:Clinical data
92:
88:
83:
79:
74:
66:
58:
48:
42:
39:This article
37:
33:
28:
27:
22:
3851:
3837:Furazolidone
3827:Policresulen
3770:
3730:Flutrimazole
3715:Butoconazole
3695:Ketoconazole
3665:Clotrimazole
3625:Sulfonamides
3587:Oxyquinoline
3363:tea tree oil
3348:lemon myrtle
3261:ethylparaben
3191:griseofulvin
3052:Benzylamines
2993:
2941:ravuconazole
2936:albaconazole
2928:voriconazole
2923:posaconazole
2913:itraconazole
2903:hexaconazole
2821:neticonazole
2811:luliconazole
2806:ketoconazole
2796:flutrimazole
2781:eberconazole
2771:clotrimazole
2756:butoconazole
2605:Racecadotril
2561:
2554:
2514:
2499:antiallergic
2497:
2459:Prednisolone
2450:
2434:+simethicone
2421:
2397:
2337:Crospovidone
2285:Oxyquinoline
2283:
2267:
2251:
2238:Nifuroxazide
2230:
2206:Sulfonamides
2204:
2191:Streptomycin
2160:
2133:
1967:Tetracycline
1952:Oxyquinoline
1941:
1887:Clotrimazole
1760:the original
1755:
1746:
1738:
1735:the original
1695:
1691:
1635:
1631:
1621:
1576:
1572:
1562:
1529:
1525:
1518:
1491:
1487:
1477:
1468:
1459:
1450:
1412:
1408:
1402:
1386:(12): 1412.
1383:
1380:EFSA Journal
1379:
1358:the original
1353:
1344:
1335:
1326:
1304:(2): 87–99.
1301:
1297:
1291:
1276:
1267:
1258:the original
1248:
1229:
1223:
1191:(1): 61–78.
1188:
1184:
1162:10665/325771
1152:
1143:
1124:
1097:. Retrieved
1051:
1041:
1037:
1034:Streptomyces
1033:
1025:
1017:
1013:
1011:
1001:
998:Streptomyces
997:
995:
987:biosynthesis
960:
954:
948:
942:
939:Streptomyces
938:
932:
929:Biochemistry
916:
908:
902:
895:
883:
876:
846:
830:
818:
810:
790:
770:
764:
758:
752:
746:
744:
729:Streptomyces
727:
724:fermentation
717:
709:fungal death
687:
683:preservative
654:
650:
649:
275:
271:
267:
263:
259:
255:
251:
247:
243:
239:
235:
231:
227:
223:
65:
55:January 2022
52:
40:
3902:Antifungals
3748:Terconazole
3725:Oxiconazole
3720:Omoconazole
3705:Azanidazole
3690:Tioconazole
3685:Isoconazole
3643:Antifungals
3610:Acetic acid
3605:Lactic acid
3577:Dequalinium
3555:derivatives
3519:Clindamycin
3514:Mepartricin
3509:Carfecillin
3481:Antibiotics
3468:antiseptics
3403:from market
3382:pentamidine
3343:lemon grass
3301:taurolidine
3271:polynoxylin
3172:flucytosine
3116:caspofungin
3040:terbinafine
3026:Allylamines
2888:fluconazole
2880:terconazole
2875:fluconazole
2846:tioconazole
2841:sulconazole
2831:oxiconazole
2826:omoconazole
2801:isoconazole
2776:croconazole
2734:inhibitors)
2732:demethylase
2689:Antifungals
2631:from market
2537:Balsalazide
2425:Eluxadoline
2392:(paregoric)
2347:Diosmectite
2342:Attapulgite
2319:(including
2302:Intestinal
2181:Polymyxin B
2176:Paromomycin
2151:Fidaxomicin
2135:Antibiotics
2111:Rehydration
2042:Epinephrine
2037:Benzydamine
2032:Becaplermin
1957:Polynoxylin
1937:Minocycline
1922:Mepartricin
1902:Doxycycline
1859:antiseptics
1817:prophylaxis
1465:"Natamycin"
1093:"Natamycin"
1054:Whole Foods
910:Aspergillus
868:metabolites
814:sorbic acid
781:oral thrush
772:Penicillium
754:Aspergillus
671:conjunctiva
546: g·mol
492:100.028.803
206:Identifiers
100:Trade names
21:E235 series
3912:Macrolides
3896:Categories
3847:Protiofate
3817:Clodantoin
3792:Ciclopirox
3680:Ornidazole
3670:Miconazole
3652:Imidazoles
3567:Clioquinol
3524:Pentamycin
3499:Hachimycin
3489:Candicidin
3372:atovaquone
3353:orange oil
3316:tolnaftate
3311:tolciclate
3296:sulbentine
3266:haloprogin
3246:ciclopirox
3211:tavaborole
3203:inhibitors
3189:Systemic:
3170:Systemic:
3131:rezafungin
3126:micafungin
3121:cilofungin
3105:Systemic:
3099:inhibitors
3082:amorolfine
3061:butenafine
3018:inhibitors
3002:Systemic:
2979:ergosterol
2886:Systemic:
2816:miconazole
2766:climbazole
2751:bifonazole
2742:Imidazoles
2718:inhibitors
2715:Ergosterol
2610:Kaopectate
2600:Octreotide
2595:Crofelemer
2532:Olsalazine
2527:Mesalazine
2484:Budesonide
2479:Tixocortol
2469:Prednisone
2430:Loperamide
2304:adsorbents
2259:Miconazole
2232:Nitrofuran
2196:Vancomycin
2092:intestinal
2046:Adrenalone
1932:Miconazole
1912:Hexetidine
1099:8 December
1060:References
1042:natalensis
979:mycosamine
950:S. lydicus
898:ergosterol
598:0.39 mg/ml
551:3D model (
539:Molar mass
382:8O0C852CPO
353:ChemSpider
288:CAS Number
215:IUPAC name
16:Antifungal
3832:Nifuratel
3771:Natamycin
3740:Triazoles
3675:Econazole
3553:Quinoline
3543:Acetarsol
3536:compounds
3413:Phase III
3401:Withdrawn
3358:patchouli
3306:ticlatone
3209:Topical:
3080:Topical:
3059:Topical:
3035:naftifine
3033:Topical:
3006:, hamycin
2994:natamycin
2987:Topical:
2960:abafungin
2958:Topical:
2951:Thiazoles
2934:Unknown:
2868:Topical:
2861:Triazoles
2786:econazole
2749:Topical:
2641:Phase III
2629:Withdrawn
2590:Ceratonia
2415:Difenoxin
2409:+atropine
2275:Acetarsol
2269:Arsenical
2253:Imidazole
2243:Nifurzide
2186:Rifaximin
2161:Natamycin
2156:Kanamycin
2022:Amlexanox
1942:Natamycin
1855:Infection
1825:Dectaflur
1698:: 25–33.
1429:264007289
1318:257086547
1038:natamycin
1020:to honor
1018:pimaricin
967:macrolide
941:species:
907:yeast to
886:resistant
823:, it has
806:cellulose
701:macrolide
693:pregnancy
655:pimaricin
651:Natamycin
297:7681-93-8
135:Eye drops
128:Routes of
120:Monograph
114:Drugs.com
70:Natamycin
47:talk page
3922:Epoxides
3917:Polyenes
3886:Medicine
3766:Nystatin
3758:Polyenes
3256:dimazole
2999:nystatin
2981:binding)
2707:membrane
2398:crosses
2385:Morphine
2374:laudanum
2312:Charcoal
2171:Nystatin
2166:Neomycin
2146:Colistin
2101:agents (
1947:Neomycin
1714:25801968
1670:17905880
1613:22733749
1546:19228256
1510:18165687
1283:Archived
1278:NBC News
1215:26512010
1151:(2019).
1024:, where
937:by some
825:E number
804:such as
766:Fusarium
679:eyedrops
657:, is an
434:E number
362:10468784
333:DrugBank
142:ATC code
3822:Inosine
3534:Arsenic
3377:dapsone
2989:hamycin
2380:Codeine
2361:opioids
2317:Bismuth
1907:Eugenol
1830:Olaflur
1661:2168226
1640:Bibcode
1604:3396478
1581:Bibcode
1554:2873514
1206:4700089
1008:History
971:polyene
888:fungi.
777:lozenge
748:Candida
741:Medical
705:polyene
667:eyelids
574:Density
544:665.733
509:Formula
342:DB00826
308:PubChem
192: (
190:S01AA10
182: (
180:G01AA02
172: (
170:D01AA02
162: (
160:A07AA03
158:)
152: (
150:A01AB10
3872:Portal
3396:WHO-EM
3224:Others
3074:Others
2726:Azoles
2624:WHO-EM
2332:Kaolin
2327:Pectin
1814:Caries
1712:
1668:
1658:
1611:
1601:
1552:
1544:
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1469:RxList
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1316:
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914:cell.
866:. The
864:tumors
843:Safety
769:, and
675:cornea
673:, and
607:SMILES
413:ChEMBL
402:C08073
322:441382
3810:Other
3785:Other
2705:Wall/
2015:Other
1550:S2CID
1425:S2CID
1314:S2CID
1004:L10.
819:As a
798:brine
627:InChI
553:JSmol
439:E235
3466:and
2695:and
2097:and
1857:and
1710:PMID
1666:PMID
1609:PMID
1542:PMID
1506:PMID
1234:ISBN
1211:PMID
1129:ISBN
1101:2017
977:and
959:and
831:The
787:Food
736:Uses
703:and
393:KEGG
373:UNII
110:AHFS
3472:G01
3368:PCP
2697:J02
2693:D01
2400:BBB
2103:A07
1805:A01
1700:doi
1696:173
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1648:doi
1599:PMC
1589:doi
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1534:doi
1530:106
1496:doi
1492:283
1417:doi
1388:doi
1306:doi
1201:PMC
1193:doi
1189:100
1157:hdl
923:ppm
695:or
458:EPA
312:CID
274:,26
270:,25
266:,24
262:,22
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254:,18
250:,16
246:,14
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178:),
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Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
