Array ( [0] => {{Short description|Chemical compound}} [1] => {{Use dmy dates|date=August 2023}} [2] => {{cs1 config |name-list-style=vanc |display-authors=6}} [3] => {{Infobox drug [4] => | Verifiedfields = changed [5] => | verifiedrevid = 462252182 [6] => | image = Micafungin.svg [7] => | width = 250 [8] => | alt = [9] => | image2 = Micafungin ball-and-stick.png [10] => | alt2 = [11] => [12] => [13] => | pronounce = [14] => | tradename = Mycamine [15] => | Drugs.com = {{drugs.com|monograph|mycamine}} [16] => | MedlinePlus = [17] => | DailyMedID = Micafungin [18] => | pregnancy_AU = [19] => | pregnancy_AU_comment = [20] => | pregnancy_category = [21] => | routes_of_administration = [[Intravenous]] [22] => | class = [23] => | ATCvet = [24] => | ATC_prefix = J02 [25] => | ATC_suffix = AX05 [26] => | ATC_supplemental = [27] => [28] => [29] => | legal_AU = [30] => | legal_AU_comment = [31] => | legal_BR = [32] => | legal_BR_comment = [33] => | legal_CA = [34] => | legal_CA_comment = [35] => | legal_DE = [36] => | legal_DE_comment = [37] => | legal_NZ = [38] => | legal_NZ_comment = [39] => | legal_UK = [40] => | legal_UK_comment = [41] => | legal_US = Rx-only [42] => | legal_US_comment = [43] => | legal_EU = [44] => | legal_EU_comment = [45] => | legal_UN = [46] => | legal_UN_comment = [47] => | legal_status = Rx-only [48] => [49] => [50] => | bioavailability = [51] => | protein_bound = 99.8% [52] => | metabolism = Via catechol-O-methyltransferase pathway [53] => | metabolites = [54] => | onset = [55] => | elimination_half-life = 11–17 hours [56] => | duration_of_action = [57] => | excretion = 40% feces, <15% urine [58] => [59] => [60] => | CAS_number_Ref = {{cascite|correct|??}} [61] => | CAS_number = 235114-32-6 [62] => | CAS_supplemental = [63] => | PubChem = 477468 [64] => | IUPHAR_ligand = [65] => | DrugBank_Ref = {{drugbankcite|correct|drugbank}} [66] => | DrugBank = DB01141 [67] => | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} [68] => | ChemSpiderID = 21106351 [69] => | UNII_Ref = {{fdacite|correct|FDA}} [70] => | UNII = R10H71BSWG [71] => | KEGG_Ref = {{keggcite|changed|kegg}} [72] => | KEGG = D02465 [73] => | ChEBI = [74] => | ChEMBL_Ref = {{ebicite|changed|EBI}} [75] => | ChEMBL = 1201351 [76] => | NIAID_ChemDB = [77] => | PDB_ligand = [78] => | synonyms = [79] => [80] => [81] => | IUPAC_name = {5-[(1''S'',2''S'')-2-[(3''S'',6''S'',9''S'',11''R'',15''S'',18''S'',20''R'',21''R'',24''S'',25''S'',26''S'')-3-[(1''R'')-2-carbamoyl-1-hydroxyethyl]-11,20,21,25-tetrahydroxy-15-[(1''R'')-1-hydroxyethyl]-26-methyl-2,5,8,14,17,23-hexaoxo-18-[(4-{5-[4-(pentyloxy)phenyl]-1,2-oxazol-3-yl}benzene)amido]-1,4,7,13,16,22-hexaazatricyclo[22.3.0.09,13]heptacosan-6-yl]-1,2-dihydroxyethyl]-2-hydroxyphenyl}oxidanesulfonic acid [82] => | C=56 | H=71 | N=9 | O=23 | S=1 [83] => | SMILES = CCCCCOc1ccc(-c2cc(-c3ccc(C(=O)N[C@H]4C[C@@H](O)[C@@H](O)N=C(O)[C@@H]5[C@@H](O)[C@@H](C)CN5C(=O)[C@H]([C@H](O)CC(=N)O)N=C(O)[C@H]([C@H](O)[C@@H](O)c5ccc(O)c(OS(=O)(=O)O)c5)N=C(O)[C@@H]5C[C@@H](O)CN5C(=O)[C@H]([C@H](C)O)N=C4O)cc3)no2)cc1 [84] => | StdInChI_Ref = {{stdinchicite|correct|chemspider}} [85] => | StdInChI = 1S/C56H71N9O23S/c1-4-5-6-17-86-32-14-11-28(12-15-32)39-21-33(63-87-39)27-7-9-29(10-8-27)49(75)58-34-20-38(70)52(78)62-54(80)45-46(72)25(2)23-65(45)56(82)43(37(69)22-41(57)71)60-53(79)44(48(74)47(73)30-13-16-36(68)40(18-30)88-89(83,84)85)61-51(77)35-19-31(67)24-64(35)55(81)42(26(3)66)59-50(34)76/h7-16,18,21,25-26,31,34-35,37-38,42-48,52,66-70,72-74,78H,4-6,17,19-20,22-24H2,1-3H3,(H2,57,71)(H,58,75)(H,59,76)(H,60,79)(H,61,77)(H,62,80)(H,83,84,85)/t25-,26-,31+,34-,35-,37+,38+,42-,43-,44-,45-,46-,47-,48-,52+/m0/s1 [86] => | StdInChI_comment = [87] => | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} [88] => | StdInChIKey = PIEUQSKUWLMALL-NFGJWQNFSA-N [89] => | density = [90] => | density_notes = [91] => | melting_point = [92] => | melting_high = [93] => | melting_notes = [94] => | boiling_point = [95] => | boiling_notes = [96] => | solubility = [97] => | sol_units = [98] => | specific_rotation = [99] => }} [100] => [101] => '''Micafungin''', sold under the brand name '''Mycamine''', is an [[echinocandin]] [[antifungal medication]] used to treat and prevent invasive fungal infections including [[candidemia]], abscesses, and [[esophageal candidiasis]]. It inhibits the production of [[Beta-glucan|beta-1,3-glucan]], an essential component of fungal [[cell walls]] that is not found in mammals. [102] => [103] => Administered [[intravenously]], Micafungin received final approval from the U.S. [[Food and Drug Administration]] (FDA) in March 2005, and gained approval in the European Union in April 2008. It is on the ''[[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]]''.{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 22nd list (2021) | year = 2021 | hdl = 10665/345533 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2021.02 | hdl-access=free }} [104] => [105] => In August 2023, Mycamine was acquired from [[Astellas Pharma]] by [[Sandoz]].{{Cite web | vauthors = Dharma RK |date=28 August 2023 |title=Sandoz concludes acquisition of Mycamine antifungal agent |url=https://www.pharmaceutical-technology.com/news/sandoz-acquisition-mycamine-antifungal-astellas/ |access-date=29 August 2023 |website=Pharmaceutical Technology |language=en-US}} [106] => [107] => == Indications == [108] => Micafungin is [[indicated]] for the treatment of [[candidemia]], acute disseminated [[candidiasis]], [[Candida (genus)|''Candida'']] [[peritonitis]], [[abscesses]] and [[esophageal candidiasis]]. [109] => [110] => Micafungin works by way of concentration-dependent inhibition of 1,3-beta-D-glucan synthase resulting in reduced formation of 1,3-beta-D-glucan, which is an essential polysaccharide comprising one-third of the majority of ''Candida'' spp. cell walls. This decreased glucan production leads to osmotic instability and thus cellular lysis. [111] => {{cite journal | vauthors = Pappas PG, Rotstein CM, Betts RF, Nucci M, Talwar D, De Waele JJ, Vazquez JA, Dupont BF, Horn DL, Ostrosky-Zeichner L, Reboli AC, Suh B, Digumarti R, Wu C, Kovanda LL, Arnold LJ, Buell DN | title = Micafungin versus caspofungin for treatment of candidemia and other forms of invasive candidiasis | journal = Clinical Infectious Diseases | volume = 45 | issue = 7 | pages = 883–93 | date = October 2007 | pmid = 17806055 | doi = 10.1086/520980 | doi-access = free }} [112] => {{cite journal | vauthors = Pettengell K, Mynhardt J, Kluyts T, Lau W, Facklam D, Buell D | title = Successful treatment of oesophageal candidiasis by micafungin: a novel systemic antifungal agent | journal = Alimentary Pharmacology & Therapeutics | volume = 20 | issue = 4 | pages = 475–81 | date = August 2004 | pmid = 15298643 | doi = 10.1111/j.1365-2036.2004.02083.x | collaboration = FK463 South African Study Group | s2cid = 31500007 | doi-access = free }} [113] => [114] => == Dosage == [115] => The metabolism of micafungin occurs hepatically via acryp sulfatase followed by secondary metabolism by a transferase. Precautions should be taken with regards to dosing, as micafungin weakly inhibits CYP3A4.{{cite journal | vauthors = Carver PL | title = Micafungin | journal = The Annals of Pharmacotherapy | volume = 38 | issue = 10 | pages = 1707–21 | date = October 2004 | pmid = 15340133 | doi = 10.1345/aph.1D301 | s2cid = 265942428 }}{{cite journal | vauthors = Kohno S, Masaoka T, Yamaguchi H, Mori T, Urabe A, Ito A, Niki Y, Ikemoto H | title = A multicenter, open-label clinical study of micafungin (FK463) in the treatment of deep-seated mycosis in Japan | journal = Scandinavian Journal of Infectious Diseases | volume = 36 | issue = 5 | pages = 372–9 | year = 2004 | pmid = 15287383 | doi = 10.1080/00365540410020406 | s2cid = 10873612 }} [116] => [117] => == Dosage forms == [118] => Micafungin is a natural antifungal product derived from other [[fungus|fungi]] as a defense mechanism for competition of nutrients, etc. To be specific, micafungin is derived from FR901379, and is produced by ''[[Coleophoma empetri]]''.{{cite journal | vauthors = Hashimoto S | title = Micafungin: a sulfated echinocandin | journal = The Journal of Antibiotics | volume = 62 | issue = 1 | pages = 27–35 | date = January 2009 | pmid = 19132058 | doi = 10.1038/ja.2008.3 | doi-access = free }}{{cite journal |doi=10.1351/pac200779040603 |year = 2007 |title = Discovery of micafungin (FK463): A novel antifungal drug derived from a natural product lead |journal = Pure and Applied Chemistry |volume = 79 |issue = 4 |pages = 603–614 | vauthors = Fujie A |doi-access = free }} [119] => [120] => == References == [121] => {{reflist}} [122] => [123] => == Further reading == [124] => {{refbegin}} [125] => * {{cite journal | vauthors = Eschenauer G, Depestel DD, Carver PL | title = Comparison of echinocandin antifungals | journal = Therapeutics and Clinical Risk Management | volume = 3 | issue = 1 | pages = 71–97 | date = March 2007 | pmid = 18360617 | pmc = 1936290 | doi = 10.2147/tcrm.2007.3.1.71 | doi-access = free }} [126] => {{refend}} [127] => [128] => {{Antifungals}} [129] => {{Portal bar | Medicine}} [130] => [131] => [[Category:Antifungals]] [132] => [[Category:Echinocandins]] [133] => [[Category:Astellas Pharma]] [134] => [[Category:World Health Organization essential medicines]] [135] => [[Category:Pentyl compounds]] [] => )
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Micafungin

{{Infobox drug | Verifiedfields = changed | verifiedrevid = 462252182 | image = Micafungin. svg | width = 250 | alt = | image2 = Micafungin ball-and-stick.

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