Misplaced Pages

:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Micafungin: Difference between pages - Misplaced Pages

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
(Difference between pages)
Page 1
Page 2
Content deleted Content addedVisualWikitext
Revision as of 12:34, 24 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 456840779 of page Micafungin for the Chem/Drugbox validation project (updated: 'ChEMBL', 'KEGG').  Latest revision as of 14:22, 24 March 2024 edit JWBE (talk | contribs)Extended confirmed users10,126 edits added Category:Pentyl compounds using HotCat 
Line 1: Line 1:
{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Use dmy dates|date=August 2023}}
{{Drugbox
{{cs1 config |name-list-style=vanc |display-authors=6}}
{{Infobox drug
| Verifiedfields = changed | Verifiedfields = changed
| verifiedrevid = 462252182
| Watchedfields = changed
| verifiedrevid = 400310735
| IUPAC_name = {5--11,20,21,25-tetrahydroxy-15--26-methyl-2,5,8,14,17,23-hexaoxo-18--1,2-oxazol-3-yl}benzene)amido]-1,4,7,13,16,22-hexaazatricycloheptacosan-6-yl]-1,2-dihydroxyethyl]-2-hydroxyphenyl}oxidanesulfonic acid
| image = Micafungin.svg | image = Micafungin.svg
| width = 250 | width = 250
| alt =
| image2 = Micafungin ball-and-stick.png
| alt2 =


<!--Clinical data--> <!-- Clinical data -->
| pronounce =
| tradename = Mycamine | tradename = Mycamine
| Drugs.com = {{drugs.com|monograph|mycamine}} | Drugs.com = {{drugs.com|monograph|mycamine}}
| MedlinePlus =
| licence_EU = Mycamine
| licence_US = Micafungin | DailyMedID = Micafungin
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_AU_comment =
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = C | pregnancy_category =
| routes_of_administration = ]
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> | class =
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> | ATCvet =
| ATC_prefix = J02
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| ATC_suffix = AX05
| ATC_supplemental =

<!-- Legal status -->
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled -->
| legal_AU_comment =
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
| legal_BR_comment =
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA_comment =
| legal_DE = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment =
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment =
| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->
| legal_UK_comment =
| legal_US = Rx-only
| legal_US_comment =
| legal_EU =
| legal_EU_comment =
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment =
| legal_status = Rx-only | legal_status = Rx-only
| routes_of_administration = Intravenous


<!--Pharmacokinetic data--> <!-- Pharmacokinetic data -->
| bioavailability = | bioavailability =
| protein_bound = 99.8% | protein_bound = 99.8%
| metabolism = Via catechol-O-methyltransferase pathway | metabolism = Via catechol-O-methyltransferase pathway
| metabolites =
| onset =
| elimination_half-life = 11–17 hours | elimination_half-life = 11–17 hours
| duration_of_action =
| excretion = 40% feces, <15% urine | excretion = 40% feces, <15% urine


<!--Identifiers--> <!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 235114-32-6 | CAS_number = 235114-32-6
| CAS_supplemental =
| ATC_prefix = J02
| ATC_suffix = AX05
| PubChem = 477468 | PubChem = 477468
| IUPHAR_ligand =
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01141 | DrugBank = DB01141
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 21106351 | ChemSpiderID = 21106351
| UNII_Ref = {{fdacite|changed|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = R10H71BSWG | UNII = R10H71BSWG
| KEGG_Ref = {{keggcite|changed|kegg}} | KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = <!-- blanked - oldvalue: D02465 --> | KEGG = D02465
| ChEBI =
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 1201351 --> | ChEMBL = 1201351
| C=56 | H=71 | N=9 | O=23 | S=1 | NIAID_ChemDB =
| PDB_ligand =
| molecular_weight = 1270.28 g/mol
| synonyms =
| InChI = 1/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

| InChIKey = PIEUQSKUWLMALL-NFGJWQNFBT
<!-- Chemical and physical data -->
| IUPAC_name = {5--11,20,21,25-tetrahydroxy-15--26-methyl-2,5,8,14,17,23-hexaoxo-18--1,2-oxazol-3-yl}benzene)amido]-1,4,7,13,16,22-hexaazatricycloheptacosan-6-yl]-1,2-dihydroxyethyl]-2-hydroxyphenyl}oxidanesulfonic acid
| C=56 | H=71 | N=9 | O=23 | S=1
| SMILES = CCCCCOc1ccc(-c2cc(-c3ccc(C(=O)N4C(O)(O)N=C(O)5(O)(C)CN5C(=O)((O)CC(=N)O)N=C(O)((O)(O)c5ccc(O)c(OS(=O)(=O)O)c5)N=C(O)5C(O)CN5C(=O)((C)O)N=C4O)cc3)no2)cc1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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 | 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
| StdInChI_comment =
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = PIEUQSKUWLMALL-NFGJWQNFSA-N | StdInChIKey = PIEUQSKUWLMALL-NFGJWQNFSA-N
| density =
| density_notes =
| melting_point =
| melting_high =
| melting_notes =
| boiling_point =
| boiling_notes =
| solubility =
| sol_units =
| specific_rotation =
}} }}

'''Micafungin''', sold under the brand name '''Mycamine''', is an ] ] used to treat and prevent invasive fungal infections including ], abscesses, and ]. It inhibits the production of ], an essential component of fungal ] that is not found in mammals.

Administered ], Micafungin received final approval from the U.S. ] (FDA) in March 2005, and gained approval in the European Union in April 2008. It is on the '']''.<ref name="WHO22nd">{{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 }}</ref>

In August 2023, Mycamine was acquired from ] by ].<ref>{{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}}</ref>

== Indications ==
Micafungin is ] for the treatment of ], acute disseminated ], ] ], ] and ].

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.
<ref>{{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 }}</ref>
<ref>{{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 }}</ref>

== Dosage ==
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.<ref>{{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 }}</ref><ref>{{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 }}</ref>

== Dosage forms ==
Micafungin is a natural antifungal product derived from other ] as a defense mechanism for competition of nutrients, etc. To be specific, micafungin is derived from FR901379, and is produced by '']''.<ref>{{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 }}</ref><ref>{{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 }}</ref>

== References ==
{{reflist}}

== Further reading ==
{{refbegin}}
* {{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 }}
{{refend}}

{{Antifungals}}
{{Portal bar | Medicine}}

]
]
]
]
]