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{{chembox {{chembox
| verifiedrevid = 400736296
| ImageFile = Perimycin A.png | ImageFile = Perimycin A.png
| ImageSize = 250px | ImageSize = 250px
| IUPACName = (1R,3S,5S,7R,9R,13R,17R,18S,19E,21E,23Z,25Z,27E,29E,31E,33R,35S,36R,37S)-33-oxy-1,3,5,7,9,13,37-heptahydroxy-17--7-oxoheptan-2-yl]-18,36-dimethyl-16,39-dioxabicyclononatriaconta-19,21,23,25,27,29,31-heptaene-11,15-dione
| IUPACName =
| OtherNames = 4ʼ-Amino-3ʼ-deamino-18-decarboxy-40-demethyl-4ʼ-deoxy-3,7-dideoxo-3,3ʼ,7-trihydroxy-N47,18,dimethyl-5-oxocandicidin-<small>D</small>-cyclic-15,19-hemiacetal<ref name="druglead">{{cite web|url=http://www.druglead.com/cds/Perimycin.html|title=Perimycin|year=2009|publisher=DrugLead US FDA&EMEA|accessdate=25 January 2010}}</ref> | OtherNames = 4ʼ-Amino-3ʼ-deamino-18-decarboxy-40-demethyl-4ʼ-deoxy-3,7-dideoxo-3,3ʼ,7-trihydroxy-N47,18,dimethyl-5-oxocandicidin-<small>D</small>-cyclic-15,19-hemiacetal
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 62327-61-1 | CASNo = 62327-61-1
⚫ | PubChem =
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | SMILES = O=C1C(O)CC(OC((C)CCC(O)CC(C4=CC=C(NC)C=C4)=O)()(C)/C=C/C=C/C=C/C=C/C=C/C=C/C=C/(O3()(O)(O)(N)(C)O3)C((C)(O)C2)()O2(O)C(O)C(O)C(O)C(O)C1)=O
| UNII = J1A6A7WH82
⚫ | PubChem = 10534218
| ChemSpiderID = 16736162
| StdInChI=1S/C59H88N2O17/c1-36-18-16-14-12-10-8-6-7-9-11-13-15-17-19-49(76-58-56(73)55(72)54(60)39(4)75-58)33-52-38(3)51(70)35-59(74,78-52)34-48(68)30-46(66)28-44(64)26-43(63)27-45(65)29-47(67)32-53(71)77-57(36)37(2)20-25-42(62)31-50(69)40-21-23-41(61-5)24-22-40/h6-19,21-24,36-39,42-44,46-49,51-52,54-58,61-64,66-68,70,72-74H,20,25-35,60H2,1-5H3/b7-6-,10-8-,11-9+,14-12+,15-13+,18-16+,19-17+/t36-,37-,38+,39+,42?,43+,44-,46-,47+,48-,49-,51-,52-,54+,55-,56-,57-,58-,59+/m0/s1
| StdInChIKey = SIJFZOSSGXKJCI-FTNWOYNKSA-N
⚫ | SMILES = O=C1C(O)CC(OC((C)CCC(O)CC(C4=CC=C(NC)C=C4)=O)()(C)/C=C/C=C/C=C/C=C/C=C/C=C/C=C/(O3()(O)(O)(N)(C)O3)C((C)(O)C2)()O2(O)C(O)C(O)C(O)C(O)C1)=O
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>59</sub>H<sub>88</sub>N<sub>2</sub>O<sub>17</sub> | Formula = C<sub>59</sub>H<sub>88</sub>N<sub>2</sub>O<sub>17</sub>
| MolarMass = 1097.33 g/mol | MolarMass = 1097.33 g/mol
| Appearance = Amorphous, golden-yellow solid | Appearance = Amorphous, golden-yellow solid
| Density = | Density =
| MeltingPt = Indefinite | MeltingPt = Indefinite
| BoilingPt = | BoilingPt =
| Solubility = | Solubility =
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
}} }}
}} }}
'''Perimycin''' (also known as '''aminomycin''' and '''fungimycin''') is ] ] produced by ''] coelicolor'' var. aminophilus.<ref name="Hamilton">{{cite journal |author=Hamilton-Miller JM |title=Chemistry and biology of the polyene macrolide antibiotics |journal=Bacteriological Reviews |volume=37 |issue=2 |pages=166–96 |year=1973 |month=June |pmid=4578757 |pmc=413810}}</ref><ref name="aromatic">{{cite journal |author=Liu CM, McDaniel LE, Schaffner CP |title=Fungimycin, biogenesis of its aromatic moiety |journal=The Journal of Antibiotics |volume=25 |issue=3 |pages=187–8 |year=1972 |month=March |pmid=5034814 |url=http://www.journalarchive.jst.go.jp/jnlpdf.php?cdjournal=antibiotics1968&cdvol=25&noissue=3&startpage=187&lang=en&from=jnlabstract}}</ref><ref name="Lee">{{cite journal |author=Lee CH, Schaffner CP |title=Perimycin. The structure of some degradation products |journal=Tetrahedron |volume=25 |issue=10 |pages=2229–32 |year=1969 |month=May |pmid=5788396 |doi=10.1016/S0040-4020(01)82770-8}}</ref><ref name="Pawlak">{{cite journal |author=Pawlak J, Sowiński P, Borowski E, Gariboldi P |title=Stereostructure of perimycin A |journal=The Journal of Antibiotics |volume=48 |issue=9 |pages=1034–8 |year=1995 |month=September |pmid=7592049 |url=http://www.journalarchive.jst.go.jp/english/jnlabstract_en.php?cdjournal=antibiotics1968&cdvol=48&noissue=9&startpage=1034}}</ref> The compound exhibits ] properties.<ref name="druglead" /> '''Perimycin''', also known as '''aminomycin''' and '''fungimycin''', is ] produced by '']'' var. aminophilus.<ref name="Hamilton">{{cite journal |author=Hamilton-Miller JM |title=Chemistry and biology of the polyene macrolide antibiotics |journal=Bacteriological Reviews |volume=37 |issue=2 |pages=166–96 |date=June 1973 |doi=10.1128/br.37.2.166-196.1973 |pmid=4578757 |pmc=413810}}</ref><ref name="aromatic">{{cite journal |vauthors=Liu CM, McDaniel LE, Schaffner CP |title=Fungimycin, biogenesis of its aromatic moiety |journal=The Journal of Antibiotics |volume=25 |issue=3 |pages=187–8 |date=March 1972 |pmid=5034814 |doi=10.7164/antibiotics.25.187 |doi-access=free }}</ref><ref name="Lee">{{cite journal |vauthors=Lee CH, Schaffner CP |title=Perimycin. The structure of some degradation products |journal=Tetrahedron |volume=25 |issue=10 |pages=2229–32 |date=May 1969 |pmid=5788396 |doi=10.1016/S0040-4020(01)82770-8}}</ref><ref name="Pawlak">{{cite journal |vauthors=Pawlak J, Sowiński P, Borowski E, Gariboldi P |title=Stereostructure of perimycin A |journal=The Journal of Antibiotics |volume=48 |issue=9 |pages=1034–8 |date=September 1995 |pmid=7592049 |doi=10.7164/antibiotics.48.1034 |doi-access=free }}</ref> The compound exhibits ] properties.{{citation needed|date=September 2015}}
__TOC__
== Composition ==
⚫ Perimycin is produced naturally as a mixture of three types: A, B and C, with type A being the major component. All types consist of a ] core with a ] sugar moiety. The variations occur at the end of the core opposite the perosamine moiety. Perimycin A has an aromatic group in this position, whereas the identities of the analogous groups in the other perimycin types are currently undetermined.{{cn|date=December 2022}}


==Composition== == Usage ==
⚫ Polyene antibiotics in general are often toxic to humans and have poor ]. Thus, with the notable exception of ], they are often not used clinically. Perimycin has been shown to be an effective antifungal compound, but is not widely used in clinical settings.<ref name="Elmer">{{cite journal|doi=10.1016/j.ajo.2009.01.020|pmid=19327742|last=Elmer|first=Y. Tu |author2=Charlotte E. Joslina |author3=Lisa M. Nijmc |author4=Robert S. Federd |author5=Sandeep Jaina |author6=Megan E. Shoffe|title=Polymicrobial Keratitis: Acanthamoeba and Infectious Crystalline Keratopathy|date=July 2009|journal=American Journal of Ophthalmology|volume=148|issue=1|pages=13–19.e2|pmc=2830559}}</ref>
⚫ Perimycin is produced naturally as a mixture of three types: A, B and C, with type A a being the major component. All types consist of a ] core with a ] sugar moiety. The variations occur at the end of the core opposite the perosamine moiety. Perimycin A has an aromatic group in this position, whereas the identities of the analogous groups in the other perimycin types are currently undetermined.<ref name="druglead" />


==Usage== == References ==
⚫ Polyene antibiotics in general are often toxic to humans and have poor ]. Thus, with the notable exception of ], they are often not used clinically. Perimycin has been shown to be an effective antifungal compound, but is not widely used in clinical settings.<ref name="Elmer">{{cite journal|doi=10.1016/j.ajo.2009.01.020|last=Elmer|first=Y. Tu|coauthors=Charlotte E. Joslina, Lisa M. Nijmc, Robert S. Federd, Sandeep Jaina and Megan E. Shoffe|title=Polymicrobial Keratitis: Acanthamoeba and Infectious Crystalline Keratopathy|date=July 2009|journal=American Journal of Ophthalmology|volume=148|issue=1|pages=13–19.e2|url=http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6VK5-4VXT0YX-D&_user=86629&_coverDate=07/31/2009&_rdoc=1&_fmt=high&_orig=search&_sort=d&_docanchor=&view=c&_acct=C000006878&_version=1&_urlVersion=0&_userid=86629&md5=2dd4dde9b9af3b84b4551fcdba9e534d|accessdate=28 January 2010}}</ref>

==References==
{{reflist}} {{reflist}}


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