Cilofungin

Cilofungin
Names

IUPAC name N-[(11R,20R,21R,25S,26S)-6-[(1S,2S)-1,2-Dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-3,15-bis(1-hydroxyethyl)-26-methyl-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexaazatricyclo[22.3.0.0^9,13]heptacosan-18-yl]-4-(octyloxy)benzamide
Other names 1-[(4R,5R)-4,5-Dihydroxy-N²-[p-(octyloxy)benzoyl]-L-ornithine]echinocandin B^[1] (4R,5R)-4,5-Dihydroxy-N²-[p-(octyloxy)benzoyl]-L-ornithyl-L-threonyl-trans-4-hydroxy-L-prolyl-(S)-4-hydroxy-4-(p-hydroxyphenyl)-L-threonyl-L-threonyl-(3S,4S)-3-hydroxy-4-methyl-L-proline cyclic (6→1)-peptide^[1]
Identifiers
CAS Number	79404-91-4 ^checkY
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL2103748 ^☒N
ChemSpider	5293334 ^☒N
MeSH	Cilofungin
PubChem CID	6918120
UNII	8ZJC54A39X ^checkY
CompTox Dashboard (EPA)	DTXSID901027438 Edit this at Wikidata
InChI InChI=1S/C49H71N7O17/c1-5-6-7-8-9-10-19-73-31-17-13-28(14-18-31)42(65)50-32-21-34(61)45(68)54-47(70)38-39(62)24(2)22-56(38)49(72)36(26(4)58)52-46(69)37(41(64)40(63)27-11-15-29(59)16-12-27)53-44(67)33-20-30(60)23-55(33)48(71)35(25(3)57)51-43(32)66/h11-18,24-26,30,32-41,45,57-64,68H,5-10,19-23H2,1-4H3,(H,50,65)(H,51,66)(H,52,69)(H,53,67)(H,54,70)/t24-,25+,26+,30+,32-,33-,34+,35-,36-,37-,38-,39-,40-,41-,45+/m0/s1^☒N Key: ZKZKCEAHVFVZDJ-MTUMARHDSA-N^☒N InChI=1/C49H71N7O17/c1-5-6-7-8-9-10-19-73-31-17-13-28(14-18-31)42(65)50-32-21-34(61)45(68)54-47(70)38-39(62)24(2)22-56(38)49(72)36(26(4)58)52-46(69)37(41(64)40(63)27-11-15-29(59)16-12-27)53-44(67)33-20-30(60)23-55(33)48(71)35(25(3)57)51-43(32)66/h11-18,24-26,30,32-41,45,57-64,68H,5-10,19-23H2,1-4H3,(H,50,65)(H,51,66)(H,52,69)(H,53,67)(H,54,70)/t24-,25+,26+,30+,32-,33-,34+,35-,36-,37-,38-,39-,40-,41-,45+/m0/s1 Key: ZKZKCEAHVFVZDJ-MTUMARHDBF
SMILES O=C2N5[C@H](C(=O)N[C@H](O)[C@H](O)C[C@H](NC(=O)c1ccc(OCCCCCCCC)cc1)C(=O)N[C@H](C(=O)N4[C@H](C(=O)N[C@H](C(=O)N[C@H]2[C@H](O)C)[C@H](O)[C@@H](O)c3ccc(O)cc3)C[C@@H](O)C4)[C@H](O)C)[C@@H](O)[C@@H](C)C5
Properties
Chemical formula	C₄₉H₇₁N₇O₁₇
Molar mass	1030.12474
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ☒N verify (what is ^checkY☒N ?) Infobox references

Chemical compound

Cilofungin (INN)^[1] is the first clinically applied member of the echinocandin family of antifungal drugs. It was derived from a fungus in the genus Aspergillus . It accomplishes this by interfering with an invading fungus' ability to synthesize the cell wall (specifically, it inhibits the synthesis of (1→3)-β-D-glucan).^[2]

References

[edit ]

^ ^a ^b ^c "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names (Rec. INN): List 29" (PDF). World Health Organization.
^ Hudler, George (1998). Magical Mushrooms, Mischievous Molds . Princeton, New Jersey: Princeton University Press. pp. 112. ISBN 978-0-691-07016-2.

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Antifungals (D01 and J02)

Wall/
membrane

Ergosterol
inhibitors

Azoles (lanosterol 14α-
demethylase inhibitors)

Imidazoles	Topical: bifonazole ^‡ butoconazole chlormidazole ^‡ climbazole clotrimazole ^# croconazole ^‡ eberconazole econazole fenticonazole ^‡ flutrimazole isoconazole ketoconazole luliconazole miconazole ^# neticonazole ^‡ omoconazole ^‡ oxiconazole sertaconazole sulconazole tioconazole Systemic: ketoconazole
Triazoles	Topical: efinaconazole fluconazole ^# terconazole Systemic: fluconazole ^# fosfluconazole fosravuconazole hexaconazole ^‡ isavuconazole itraconazole ^# oteseconazole posaconazole voriconazole ^# Unknown: albaconazole ^‡ ravuconazole ^†
Thiazoles	Topical: abafungin ^‡

Polyene antimycotics
(ergosterol binding)

Topical: hamycin ^‡
natamycin
nystatin ^#
Systemic: amphotericin B ^#, hamycin^‡

Squalene monooxygenase
inhibitors

Allylamines	Topical: naftifine terbinafine Systemic: terbinafine
Benzylamines	Topical: butenafine

Others

Topical: amorolfine

β-glucan synthase
inhibitors

Intracellular

Pyrimidine analogues/ thymidylate synthase inhibitors	Systemic: flucytosine ^#
Mitotic inhibitors	Systemic: griseofulvin ^#
Aminoacyl tRNA synthetase inhibitors	Topical: tavaborole

Others

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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