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SML2268

Sigma-Aldrich

Micafungin sodium

≥97% (HPLC), powder, β(1,3)-D-Glucan synthase inhibitor

Synonym(s):

1-[(4R,5R)-4,5-Dihydroxy-N2-[4-[5-[4-(pentyloxy)phenyl]-3-isoxazolyl]benzoyl]-L-ornithine]-4-[(4S)-4-hydroxy-4-[4-hydroxy-3-(sulfooxy)phenyl]-L-threonine]pneumocandin A0 sodium salt

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About This Item

Empirical Formula (Hill Notation):
C56H70N9O23S · Na
CAS Number:
208538-73-2
Molecular Weight:
1292.26
MDL number:
MFCD08067752
UNSPSC Code:
12352200
NACRES:
NA.77

product name

Micafungin sodium, ≥97% (HPLC)

assay

≥97% (HPLC)

form

powder

storage condition

protect from light

color

white to beige

solubility

H2O: 2 mg/mL, clear (warmed)

shipped in

wet ice

storage temp.

−20°C

SMILES string

O=C(N[C@H]1C[C@@H](O)[C@@H](O)NC([C@@H]2[C@@H](O)[C@@H](C)CN2C([C@H]([C@H](O)CC(N)=O)NC([C@@H](NC([C@]3([H])C[C@@H](O)CN3C([C@H]([C@H](O)C)NC1=O)=O)=O)[C@H](O)[C@H](C4=CC(OS(=O)([O-])=O)=C(O)C=C4)O)=O)=O)=O)C5=CC=C(C6=NOC(C7=CC=C(OCCCCC)C=C7)=C6)C=C5.[Na+

InChI

1S/C56H71N9O23S.Na/c1-4-5-6-16-86-32-9-7-8-29(17-32)39-21-33(63-87-39)27-10-12-28(13-11-27)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)30-14-15-36(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;/h7-15,17-18,21,25-26,31,34-35,37-38,42-48,52,66-70,72-74,78H,4-6,16,19-20,22-24H2,1-3H3,(H2,57,71)(H,58,75)(H,59,76)(H,60,79)(H,61,77)(H,62,80)(H,83,84,85);/q;+1/p-1/t25?,26-,31-,34+,35+,37-,38-,42?,43+,44?,45+,46+,47+,48+,52?;/m1./s1

InChI key

DDVWCESGUGLBJI-OZMKZJPFSA-M

Application

Micafungin sodium has been used as an anti-fungal agent to test its effectiveness against multidrug-resistant C. auris by in vitro minimum inhibitory concentration (MIC) assay.

Biochem/physiol Actions

Micafungin is a semisynthetic echinocandin antifungal. Micafungin works by inhibiting the enzyme β(1,3)-D-Glucan synthase and thereby disturbing the integrity of the fungal cell wall. This enzyme does not exist in mammalian systems.
Micafungin is used for first-line treatment of invasive and esophageal candidiasis in addition to prophylaxis of Candida infections in both adults and children.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Roeland E Wasmann et al.
Clinical pharmacokinetics, 57(3), 267-286 (2017-08-10)
Micafungin is a selective inhibitor of the synthesis of fungal 1,3-β-D-glucan, an essential component of the fungal cell wall. It is available as a powder for infusion only and is registered for the treatment of invasive and esophageal candidiasis in
David S Perlin
Future microbiology, 6(4), 441-457 (2011-04-30)
It has been nearly a decade since caspofungin was approved for clinical use as the first echinocandin class antifungal agent, followed by micafungin and anidulafungin. The echinocandin drugs target the fungal cell wall by inhibiting the synthesis of β-1,3-D-glucan, a
Giardia hinders growth by disrupting nutrient metabolism independent of inflammatory enteropathy.
Giallourou, et al.
Nature Communications, 14, 2840-2840 (2023)
David Andes et al.
Antimicrobial agents and chemotherapy, 55(5), 2113-2121 (2011-02-09)
Echinocandins have become a first-line therapy for invasive candidiasis (IC). Using phase 3 trial data for patients with IC, pharmacokinetic-pharmacodynamic (PK-PD) relationships for efficacy for micafungin were examined. Micafungin exposures were estimated using a population pharmacokinetic model, and univariable and
Akash Patil et al.
The Journal of pharmacy and pharmacology, 69(12), 1635-1660 (2017-07-27)
Echinocandins are the newest addition of the last decade to the antifungal armamentarium, which, owing to their unique mechanism of action, selectively target the fungal cells without affecting mammalian cells. Since the time of their introduction, they have come to
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