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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 Code

11 - Combustible Solids

WGK

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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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
G Kofla et al.
European journal of medical research, 16(4), 159-166 (2011-04-14)
Echinocandins represent the newest class of antifungal agents. Currently, three echinocandins, anidulafungin, caspofungin and micafungin are licensed for clinical use in various indications. They act as inhibitors of β-(1,3)-glucan synthesis in the fungal cell wall and have a favorable pharmacological
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
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
Jonothan Rosario-Colon et al.
International journal of molecular sciences, 22(11) (2021-07-03)
Candida auris is a multidrug-resistant fungal pathogen that can cause disseminated bloodstream infections with up to 60% mortality in susceptible populations. Of the three major classes of antifungal drugs, most C. auris isolates show high resistance to azoles and polyenes

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