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Merck

P0440

Pimaricin preparation

~2.5% (γ-irradiated Pimaricin), aqueous suspension

Sinónimos:

Pimaricin, Tennecetin, Natamycin preparation

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Fórmula empírica (notación de Hill):
C33H47NO13
Número CAS:
7681-93-8
Peso molecular:
665.73
UNSPSC Code:
51102829
NACRES:
NA.85
PubChem Substance ID:
24898105
MDL number:
MFCD00135085
Beilstein/REAXYS Number:
1614878

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Nombre del producto

Pimaricin preparation, ~2.5% (γ-irradiated Pimaricin), aqueous suspension

InChI

1S/C33H47NO13/c1-18-10-8-6-4-3-5-7-9-11-21(45-32-30(39)28(34)29(38)19(2)44-32)15-25-27(31(40)41)22(36)17-33(42,47-25)16-20(35)14-24-23(46-24)12-13-26(37)43-18/h3-9,11-13,18-25,27-30,32,35-36,38-39,42H,10,14-17,34H2,1-2H3,(H,40,41)/b4-3+,7-5+,8-6+,11-9+,13-12+/t18-,19-,20+,21+,22+,23-,24-,25+,27-,28+,29-,30+,32+,33-/m1/s1

SMILES string

[H][C@]12C[C@@H](O[C@@H]3O[C@H](C)[C@@H](O)[C@H](N)[C@@H]3O)\C=C\C=C\C=C\C=C\C[C@@H](C)OC(=O)\C=C\[C@@]4([H])O[C@]4([H])C[C@H](O)C[C@](O)(C[C@H](O)[C@H]1C(O)=O)O2

InChI key

NCXMLFZGDNKEPB-FFPOYIOWSA-N

form

aqueous suspension

concentration

~2.5% (γ-irradiated Pimaricin)

solubility

DMSO: soluble

density

1.0 g/mL at 20 °C (lit.)

antibiotic activity spectrum

fungi
yeast

mode of action

cell membrane | interferes

storage temp.

2-8°C

Quality Level

200

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Application

Pimaricin is an amphoteric antibiotic from Streptomyces natalensis or S. chattanoogensis. It is used for a variety of fungal infections, mainly topically. It is used as an ergosterol and cholesterol binding agent to study lipid bilayer dynamics, especially in fungal cells. It is used to study pimaricin biosynthesis and as a fungicide in agar media.

Biochem/physiol Actions

An antifungal polyene macrolide that binds specifically to ergosterol and blocks fungal growth. However, unlike nystatin and filipin, pimaricin does not change the permeability of the plasma membrane.

General description

This product is a saline suspension with approximately 2.5% pimaricin γ-irradiated.

Pimaricin is a polyene antifungal antibiotic produced by Streptomyces natalensis from soil near Pietermaritzburg, South Africa.1 Pimaricin has antimicrobial activity similar to that of nystatin. In addition, it is active against Trichomonas vaginalis. Pimaricin is used in the treatment of candidiasis, trichomoniasis, fungal keratitis and aspergillosis. It has also been used as a food additive in some countries. In some studies, it has been shown to decrease the amount of mold upon which the Dermatophagoides pteronyssinus (house-dust mite) is dependent.2

Other Notes

20ml
Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage.Light Sensitive

Preparation Note

The product can be further diluted with 0.5 M sodium chloride giving a suspension as well. The product can also be further diluted into an organic solvent such as dimethylformamide (may also be soluble in DMSO).

The product and any aqueous dilutions will be suspensions and should not be sterile filtered.
The product is not degraded by a single freeze-thaw cycle. The diluted product should be aliquoted and stored frozen.

Clase de almacenamiento

10 - Combustible liquids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
0000447888
0000447890
0000447890
0000447888
0000410482

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Eliseo Recio et al.
The Journal of biological chemistry, 279(40), 41586-41593 (2004-07-03)
A chemically novel autoinducer (PI factor) has been purified from cultures of the pimaricin producer Streptomyces natalensis ATCC27448. The chemical structure of the PI molecule was identified as 2,3-diamino-2,3-bis (hydroxymethyl)-1,4-butanediol. Pimaricin biosynthesis in S. natalensis npi287, a mutant impaired in
J C Pedersen
Applied and environmental microbiology, 58(3), 1064-1066 (1992-03-01)
Fungal inhibition in four commonly used agar media was improved by substituting natamycin (pimaricin) for cycloheximide. The recovery of bacteria was not affected by natamycin, whereas fungal contamination from a variety of samples was significantly suppressed. Furthermore, natamycin lacks the
F N Arroyo-López et al.
International journal of food microbiology, 155(3), 257-262 (2012-03-01)
The present work uses a logistic/probabilistic model to obtain the growth/no growth interfaces of Saccharomyces cerevisiae, Wickerhamomyces anomalus and Candida boidinii (three yeast species commonly isolated from table olives) as a function of the diverse combinations of natamycin (0-30 mg/L)
Prajna Lalitha et al.
Cornea, 31(6), 662-667 (2012-02-16)
To analyze the minimum inhibitory concentration (MIC) of isolates from fungal keratitis to natamycin and voriconazole and to assess the relationship between organism, MIC, and clinical outcome. Data were collected as part of a randomized, controlled, double-masked clinical trial. Main
Chau-Minh Phan et al.
Eye & contact lens, 39(2), 162-168 (2013-02-09)
To investigate the uptake and release of the antifungal ocular drug, natamycin from commercially available conventional hydrogel (CH) and silicone hydrogel (SH) contact lens (CL) materials and to evaluate the effectiveness of this delivery method. Five commercial SH CLs (balafilcon
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