P0440

Pimaricin preparation

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

• Synonym(s): Pimaricin, Tennecetin, Natamycin preparation
• Empirical Formula (Hill Notation): C₃₃H₄₇NO₁₃
• CAS Number: 7681-93-8
• Molecular Weight: 665.73
• Beilstein: 1614878
• MDL number: MFCD00135085
• UNSPSC Code: 51102829
• PubChem Substance ID: 24898105
• NACRES: NA.85

Properties

• 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
• 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: 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
• InChI key: NCXMLFZGDNKEPB-FFPOYIOWSA-N

Description

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

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.

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.

Storage and Stability

The product is not degraded by a single freeze-thaw cycle. The diluted product should be aliquoted and stored frozen.

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

Safety Information

• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 2
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves