Спирамицин III

Description

Spiramycin III (Spiramycin III, foromacidin C) is one of the three components of the antibiotic spiramycin, a 16-membered macrolide. The producer is the actinomycete Streptomyces ambofaciens. Commercial spiramycin is a mixture of spiramycins I, II and III in a ratio of approximately 2: 1: 1. All three differ in the hydroxyl substituent in position 3 of the macrolactone ring: in form I it is free hydroxyl, in form II it is acetate, in form III it is propanoate. The antibacterial activity of form I is higher than that of forms II and III.

Basic Attributes

• CAS No.: 24916-52-7
• Chemical formula: C46H78N2O15
• Molecular weight: 899.11600; exact weight: 899.12
• DSSTox ID: DTXSID9023596
• HS code: 2941907000
• Synonyms: spiramycin C, spiramycin 3, foromacidin C, leukomycin V, 9-O-[(2R,5S,6R)-5-(dimethylamino)tetrahydro-6-methyl-2H-pyran-2-yl]-, 3-propanoate; leukomycin V derivative - oxacyclohexadecane
• Additional registration numbers from the card: 1403-59-4, 1405-27-2, 11001-07-3, 13441-33-3, 13445-44-8, 13429-99-7, 23410-82-4, 33299-71-7, 708989-56-4, 203005-19-0

Structure

The molecule is built from the platenolide macrolactone core and three sugar residues: forosamine, mycaminose and mycarose. Forosamine is an amino sugar attached at position 9, which is reflected in the systematic name through the fragment 5-(dimethylamino)tetrahydro-6-methyl-2H-pyran-2-yl.

Physico-chemical characteristics

• Density: 1.2 g/cm³
• Melting point: 128–131 °C
• Boiling point: 923.6 °C at 760 mm Hg. Art.
• Flash point: 512.4 °C
• Refractive index: 1.542
• Steam pressure: 0 mmHg Art. at 25 °C
• PSA: 201.45000
• XLogP3: 3.28600

The boiling and flash point values ​​for a thermolabile macrolide are of a calculated nature: at such temperatures the compound decomposes. Zero vapor pressure at 25 °C reflects the practical non-volatility of the substance. A polar area of ​​over 200 Ų is characteristic of glycosylated macrolides.

Pharmacological group and mechanism

Spiramycin is a macrolide antibiotic. The mechanism is binding to the 50S subunit of the bacterial ribosome and inhibition of protein synthesis. The spectrum covers gram-positive bacteria; A separate feature of spiramycin is its activity against the protozoan Toxoplasma gondii, which is the basis for its use in toxoplasmosis, including in pregnant women. Known under the names Rovamycine, formacidin, kitasamycin.

Scope of application

• standard sample for monitoring the composition and activity of commercial spiramycin using HPLC methods
• reference for determining residual amounts of antibiotics in livestock products
• object of research on macrolide biosynthesis and structure-activity relationships

Storage and handling

Macrolides are hydrolyzed in an acidic environment through glycosidic bonds. Keep the container tightly closed in a dry and dark place. As an antibacterial substance, the product requires measures to prevent spraying and entry into wastewater: subinhibitory concentrations of antibiotics in the environment contribute to the selection of resistant strains. Work with gloves, glasses and, when hanging powder, in a respirator.