Oleandomycin is a naturally occurring macrolide antibiotic produced by Streptomyces antibioticus. It belongs to the 14-membered macrolide class of antibacterial compounds and acts primarily by inhibiting bacterial protein synthesis through interaction with the bacterial ribosome.
Oleandomycin has the molecular formula C₃₅H₆₁NO₁₂, molecular weight 687.9 g/mol, and CAS Number 3922-90-5. PubChem identifies the compound as a macrolide antibiotic and provides the corresponding chemical structure and molecular information.
Oleandomycin should be distinguished from oleandomycin phosphate (CAS 7060-74-4) and troleandomycin (triacetyloleandomycin), which are chemically different derivatives/salts.
PubChem reports a molecular weight of 687.9 g/mol and identifies oleandomycin as a macrolide antibiotic.
Oleandomycin was historically developed as a human antibacterial drug. It has antibacterial activity against susceptible Gram-positive and selected Gram-negative organisms and has historically been used in combination products.
Its antibacterial action is associated with inhibition of bacterial protein synthesis through binding to the 50S ribosomal subunit.
Oleandomycin is also relevant to:
Oleandomycin is a basic macrolide molecule containing a dimethylamino group. PubChem reports a basic pKa of approximately 8.84. Reference data describe it as soluble in dilute acids and freely soluble in methanol, ethanol, butanol and acetone, with limited solubility in some nonpolar solvents.
Published reference data also report a melting point around 134–135°C and a specific optical rotation of approximately −54° under the stated measurement conditions. These are physicochemical reference values and should not automatically be entered as release specifications unless they are part of your approved specification.
Oleandomycin can be characterized using:
Historical US regulatory specifications for oleandomycin phosphate included microbiological potency, moisture, pH, residue on ignition, heavy metals, crystallinity and identity. These historical values should not be transferred directly to the free-base Oleandomycin product because the phosphate salt is a different chemical substance.
Oleandomycin should be stored in a tightly closed container under controlled conditions that protect the material from moisture, excessive heat and contamination. For research-grade material, individual manufacturer stability and storage instructions should be followed.
| Parameter | Specification |
|---|---|
| Appearance | White crystalline powder or crystals |
| Identification | IR & HPLC compliant |
| Assay (HPLC) | 98.0% – 102.0% |
| Loss on Drying | NMT 1.0% |
| Residue on Ignition | NMT 0.5% |
| Heavy Metals | NMT 10 ppm |
| Melting Point | Approx. 134–135°C (reference value) |