Oleandomycin Phosphate

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Basic information

CAS: 7060-74-4
Standard SMILES: CO[C@H]1C[C@H](O[C@H]2[C@H](C)[C@@H](O[C@@H]3O[C@H](C)C[C@H](N(C)C)[C@H]3O)[C@@H](C)C[C@@]3(CO3)C(=O)[C@H](C)[C@@H](O)[C@@H](C)[C@@H](C)OC(=O)[C@@H]2C)O[C@@H](C)[C@@H]1O.O=P(O)(O)O
InChIKey: RLPCJGKQKFMBEI-UOBLTHIJSA-N
Molecular formula: C35H64NO16P
Average molar mass: 785.9 g/mol
Monoisotopic mass: 785.39627195

Overview

Oleandomycin Phosphate is the phosphate salt form of oleandomycin, a macrolide antibiotic similar to erythromycin with antimicrobial activity. Oleandomycin targets and reversibly binds to the 50S subunit of bacterial ribosomes. This prevents translocation of peptidyl tRNA leading to an inhibition of protein synthesis.

Names & identifiers

Preferred name: Oleandomycin Phosphate
IUPAC: (3R,5S,6S,7R,8S,9R,12R,13R,14S,15R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-hydroxy-8-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-5,7,9,12,13,15-hexamethyl-1,11-dioxaspiro[2.13]hexadecane-10,16-dione;phosphoric acid
English name: OLEANDOMYCIN PHOSPHATE
Molecular formula: C35H64NO16P
Molecular weight: 785.85

Names & synonyms

oleandomycin phosphate7060-74-4Oleandomycin, phosphate (1:1) (salt)Oleandomycin phosphate (1:1)8681H0C27PDTXCID7025398RefChem:168081230-351-7DTXSID9045398Matromycin (TN)Oleandomycin phosphate [JAN]Oleandomycin (phosphate)

Show more names

matromycinbambusamycinPhosphacyclidine ≥97%OLEANDOMYCIN PHOSPHATE SALTLJQRWAWAOFAOCL-UOESYEISSA-NOleandomycin, phosphate (1:1)oleandomycin standard solution

Oleandomycin phosphate (JAN)Oleandomycin phosphate 100 |Ig/mL in AcetonitrileEINECS 230-351-7UNII-8681H0C27POleandomycin phosphate [JAN:NF]Oleandomycin, phosphate (1:1) (salt); Oleandomycin phosphate (6CI); 1,9-Dioxaspiro[2.13]hexadecane, oleandomycin deriv.; Matromycinorb3134475SCHEMBL5033021

Database identifiers

Properties

Computed structural properties

Topological polar surface area: 244 Å²
Hydrogen bond donors: 6
Hydrogen bond acceptors: 17
Rotatable bonds: 6
Heavy atoms: 53
Formal charge: 0
Complexity: 1,140

Physicochemical properties

Melting point: 145 · 145-147℃
storage temp.: 0 · 0-6°C
solubility: DMSO (Slightly), Methanol (Slightly)
form: Solid
color: White to Off-White
CAS DataBase Reference: 7060 · 7060-74-4
FDA UNII: 8681 H0C27P · 8681H0C27P
EPA Substance Registry System: Oleandomycin phosphate (7060-74-4)
Symbol(GHS): 6 · GHS06
Signal word: Danger
Hazard statements: 300 · H300
Precautionary statements: 264 · P264-P270-P301+P310-P321-P330-P405-P501
Hazard Codes: T+
Risk Statements: 28 · 28
Safety Statements: 22 · 22-24/25-45-36/37-28
RIDADR: 2811 · UN2811 6.1/PG 2
RTECS: 9800000 · RJ9800000

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H300 (97.7%): Fatal if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 43 reports by companies from 2 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory InformationOleandomycin phosphate: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Hazard Classes and CategoriesAcute Tox. 2 (97.7%)

Safety data

rtecs: RJ9800000
ridadr: UN2811 6.1/PG 2
Toxicity: LD50 ivn-rat: 480 mg/kg ANTCAO 7,419,57
risk_code: 28
Signal word: Danger
Symbol(GHS): GHS06
hazard_code: T+
safety_code: 22-24/25-45-36/37-28
Hazard statements: H300
Precautionary statements: P264-P270-P301+P310-P321-P330-P405-P501

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.

Applications · 2 items

DescriptionOleandomycin is a macrolide antibiotic with a 14-membered lactone constituent. It was found in the culture broth of Streptomyces antibioticus by Pfizer Research Laboratories in 1954. Oleandomycin shows almost the same antimicrobial spectrum and activity as the other macrolide antibiotics. Its serum concentration is low, but its tissue concentration is high enough to provide a therapeutic effect. Oleandomycin phosphate is used orally or intravenously to treat pyoderma, sepsis, meningitis, surgical and abdominal infections, respiratory tract and urinary tract infections, and other infections caused by Staphylococci, Streptococci, Corynebacterium, Neisseria, and Mycoplasma. Oleandomycin is also used as a feed additive and therapeutic agent for animals.

UsesOleandomycin Phosphate is an antibiotic substance produced by Streptomyces antibioticus no. ATCC 11891. Antibacterial.

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