All Photos(2)
Synonym(s):
MK-2764 tosylate, (4S,4aS,5aR,12aS)-4,7-bis(Dimethylamino)-9-(2,2-dimethylpropylaminomethyl)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12aoctahydrotetracene-2-carboxamide, 4-methylbenzenesulfonate, Amadacycline tosylate, BAY 73-7388 tosylate, MK 2764 tosylate, MK2764 tosylate, PTK 0796 tosylate, PTK-0796 tosylate, PTK0796 tosylate
Empirical Formula (Hill Notation):
C29H40N4O7·C7H8O3S
CAS Number:
Molecular Weight:
728.85
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.21
Recommended Products
Quality Level
Assay
≥97% (HPLC)
form
powder
storage condition
desiccated
color
yellow to orange
solubility
H2O: 2 mg/mL, clear
storage temp.
-10 to -25°C
Biochem/physiol Actions
Omadacycline (amadacycline, PTK 0796) is an orally active, potent tetracycline-class antibacterial against broad gram-positive and some gram-negative bacteria, including strains expressing the two main forms of tetracycline resistance (efflux and ribosomal protection). Omadacycline is also active against Haemophilus influenzae (H. influenzae) and atypical and anaerobic pathogens, including Legionella pneumophila, Mycoplasma spp., Ureaplasma spp., Bacteroides spp., and Clostridioides difficile. Unlike tetracycline, Omadacycline is active in vitro in the presence of the ribosomal protection protein Tet(O), despite its ribosomal binding site is similar to that of tetracycline.
Caution
Hygroscopic
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Lact. - Repr. 2
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Regulatory Information
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Mechanism of action of the novel aminomethylcycline antibiotic omadacycline
Antimicrobial Agents and Chemotherapy, 58(3), 1279-1283 (2014)
James A Karlowsky et al.
Clinical infectious diseases : an official publication of the Infectious Diseases Society of America, 69(Suppl 1), S6-S15 (2019-08-02)
Omadacycline is a novel aminomethylcycline antimicrobial and semisynthetic derivative of tetracycline. In vitro, omadacycline displays potent activity against gram-positive and many gram-negative bacteria, including methicillin-resistant Staphylococcus aureus, Streptococcus pneumoniae, β-hemolytic streptococci, vancomycin-resistant Enterococcus, and Enterobacteriaceae. Omadacycline is also active against
A B Macone et al.
Antimicrobial agents and chemotherapy, 58(2), 1127-1135 (2013-12-04)
Omadacycline is the first intravenous and oral 9-aminomethylcycline in clinical development for use against multiple infectious diseases including acute bacterial skin and skin structure infections (ABSSSI), community-acquired bacterial pneumonia (CABP), and urinary tract infections (UTI). The comparative in vitro activity
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