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SML3782

Sigma-Aldrich

Omadacycline tosylate

≥97% (HPLC)

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

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About This Item

Empirical Formula (Hill Notation):
C29H40N4O7·C7H8O3S
CAS Number:
1075240-43-5
Molecular Weight:
728.85
MDL number:
MFCD28167752
UNSPSC Code:
51111800
UNSPSC Code:
12352200
NACRES:
NA.21

Quality Level

100

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

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H361d,H362

Hazard Classifications

Lact. - Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Mechanism of action of the novel aminomethylcycline antibiotic omadacycline
Antimicrobial Agents and Chemotherapy, 58(3), 1279-1283 (2014)
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
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

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