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Chemical Structure| 389139-89-3 Chemical Structure| 389139-89-3

Structure of Omadacycline
CAS No.: 389139-89-3

Chemical Structure| 389139-89-3

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Omadacycline (PTK 0796), a first-in-class orally active aminomethylcycline antibacterial, is a member of the tetracycline class of antibiotics. It inhibits bacterial protein synthesis by binding to the 30S ribosomal subunit and has broad-spectrum antibacterial activity against aerobic and anaerobic Gram-positive and Gram-negative bacteria, as well as atypical bacteria. Omadacycline is used for researching acute bacterial skin and skin-structure infections, community-acquired pneumonia, and urinary tract infections.

Synonyms: PTK 0796; Amadacycline; MK-2764

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Product Details of Omadacycline

CAS No. :389139-89-3
Formula : C29H40N4O7
M.W : 556.65
SMILES Code : O=C(C1=C(O)[C@@H](N(C)C)[C@@](C[C@@]2([H])C(C(C3=C(O)C(CNCC(C)(C)C)=CC(N(C)C)=C3C2)=O)=C4O)([H])[C@@]4(O)C1=O)N
Synonyms :
PTK 0796; Amadacycline; MK-2764
MDL No. :MFCD19443723
InChI Key :VJYKVCURWJGLPG-IQZGDKDPSA-N
Pubchem ID :54697325

Safety of Omadacycline

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H361-H362
Precautionary Statements:P201-P202-P260-P263-P264-P270-P280-P308+P313-P405-P501

Isoform Comparison

Biological Activity

Description
Omadacycline (PTK 0796), a novel orally active aminomethylcycline antibacterial, belongs to the tetracycline class of antibiotics. It functions by inhibiting bacterial protein synthesis through binding to the 30S ribosomal subunit. With broad-spectrum antibacterial activity against aerobic and anaerobic Gram-positive and Gram-negative bacteria, as well as atypical bacteria, Omadacycline is applicable in research related to acute bacterial skin and skin-structure infections, community-acquired pneumonia, and urinary tract infections [1][2][3][4].

In Vitro:

Cell Line
Concentration Treated Time Description References
Bacillus anthracis 0.008–0.25 µg/mL 18 hours To evaluate the in vitro activity of Omadacycline against Bacillus anthracis, results showed an MIC range of ≤0.008–0.25 µg/mL against 53 B. anthracis isolates, with an MIC50/MIC90 of 0.015/0.03 µg/mL. Antimicrob Agents Chemother. 2024 Sep 4;68(9):e0059524.
Mycobacterium abscessus 0.5 mg/L and 1 mg/L 24 hours and 48 hours Determine the minimum inhibitory concentration of Omadacycline against Mycobacterium abscessus Int J Antimicrob Agents. 2023 Jul;62(1):106847.
Clostridioides difficile spores 25 mg/L 24 to 96 hours Evaluate the sporicidal effect of Omadacycline combined with germinants on C. difficile spores, showing significant spore eradication between 24 to 48 hours, particularly in R027 strains with spore eradication rates of 99.4% to 99.8%. Antimicrob Agents Chemother. 2023 May 1;65(5):e01431-20.
Rapidly growing mycobacteria (RGM) 0.004 to 0.25 mg/ml (80% inhibition) and 0.06 to 1 mg/ml (100% inhibition) 3 days To test the in vitro activity of Omadacycline against rapidly growing mycobacteria, results showed that Omadacycline was active against all RGM species, with MIC50 ranges of 0.004 to 0.25 mg/ml (80% inhibition) and 0.06 to 1 mg/ml (100% inhibition). Antimicrob Agents Chemother. 2021 Feb 17;65(3):e01947-20.
THP-1 cells 0.5 mg/L to 128 mg/L 7 days Determine the minimum inhibitory concentration (MIC) of Omadacycline against M. kansasii, showing MIC of the reference strain was 4 mg/L and clinical strains ranged from 8 to 32 mg/L Antimicrob Agents Chemother. 2022 Sep 20;66(9):e0068722.
Mycobacterium tuberculosis H37Rv 16 mg/L 7 days To evaluate the bactericidal effect of Omadacycline on drug-susceptible and MDR-TB strains, results showed that it killed 4.39 log10 CFU/mL in 7 days Antimicrob Agents Chemother. 2024 Feb 7;68(2):e0108023.
MDR-TB clinical strain (16D) 4 mg/L 7 days To evaluate the bactericidal effect of Omadacycline on MDR-TB strain, results showed that it killed 4.39 log10 CFU/mL in 7 days Antimicrob Agents Chemother. 2024 Feb 7;68(2):e0108023.
Mycobacterium abscessus subsp. abscessus 0.063 to 256 mg/L 7 days To assess the in vitro activity of omadacycline against M. abscessus and compare it with the activity of tigecycline. Results showed that omadacycline inhibited mycobacterial growth at 4 mg/L and achieved mycobacterial killing at concentrations ≥16 mg/L. J Antimicrob Chemother. 2019 Oct 1;74(10):2930-2933.
Slowly growing mycobacteria (SGM) 8 to >16 mg/ml 7 to 8 days To test the in vitro activity of Omadacycline against slowly growing mycobacteria, results showed that Omadacycline MICs were higher for SGM, ranging from 8 to >16 mg/ml. Antimicrob Agents Chemother. 2021 Feb 17;65(3):e01947-20.
Mycoplasma genitalium 0.5 mg/mL To evaluate the in vitro activity of Omadacycline against Mycoplasma genitalium, results showed potent activity against all tested strains, including those resistant to tetracyclines, macrolides, and quinolones. Microbiol Spectr. 2022 Dec 21;10(6):e0365422.
S. aureus and S. epidermidis biofilms 0.5 to 1 mg/ml To evaluate the inhibitory effect of Omadacycline alone or in combination with rifampin on biofilm formation by S. aureus and S. epidermidis, showing low biofilm MICs of 0.5 to 1 mg/ml for S. aureus Antimicrob Agents Chemother. 2022 Jan 18;66(1):e0170321.

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
BALB/c mice Inhalation anthrax model Intraperitoneal injection 0.75, 2.5, 3.75, 5, 7.5, and 15 mg/kg Every 12 hours for 14 days To evaluate the efficacy of Omadacycline for PEP against inhalation anthrax caused by ciprofloxacin-resistant Bacillus anthracis, results showed that Omadacycline significantly increased survival compared to the vehicle control group and the ciprofloxacin treatment group. Antimicrob Agents Chemother. 2024 Sep 4;68(9):e0059524.
Rats MRSA osteomyelitis model Intraperitoneal 20 mg/kg Once daily for 21 days To evaluate the efficacy of Omadacycline alone or in combination with rifampin in a MRSA osteomyelitis model, showing that Omadacycline alone reduced bacterial load, but the combination with rifampin was more effective, and no emergence of rifampin resistance was observed Antimicrob Agents Chemother. 2022 Jan 18;66(1):e0170321.
Mice Lung infection model Oral 300mg/day Once daily for four weeks Evaluate the efficacy of Omadacycline against pulmonary Mycobacterium abscessus infection Int J Antimicrob Agents. 2023 Jul;62(1):106847.

Clinical Trial:

NCT Number Conditions Phases Recruitment Completion Date Locations
NCT04714411 Diabetic Foot Infection RECRUITING 2025-08-18 Methodist Dallas Medical Cente... More >>r, Dallas, Texas, 75203, United States|Methodist Charlton Medical Center, Dallas, Texas, 75237, United States Less <<
NCT04160260 Community-acquired Pneumonia PHASE1 COMPLETED 2020-04-13 Site 105, Birmingham, Alabama,... More >> 35215, United States|Site 102, San Diego, California, 92123, United States|Site 104, San Diego, California, 92123, United States|Site 111, Clearwater, Florida, 33756, United States|Site 116, Clearwater, Florida, 33756, United States|Site 106, Doral, Florida, 33166, United States|Site 108, Miami, Florida, 33155, United States|Site 110, Miami, Florida, 33165, United States|Site 112, West Palm Beach, Florida, 33409, United States|Site 103, Butte, Montana, 59701, United States|Site 114, Las Vegas, Nevada, 89106, United States|Site 101, Sherman, Texas, 75092, United States|Site 109, Madison, Wisconsin, 53717, United States Less <<

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

1.80mL

0.36mL

0.18mL

8.98mL

1.80mL

0.90mL

17.96mL

3.59mL

1.80mL

References

 

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