Structure of Omadacycline
CAS No.: 389139-89-3
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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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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 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H361-H362 |
Precautionary Statements: | P201-P202-P260-P263-P264-P270-P280-P308+P313-P405-P501 |
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. | PMC11373220 |
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 | PMC10330927 |
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%. | PMC8092874 |
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). | PMC8092516 |
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 | PMC9487483 |
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 | PMC10848755 |
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 | PMC10848755 |
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. | PMC7183808 |
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. | PMC8092516 |
Mycoplasma genitalium | #0.5mg/mL | Not used | 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. | PMC9769859 |
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 | PMC8765317 |
In Vivo:
Species
|
Animal Model
|
Administration | Dosage | Frequency | Description | References |
Mice | Lung infection model | Oral | 300mg/day | Once daily for four weeks | Evaluate the efficacy of Omadacycline against pulmonary Mycobacterium abscessus infection | PMC10330927 |
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. | PMC11373220 |
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 | PMC8765317 |
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 << |
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 |
Tags: Omadacycline | PTK 0796 | Amadacycline | PTK0796 | PTK-0796 | Antibiotic | tetracycline | antibacterial | agent | broad | spectrum | Gram-positive | Gram-negative | anaerobic | atypical | skin-structure | infections | community-acquired | pneumonia | aminomethylcycline | 389139-89-3
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P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
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P243 | Take precautionary measures against static discharge. |
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P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
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P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
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H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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