Omadacycline hydrochloride

• CAT Number: I012056
• CAS Number: 1196800-39-1
• Molecular Formula: C29 H40 N4 O7 . x Cl H
• Purity: ≥95%
• Synonyms: PTK 0796; Omadacycline hydrochloride; 2-​Naphthacenecarboxami​de, 4,​7-​bis(dimethylamino)​-​9-​[[(2,​2-​dimethylpropyl)​amino]​methyl]​-​1,​4,​4a,​5,&#82
• Target: Bacterial; Antibiotic
• Storage: Room temperature
• Related CAS: 389139-89-3(free base)
• IUPAC Name: (4S,4aS,5aR,12aR)-4,7-bis(dimethylamino)-9-[(2,2-dimethylpropylamino)methyl]-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide;hydrochloride
• InChI: InChI=1S/C29H40N4O7.ClH/c1-28(2,3)12-31-11-14-10-17(32(4)5)15-8-13-9-16-21(33(6)7)24(36)20(27(30)39)26(38)29(16,40)25(37)18(13)23(35)19(15)22(14)34;/h10,13,16,21,31,34-35,38,40H,8-9,11-12H2,1-7H3,(H2,30,39);1H/t13-,16-,21-,29-;/m0./s1
• InChIKey: XFPTUHUKKFUSNF-XGLFQKEBSA-N
• SMILES: CC(C)(C)CNCC1=CC(=C2C[C@H]3C[C@H]4[C@@H](C(=O)C(=C([C@]4(C(=O)C3=C(C2=C1O)O)O)O)C(=O)N)N(C)C)N(C)C.Cl

Omadacycline Hydrochloride（Cat No.:I012056）is a modern tetracycline-class antibiotic designed to treat bacterial infections, including community-acquired bacterial pneumonia (CABP) and acute bacterial skin and skin structure infections (ABSSSI). It works by inhibiting bacterial protein synthesis, effectively combating a wide range of gram-positive and gram-negative bacteria, including drug-resistant strains like MRSA and Streptococcus pneumoniae. Available in both oral and intravenous forms, Omadacycline provides flexibility in treatment settings. Its broad-spectrum activity and effectiveness against resistant pathogens make it a valuable option in managing complex infections with a convenient dosing regimen.

Overview of Clinical Research

Originator: Paratek Pharmaceuticals
Developer: Merck & Co; Paratek Pharmaceuticals
Class: Antibacterials; Small molecules; Tetracyclines
Mechanism of Action: Protein synthesis inhibitors
Orphan Drug Status: No
New Molecular Entity: Yes

Reference

1. Antimicrob Agents Chemother. 2017 Apr 24;61(5). pii: e02368-16. doi:
10.1128/AAC.02368-16. Print 2017 May.
In Vivo Pharmacodynamic Evaluation of Omadacycline (PTK 0796) against
Streptococcus pneumoniae in the Murine Pneumonia Model.
Lepak AJ(1), Zhao M(1)(2), Marchillo K(2), VanHecker J(2), Andes DR(3)(4)(2).
Author information:
(1)Department of Medicine, University of Wisconsin School of Medicine and Public
Health, Madison, Wisconsin, USA.
(2)William S. Middleton Memorial VA Hospital, Madison, Wisconsin, USA.
(3)Department of Medicine, University of Wisconsin School of Medicine and Public
Health, Madison, Wisconsin, USA .
(4)Department of Medical Microbiology and Immunology, University of Wisconsin,
Madison, Wisconsin, USA.
Omadacycline is a novel aminomethylcycline antibiotic in clinical development for
community-acquired bacterial pneumonia (CABP). We used a neutropenic murine
pneumonia infection model to characterize the in vivo pharmacodynamic activity of
omadacycline against Streptococcus pneumoniae Four strains with various
phenotypic resistances to other antimicrobials, including tetracyclines, were
utilized. Drug concentration measurements were performed in the plasma and
epithelial lining fluid (ELF) after administration of 0.5, 2, 8, and 32 mg/kg.
Pharmacokinetic parameters were calculated using a noncompartmental model and
were linear over the dose range. Penetration into ELF ranged from 72 to 102%.
Omadacycline demonstrated net cidal activity in relation to the initial burden
against all four strains. The pharmacokinetic/pharmacodynamic index AUC/MIC
correlated well with efficacy (R2 = 0.74). The plasma 24-h static dose AUC/MIC
values were 16 to 20 (24-h ELF AUC/MIC of 14 to 18). A 1-log10 kill was achieved
at 24-h plasma AUC/MIC values of 6.1 to 180 (24-h ELF AUC/MIC values 6.0 to 200).
A 2-log10 kill was achieved at 24-h plasma AUC/MIC values of 19 to 56 (24-h ELF
AUC/MIC of 17 to 47). The targets identified in this study in combination with in
vitro potency and favorable human pharmacokinetics make omadacycline an
attractive candidate for further development and study in patients with CABP.
2. Antimicrob Agents Chemother. 2016 Nov 21;60(12):7502-7504. Print 2016 Dec.
In Vitro Activities of Omadacycline (PTK 0796) and Other Antimicrobial Agents
against Human Mycoplasmas and Ureaplasmas.
Waites KB(1), Crabb DM(2), Liu Y(3), Duffy LB(2).
Author information:
(1)Department of Pathology, University of Alabama at Birmingham, Birmingham,
Alabama, USA .
(2)Department of Pathology, University of Alabama at Birmingham, Birmingham,
Alabama, USA.
(3)Institute of Antibiotics, Huashan Hospital, Institute of Biomedical Sciences,
Fudan University, Shanghai, China.
In vitro activities of omadacycline, a new aminomethylcycline, were determined
for Mycoplasma and Ureaplasma spp. and compared with those of azithromycin,
clindamycin, moxifloxacin, tetracycline, and doxycycline. All omadacycline MICs
were <2 μg/ml. MIC90s were 0.063 μg/ml for Mycoplasma hominis, 0.25 μg/ml for
Mycoplasma pneumoniae, and 2 μg/ml for Ureaplasma spp. Omadacycline had the
lowest MIC90 among all drugs tested against M. hominis Omadacycline activity was
not affected by macrolide, tetracycline, or fluoroquinolone resistance.