Omadacycline
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MedKoo CAT#: 326705

CAS#: 389139-89-3 (free base)

Description: Omadacycline, also known as PTK 0796 and Amadacyclin, is a novel first-in-class aminomethylcycline with potent activity against important skin and pneumonia pathogens, including community-acquired methicillin-resistant Staphylococcus aureus (MRSA), β-hemolytic streptococci, penicillin-resistant Streptococcus pneumoniae, Haemophilus influenzae, and Legionella. Omadacycline is active against strains expressing the two main forms of tetracycline resistance (efflux and ribosomal protection). The primary effect of omadacycline is on bacterial protein synthesis, inhibiting protein synthesis with a potency greater than that of tetracycline. The binding site for omadacycline is similar to that for tetracycline.

Chemical Structure

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Omadacycline
CAS# 389139-89-3 (free base)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 326705
Name: Omadacycline
CAS#: 389139-89-3 (free base)
Chemical Formula: C29H40N4O7
Exact Mass: 556.29
Molecular Weight: 556.660
Elemental Analysis: C, 62.57; H, 7.24; N, 10.07; O, 20.12

Price and Availability

Size Price Availability Quantity
1mg USD 90 Ready to ship
5mg USD 150 Ready to ship
10mg USD 250 Ready to ship
25mg USD 550 Ready to ship
50mg USD 850 Ready to ship
100mg USD 1450 Ready to ship
200mg USD 2450 Ready to ship
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Related CAS #: 389139-89-3 (free base)   1196800-40-4 (mesylate)   1075240-43-5 (tosylate)   1196800-39-1 (HCl)  

Synonym: PTK 0796; PTK-0796; PTK0796; Amadacyclin; Omadacycline; Nuzyra.

IUPAC/Chemical Name: (4S,4aS,5aR,12aS)-4,7-bis(Dimethylamino)-9-(((2,2-dimethylpropyl)amino)methyl)- 3,10,12,12a- tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2- carboxamide

InChi Key: JEECQCWWSTZDCK-IQZGDKDPSA-N

InChi Code: InChI=1S/C29H40N4O7/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/h10,13,16,21,31,34,36-37,40H,8-9,11-12H2,1-7H3,(H2,30,39)/t13-,16-,21-,29-/m0/s1

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

Appearance: Solid powder

Purity: >95% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target: Omadacycline (PTK 0796), a first-in-class active aminomethylcycline antibacterial.
In vitro activity: A series of nonclinical in vitro studies were undertaken with omadacycline with the objective of evaluating the potential for cardiovascular toxicity. The effects of omadacycline on the hERG tail current were recorded from human embryonic kidney (HEK293) cells. Omadacycline (10 μM, 5.57 μg/ml) inhibited the ligand binding activity of one subtype of muscarinic acetylcholine receptor (M2) by 82%; there was no substantial effect on muscarinic receptor M3 or nicotinic acetylcholine receptors. Omadacycline did not inhibit or stimulate the ligand binding activity of adrenergic receptors or any other receptor target by more than 20% (Table 1). In vehicle-treated cells (n = 4), approximately 10 min of exposure to 100% bath solution produced a residual tail current of 91.1% ± 5.0% of the control values. Omadacycline at 100, 250, 500, and 1,000 μg/ml inhibited the hERG tail current in a concentrationdependent manner, and the inhibition began to plateau at higher concentrations. A significant inhibition of the tail current was observed at concentrations of 250 μg/ml and above (P < 0.01) compared with the results obtained with the vehicle-treated group. When the results for the omadacycline- and vehicle-treated groups were compared, omadacycline at 100 μg/ml had no significant inhibitory effect on the hERG tail current. The IC25 value for omadacycline was 166 μg/ml (Fig. 1). Importantly, omadacycline has a low potential for cardiovascular toxicity in human subjects related to blockade of the hERG channel. Antimicrob Agents Chemother. 2016 Sep; 60(9): 5247–5253. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4997885/
In vivo activity: Administration of omadacycline in conscious male cynomolgus monkeys was associated with a mildly increased arterial blood pressure (systolic, diastolic, and mean) for the 30-min interval ending at infusion termination (the time of the maximum plasma concentration [Cmax]) compared with that achieved with the vehicle (Fig. 5). The greatest increase was observed in the medium-dose and high-dose groups (20 and 40 mg/kg, respectively), with mean blood pressures being 23 and 17 mm Hg greater, respectively, than those in monkeys treated with the vehicle. Blood pressure trended toward baseline values after the maximum increases at 0.5 h after dose initiation. Increases in heart rate were observed among the animals in all omadacycline treatment groups (Fig. 5). The increase in heart rate compared with the heart rate in the vehicle-treated group was greatest (58 bpm) at 0.5 h postdosing in the group treated with an omadacycline dose of 20 mg/kg, but the increases for the groups treated with doses of 5 and 40 mg/kg were 37 and 27 bpm, respectively, compared with the heart rate for the animals in the vehicle-treated group. In summary, the findings from these nonclinical studies suggest that omadacycline can attenuate the parasympathetic influence on heart rate in a concentration-dependent manner. Antimicrob Agents Chemother. 2016 Sep; 60(9): 5247–5253. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4997885/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 1.0 1.80

Preparing Stock Solutions

The following data is based on the product molecular weight 556.66 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Kohlhoff SA, Huerta N, Hammerschlag MR. In Vitro Activity of Omadacycline against Chlamydia pneumoniae. Antimicrob Agents Chemother. 2019 Jan 29;63(2):e01907-18. doi: 10.1128/AAC.01907-18. PMID: 30509942; PMCID: PMC6355552. 2. Tanaka SK, Villano S. In Vitro and In Vivo Assessments of Cardiovascular Effects with Omadacycline. Antimicrob Agents Chemother. 2016 Aug 22;60(9):5247-53. doi: 10.1128/AAC.00320-16. PMID: 27324778; PMCID: PMC4997885. 3. Steenbergen J, Tanaka SK, Miller LL, Halasohoris SA, Hershfield JR. In Vitro and In Vivo Activity of Omadacycline against Two Biothreat Pathogens, Bacillus anthracis and Yersinia pestis. Antimicrob Agents Chemother. 2017 Apr 24;61(5):e02434-16. doi: 10.1128/AAC.02434-16. PMID: 28223382; PMCID: PMC5404541.
In vitro protocol: 1. Kohlhoff SA, Huerta N, Hammerschlag MR. In Vitro Activity of Omadacycline against Chlamydia pneumoniae. Antimicrob Agents Chemother. 2019 Jan 29;63(2):e01907-18. doi: 10.1128/AAC.01907-18. PMID: 30509942; PMCID: PMC6355552. 2. Tanaka SK, Villano S. In Vitro and In Vivo Assessments of Cardiovascular Effects with Omadacycline. Antimicrob Agents Chemother. 2016 Aug 22;60(9):5247-53. doi: 10.1128/AAC.00320-16. PMID: 27324778; PMCID: PMC4997885.
In vivo protocol: 1. Tanaka SK, Villano S. In Vitro and In Vivo Assessments of Cardiovascular Effects with Omadacycline. Antimicrob Agents Chemother. 2016 Aug 22;60(9):5247-53. doi: 10.1128/AAC.00320-16. PMID: 27324778; PMCID: PMC4997885. 2. Steenbergen J, Tanaka SK, Miller LL, Halasohoris SA, Hershfield JR. In Vitro and In Vivo Activity of Omadacycline against Two Biothreat Pathogens, Bacillus anthracis and Yersinia pestis. Antimicrob Agents Chemother. 2017 Apr 24;61(5):e02434-16. doi: 10.1128/AAC.02434-16. PMID: 28223382; PMCID: PMC5404541.

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11: Pagano P, Marra A, Shinabarger D, Pillar C. In vitro activity of omadacycline and levofloxacin against Escherichia coli, Klebsiella pneumoniae and Staphylococcus saprophyticus in human urine supplemented with calcium and magnesium. J Antimicrob Chemother. 2020 Aug 1;75(8):2160-2163. doi: 10.1093/jac/dkaa138. PMID: 32428235; PMCID: PMC7366199.


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15: Lakota EA, Van Wart SA, Trang M, Tzanis E, Bhavnani SM, Safir MC, Friedrich L, Steenbergen JN, Ambrose PG, Rubino CM. Population Pharmacokinetic Analyses for Omadacycline Using Phase 1 and 3 Data. Antimicrob Agents Chemother. 2020 Jun 23;64(7):e02263-19. doi: 10.1128/AAC.02263-19. PMID: 32340986; PMCID: PMC7318031.


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