Omadacycline | CAS#389139-89-3 | antibiotic

MedKoo Cat#: 326705 | Name: Omadacycline

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Omadacycline

CAS#389139-89-3 (free base)

Theoretical Analysis

MedKoo Cat#: 326705

Name: Omadacycline

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

Chemical Formula: C29H40N4O7

Exact Mass: 556.2897

Molecular Weight: 556.66

Elemental Analysis: C, 62.57; H, 7.24; N, 10.07; O, 20.12

Price and Availability

Size	Price	Availability
1mg	USD 90.00	Ready to ship
5mg	USD 150.00	Ready to ship
10mg	USD 250.00	Ready to ship
25mg	USD 550.00	Ready to ship
50mg	USD 850.00	Ready to ship
100mg	USD 1,450.00	Ready to ship
200mg	USD 2,450.00	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

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#A20T10K19

QC Data

View QC data: current batch, Lot#A20T10K19

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

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/

	Solvent	mg/mL	mM
Solubility
	DMSO	1.0	1.80

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

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:

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.

: Kovacs SJ, Ting L, Praestgaard J, Sunkara G, Sun H, Stein DS, Tanaka SK, Villano S. An Open-Label Study of the Impact of Hepatic Impairment on the Pharmacokinetics and Safety of Single Oral and Intravenous Doses of Omadacycline. Antimicrob Agents Chemother. 2020 Aug 24:AAC.01650-20. doi: 10.1128/AAC.01650-20. Epub ahead of print. PMID: 32839218. 2: McKenna M. The antibiotic paradox: why companies can't afford to create life- saving drugs. Nature. 2020 Aug;584(7821):338-341. doi: 10.1038/d41586-020-02418-x. PMID: 32814891. 3: Riccardi N, Monticelli J, Antonello RM, Di Lallo G, Frezza D, Luzzati R, Di Bella S. Therapeutic Options for Infections due to vanB Genotype Vancomycin- Resistant Enterococci. Microb Drug Resist. 2020 Aug 14. doi: 10.1089/mdr.2020.0171. Epub ahead of print. PMID: 32799629. 4: Yang Y, Bian L, Hang X, Yan C, Huang Y, Ye F, Zhang G, Jin G, Bi H. In vitro activity of new tetracycline analogues omadacycline and eravacycline against clinical isolates of Helicobacter pylori collected in China. Diagn Microbiol Infect Dis. 2020 Jul 8;98(3):115129. doi: 10.1016/j.diagmicrobio.2020.115129. Epub ahead of print. PMID: 32739761. 5: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006–. Omadacycline. 2020 Jul 20. PMID: 30601611. 6: Shutter MC, Akhondi H. Tetracycline. 2020 Jul 6. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2020 Jan–. PMID: 31751095. 7: Wang Z, Lin Z, Bai B, Xu G, Li P, Yu Z, Deng Q, Shang Y, Zheng J. Eravacycline susceptibility was impacted by genetic mutation of 30S ribosome subunits, and branched-chain amino acid transport system II carrier protein, Na/Pi cotransporter family protein in Staphylococcus aureus. BMC Microbiol. 2020 Jul 1;20(1):189. doi: 10.1186/s12866-020-01869-6. PMID: 32611319; PMCID: PMC7329441. 8: Iregui A, Landman D, Quale J. Activity of Omadacycline and Other Tetracyclines Against Contemporary Gram-Negative Pathogens from New York City Hospitals. Microb Drug Resist. 2020 Jun 22. doi: 10.1089/mdr.2019.0423. Epub ahead of print. PMID: 32580619. 9: Lutgring JD, Balbuena R, Reese N, Gilbert SE, Ansari U, Bhatnagar A, Boyd S, Campbell D, Cochran J, Haynie J, Ilutsik J, Longo C, Swint S, Rasheed JK, Brown AC, Karlsson M. Antibiotic Susceptibility of NDM-Producing Enterobacterales Collected in the United States in 2017 and 2018. Antimicrob Agents Chemother. 2020 Aug 20;64(9):e00499-20. doi: 10.1128/AAC.00499-20. PMID: 32540972; PMCID: PMC7449154. 10: Begum K, Bassères E, Miranda J, Lancaster C, Gonzales-Luna AJ, Carlson TJ, Rashid T, Eyre DW, Wilcox MH, Alam MJ, Garey KW. In Vitro Activity of Omadacycline, a New Tetracycline Analog, and Comparators against Clostridioides difficile. Antimicrob Agents Chemother. 2020 Jul 22;64(8):e00522-20. doi: 10.1128/AAC.00522-20. PMID: 32513796. 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. 12: Gasparrini AJ, Markley JL, Kumar H, Wang B, Fang L, Irum S, Symister CT, Wallace M, Burnham CD, Andleeb S, Tolia NH, Wencewicz TA, Dantas G. Tetracycline-inactivating enzymes from environmental, human commensal, and pathogenic bacteria cause broad-spectrum tetracycline resistance. Commun Biol. 2020 May 15;3(1):241. doi: 10.1038/s42003-020-0966-5. PMID: 32415166; PMCID: PMC7229144. 13: Mendes RE, Huband MD, Streit JM, Castanheira M, Flamm RK. Omadacycline invitro activity against a molecularly characterized collection of clinical isolates with known acquired tetracycline resistance mechanisms. Diagn Microbiol Infect Dis. 2020 Jul;97(3):115054. doi: 10.1016/j.diagmicrobio.2020.115054. Epub 2020 Apr 2. PMID: 32376058. 14: Dong D, Zheng Y, Chen Q, Guo Y, Yang Y, Wu S, Zhu D, Deng D, Bradford PA, Reinhart H, Hu F. In vitro activity of omadacycline against pathogens isolated from Mainland China during 2017-2018. Eur J Clin Microbiol Infect Dis. 2020 Aug;39(8):1559-1572. doi: 10.1007/s10096-020-03877-w. Epub 2020 Apr 30. PMID: 32356026. 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. 16: Andrei S, Droc G, Stefan G. FDA approved antibacterial drugs: 2018-2019. Discoveries (Craiova). 2019 Dec 31;7(4):e102. doi: 10.15190/d.2019.15. PMID: 32309620; PMCID: PMC7086080. 17: VanScoy BD, Lakota EA, Conde H, McCauley J, Friedrich L, Steenbergen JN, Ambrose PG, Bhavnani SM. Pharmacokinetic-Pharmacodynamic Characterization of Omadacycline against Haemophilus influenzae Using a One-Compartment In Vitro Infection Model. Antimicrob Agents Chemother. 2020 May 21;64(6):e02265-19. doi: 10.1128/AAC.02265-19. PMID: 32284378; PMCID: PMC7269464. 18: Muñoz-Egea MC, Carrasco-Antón N, Esteban J. State-of-the-art treatment strategies for nontuberculous mycobacteria infections. Expert Opin Pharmacother. 2020 Jun;21(8):969-981. doi: 10.1080/14656566.2020.1740205. Epub 2020 Mar 21. PMID: 32200657. 19: John J Jr. The treatment of resistant staphylococcal infections. F1000Res. 2020 Feb 26;9:F1000 Faculty Rev-150. doi: 10.12688/f1000research.17718.1. PMID: 32148777; PMCID: PMC7047908. 20: Dubois J, Dubois M, Martel JF. In Vitro and Intracellular Activities of Omadacycline against Legionella pneumophila. Antimicrob Agents Chemother. 2020 Apr 21;64(5):e01972-19. doi: 10.1128/AAC.01972-19. PMID: 32094130; PMCID: PMC7179622.