Omadacycline HCl | CAS#1196800-39-1

MedKoo Cat#: 330044 | Name: Omadacycline HCl

Featured

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 HCl

CAS#1196800-39-1 (HCl)

Theoretical Analysis

MedKoo Cat#: 330044

Name: Omadacycline HCl

CAS#: 1196800-39-1 (HCl)

Chemical Formula: C29H41ClN4O7

Exact Mass: 0.0000

Molecular Weight: 593.12

Elemental Analysis: C, 58.73; H, 6.97; Cl, 5.98; N, 9.45; O, 18.88

Price and Availability

Size	Price	Availability
50mg	USD 2,650.00	2 Weeks
100mg	USD 4,250.00	2 Weeks
200mg	USD 6,950.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

389139-89-3 (free base) 1196800-40-4 (mesylate) 1075240-43-5 (tosylate) 1196800-39-1 (HCl)

Synonym

Omadacycline HCl; Omadacycline hydrochloride; PTK 0796; PTK-0796; PTK0796; Amadacyclin; Omadacycline; Nuzyra.

IUPAC/Chemical Name

(4S,4aS,5aR,12aS)-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-9-((neopentylamino)methyl)-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide hydrochloride

InChi Key

HXMCZSICOWSBRX-XGLFQKEBSA-N

InChi Code

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;/h10,13,16,21,31,34,36-37,40H,8-9,11-12H2,1-7H3,(H2,30,39);1H/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.[HCl]

Appearance

Solid powder

Purity

>98% (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

Shelf Life

>3 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

Instruction

View handling instruction

Biological target:

Omadacycline, also known as PTK 0796 and Amadacyclin, is a novel first-in-class aminomethylcycline.

In vitro activity:

Here, this study performed in vitro susceptibility testing on 10 Mycoplasma genitalium isolates against omadacycline, minocycline, tetracycline, doxycycline, moxifloxacin, levofloxacin, and azithromycin. Omadacycline was the most potent agent, with all MICs of ≤0.5 μg/mL. MICs were not affected by resistance to other agents, including resistance to other tetracycline class drugs. Reference: Microbiol Spectr. 2022 Dec 21;10(6):e0365422. https://pubmed.ncbi.nlm.nih.gov/36314935/

In vivo activity:

In vivo efficacy of omadacycline was demonstrated using an intraperitoneal infection model in mice. A single intravenous dose of omadacycline exhibited efficacy against Streptococcus pneumoniae, Escherichia coli, and Staphylococcus aureus, including tet(M) and tet(K) efflux-containing strains and MRSA strains. The 50% effective doses (ED50s) for Streptococcus pneumoniae obtained ranged from 0.45 mg/kg to 3.39 mg/kg, the ED50s for Staphylococcus aureus obtained ranged from 0.30 mg/kg to 1.74 mg/kg, and the ED50 for Escherichia coli was 2.02 mg/kg. Reference: Antimicrob Agents Chemother. 2014;58(2):1127-35. https://pubmed.ncbi.nlm.nih.gov/24295985/

	Solvent	mg/mL	mM
Solubility
	DMSO	105.0	177.03
	Water	50.0	84.30

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 593.12 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. Waites KB, Crabb DM, Atkinson TP, Geisler WM, Xiao L. Omadacycline Is Highly Active In Vitro against Mycoplasma genitalium. Microbiol Spectr. 2022 Dec 21;10(6):e0365422. doi: 10.1128/spectrum.03654-22. Epub 2022 Oct 31. PMID: 36314935; PMCID: PMC9769859. 2. Serio AW, Tanaka SK, Wright K, Garrity-Ryan L. Sub-growth-inhibitory concentrations of omadacycline inhibit Staphylococcus aureus haemolytic activity in vitro. JAC Antimicrob Resist. 2021 Dec 22;4(1):dlab190. doi: 10.1093/jacamr/dlab190. PMID: 34988444; PMCID: PMC8693163. 3. Leahy RG, Serio AW, Wright K, Traczewski MM, Tanaka SK. Activity of omadacycline in vitro against Clostridioides difficile and preliminary efficacy assessment in a hamster model of C. difficile-associated diarrhoea. J Glob Antimicrob Resist. 2022 Sep;30:96-99. doi: 10.1016/j.jgar.2022.04.019. Epub 2022 Apr 29. PMID: 35500838. 4. Macone AB, Caruso BK, Leahy RG, Donatelli J, Weir S, Draper MP, Tanaka SK, Levy SB. In vitro and in vivo antibacterial activities of omadacycline, a novel aminomethylcycline. Antimicrob Agents Chemother. 2014;58(2):1127-35. doi: 10.1128/AAC.01242-13. Epub 2013 Dec 2. PMID: 24295985; PMCID: PMC3910882.

In vitro protocol:

In vivo protocol:

1. Leahy RG, Serio AW, Wright K, Traczewski MM, Tanaka SK. Activity of omadacycline in vitro against Clostridioides difficile and preliminary efficacy assessment in a hamster model of C. difficile-associated diarrhoea. J Glob Antimicrob Resist. 2022 Sep;30:96-99. doi: 10.1016/j.jgar.2022.04.019. Epub 2022 Apr 29. PMID: 35500838. 2. Macone AB, Caruso BK, Leahy RG, Donatelli J, Weir S, Draper MP, Tanaka SK, Levy SB. In vitro and in vivo antibacterial activities of omadacycline, a novel aminomethylcycline. Antimicrob Agents Chemother. 2014;58(2):1127-35. doi: 10.1128/AAC.01242-13. Epub 2013 Dec 2. PMID: 24295985; PMCID: PMC3910882.

: 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.