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MedKoo Cat#: 592757 | Name: Omadacycline tosylate
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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 tosylate
Omadacycline tosylate
CAS#1075240-43-5 (tosylate)

Theoretical Analysis

MedKoo Cat#: 592757

Name: Omadacycline tosylate

CAS#: 1075240-43-5 (tosylate)

Chemical Formula: C36H48N4O10S

Exact Mass: 728.3091

Molecular Weight: 728.86

Elemental Analysis: C, 59.33; H, 6.64; N, 7.69; O, 21.95; S, 4.40

Price and Availability

Size Price Availability Quantity
5mg USD 450.00 2 Weeks
10mg USD 750.00 2 Weeks
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Related CAS #
389139-89-3 (free base) 1196800-40-4 (mesylate) 1075240-43-5 (tosylate) 1196800-39-1 (HCl)
Synonym
Amadacyclin tosylate, Omadacycline tosylate; Nuzyra; PTK-0796; PTK 0796; PTK0796;
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 4-methylbenzenesulfonate
InChi Key
SETFNHZTVGTBHC-XGLFQKEBSA-N
InChi Code
InChI=1S/C29H40N4O7.C7H8O3S/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;1-6-2-4-7(5-3-6)11(8,9)10/h10,13,16,21,31,34,36-37,40H,8-9,11-12H2,1-7H3,(H2,30,39);2-5H,1H3,(H,8,9,10)/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.O=S(C5=CC=C(C)C=C5)(O)=O
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

Preparing Stock Solutions

The following data is based on the product molecular weight 728.86 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
1: Rodvold KA, Burgos RM, Tan X, Pai MP. Omadacycline: A Review of the Clinical Pharmacokinetics and Pharmacodynamics. Clin Pharmacokinet. 2019 Nov 27. doi: 10.1007/s40262-019-00843-4. [Epub ahead of print] Review. PubMed PMID: 31773505. 2: Shutter MC, Akhondi H. Tetracycline. 2019 Oct 28. StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2019 Jan-. Available from http://www.ncbi.nlm.nih.gov/books/NBK549905/ PubMed PMID: 31751095. 3: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012-. Available from http://www.ncbi.nlm.nih.gov/books/NBK548040/ PubMed PMID: 31643371. 4: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012-. Available from http://www.ncbi.nlm.nih.gov/books/NBK547890/ PubMed PMID: 31643226. 5: Lefamulin (Xenleta) for community-acquired bacterial pneumonia. Med Lett Drugs Ther. 2019 Sep 23;61(1581):145-148. Review. PubMed PMID: 31599865. 6: Koulenti D, Xu E, Mok IYS, Song A, Karageorgopoulos DE, Armaganidis A, Lipman J, Tsiodras S. Novel Antibiotics for Multidrug-Resistant Gram-Positive Microorganisms. Microorganisms. 2019 Aug 18;7(8). pii: E270. doi: 10.3390/microorganisms7080270. Review. PubMed PMID: 31426596; PubMed Central PMCID: PMC6723731. 7: Burgos RM, Rodvold KA. Omadacycline: a novel aminomethylcycline. Infect Drug Resist. 2019 Jul 2;12:1895-1915. doi: 10.2147/IDR.S171352. eCollection 2019. Review. PubMed PMID: 31308710; PubMed Central PMCID: PMC6613460. 8: Jaffa RK, Pillinger KE, Roshdy D, Isip JA, Pasquale TR. Novel developments in the treatment of acute bacterial skin and skin structure infections. Expert Opin Pharmacother. 2019 Aug;20(12):1493-1502. doi: 10.1080/14656566.2019.1617851. Epub 2019 May 30. Review. PubMed PMID: 31145645. 9: Bassetti M, Peghin M, Castaldo N, Giacobbe DR. The safety of treatment options for acute bacterial skin and skin structure infections. Expert Opin Drug Saf. 2019 Aug;18(8):635-650. doi: 10.1080/14740338.2019.1621288. Epub 2019 Jun 13. Review. PubMed PMID: 31106600. 10: Baker DE. Omadacycline. Hosp Pharm. 2019 Apr;54(2):80-87. doi: 10.1177/0018578718823730. Epub 2019 Jan 22. Review. PubMed PMID: 30923399; PubMed Central PMCID: PMC6431718. 11: Bondeelle L, Bergeron A, Wolff M. [The role of new antibiotics in the treatment of acute adult community acquired pneumonia]. Rev Mal Respir. 2019 Jan;36(1):104-117. doi: 10.1016/j.rmr.2018.04.010. Epub 2019 Jan 10. Review. French. PubMed PMID: 30638789. 12: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006-. Available from http://www.ncbi.nlm.nih.gov/books/NBK535602/ PubMed PMID: 30601611. 13: Markham A, Keam SJ. Omadacycline: First Global Approval. Drugs. 2018 Dec;78(18):1931-1937. doi: 10.1007/s40265-018-1015-2. Review. PubMed PMID: 30471003. 14: Barber KE, Bell AM, Wingler MJB, Wagner JL, Stover KR. Omadacycline Enters the Ring: A New Antimicrobial Contender. Pharmacotherapy. 2018 Dec;38(12):1194-1204. doi: 10.1002/phar.2185. Epub 2018 Nov 15. Review. Erratum in: Pharmacotherapy. 2019 Feb;39(2):207. PubMed PMID: 30290000; PubMed Central PMCID: PMC6587716. 15: Cho JC, Childs-Kean LM, Zmarlicka MT, Crotty MP. Return of the tetracyclines: omadacycline, a novel aminomethylcycline antimicrobial. Drugs Today (Barc). 2018 Mar;54(3):209-217. doi: 10.1358/dot.2018.54.3.2800620. Review. PubMed PMID: 29771255. 16: Montravers P, Tran-Dinh A, Tanaka S. The role of omadacycline in skin and soft tissue infections. Curr Opin Infect Dis. 2018 Apr;31(2):148-154. doi: 10.1097/QCO.0000000000000429. Review. PubMed PMID: 29251672. 17: Abbas M, Paul M, Huttner A. New and improved? A review of novel antibiotics for Gram-positive bacteria. Clin Microbiol Infect. 2017 Oct;23(10):697-703. doi: 10.1016/j.cmi.2017.06.010. Epub 2017 Jun 19. Review. PubMed PMID: 28642145. 18: Amalakuhan B, Echevarria KL, Restrepo MI. Managing community acquired pneumonia in the elderly - the next generation of pharmacotherapy on the horizon. Expert Opin Pharmacother. 2017 Aug;18(11):1039-1048. doi: 10.1080/14656566.2017.1340937. Epub 2017 Jun 21. Review. PubMed PMID: 28598693; PubMed Central PMCID: PMC6092187. 19: Petković H, Lukežič T, Šušković J. Biosynthesis of Oxytetracycline by Streptomyces rimosus:Past, Present and Future Directions in the Developmentof Tetracycline Antibiotics. Food Technol Biotechnol. 2017 Mar;55(1):3-13. doi: 10.17113/ftb.55.01.17.4617. Review. PubMed PMID: 28559729; PubMed Central PMCID: PMC5434370. 20: Villano S, Steenbergen J, Loh E. Omadacycline: development of a novel aminomethylcycline antibiotic for treating drug-resistant bacterial infections. Future Microbiol. 2016 Oct;11:1421-1434. Epub 2016 Aug 19. Review. PubMed PMID: 27539442.