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About This Item
Empirical Formula (Hill Notation):
C29H40N4O7
CAS Number:
Molecular Weight:
556.65
MDL number:
UNSPSC Code:
41116107
NACRES:
NA.76
Recommended Products
Quality Level
Assay
≥98% (HPLC)
form
powder
antibiotic activity spectrum
Gram-negative bacteria
Gram-positive bacteria
Mode of action
protein synthesis | interferes
storage temp.
−20°C
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
InChI key
JEECQCWWSTZDCK-IQZGDKDPSA-N
General description
Omadacycline is an aminomethylcycline, a novel semisynthetic tetracycline-class antibiotic drug.(1)(2) It is distinguished from other tetracycline-class drugs like tigecycline and eravacycline at the C9 position with an aminomethyl substitution.(2)
Application
Mode of Action: Interferes with protein synthesis Antibiotic Activity Spectrum: Gram-negative bacteria and Gram-positive bacteria.
Biochem/physiol Actions
Omadacycline displays antimicrobial activities against a broad spectrum of organisms including Gram-positive, Gram-negative, anaerobic, and atypical bacteria.(3)(4) It inhibits bacterial protein synthesis by binding on the 30S subunit of the bacterial ribosome.(1)(2) Omadacycline is also effective against tetracycline efflux proteins in in vitro studies and protects against bacterial tetracycline resistance.(4) It has improved efficacy than other tetracycline drugs against acute bacterial skin and skin structure infections (ABSSSIs) and community-acquired bacterial pneumonia (CABP).(1)(2)(5) In nonclinical and ex vivo studies, omadacycline displays a low potential for cardiovascular toxicity.(6)
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Lact. - Repr. 2
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
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Monique R Bidell et al.
Pharmacotherapy, 41(11), 915-931 (2021-09-25)
Oral tetracyclines have been used in clinical practice for over 60 years. One of the most common indications for use of oral tetracyclines is for treatment of adult outpatients with skin and soft infections (SSTIs), including acute bacterial skin and skin
S Ken Tanaka et al.
Bioorganic & medicinal chemistry, 24(24), 6409-6419 (2016-07-30)
Omadacycline is novel, aminomethyl tetracycline antibiotic being developed for oral and intravenous (IV) administration for the treatment of community-acquired bacterial infections. Omadacycline is characterized by an aminomethyl substituent at the C9 position of the core 6-member ring. Modifications at this
S Ken Tanaka et al.
Antimicrobial agents and chemotherapy, 60(9), 5247-5253 (2016-06-22)
Omadacycline is a first-in-class aminomethylcycline antibiotic with a broad spectrum of activity against Gram-positive and Gram-negative aerobes and anaerobes and atypical bacterial pathogens. A series of nonclinical studies, including mammalian pharmacologic receptor binding studies, human ether-a-go-go-related gene (hERG) channel binding
Rodrigo M Burgos et al.
Infection and drug resistance, 12, 1895-1915 (2019-07-17)
Tetracyclines have come a long way since they became available almost seven decades ago, with numerous enhancements allowing new agents to overcome bacterial mechanisms of resistance. However, these enhancements come with toxicities and pharmacokinetic disadvantages such as the gastrointestinal side-effects
James A Karlowsky et al.
Clinical infectious diseases : an official publication of the Infectious Diseases Society of America, 69(Suppl 1), S6-S15 (2019-08-02)
Omadacycline is a novel aminomethylcycline antimicrobial and semisynthetic derivative of tetracycline. In vitro, omadacycline displays potent activity against gram-positive and many gram-negative bacteria, including methicillin-resistant Staphylococcus aureus, Streptococcus pneumoniae, β-hemolytic streptococci, vancomycin-resistant Enterococcus, and Enterobacteriaceae. Omadacycline is also active against
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