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SBR00042

Sigma-Aldrich

Omadacycline

≥98% (HPLC)

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About This Item

Empirický vzorec (Hillův zápis):
C29H40N4O7
Číslo CAS:
389139-89-3
Molekulová hmotnost:
556.65
MDL number:
MFCD19443723
UNSPSC Code:
41116107
NACRES:
NA.76

Quality Level

100

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)

pictograms

Health hazard
GHS08

signalword

Warning

Hazard Classifications

Lact. - Repr. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Osvědčení o analýze (COA)

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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
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
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
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
A B Macone et al.
Antimicrobial agents and chemotherapy, 58(2), 1127-1135 (2013-12-04)
Omadacycline is the first intravenous and oral 9-aminomethylcycline in clinical development for use against multiple infectious diseases including acute bacterial skin and skin structure infections (ABSSSI), community-acquired bacterial pneumonia (CABP), and urinary tract infections (UTI). The comparative in vitro activity
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