Tigecycline

Names

[ CAS No. ]:
220620-09-7

[ Name ]:
Tigecycline

[Synonym ]:
WAY-GAR 936
TIGECYCLINE POWDER
9-t-Butylglycylamido-minocycline hydrate
2-Naphthacenecarboxamide, 4,7-bis(dimethylamino)-9-((((1,1-dimethylethyl)amino)acetyl)amino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-, (4S,4aS,5aR,12aS)-
Tigercycline
(4S,4aS,5aR,12aS)-9-{[(tert-butylamino)acetyl]amino}-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
2-naphthacenecarboxamide, 4,7-bis(dimethylamino)-9-[[[(1,1-dimethylethyl)amino]acetyl]amino]-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-, (4S,4aS,5aR,12aS)-
2-NAPHTHACENECARBOXAMIDE
(4S,4aS,5aR,12aS)-9-[(N-tert-Butylglycyl)amino]-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
Glycylcycline
(4S,4aS,5aR,12aS)-4,7-Bis(dimethylamino)-3,10,12,12a-tetrahydroxy-9-{[N-(2-methyl-2-propanyl)glycyl]amino}-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-2-tetracenecarboxamide
2-Naphthacenecarboxamide, 4,7-bis(dimethylamino)-9-[[2-[(1,1-dimethylethyl)amino]acetyl]amino]-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-, (4S,4aS,5aR,12aS)-
Tygacil
MFCD00935753
Tigecycline
TIGECYCLINE GLYCYLCYCLINE
Tegecycline

Biological Activity

[Description]:

Tigecycline is a first-in-class, broad spectrum antibiotic with activity against antibiotic-resistant organisms.Target: AntibacterialTigecycline is active against a broad range of gram-negative and gram-positive bacterial species including clinically important multidrug-resistant nosocomial and community-acquired bacterial pathogens. Tigecycline has been shown to inhibit the translation elongation step by binding to the ribosome 30S subunit and preventing aminoacylated tRNAs to accommodate in the ribosomal A site [1]. Tigecycline has also been found to be effective for the treatment of community- as well as hospital-acquired and ventilator-associated pneumonia and bacteremia, sepsis with shock and urinary tract infections. Tigecycline appears to be a valuable treatment option for the management of superbugs, especially where conventional therapy has failed [2].Fifteen patients received tigecycline for 16 episodes of CPKP infection. The main infections were pneumonia (31%), urinary tract infection (31%), peritonitis (20%), catheter-related bacteraemia (12%), and meningitis (6%). Most infections were complicated with severe sepsis (44%), septic shock (12%), and/or bacteraemia (19%). The daily maintenance dose of tigecycline was 200 mg in 10 episodes and 100 mg in 6 episodes. The overall 30-day mortality rate was 25%. Univariate analysis showed that mortality was significantly associated (p < 0.01) with mean APACHE II and SOFA scores and the presence of immunosuppression, but not with the tigecycline dose [3].

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Anti-infection >> Bacterial

Research Areas >> Infection

Natural Products >> Alkaloid

[References]

[1]. Seputiene V, et al. Tigecycline - how powerful is it in the fight against antibiotic-resistant bacteria? Medicina (Kaunas). 2010;46(4):240-8.

[2]. Bhattacharya M, et al. Tigecycline. J Postgrad Med. 2009 Jan-Mar;55(1):65-8.

[3]. Moreno BB, et al. Tigecycline therapy for infections due to carbapenemase-producing Klebsiella pneumoniae in critically ill patients. Scand J Infect Dis. 2013 Dec 20.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
890.9±65.0 °C at 760 mmHg

[ Melting Point ]:
164-166°C

[ Molecular Formula ]:
C₂₉H₃₉N₅O₈

[ Molecular Weight ]:
585.649

[ Flash Point ]:
492.6±34.3 °C

[ Exact Mass ]:
585.279846

[ PSA ]:
205.76000

[ LogP ]:
-1.30

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.675

[ Storage condition ]:
Amber Vial, -20°C Freezer

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H319-H360

[ Precautionary Statements ]:
P201-P280-P305 + P351 + P338-P308 + P313

[ Hazard Codes ]:
Xn

[ Safety Phrases ]:
S24/25

[ RIDADR ]:
UN 3077 9 / PGIII

[ WGK Germany ]:
3

[ HS Code ]:
3004909090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 3004909090

Related Compounds

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