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Tigecycline

HCID 54686904
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Grundinformationen

CAS
220620-09-7
Standard-SMILES
CN(C)c1cc(NC(=O)CNC(C)(C)C)c(O)c2c1C[C@H]1C[C@H]3[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]3(O)C(=O)C1=C2O
InChIKey
FPZLLRFZJZRHSY-HJYUBDRYSA-N
Summenformel
C29H39N5O8
Durchschnittliche Molmasse
585,6 g/mol
Monoisotopische Masse
585,27986322

Überblick

Tigecycline is tetracycline in which the hydroxy group at position 5 and the methyl group at position 6 are replaced by hydrogen, and with a dimethylamino substituent and an (N-tert-butylglycyl)amino substituent at positions 7 and 9, respectively. A glycylcycline antibiotic, it has activity against a broad range of Gram-positive and Gram-negative bacteria, including tetracycline-resistant organisms. It is used for the intravenous treatment of complicated skin and skin structure infections caused by susceptible organisms. It has a role as an antibacterial drug. It is a tertiary alpha-hydroxy ketone and a member of tetracyclines. It is a conjugate base of a tigecycline(1+).

Namen und Bezeichner

Bevorzugter Name
Tigecycline
IUPAC
(4S,4aS,5aR,12aR)-9-[[2-(tert-butylamino)acetyl]amino]-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
Englischer Name
Tigecycline
Summenformel
C29H39N5O8
Molmasse
585.65

Namen und Synonyme

Tigecycline220620-09-7TygacilWAY-GAR-936TBG-MINOGAR-936GAR-936,TigecyclineTigilcyclineTygacil(TM)GAR 936Tygacil (TN)(4S,4aS,5aR,12aS)-9-(2-(tert-butylamino)acetamido)-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
Weitere Namen anzeigen
TigTigercycline(4s,4as,5ar,12as)-4,7-bis(dimethylamino)-9-[(tert-butylamino)acetamido]-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracen-2-carboxamideecycLCS-131TigecycLigecyclineTegecycline
tiglicyclineTigeciclinaDTXSID20485819-t-butylglycylamido-minocyclineMFCD00935753(4S,4aS,5aR,12aR)-9-[[2-(tert-butylamino)acetyl]amino]-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide(4S,4aS,5aR,12aS)-9-(2-(tert-butylamino)acetamido)-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamideTIGECYCLINE [EMA EPAR]

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,1
Polarare Oberfläche (TPSA)
206 Ų
H-Brücken-Donoren
7
H-Brücken-Akzeptoren
11
Frei drehbare Bindungen
7
Schwere Atome
42
Formalladung
0
Komplexität
1.240

Experimentelle und physikochemische Eigenschaften

Drugs · 3 Einträge

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Antibiotics

Physikochemische Eigenschaften

Schmelzpunkt
164 · 164-166°C
Siedepunkt
890.9 · 890.9±65.0 °C(Predicted)
Dichte
1.45 · 1.45±0.1 g/cm3(Predicted)
storage temp.
-20 °C · Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
Löslichkeit
Soluble in DMSO (up to at least 25 mg/ml).
pka
4.5 · 4.50±1.00(Predicted)
Aggregatzustand
Orange powder
Farbe
Orange
Merck
14 · 14,9432
Stabilität
1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.
InChIKey
FPZLLRFZJZRHSY-HJYUBDRYSA-N

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Sicherheitsdaten

wgk
WGK 3
ridadr
3077
hs_code
29419090
RTECS-Nr.
QI7619500
safety_code
24/25
hazard_class
9
packing_group
III
Speicherklasse
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Giftige Stoffe Daten
220620-09-7(Hazardous Substances Data)
Hazard Classifications
Aquatic Acute 1Aquatic Chronic 2Eye Dam. 1Repr. 1BSkin Sens. 1

Chemie und Industrie

Pharmakologische Informationen

ATC CodeJ01AA12
Protein Binding71% to 89%
Pharmacodynamics · 1 Eintrag

Tigecycline is the first clinically-available drug in a new class of antibiotics called the glycylcyclines. Glycylcyclines are a new class of antibiotics derived from tetracycline. These tetracycline analogues are specifically designed to overcome two common mechanisms of tetracycline resistance, namely resistance mediated by acquired efflux pumps and/or ribosomal protection. Glycylcycline antibiotics have a similar mechanism of action as tetracycline antibiotics. Both classes of antibiotics bind to the 30S ribosomal subunit to prevent the amino-acyl tRNA from binding to the A site of the ribosome. However, the glycylcyclines appear to bind more effectively than the tetracyclines.

Mechanism of Action · 1 Eintrag

Tigecycline, a glycylcycline, inhibits protein translation in bacteria by binding to the 30S ribosomal subunit and blocking entry of amino-acyl tRNA molecules into the A site of the ribosome. This prevents incorporation of amino acid residues into elongating peptide chains. Tigecycline carries a glycylamido moiety attached to the 9-position of minocycline. The substitution pattern is not present in any naturally occurring or semisynthetic tetracycline and imparts certain microbiologic properties to tigecycline. Tigecycline is not affected by the two major tetracycline resistance mechanisms, ribosomal protection and efflux. Accordingly, tigecycline has demonstrated in vitro and in vivo activity against a broad spectrum of bacterial pathogens. There has been no cross resistance observed between tigecycline and other antibiotics. Tigecycline is not affected by resistance mechanisms such as beta-lactamases (including extended spectrum beta-lactamases), target site modifications, macrolide efflux pumps or enzyme target changes (e.g. gyrase/topoisomerase). In vitro studies have not demonstrated antagonism between tigecycline and other commonly used antibacterial drugs. In general, tigecycline is considered bacteriostatic.

Biological Half-Life27-43 hours
Metabolism/Metabolites · 1 Eintrag

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Datenbank-Bezeichner

CAS
220620-09-7
PubChem CID
54686904
DTXSID
DTXSID2048581
ChEMBL
CHEMBL376140
ChEBI
CHEBI:149836
UNII
70JE2N95KR
Nikkaji
J1.112.522K
SMILES
C1(=O)[C@]2(O)[C@@]([H])(C[C@@]3([H])C(=C2O)C(=O)C2=C(C(N(C)C)=CC(NC(CNC(C)(C)C)=O)=C2O)C3)[C@H](N(C)C)C(O)=C1C(N)=O
CAS Datenbank
220620 · 220620-09-7(CAS DataBase Reference)

Tigecycline is not extensively metabolized. In vitro studies with tigecycline using human liver microsomes, liver slices, and hepatocytes led to the formation of only trace amounts of metabolites. A glucuronide, an N-acetyl metabolite, and a tigecycline epimer (each at no more than 10% of the administered dose) are the primary metabolites.

Anwendungen · 2 Einträge

BeschreibungThe emergence of drug-resistant bacteria has diminished the clinical utility of the tetracyclines. Research to circumvent the efflux and ribosomal protection mechanisms of bacteria has led to the development of the glycylcyclines. Tigecycline is the first glycylcycline antibiotic to launch for the parenteral treatment of baterial infection, including complicated intra-abdominal and skin infections. Its mechanism of action involves inhibiting protein translation in bacteria by binding to the 30S ribosomal subunit and blocking entry of amino-acyl tRNA molecules into the A site of the ribosome to effectively prevent incorporation of amino acid residues into elongating peptide chains. Presumably, ribosomal protection proteins are ineffective against tigecycline due to its higher affinity for ribosomal binding compared to tetracyclines (approximately 16-fold). In addition, tigecycline may be resistant to efflux mechanisms by either their inability to translocate it across the cytoplasmic membrane due to steric complications or simply by their failure to recognize the molecule.

VerwendenTigecycline is a semi-synthetic tetracycline prepared by the introduction of a tert-butylaminoacetamido group into a previously unexplored and un-substituted region of existing tetracyclines. Like other tetracyclines, tigecycline acts by reversibly binding to the 30S ribosomal subunit and inhibits protein translation by blocking entry of aminoacyl-tRNA into the ribosome A site. The enhanced activity can be attributed to stronger binding affinity, thus minimising the impact of existing mechanisms of resistance. Tigecycline is regarded as the first of a new class of glycylcyline antibiotics. Critical comparison to the tetracycline class appears to be lacking in the literature.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

156263-28-4N-t-Butylglycine sodium saltTigecycline Metabolite M6 (9-AniMoMinocycline)2-Methyl-2-propanaminN,N-DimethylacetamidNatriumiodid
Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: Tetracycline in which the hydroxy group at position 5 and the methyl group at position 6 are replaced by hydrogen, and with a dimethylamino substituent and an (N-tert-butylglycyl)amino substituent at positions 7 and 9, respe tively. A glycylcycline antibiotic, it has activity against a broad range of Gram-positive and Gram-negative bacteria, including tetracycline-resistant organisms. It is used for the intravenous treatment of complicated skin and skin structure infections ca sed by susceptible organisms.