Grundinformationen
- CAS
73384-59-5- Standard-SMILES
CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(CSc3nc(=O)c(=O)[nH]n3C)CS[C@H]12)c1csc(N)n1- InChIKey
VAAUVRVFOQPIGI-SPQHTLEESA-N- Summenformel
- C18H18N8O7S3
- Durchschnittliche Molmasse
- 554,6 g/mol
- Monoisotopische Masse
- 554,04605846
Überblick
Ceftriaxone is a third-generation cephalosporin compound having 2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetylamino and [(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl side-groups. It has a role as an EC 3.5.2.6 (beta-lactamase) inhibitor, an antibacterial drug and a drug allergen. It is a cephalosporin, an oxime O-ether, a member of 1,3-thiazoles and a member of 1,2,4-triazines. It is a conjugate acid of a ceftriaxone(1-).
Namen und Bezeichner
- Bevorzugter Name
- Ceftriaxone
- IUPAC
- (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(2-methyl-5,6-dioxo-1H-1,2,4-triazin-3-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- Lokaler Name
- Ceftriaxon
- Englischer Name
- CEFTRIAXONE
- Summenformel
- C18H18N8O7S3
- Molmasse
- 554.58
Namen und Synonyme
ceftriaxone73384-59-5RocephinBiotraksonCeftriaxonaCeftriaxonCeftriaxonumCeftriazoneRocephineRocefinCefatriaxoneCHEBI:29007
Weitere Namen anzeigen
Ceftriazone sodiuMCeftriaxone Sodium Ep Impurity ARocephin(e)Cefatriaxone FromRo 13-9904 free acid
(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(2-methyl-5,6-dioxo-1H-1,2,4-triazin-3-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid75J73V1629DTXSID0022773Rocefalin(6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-8-oxo-3-(((1,2,5,6-tetrahydro-2-methyl-5,6-dioxo-1,2,4-triazin-3-yl)thio)methyl)-, (6R-(6alpha,7beta(Z)))-Anhydrous Ceftriaxone Sodium(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Datenbank-Bezeichner
- CAS
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -1,3
- Polarare Oberfläche (TPSA)
- 288 Ų
- H-Brücken-Donoren
- 4
- H-Brücken-Akzeptoren
- 13
- Frei drehbare Bindungen
- 8
- Schwere Atome
- 36
- Formalladung
- 0
- Komplexität
- 1.110
Experimentelle und physikochemische Eigenschaften
Drugs
Pharmaceuticals -> Used in Switzerland
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
LogP-1.7
Solubility1.05e-01 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Cephalosporins
Medicines for bacterial central nervous system infections
Melting Point
>155 °C
> 155 °C
Physical DescriptionSolid
Collision Cross Section215.06 Ų [M+H]+
Physikochemische Eigenschaften
- Schmelzpunkt
- 155 °C · 155 °C
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Danger
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P233, P260, P261, P264, P264+P265, P271, P272, P280, P284, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 5 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Toxikologische Informationen
TreatmentIn the case of overdosage, drug concentration would not be reduced by hemodialysis or peritoneal dialysis. There is no specific antidote. Treatment of overdosage should be symptomatic (RxList, A308).
Health Effects
Some observed adverse reactions ( < 0.1%) include abdominal pain, agranulocytosis, allergic pneumonitis, anaphylaxis, basophilia, biliary lithiasis, bronchospasm, colitis, dyspepsia, epistaxis, flatulence, gallbladder sludge, glycosuria, hematuria, jaundice, leukocytosis, lymphocytosis, monocytosis, nephrolithiasis, palpitations, a decrease in the prothrombin time, renal precipitations, seizures, and serum sickness (RxList, A308).
Hepatotoxicity
Parenteral administration of ceftriaxone has been associated with development of biliary sludge in 3% to 46% of patients. The incidence may be higher in children than adults and is associated with higher doses and longer courses of treatment and possibly with fasting or dehydration. The syndrome is referred to as “pseudolithiasis” as the sludge and stones consist largely of ceftriaxone and they resolve spontaneously when the drug is stopped, indicating that surgery can be avoided. Most cases occur with minimal or no symptoms. Frank symptoms of cholecystitis are reported in up to 5% of patients who develop pseudo-lithiasis. Typically, serum enzymes and bilirubin levels remain normal even with biliary colic, but in rare instances there is cholestatic jaundice or gallstone pancreatitis that can be severe and require surgical intervention. Sludge and symptoms of gallbladder disease can arise within a few days of starting therapy, but typically resolve rapidly once ceftriaxone is stopped, although sludge and gallstones may be detectable by ultrasound for several months.
Chemie und Industrie
Pharmakologische Informationen
ATC Code
J01DD04
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
J01DD04
Protein BindingCeftriaxone is 95% protein bound.
Pharmacodynamics
Ceftriaxone is a cephalosporin/cephamycin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. Ceftriaxone has <i>in vitro</i> activity against gram-positive aerobic, gram-negative aerobic, and anaerobic bacteria. The bactericidal activity of ceftriaxone results from the inhibition of cell wall synthesis and is mediated through ceftriaxone binding to penicillin-binding proteins (PBPs). Ceftriaxone is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended-spectrum beta-lactamases. However, resistance to ceftriaxone usually occurs through beta-lactamase hydrolysis, altered PBPs, or reduced bacterial cell permeability. Ceftriaxone should not be mixed with or giving in the same IV line as diluents/products containing calcium as they may cause ceftriaxone to precipitate. Ceftriaxone use may also cause biliary sludge or gallbladder pseudolithiasis.
Mechanism of Action
Ceftriaxone works by inhibiting the mucopeptide synthesis in the bacterial cell wall. The beta-lactam moiety of ceftriaxone binds to carboxypeptidases, endopeptidases, and transpeptidases in the bacterial cytoplasmic membrane. These enzymes are involved in cell-wall synthesis and cell division. Binding of ceftriaxone to these enzymes causes the enzyme to lose activity; therefore, the bacteria produce defective cell walls, causing cell death.
Biological Half-LifeThe elimination half-life of ceftriaxone is 5.8-8.7 hours. The half-life of ceftriaxone in the middle ear fluid has been estimated to be 25 hours.
Metabolism/Metabolites
Metabolism of ceftriaxone is negligible.
Ceftriaxone is eliminated unchanged in the urine by glomerular filtration (60%) and bile (40%) (A633). Route of Elimination: Thirty-three percent to 67% of a ceftriaxone dose was excreted in the urine as unchanged drug and the remainder was secreted in the bile and ultimately found in the feces as microbiologically inactive compounds. Half Life: 5.8-8.7 hours
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