Grundinformationen
- CAS
3485-14-1- Standard-SMILES
CC1(C)S[C@@H]2[C@H](NC(=O)C3(N)CCCCC3)C(=O)N2[C@H]1C(=O)O- InChIKey
HGBLNBBNRORJKI-WCABBAIRSA-N- Summenformel
- C15H23N3O4S
- Durchschnittliche Molmasse
- 341,4 g/mol
- Monoisotopische Masse
- 341,1409274
Namen und Bezeichner
- Bevorzugter Name
- Cyclacillin
- IUPAC
- (2S,5R,6R)-6-[(1-aminocyclohexanecarbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- Lokaler Name
- Ciclacillin
- Englischer Name
- CYCLACILLIN (200 MG)
- Summenformel
- C15H23N3O4S
- Molmasse
- 341.43
Namen und Synonyme
CYCLACILLINciclacillinVastcillin3485-14-1AminocyclohexylpenicillinBastcillinCyclapenUltracillinWyvitalCitosarinSyngacillinCalthor
Weitere Namen anzeigen
wy4508VatracinNSC 88789CICLACILIN
VipicilCyclapen-WCiclacillineCiclacillinumCiclacilina(1-Aminocyclohexyl)penicillinWy-45086-(1-Aminocyclohexanecarboxamido)penicillanic acid
Datenbank-Bezeichner
- CAS
3485-14-1- PubChem CID
- 19003
- DTXSID
DTXSID9022861- ChEMBL
CHEMBL1200356- ChEBI
CHEBI:31444- UNII
- 72ZJ154X86
- EC Number
- 222-470-8
- Nikkaji
- J3.403G
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,3
- Polarare Oberfläche (TPSA)
- 138 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 6
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 23
- Formalladung
- 0
- Komplexität
- 559
Experimentelle und physikochemische Eigenschaften
LogP
1.31
0.4
Solubility1.90e+00 g/L
Melting Point182-183 °C
Physical DescriptionSolid
Dissociation Constants2.68
Physikochemische Eigenschaften
- Schmelzpunkt
- 182 · 182-183° (anhydrate) (Hou, Poole); mp 156-158° (dec) (Alburn et al.)
- Siedepunkt
- 649.6 · 649.6±55.0 °C(Predicted)
- Dichte
- 1.4 · 1.40±0.1 g/cm3(Predicted)
- Löslichkeit
- Aqueous Acid (Slightly), DMSO (Slightly), Methanol (Slightly)
- Aggregatzustand
- Solid
- pka
- 1 · pK1, pK2 in water: 2.68, 7.50; in 50% dioxane: 4.16, 7.04(at 25℃)
- Farbe
- White to Off-White
Chemie und Industrie
Pharmakologische Informationen
Pharmacodynamics
Cyclacillin, a penicillin, is a cyclohexylamido analog of penicillanic acid. Cyclacillin is more resistant to beta-lactamase hydrolysis than ampicillin, is much better absorbed when given by mouth and, as a result, the levels reached in the blood and in the urine are considerably higher than those obtained with the same dose of ampicillin. Cyclacillin has been replaced by newer penicillin treatments.
Mechanism of Action
The bactericidal activity of cyclacillin results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs). Cyclacillin is stable in the presence of a variety of b-lactamases, including penicillinases and some cephalosporinases.
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and ExcretionModerately absorbed.
Cellular LocationsCytoplasm；Membrane
Anwendungen
BeschreibungCiclacillin was synthesized by Wyeth Laboratories in 1967 in the course of studies on the improvement of oral absorption of ampicillin. Although its antibacterial activity is one-sixteenth to one-half that of ampicillin, it shows a four to tenfold higher oral absorption and higher urinary excretion. Ciclacillin shows less tendency than ampicillin to cause diarrhea and is used for therapy of pyoderma, wound infection, respiratory and urinary tract infections, as well as ear and nose, and other infections caused by Staphylococcus, Streptococcus, Escherichia coli, Citrobacter, Klebsiella, Proteus, and Haemophilus influenzae.
VerwendenAntibacterial.
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