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Basic information
- 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- Molecular formula
- C15H23N3O4S
- Average molar mass
- 341.4 g/mol
- Monoisotopic mass
- 341.1409274
Names & identifiers
- Preferred 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
- English name
- CYCLACILLIN (200 MG)
- Molecular formula
- C15H23N3O4S
- Molecular weight
- 341.43
Names & synonyms
CYCLACILLINciclacillinVastcillin3485-14-1AminocyclohexylpenicillinBastcillinCyclapenUltracillinWyvitalCitosarinSyngacillinCalthor
Show more names
wy4508VatracinNSC 88789CICLACILIN
VipicilCyclapen-WCiclacillineCiclacillinumCiclacilina(1-Aminocyclohexyl)penicillinWy-45086-(1-Aminocyclohexanecarboxamido)penicillanic acid
Database identifiers
- CAS
3485-14-1- PubChem CID
- 19003
- DTXSID
DTXSID9022861- ChEMBL
CHEMBL1200356- ChEBI
CHEBI:31444- UNII
- 72ZJ154X86
- EC Number
- 222-470-8
- Nikkaji
- J3.403G
Properties
Computed structural propertiesFilling in
- XLogP
- 1.3
- Topological polar surface area
- 138 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 3
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 559
Experimental & physicochemical properties
LogP
1.31
0.4
Solubility1.90e+00 g/L
Melting Point182-183 °C
Physical DescriptionSolid
Dissociation Constants2.68
Physicochemical properties
- Melting point
- 182 · 182-183° (anhydrate) (Hou, Poole); mp 156-158° (dec) (Alburn et al.)
- alpha
- 25 · D25 +268° (water)
- Boiling point
- 649.6 · 649.6±55.0 °C(Predicted)
- Density
- 1.4 · 1.40±0.1 g/cm3(Predicted)
- solubility
- Aqueous Acid (Slightly), DMSO (Slightly), Methanol (Slightly)
- pka
- 1 · pK1, pK2 in water: 2.68, 7.50; in 50% dioxane: 4.16, 7.04(at 25℃)
- form
- Solid
Chemistry & industry
Pharmacology
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 Cyclacillin has been replaced by newer penicillin treatments.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
Applications
DescriptionCiclacillin 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.
UsesAntibacterial.
UsesCyclacillin is an aminosalicylic semisynthetic penicillin; Antibiotic.
Upstream & downstream products
Related reactions
1 records
Compound notes
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