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| Targets |
Cyclacillin targets bacterial cell wall synthesis by binding to specific penicillin-binding proteins (PBPs). This binding inhibits the transpeptidation reaction during peptidoglycan synthesis, a critical step in bacterial cell wall formation. By disrupting cell wall integrity, Cyclacillin leads to bacterial lysis and cell death. Its mechanism is bactericidal. The compound is a β-lactam antibiotic.
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| ln Vitro |
Cyclacillin (0-125 μg/mL) suppresses a number of infections excluding Klebsiella and Enterobacteriaceae, with MIC values ranging from 0.24 μg/mL to 7.8 μg/mL[1].
In vitro, Cyclacillin displays broad-spectrum antimicrobial activity against a range of Gram-positive and Gram-negative bacteria. As a penicillin derivative, it is expected to be effective against susceptible strains of Streptococcus, Staphylococcus, and various Gram-negative organisms. Its in vitro activity is typically assessed by determining the minimum inhibitory concentration (MIC) against clinical isolates. |
| ln Vivo |
Mice given a single dose of cyclacillin (0–287 mg/kg) exhibit oral activity and recover from injections of both Gram-positive and Gram-negative bacteria [1]. Rat intestinal tissue absorbs cicracillin (10 mg/kg; intravenous injection; single dose) at comparatively low concentrations (less than 1 mg/mL), exhibiting solely Michaelis-Menten kinetics [2].
In vivo, Cyclacillin is effective in treating bacterial infections in animal models and has been used clinically for various infections. It is an orally bioactive antibiotic. The compound's in vivo efficacy is related to its ability to achieve therapeutic concentrations in plasma and tissues, as well as its bactericidal activity against the infecting organisms. |
| Enzyme Assay |
In cell-free assays, Cyclacillin's activity is evaluated by measuring its ability to inhibit the transpeptidase activity of penicillin-binding proteins (PBPs). Purified PBPs are incubated with a fluorescent or radiolabeled substrate in the presence of varying concentrations of Cyclacillin. The inhibition of substrate binding or enzymatic activity is measured, and the IC50 or binding affinity is calculated.
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| Cell Assay |
In vitro cell-based experiments with Cyclacillin involve standard antimicrobial susceptibility testing using the broth microdilution method. Bacterial cultures (e.g., Staphylococcus aureus, Escherichia coli) are grown in Mueller-Hinton broth and incubated with serial two-fold dilutions of the antibiotic in 96-well plates. After 16-20 hours of incubation at 35°C, the minimum inhibitory concentration (MIC) is determined as the lowest concentration that inhibits visible bacterial growth.
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| Animal Protocol |
In vivo animal experiments with Cyclacillin typically involve mouse models of systemic infection. Mice are infected with a lethal dose of a pathogenic bacterium (e.g., Streptococcus pneumoniae or Escherichia coli) and then treated with Cyclacillin administered orally or parenterally at various doses. The survival rate is monitored over a period of several days, and the 50% effective dose (ED50) is calculated.
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| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
Moderate absorption. Cyclacillin is an orally bioavailable aminopenicillin. It was designed to offer enhanced oral bioavailability and improved patient compliance compared to traditional penicillins. Its pharmacokinetic properties include good absorption from the gastrointestinal tract and distribution to various tissues. The compound is excreted primarily via the kidneys. No specific PK parameters (e.g., half-life, Cmax) are provided in the search results. |
| Toxicity/Toxicokinetics |
Cyclacillin is generally well-tolerated as a penicillin antibiotic. Common adverse effects may include gastrointestinal disturbances, hypersensitivity reactions (including rash and anaphylaxis), and, rarely, hematological effects. As with other penicillins, it is contraindicated in patients with a history of penicillin allergy. The compound is for research use only and is not intended for human therapeutic use outside of approved indications.
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| References |
[1]. Warren GH. Cyclacillin: microbiological and pharmacological properties and use in chemotherapy of infection - a critical appraisal. Chemotherapy. 1976;22(3-4):154-82.
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| Additional Infomation |
Cyclacillin is a penicillin antibiotic with antibacterial activity. It is a cyclohexylamide analog of penicillinic acid. Cyclacillin is a semi-synthetic β-lactam aminocyclohexylpenicillin antibiotic. Cyclacillin has bactericidal activity by binding to specific penicillin-binding proteins, thereby inhibiting transpeptidation during peptidoglycan synthesis. This leads to the disruption of bacterial cell wall structure, causing bacterial cell wall instability and ultimately cell lysis. Cyclacillin is sensitive to β-lactamases. It is a cyclohexylamide analog of penicillin. Indications: Used to treat bacterial infections caused by susceptible bacteria. Mechanism of Action: Cyclacillin's bactericidal activity derives from its affinity for penicillin-binding proteins (PBPs), thereby inhibiting cell wall synthesis. Cyclacillin is stable in the presence of various β-lactamases, including penicillinases and certain cephalosporinases. Pharmacodynamics: Cyclacillin is a penicillin, a cyclohexylamide analog of penicillinic acid. Compared to ampicillin, Cyclacillin is more resistant to β-lactamase hydrolysis and has a higher oral absorption rate. Therefore, at the same dose, the concentration of Cyclacillin in blood and urine is much higher than that of ampicillin. Cyclacillin has been replaced by newer penicillin drugs.
Cyclacillin is a semi-synthetic aminopenicillin antibiotic with a molecular formula of C15H23N3O4S and a molecular weight of 341.43. It is also known as Ciclacillin or Wy-4508. The compound is a derivative of ampicillin designed for improved oral bioavailability. It has been used in both human and veterinary medicine. It is available for research purposes only and is not currently marketed in many countries. |
| Molecular Formula |
C15H23N3O4S
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| Molecular Weight |
341.43
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| Exact Mass |
341.141
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| CAS # |
3485-14-1
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| PubChem CID |
19003
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| Appearance |
White to off-white solid powder
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| Density |
1.4g/cm3
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| Boiling Point |
649.6ºC at 760mmHg
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| Melting Point |
182-183° (anhydrate) (Hou, Poole); mp 156-158° (dec) (Alburn et al.)
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| Index of Refraction |
1.631
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| LogP |
1.308
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
23
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| Complexity |
559
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| Defined Atom Stereocenter Count |
3
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| SMILES |
CC1([C@@H](N2C([C@@H](NC(C3(N)CCCCC3)=O)[C@H]2S1)=O)C(O)=O)C
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| InChi Key |
HGBLNBBNRORJKI-WCABBAIRSA-N
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| InChi Code |
InChI=1S/C15H23N3O4S/c1-14(2)9(12(20)21)18-10(19)8(11(18)23-14)17-13(22)15(16)6-4-3-5-7-15/h8-9,11H,3-7,16H2,1-2H3,(H,17,22)(H,20,21)/t8-,9+,11-/m1/s1
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| Chemical Name |
(2S,5R,6R)-6-[(1-aminocyclohexanecarbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
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| Synonyms |
Bastcillin; CYCLACILLIN; Ciclacillin
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.9289 mL | 14.6443 mL | 29.2886 mL | |
| 5 mM | 0.5858 mL | 2.9289 mL | 5.8577 mL | |
| 10 mM | 0.2929 mL | 1.4644 mL | 2.9289 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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