Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Cyclacillin
- DrugBank Accession Number
- DB01000
- Background
A cyclohexylamido analog of penicillanic acid.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Cyclacillin (DB01000)
- Weight
- Average: 341.426
Monoisotopic: 341.140926929 - Chemical Formula
- C15H23N3O4S
- Synonyms
- (1-aminocyclohexyl)penicillin
- (2S,5R,6R)-6-{[(1-aminocyclohexyl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- 6-(1-aminocyclohexanecarboxamido)penicillanic acid
- 6-(1-aminocyclohexylcarboxamido)penicillanic acid
- Ciclacilina
- Ciclacillin
- Ciclacilline
- Ciclacillinum
- Cyclacillin
Pharmacology
- Indication
For the treatment of bacterial infections caused by susceptible organisms.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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 Cyclacillin has been replaced by newer penicillin treatments.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.
Target Actions Organism APenicillin-binding protein 1A inhibitorStreptococcus pneumoniae (strain ATCC BAA-255 / R6) APenicillin-binding protein 3 inhibitorStreptococcus pneumoniae APenicillin binding protein 2a inhibitorStaphylococcus aureus APenicillin-binding protein inhibitorGram positive and gram negative bacteria - Absorption
Moderately absorbed.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Symptoms of overdose include severe diarrhea, nausea and vomiting.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcemetacin Acemetacin may decrease the excretion rate of Cyclacillin which could result in a higher serum level. Acenocoumarol Cyclacillin may increase the anticoagulant activities of Acenocoumarol. Ambroxol The risk or severity of methemoglobinemia can be increased when Cyclacillin is combined with Ambroxol. Amikacin The serum concentration of Amikacin can be decreased when it is combined with Cyclacillin. Articaine The risk or severity of methemoglobinemia can be increased when Cyclacillin is combined with Articaine. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Bastcillin / Calthor / Citosarin / Cyclapen (Wyeth) / Cyclapen-W (Wyeth) / Syngacillin / Ultracillin / Vastcillin (Takeda) / Vipicil (Wyeth) / Wybital (Wyeth) / Wyvital
Categories
- ATC Codes
- J01CR50 — Combinations of penicillins
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Lactams
- Sub Class
- Beta lactams
- Direct Parent
- Penicillins
- Alternative Parents
- N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Cyclohexylamines / Thiazolidines / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Amino acids / Azetidines / Thiohemiaminal derivatives / Monocarboxylic acids and derivatives show 8 more
- Substituents
- Aliphatic heteropolycyclic compound / Alpha-amino acid amide / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Azacycle / Azetidine / Carbonyl group / Carboxamide group show 21 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- penicillin (CHEBI:31444)
- Affected organisms
- Enteric bacteria and other eubacteria
- Streptococcus pneumoniae
- Haemophilus influenzae
Chemical Identifiers
- UNII
- 72ZJ154X86
- CAS number
- 3485-14-1
- InChI Key
- HGBLNBBNRORJKI-WCABBAIRSA-N
- InChI
- 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
- IUPAC Name
- (2S,5R,6R)-6-(1-aminocyclohexaneamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- SMILES
- [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1(N)CCCCC1)C(O)=O
References
- Synthesis Reference
Alburn, H.E., Grant, N.H. and Fletcher, H. Ill; US.Patent 3,194,802; assigned to American Home Products Corporation. Robinson, C.A. and Nescio, J.J.; US.Patent 3,478,018; November 11,1969; assigned to American Home Products Corporation.
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015135
- KEGG Drug
- D01334
- KEGG Compound
- C12766
- PubChem Compound
- 19003
- PubChem Substance
- 46508073
- ChemSpider
- 17941
- BindingDB
- 50350474
- 2968
- ChEBI
- 31444
- ChEMBL
- CHEMBL1200356
- ZINC
- ZINC000003830609
- Therapeutic Targets Database
- DAP001159
- PharmGKB
- PA164743456
- Wikipedia
- Ciclacillin
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data
Pharmacoeconomics
- Manufacturers
- Wyeth ayerst laboratories
- Teva pharmaceuticals usa inc
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 182-183 °C PhysProp logP 1.31 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 1.9 mg/mL ALOGPS logP 0.56 ALOGPS logP -1.9 Chemaxon logS -2.3 ALOGPS pKa (Strongest Acidic) 3.3 Chemaxon pKa (Strongest Basic) 8.45 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 112.73 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 84.22 m3·mol-1 Chemaxon Polarizability 34.89 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.947 Blood Brain Barrier - 0.9961 Caco-2 permeable - 0.8171 P-glycoprotein substrate Substrate 0.7143 P-glycoprotein inhibitor I Non-inhibitor 0.9153 P-glycoprotein inhibitor II Non-inhibitor 0.997 Renal organic cation transporter Non-inhibitor 0.9488 CYP450 2C9 substrate Non-substrate 0.8429 CYP450 2D6 substrate Non-substrate 0.825 CYP450 3A4 substrate Non-substrate 0.5 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.8594 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9839 Ames test Non AMES toxic 0.8339 Carcinogenicity Non-carcinogens 0.8335 Biodegradation Not ready biodegradable 0.9667 Rat acute toxicity 1.8643 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9994 hERG inhibition (predictor II) Non-inhibitor 0.8895
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0002-9110000000-880dc522fc28c1bba7cb Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-001l-2903000000-f415e0b665a8687bc221 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03dj-0490000000-d3dd5d6b6a1f6128cfca Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0lea-2900000000-b1e74bcbb6952605d13d Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0h2e-3952000000-299df981132e1723f3d4 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0bta-3901000000-0805bf556882a895abe7 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-00dl-5931000000-797dae9e12f867ae15e7 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 182.0519692 predictedDarkChem Lite v0.1.0 [M-H]- 183.5814692 predictedDarkChem Lite v0.1.0 [M-H]- 184.36284 predictedDeepCCS 1.0 (2019) [M+H]+ 181.4028692 predictedDarkChem Lite v0.1.0 [M+H]+ 183.7705692 predictedDarkChem Lite v0.1.0 [M+H]+ 186.72084 predictedDeepCCS 1.0 (2019) [M+Na]+ 181.2904692 predictedDarkChem Lite v0.1.0 [M+Na]+ 193.69182 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Cell wall formation.
- Specific Function
- penicillin binding
- Gene Name
- pbpA
- Uniprot ID
- Q8DR59
- Uniprot Name
- Penicillin-binding protein 1A
- Molecular Weight
- 79700.9 Da
References
- Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [Article]
- Kind
- Protein
- Organism
- Streptococcus pneumoniae
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors.
- Specific Function
- serine-type D-Ala-D-Ala carboxypeptidase activity
- Gene Name
- pbp3
- Uniprot ID
- Q75Y35
- Uniprot Name
- Penicillin-binding protein 3
- Molecular Weight
- 45209.84 Da
References
- Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [Article]
- Kind
- Protein
- Organism
- Staphylococcus aureus
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Not Available
- Specific Function
- penicillin binding
- Gene Name
- mecA
- Uniprot ID
- C1KC03
- Uniprot Name
- Penicillin binding protein 2a
- Molecular Weight
- 54918.915 Da
References
- Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [Article]
- Kind
- Protein group
- Organism
- Gram positive and gram negative bacteria
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors.
- Specific Function
- beta-lactamase activity
Components:
References
- Murphy TF, Barza M, Park JT: Penicillin-binding proteins in Clostridium perfringens. Antimicrob Agents Chemother. 1981 Dec;20(6):809-13. doi: 10.1128/aac.20.6.809. [Article]
- Park M, Rafii F: Exposure to beta-lactams results in the alteration of penicillin-binding proteins in Clostridium perfringens. Anaerobe. 2017 Jun;45:78-85. doi: 10.1016/j.anaerobe.2017.02.004. Epub 2017 Feb 7. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine (PubMed:10454528, PubMed:10525100, PubMed:10966938, PubMed:17509700, PubMed:20722056, PubMed:33124720). Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 11.3 (PubMed:10454528, PubMed:10525100, PubMed:10966938). In intestinal epithelia, transports the quorum-sensing pentapeptide CSF (competence and sporulation factor) from Bacillus Subtilis wich induces cytoprotective heat shock proteins contributing to intestinal homeostasis (PubMed:18005709). May also contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable)
- Specific Function
- (R)-carnitine transmembrane transporter activity
- Gene Name
- SLC22A5
- Uniprot ID
- O76082
- Uniprot Name
- Organic cation/carnitine transporter 2
- Molecular Weight
- 62751.08 Da
References
- Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Electrogenic proton-coupled amino-acid transporter that transports oligopeptides of 2 to 4 amino acids with a preference for dipeptides. Transports neutral and monovalently charged peptides with a proton to peptide stoichiometry of 1:1 or 2:1 (By similarity) (PubMed:15521010, PubMed:18367661, PubMed:19685173, PubMed:26320580, PubMed:7896779, PubMed:8914574, PubMed:9835627). Primarily responsible for the absorption of dietary di- and tripeptides from the small intestinal lumen (By similarity). Mediates transepithelial transport of muramyl and N-formylated bacterial dipeptides contributing to recognition of pathogenic bacteria by the mucosal immune system (PubMed:15521010, PubMed:9835627)
- Specific Function
- dipeptide transmembrane transporter activity
- Gene Name
- SLC15A1
- Uniprot ID
- P46059
- Uniprot Name
- Solute carrier family 15 member 1
- Molecular Weight
- 78805.265 Da
References
- Ganapathy ME, Brandsch M, Prasad PD, Ganapathy V, Leibach FH: Differential recognition of beta -lactam antibiotics by intestinal and renal peptide transporters, PEPT 1 and PEPT 2. J Biol Chem. 1995 Oct 27;270(43):25672-7. [Article]
- Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [Article]
- Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Proton-coupled amino-acid transporter that transports oligopeptides of 2 to 4 amino acids with a preference for dipeptides (PubMed:16434549, PubMed:18367661, PubMed:7756356). Transports neutral and anionic dipeptides with a proton to peptide stoichiometry of 2:1 or 3:1 (By similarity). In kidney, involved in the absorption of circulating di- and tripeptides from the glomerular filtrate (PubMed:7756356). Can also transport beta-lactam antibiotics, such as the aminocephalosporin cefadroxil, and other antiviral and anticancer drugs (PubMed:16434549). Transports the dipeptide-like aminopeptidase inhibitor bestatin (By similarity). Also able to transport carnosine (PubMed:31073693). Involved in innate immunity by promoting the detection of microbial pathogens by NOD-like receptors (NLRs) (By similarity). Mediates transport of bacterial peptidoglycans across the plasma membrane or, in macrophages, the phagosome membrane: catalyzes the transport of certain bacterial peptidoglycans, such as muramyl dipeptide (MDP), the NOD2 ligand (PubMed:20406817)
- Specific Function
- dipeptide transmembrane transporter activity
- Gene Name
- SLC15A2
- Uniprot ID
- Q16348
- Uniprot Name
- Solute carrier family 15 member 2
- Molecular Weight
- 81782.77 Da
References
- Ganapathy ME, Brandsch M, Prasad PD, Ganapathy V, Leibach FH: Differential recognition of beta -lactam antibiotics by intestinal and renal peptide transporters, PEPT 1 and PEPT 2. J Biol Chem. 1995 Oct 27;270(43):25672-7. [Article]
- Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [Article]
- Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 02, 2024 21:48