Identification
- Summary
Cefacetrile is a broad-spectrum first-generation cephalosporin used for the treatment of susceptible bacterial infections.
- Generic Name
- Cefacetrile
- DrugBank Accession Number
- DB01414
- Background
A derivative of 7-aminocephalosporanic acid.
- Type
- Small Molecule
- Groups
- Experimental, Vet approved
- Structure
Structure for Cefacetrile (DB01414)
- Weight
- Average: 339.324
Monoisotopic: 339.052505853 - Chemical Formula
- C13H13N3O6S
- Synonyms
- Cefacetrile
- Cefacetrilo
- Cefacetrilum
- Cephacetrile
Pharmacology
- Indication
Cefacetrile is a broad-spectrum first generation cephalosporin antibiotic effective in Gram-positive and Gram-negative bacterial infections.
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Cefacetrile is effective against many Gram-positive bacterial strains and somewhat less effective against Gram-negative species. It works by inhibition of bacterial cell wall synthesis. It attains high serum levels and is excreted quickly via the urine.
- Mechanism of action
In vitro tests demonstrate that the bactericidal action of cephalosporins results from inhibition of cell wall synthesis. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins.
Target Actions Organism APenicillin-binding protein 1A inhibitorEscherichia coli (strain K12) APenicillin-binding protein 1B inhibitorEscherichia coli (strain K12) - Absorption
Not Available
- Volume of distribution
Vd of 0.2 to 0.5L/.kg
- Protein binding
23 to 38%
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
1.2 hours
- Clearance
Not Available
- Adverse Effects
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Not Available
- 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 softwareAbacavir Cefacetrile may decrease the excretion rate of Abacavir which could result in a higher serum level. Abciximab The therapeutic efficacy of Abciximab can be decreased when used in combination with Cefacetrile. Acamprosate The excretion of Acamprosate can be decreased when combined with Cefacetrile. Aceclofenac The risk or severity of nephrotoxicity can be increased when Cefacetrile is combined with Aceclofenac. Acemetacin The risk or severity of nephrotoxicity can be increased when Cefacetrile is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding can be increased when Cefacetrile is combined with Acenocoumarol. Acetaminophen Cefacetrile may decrease the excretion rate of Acetaminophen which could result in a higher serum level. Acetazolamide The excretion of Cefacetrile can be decreased when combined with Acetazolamide. Acetylsalicylic acid The excretion of Cefacetrile can be decreased when combined with Acetylsalicylic acid. Aclidinium Cefacetrile may decrease the excretion rate of Aclidinium which could result in a higher serum level. 
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- Not Available
Products
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Ingredient UNII CAS InChI Key Cefacetrile sodium 87TH1FJY1N 23239-41-0 GXCRUTWHNMMJEK-WYUVZMMLSA-M - International/Other Brands
- Celospor (Ciba) / Celtol (Takeda)
Categories
- ATC Codes
- J01DB10 — Cefacetrile
- Drug Categories
- Amides
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- beta-Lactams
- Cephalosporins
- First-Generation Cephalosporins
- Heterocyclic Compounds, Fused-Ring
- Lactams
- Nephrotoxic agents
- OAT1/SLC22A6 inhibitors
- OAT1/SLC22A6 Substrates
- OAT3/SLC22A8 Inhibitors
- OAT3/SLC22A8 Substrates
- Sulfur Compounds
- Thiazines
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as cephalosporin 3'-esters. These are cephalosporins that are esterified at the 3'-position.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Lactams
- Sub Class
- Beta lactams
- Direct Parent
- Cephalosporin 3'-esters
- Alternative Parents
- N-acyl-alpha amino acids and derivatives / 1,3-thiazines / Dicarboxylic acids and derivatives / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Azetidines / Carboxylic acid esters / Thiohemiaminal derivatives / Azacyclic compounds / Nitriles show 6 more
- Substituents
- Aliphatic heteropolycyclic compound / Alpha-amino acid or derivatives / Azacycle / Azetidine / Carbonitrile / Carbonyl group / Carboxamide group / Carboxylic acid / Carboxylic acid derivative / Carboxylic acid ester show 17 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- FDM21QQ344
- CAS number
- 10206-21-0
- InChI Key
- RRYMAQUWDLIUPV-BXKDBHETSA-N
- InChI
- InChI=1S/C13H13N3O6S/c1-6(17)22-4-7-5-23-12-9(15-8(18)2-3-14)11(19)16(12)10(7)13(20)21/h9,12H,2,4-5H2,1H3,(H,15,18)(H,20,21)/t9-,12-/m1/s1
- IUPAC Name
- (6R,7R)-3-[(acetyloxy)methyl]-7-(2-cyanoacetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- SMILES
- [H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)CC#N)C(O)=O
References
- Synthesis Reference
Bickel, H., Bosshardt, R., Fechtig, B., Schenker, K. and Urech, J.; U.S. Patent 3,483,197; December 9,1969; assigned to Ciba Corporation.
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015484
- KEGG Drug
- D07629
- PubChem Compound
- 91562
- PubChem Substance
- 46504767
- ChemSpider
- 82675
- ChEBI
- 135437
- ChEMBL
- CHEMBL2110602
- ZINC
- ZINC000003830496
- Therapeutic Targets Database
- DAP001172
- PharmGKB
- PA164776752
- Wikipedia
- Cefacetrile
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 168-170 Bickel, H., Bosshardt, R., Fechtig, B., Schenker, K. and Urech, J.; U.S. Patent 3,483,197; December 9,1969; assigned to Ciba Corporation. logP -0.45 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 2.43 mg/mL ALOGPS logP -0.52 ALOGPS logP -1.8 Chemaxon logS -2.2 ALOGPS pKa (Strongest Acidic) 3.11 Chemaxon pKa (Strongest Basic) -6.2 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 136.8 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 77.51 m3·mol-1 Chemaxon Polarizability 31.34 Å3 Chemaxon Number of Rings 2 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 - 0.9435 Blood Brain Barrier - 0.9965 Caco-2 permeable - 0.754 P-glycoprotein substrate Substrate 0.7774 P-glycoprotein inhibitor I Non-inhibitor 0.7686 P-glycoprotein inhibitor II Non-inhibitor 0.9626 Renal organic cation transporter Non-inhibitor 0.9013 CYP450 2C9 substrate Non-substrate 0.7919 CYP450 2D6 substrate Non-substrate 0.823 CYP450 3A4 substrate Non-substrate 0.5 CYP450 1A2 substrate Non-inhibitor 0.8122 CYP450 2C9 inhibitor Non-inhibitor 0.8282 CYP450 2D6 inhibitor Non-inhibitor 0.9145 CYP450 2C19 inhibitor Non-inhibitor 0.8132 CYP450 3A4 inhibitor Non-inhibitor 0.9152 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8735 Ames test Non AMES toxic 0.6895 Carcinogenicity Non-carcinogens 0.9237 Biodegradation Not ready biodegradable 0.9705 Rat acute toxicity 1.8811 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9933 hERG inhibition (predictor II) Non-inhibitor 0.9062
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Serine-type d-ala-d-ala carboxypeptidase activity
- Specific Function
- Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan str...
- Gene Name
- mrcA
- Uniprot ID
- P02918
- Uniprot Name
- Penicillin-binding protein 1A
- Molecular Weight
- 93635.545 Da
References
- Yotsuji A, Mitsuyama J, Hori R, Yasuda T, Saikawa I, Inoue M, Mitsuhashi S: Mechanism of action of cephalosporins and resistance caused by decreased affinity for penicillin-binding proteins in Bacteroides fragilis. Antimicrob Agents Chemother. 1988 Dec;32(12):1848-53. [Article]
- Truesdell SE, Zurenko GE, Laborde AL: Interaction of cephalosporins with penicillin-binding proteins of methicillin-resistant Staphylococcus aureus. J Antimicrob Chemother. 1989 Apr;23 Suppl D:13-9. [Article]
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Serine-type d-ala-d-ala carboxypeptidase activity
- Specific Function
- Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan str...
- Gene Name
- mrcB
- Uniprot ID
- P02919
- Uniprot Name
- Penicillin-binding protein 1B
- Molecular Weight
- 94291.875 Da
References
- Truesdell SE, Zurenko GE, Laborde AL: Interaction of cephalosporins with penicillin-binding proteins of methicillin-resistant Staphylococcus aureus. J Antimicrob Chemother. 1989 Apr;23 Suppl D:13-9. [Article]
- Yotsuji A, Mitsuyama J, Hori R, Yasuda T, Saikawa I, Inoue M, Mitsuhashi S: Mechanism of action of cephalosporins and resistance caused by decreased affinity for penicillin-binding proteins in Bacteroides fragilis. Antimicrob Agents Chemother. 1988 Dec;32(12):1848-53. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [Article]
- Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [Article]
- Jung KY, Takeda M, Shimoda M, Narikawa S, Tojo A, Kim DK, Chairoungdua A, Choi BK, Kusuhara H, Sugiyama Y, Sekine T, Endou H: Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. Life Sci. 2002 Mar 8;70(16):1861-74. [Article]
- Uwai Y, Saito H, Inui K: Rat renal organic anion transporter rOAT1 mediates transport of urinary-excreted cephalosporins, but not of biliary-excreted cefoperazone. Drug Metab Pharmacokinet. 2002;17(2):125-9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
- Gene Name
- SLC22A8
- Uniprot ID
- Q8TCC7
- Uniprot Name
- Solute carrier family 22 member 8
- Molecular Weight
- 59855.585 Da
References
- Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [Article]
- Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [Article]
- Jung KY, Takeda M, Shimoda M, Narikawa S, Tojo A, Kim DK, Chairoungdua A, Choi BK, Kusuhara H, Sugiyama Y, Sekine T, Endou H: Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. Life Sci. 2002 Mar 8;70(16):1861-74. [Article]
- Uwai Y, Saito H, Inui K: Rat renal organic anion transporter rOAT1 mediates transport of urinary-excreted cephalosporins, but not of biliary-excreted cefoperazone. Drug Metab Pharmacokinet. 2002;17(2):125-9. [Article]
Drug created at July 23, 2007 12:31 / Updated at June 12, 2021 10:52