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Identification
- Summary
Cefoperazone is a broad-spectrum cephalosporin antibiotic used for the treatment of bacterial infections in various locations, including the respiratory tract, abdomen, skin, and female genital tracts.
- Generic Name
- Cefoperazone
- DrugBank Accession Number
- DB01329
- Background
Cefoperazone is a semisynthetic broad-spectrum cephalosporin proposed to be effective against Pseudomonas infections. It is a third-generation antiobiotic agent and it is used in the treatment of various bacterial infections caused by susceptible organisms in the body, including respiratory tract infections, peritonitis, skin infections, endometritis, and bacterial septicemia. While its clinical use has been discontinued in the U.S., cefoperazone is available in several European countries most commonly under the product name, Sulperazon.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Cefoperazone (DB01329)
- Weight
- Average: 645.67
Monoisotopic: 645.142401213 - Chemical Formula
- C25H27N9O8S2
- Synonyms
- (6R,7R)-7-((R)-2-(4-Ethyl-2,3-dioxo-1-piperazinylcarboxamido)-2-(4-hydroxyphenyl)acetamido)-3-((1-methyl-1H-tetrazol-5-yl)thiomethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-2-carbonsaeure
- (6R,7R)-7-[[2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- Cefoperazone
- Cefoperazono
- Cefoperazonum
Pharmacology
- Indication
Indicated for the treatment of following infections caused by susceptible bacteria:Label
1) Respiratory tract infections caused by S. pneumoniae, H. influenzae, S. aureus (penicillinase and non-penicillinase producing strains), S. pyogenes (Group A beta-hemolytic streptococci), P. aeruginosa, Klebsiella pneumoniae, E. coli, Proteus mirabilis, and Enterobacter species.
2) Peritonitis and other intra-abdominal infections caused by E. coli, P. aeruginosa, and anaerobic gram-negative bacilli (including Bacteroides fragilis).
3) Bacterial septicemia caused by S. pneumoniae, S. agalactiae, S. aureus, Pseudomonas aeruginosa, E. coli, Klebsiella spp., Klebsiella pneumoniae, Proteus species (indole-positive and indole-negative), Clostridium spp. and anaerobic gram-positive cocci.
4) Infections of the skin and skin structures caused by S. aureus (penicillinase and non-penicillinase producing strains), S. pyogenes, and P. aeruginosa.
5) Pelvic Inflammatory Disease, Endometritis, and Other Infections of the Female Genital Tract caused by N. gonorrhoeae, S. epidermidis, S. agalactiae, E. coli, Clostridium spp., Bacteroides species (including Bacteroides fragilis), and anaerobic gram-positive cocci.
6) Urinary tract infections caused by Escherichia coli and Pseudomonas aeruginosa.
7) Enterococcal Infections. Although cefoperazone has been shown to be clinically effective in the treatment of infections caused by enterococci in cases of peritonitis and other intra-abdominal infections, infections of the skin and skin structures, pelvic inflammatory disease, endometritis and other infections of the female genital tract, and urinary tract infections, the majority of clinical isolates of enterococci tested are not susceptible to cefoperazone but fall just at or in the intermediate zone of susceptibility, and are moderately resistant to cefoperazone. However, in vitro susceptibility testing may not correlate directly with in vivo results. Despite this, cefoperazone therapy has resulted in clinical cures of enterococcal infections, chiefly in polymicrobial infections. Cefoperazone should be used in enterococcal infections with care and at doses that achieve satisfactory serum levels of cefoperazone.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Bacterial infections Combination Product in combination with: Sulbactam (DB09324) •••••••••••• Treatment of Bloodstream infections •••••••••••• Treatment of Bone and joint infections •••••••••••• Treatment of Intra-abdominal infections •••••••••••• Treatment of Lower respiratory tract infection (lrti) •••••••••••• - Contraindications & Blackbox Warnings
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Cefoperazone is a third generation cephalosporin antibiotic. Cefoperazone exerts its bactericidal effect by inhibiting the bacterial cell wall synthesis
- Mechanism of action
Like all beta-lactam antibiotics, cefoperazone binds to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, causing the inhibition of 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 APeptidoglycan synthase FtsI inhibitorEscherichia coli (strain K12) APenicillin-binding protein 1B inhibitorEscherichia coli (strain K12) APenicillin-binding protein 2 inhibitorEscherichia coli (strain K12) APenicillin-binding protein 1A inhibitorPseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228) APenicillin-binding protein 1B inhibitorPseudomonas aeruginosa AD-alanyl-D-alanine carboxypeptidase DacC inhibitorEscherichia coli (strain K12) APenicillin-binding protein 1A inhibitorEscherichia coli (strain K12) AD-alanyl-D-alanine carboxypeptidase DacA inhibitorEscherichia coli (strain K12) AD-alanyl-D-alanine carboxypeptidase DacB inhibitorEscherichia coli (strain K12) - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
The degree of reversible protein binding varies with the serum concentration from 93% at 25 mcg/mL to 90% at 250 mcg/mL and 82% at 500 mcg/mL. Cefotetan is 88% plasma protein bound.
- Metabolism
No significant quanitity of metabolites have been identified in urine.
- Route of elimination
Cefoperazone is excreted mainly in the bile.
- Half-life
The mean serum half-life is approximately 2.0 hours, independent of the route of administration.
- 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 blood in the urine, diarrhea, nausea, upper abdominal pain, 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 softwareAbacavir Cefoperazone 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 Cefoperazone. Acamprosate The excretion of Acamprosate can be decreased when combined with Cefoperazone. Aceclofenac The risk or severity of nephrotoxicity can be increased when Cefoperazone is combined with Aceclofenac. Acemetacin The risk or severity of nephrotoxicity can be increased when Cefoperazone is combined with Acemetacin. - Food Interactions
- Avoid alcohol. Ingesting alcohol with cefoperazone may precipitate a disulfuram like reaction including symptoms such as flushing, tachycardia, sweating, and headache.
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.- Product Ingredients
Ingredient UNII CAS InChI Key Cefoperazone sodium 5FQG9774WD 62893-20-3 NCFTXMQPRQZFMZ-WERGMSTESA-M - International/Other Brands
- Cefobine (Pfizer) / Cefobis (Pfizer) / Cefoperazin (Pfizer)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cefobid Powder, for solution 10 g/1 Intravenous Roerig 1982-11-18 2003-03-01 US 
Cefobid Powder, for solution 2 g/1 Intravenous Roerig 1982-11-18 2003-03-01 US Cefobid Powder, for solution 1 g/1 Intravenous Roerig 1982-11-18 2003-03-01 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image BAXCEF Cefoperazone (0.5 g) + Sulbactam (0.5 g) Injection, powder, for solution Intramuscular; Intravenous Solas Langgeng Sejahtera 2016-01-14 2026-01-14 Indonesia 
Cebactam Injection 1g Cefoperazone sodium (500 mg) + Sulbactam sodium (500 mg) Injection, powder, for solution Intramuscular; Intravenous HEALOL PHARMACEUTICALS SDN. BHD. 2020-09-08 2022-03-03 Malaysia 
CEFOPERAZONE SODIUM - SULBACTAM SODIUM Cefoperazone (500 mg) + Sulbactam (500 mg) Injection, powder, for solution Intramuscular; Intravenous Natura Laboratoria Prima 2018-12-31 2025-05-08 Indonesia CEFOPERAZONE SODIUM - SULBACTAM SODIUM Cefoperazone sodium (500 mg) + Sulbactam sodium (500 mg) Injection, powder, for solution Intramuscular; Intravenous Infion 2015-10-05 2025-05-08 Indonesia CEFOPERAZONE SODIUM - SULBACTAM SODIUM Cefoperazone sodium (500 mg) + Sulbactam sodium (500 mg) Injection, powder, for solution Intramuscular; Intravenous Etercon Pharma 2017-03-03 2026-11-01 Indonesia
Categories
- ATC Codes
- J01DD12 — Cefoperazone
- Drug Categories
- Amides
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- beta-Lactams
- Cephalosporins
- Heterocyclic Compounds, Fused-Ring
- Lactams
- Nephrotoxic agents
- OAT1/SLC22A6 inhibitors
- OAT3/SLC22A8 Inhibitors
- Sulfur Compounds
- Thiazines
- Third-Generation Cephalosporins
- Classification
- Not classified
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- 7U75I1278D
- CAS number
- 62893-19-0
- InChI Key
- GCFBRXLSHGKWDP-XCGNWRKASA-N
- InChI
- InChI=1S/C25H27N9O8S2/c1-3-32-8-9-33(21(39)20(32)38)24(42)27-15(12-4-6-14(35)7-5-12)18(36)26-16-19(37)34-17(23(40)41)13(10-43-22(16)34)11-44-25-28-29-30-31(25)2/h4-7,15-16,22,35H,3,8-11H2,1-2H3,(H,26,36)(H,27,42)(H,40,41)/t15-,16-,22-/m1/s1
- IUPAC Name
- (6R,7R)-7-[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetamido]-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- SMILES
- [H][C@]12SCC(CSC3=NN=NN3C)=C(N1C(=O)[C@@]2([H])NC(=O)[C@H](NC(=O)N1CCN(CC)C(=O)C1=O)C1=CC=C(O)C=C1)C(O)=O
References
- Synthesis Reference
Walter Cabri, "Process for the preparation of highly crystalline sodium cefoperazone." U.S. Patent US20040030127, issued February 12, 2004.
US20040030127- General References
- Jones RN, Barry AL: Cefoperazone: a review of its antimicrobial spectrum, beta-lactamase stability, enzyme inhibition, and other in vitro characteristics. Rev Infect Dis. 1983 Mar-Apr;5 Suppl 1:S108-26. [Article]
- TITCK Product Information: Cefobid (cefoperazone sodium) for intramuscular/intravenous injection [Link]
- External Links
- Human Metabolome Database
- HMDB0015424
- KEGG Compound
- C06883
- PubChem Compound
- 44185
- PubChem Substance
- 46504543
- ChemSpider
- 40206
- BindingDB
- 50390999
- 2184
- ChEBI
- 3493
- ChEMBL
- CHEMBL507674
- ZINC
- ZINC000003830432
- Therapeutic Targets Database
- DAP000450
- PharmGKB
- PA448849
- Wikipedia
- Cefoperazone
- FDA label
- Download (174 KB)
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 data4 Active Not Recruiting Other Infectious Diseases 1 somestatus stop reason just information to hide 4 Completed Treatment Anti-drug antibody development / Cholangitis, Secondary Biliary / Compliance, Treatment 1 somestatus stop reason just information to hide 4 Completed Treatment Infection 1 somestatus stop reason just information to hide 4 Unknown Status Treatment Pancreatitis,Acute Necrotizing 1 somestatus stop reason just information to hide 2 Suspended Treatment Respiratory Tract Infections (RTI) / Urinary Tract Infection 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Pfizer Inc.
- Dosage Forms
Form Route Strength Injection Intramuscular; Intravenous 1 g Injection, powder, for solution Intramuscular Injection, powder, for solution Intravenous Powder, for solution Intravenous 1 g/1 Powder, for solution Intravenous 10 g/1 Powder, for solution Intravenous 2 g/1 Injection, powder, for solution Intramuscular; Intravenous Injection, powder, for solution Intramuscular; Intravenous 1 gr Injection Parenteral 1 g Injection, powder, for solution Parenteral Injection Parenteral 2 g Powder, for solution Intravenous Injection, powder, for solution 1.088 g Injection, powder, for solution 1.12 g Powder Intravenous Injection Intramuscular; Intravenous Injection, solution Intramuscular; Intravenous Injection, powder, for solution Intramuscular; Intravenous 1 g Injection, powder, for solution Intramuscular; Intravenous 500 mg Injection Intramuscular; Intravenous Injection, powder, for solution 1 G Injection, powder, for solution 2 GM Injection, powder, for solution Injection, powder, for solution Intramuscular; Intravenous Injection, solution Intramuscular Injection Intramuscular Powder - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 188-190 Saikawa, I., Takano, S., Yoshida, C., Takashima, 0..Momonoi, K., Kuroda, S., Komatsu, M., Yasuda, T.and Kodama, Y.; British Patent 1,508,071; April 19,1978; assigned to Toyama Chemical Co., Ltd. and U.S. Patent 4,110,327; August 29,1978; also assigned to Toyama Chemical Co., Ltd. logP -0.74 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.286 mg/mL ALOGPS logP -0.11 ALOGPS logP -0.9 Chemaxon logS -3.4 ALOGPS pKa (Strongest Acidic) 3.19 Chemaxon pKa (Strongest Basic) -1.7 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 11 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 220.26 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 169.06 m3·mol-1 Chemaxon Polarizability 60.97 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.5526 Blood Brain Barrier - 0.9886 Caco-2 permeable - 0.7049 P-glycoprotein substrate Substrate 0.946 P-glycoprotein inhibitor I Non-inhibitor 0.8782 P-glycoprotein inhibitor II Non-inhibitor 0.9759 Renal organic cation transporter Non-inhibitor 0.8099 CYP450 2C9 substrate Non-substrate 0.7919 CYP450 2D6 substrate Non-substrate 0.8101 CYP450 3A4 substrate Substrate 0.5899 CYP450 1A2 substrate Non-inhibitor 0.8022 CYP450 2C9 inhibitor Non-inhibitor 0.7458 CYP450 2D6 inhibitor Non-inhibitor 0.8502 CYP450 2C19 inhibitor Non-inhibitor 0.7271 CYP450 3A4 inhibitor Non-inhibitor 0.869 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6906 Ames test Non AMES toxic 0.6584 Carcinogenicity Non-carcinogens 0.9099 Biodegradation Not ready biodegradable 0.6674 Rat acute toxicity 2.4703 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8021 hERG inhibition (predictor II) Inhibitor 0.557
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 235.7793853 predictedDarkChem Lite v0.1.0 [M+H]+ 234.7044853 predictedDarkChem Lite v0.1.0 [M+Na]+ 234.7592853 predictedDarkChem Lite v0.1.0
Targets
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- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Peptidoglycan glycosyltransferase activity
- Specific Function
- Essential cell division protein that is required for the synthesis of peptidoglycan at the division septum (PubMed:1103132, PubMed:9614966). Catalyzes the synthesis of cross-linked peptidoglycan fr...
- Gene Name
- ftsI
- Uniprot ID
- P0AD68
- Uniprot Name
- Peptidoglycan synthase FtsI
- Molecular Weight
- 63876.925 Da
References
- Matsubara N, Minami S, Matsuhashi M, Takaoka M, Mitsuhashi S: Affinity of cefoperazone for penicillin-binding proteins. Antimicrob Agents Chemother. 1980 Jul;18(1):195-9. [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
- Matsubara N, Minami S, Matsuhashi M, Takaoka M, Mitsuhashi S: Affinity of cefoperazone for penicillin-binding proteins. Antimicrob Agents Chemother. 1980 Jul;18(1):195-9. [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; PBP-2 is responsible for the determination of the rod shape of the cell. It synthesizes cross-linked peptidoglycan from lipid intermediates.
- Gene Name
- mrdA
- Uniprot ID
- P0AD65
- Uniprot Name
- Penicillin-binding protein 2
- Molecular Weight
- 70856.1 Da
References
- Matsubara N, Minami S, Matsuhashi M, Takaoka M, Mitsuhashi S: Affinity of cefoperazone for penicillin-binding proteins. Antimicrob Agents Chemother. 1980 Jul;18(1):195-9. [Article]
- Kind
- Protein
- Organism
- Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Transferase activity, transferring glycosyl groups
- 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
- Q07806
- Uniprot Name
- Penicillin-binding protein 1A
- Molecular Weight
- 91198.715 Da
References
- Matsubara N, Minami S, Matsuhashi M, Takaoka M, Mitsuhashi S: Affinity of cefoperazone for penicillin-binding proteins. Antimicrob Agents Chemother. 1980 Jul;18(1):195-9. [Article]
- Kind
- Protein
- Organism
- Pseudomonas aeruginosa
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Peptidoglycan glycosyltransferase 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
- ponB
- Uniprot ID
- Q9X6W0
- Uniprot Name
- Penicillin-binding protein 1B
- Molecular Weight
- 85486.615 Da
References
- Matsubara N, Minami S, Matsuhashi M, Takaoka M, Mitsuhashi S: Affinity of cefoperazone for penicillin-binding proteins. Antimicrob Agents Chemother. 1980 Jul;18(1):195-9. [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
- Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors.
- Gene Name
- dacC
- Uniprot ID
- P08506
- Uniprot Name
- D-alanyl-D-alanine carboxypeptidase DacC
- Molecular Weight
- 43608.595 Da
References
- Matsubara N, Minami S, Matsuhashi M, Takaoka M, Mitsuhashi S: Affinity of cefoperazone for penicillin-binding proteins. Antimicrob Agents Chemother. 1980 Jul;18(1):195-9. [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
- mrcA
- Uniprot ID
- P02918
- Uniprot Name
- Penicillin-binding protein 1A
- Molecular Weight
- 93635.545 Da
References
- Matsubara N, Minami S, Matsuhashi M, Takaoka M, Mitsuhashi S: Affinity of cefoperazone for penicillin-binding proteins. Antimicrob Agents Chemother. 1980 Jul;18(1):195-9. [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
- Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors.
- Gene Name
- dacA
- Uniprot ID
- P0AEB2
- Uniprot Name
- D-alanyl-D-alanine carboxypeptidase DacA
- Molecular Weight
- 44443.62 Da
References
- Matsubara N, Minami S, Matsuhashi M, Takaoka M, Mitsuhashi S: Affinity of cefoperazone for penicillin-binding proteins. Antimicrob Agents Chemother. 1980 Jul;18(1):195-9. [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
- Not involved in transpeptidation but exclusively catalyzes a DD-carboxypeptidase and DD-endopeptidase reaction.
- Gene Name
- dacB
- Uniprot ID
- P24228
- Uniprot Name
- D-alanyl-D-alanine carboxypeptidase DacB
- Molecular Weight
- 51797.85 Da
References
- Matsubara N, Minami S, Matsuhashi M, Takaoka M, Mitsuhashi S: Affinity of cefoperazone for penicillin-binding proteins. Antimicrob Agents Chemother. 1980 Jul;18(1):195-9. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Other/unknown
- General Function
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- Antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Albumin
- Molecular Weight
- 69365.94 Da
References
- Liu LS, Zhang YY, Wang XP: [The reaction mechanism between cefoperazone and human serum albumin]. Guang Pu Xue Yu Guang Pu Fen Xi. 2005 Sep;25(9):1490-2. [Article]
- Gulian JM, Dalmasso C, Gonard V: Interaction of beta-lactam antibiotics on bilirubin-albumin complex: comparison by three methods, total bilirubin, unbound bilirubin and erythrocyte-bound bilirubin. Chemotherapy. 1990;36(2):91-7. [Article]
- Leggett JE, Craig WA: Enhancing effect of serum ultrafiltrate on the activity of cephalosporins against gram-negative bacilli. Antimicrob Agents Chemother. 1989 Jan;33(1):35-40. [Article]
- Robertson A, Fink S, Karp W: Effect of cephalosporins on bilirubin-albumin binding. J Pediatr. 1988 Feb;112(2):291-4. [Article]
- Nerli B, Farruggia B, Pico G: A comparative study of the binding characteristics of ceftriaxone, cefoperazone and cefsulodin to human serum albumin. Biochem Mol Biol Int. 1996 Nov;40(4):823-31. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Secondary active transporter that functions as a Na(+)-independent organic anion (OA)/dicarboxylate antiporter where the uptake of one molecule of OA into the cell is coupled with an efflux of one molecule of intracellular dicarboxylate such as 2-oxoglutarate or glutarate (PubMed:11669456, PubMed:11907186, PubMed:14675047, PubMed:22108572, PubMed:23832370, PubMed:28534121, PubMed:9950961). Mediates the uptake of OA across the basolateral side of proximal tubule epithelial cells, thereby contributing to the renal elimination of endogenous OA from the systemic circulation into the urine (PubMed:9887087). Functions as a biopterin transporters involved in the uptake and the secretion of coenzymes tetrahydrobiopterin (BH4), dihydrobiopterin (BH2) and sepiapterin to urine, thereby determining baseline levels of blood biopterins (PubMed:28534121). Transports prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) and may contribute to their renal excretion (PubMed:11907186). Also mediates the uptake of cyclic nucleotides such as cAMP and cGMP (PubMed:26377792). Involved in the transport of neuroactive tryptophan metabolites kynurenate (KYNA) and xanthurenate (XA) and may contribute to their secretion from the brain (PubMed:22108572, PubMed:23832370). May transport glutamate (PubMed:26377792). Also involved in the disposition of uremic toxins and potentially toxic xenobiotics by the renal organic anion secretory pathway, helping reduce their undesired toxicological effects on the body (PubMed:11669456, PubMed:14675047). Uremic toxins include the indoxyl sulfate (IS), hippurate/N-benzoylglycine (HA), indole acetate (IA), 3-carboxy-4- methyl-5-propyl-2-furanpropionate (CMPF) and urate (PubMed:14675047, PubMed:26377792). Xenobiotics include the mycotoxin ochratoxin (OTA) (PubMed:11669456). May also contribute to the transport of organic compounds in testes across the blood-testis-barrier (PubMed:35307651)
- Specific Function
- Alpha-ketoglutarate transmembrane transporter activity
- 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]
- 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
- Inhibitor
- General Function
- Functions as an organic anion/dicarboxylate exchanger that couples organic anion uptake indirectly to the sodium gradient (PubMed:14586168, PubMed:15644426, PubMed:15846473, PubMed:16455804, PubMed:31553721). Transports organic anions such as estrone 3-sulfate (E1S) and urate in exchange for dicarboxylates such as glutarate or ketoglutarate (2-oxoglutarate) (PubMed:14586168, PubMed:15846473, PubMed:15864504, PubMed:22108572, PubMed:23832370). Plays an important role in the excretion of endogenous and exogenous organic anions, especially from the kidney and the brain (PubMed:11306713, PubMed:14586168, PubMed:15846473). E1S transport is pH- and chloride-dependent and may also involve E1S/cGMP exchange (PubMed:26377792). Responsible for the transport of prostaglandin E2 (PGE2) and prostaglandin F2(alpha) (PGF2(alpha)) in the basolateral side of the renal tubule (PubMed:11907186). Involved in the transport of neuroactive tryptophan metabolites kynurenate and xanthurenate (PubMed:22108572, PubMed:23832370). Functions as a biopterin transporters involved in the uptake and the secretion of coenzymes tetrahydrobiopterin (BH4), dihydrobiopterin (BH2) and sepiapterin to urine, thereby determining baseline levels of blood biopterins (PubMed:28534121). May be involved in the basolateral transport of steviol, a metabolite of the popular sugar substitute stevioside (PubMed:15644426). May participate in the detoxification/ renal excretion of drugs and xenobiotics, such as the histamine H(2)-receptor antagonists fexofenadine and cimetidine, the antibiotic benzylpenicillin (PCG), the anionic herbicide 2,4-dichloro-phenoxyacetate (2,4-D), the diagnostic agent p-aminohippurate (PAH), the antiviral acyclovir (ACV), and the mycotoxin ochratoxin (OTA), by transporting these exogenous organic anions across the cell membrane in exchange for dicarboxylates such as 2-oxoglutarate (PubMed:11669456, PubMed:15846473, PubMed:16455804). Contributes to the renal uptake of potent uremic toxins (indoxyl sulfate (IS), indole acetate (IA), hippurate/N-benzoylglycine (HA) and 3-carboxy-4-methyl-5-propyl-2-furanpropionate (CMPF)), pravastatin, PCG, E1S and dehydroepiandrosterone sulfate (DHEAS), and is partly involved in the renal uptake of temocaprilat (an angiotensin-converting enzyme (ACE) inhibitor) (PubMed:14675047). May contribute to the release of cortisol in the adrenals (PubMed:15864504). Involved in one of the detoxification systems on the choroid plexus (CP), removes substrates such as E1S or taurocholate (TC), PCG, 2,4-D and PAH, from the cerebrospinal fluid (CSF) to the blood for eventual excretion in urine and bile (By similarity). Also contributes to the uptake of several other organic compounds such as the prostanoids prostaglandin E(2) and prostaglandin F(2-alpha), L-carnitine, and the therapeutic drugs allopurinol, 6-mercaptopurine (6-MP) and 5-fluorouracil (5-FU) (By similarity). Mediates the transport of PAH, PCG, and the statins pravastatin and pitavastatin, from the cerebrum into the blood circulation across the blood-brain barrier (BBB). In summary, plays a role in the efflux of drugs and xenobiotics, helping reduce their undesired toxicological effects on the body (By similarity)
- Specific Function
- Organic anion transmembrane transporter activity
- Gene Name
- SLC22A8
- Uniprot ID
- Q8TCC7
- Uniprot Name
- Organic anion transporter 3
- 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]
- 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]
- Kusuhara H, Sekine T, Utsunomiya-Tate N, Tsuda M, Kojima R, Cha SH, Sugiyama Y, Kanai Y, Endou H: Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain. J Biol Chem. 1999 May 7;274(19):13675-80. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Antiporter that mediates the transport of conjugated steroids and other specific organic anions at the basal membrane of syncytiotrophoblast and at the apical membrane of proximal tubule epithelial cells, in exchange for anionic compounds (PubMed:10660625, PubMed:11907186, PubMed:15037815, PubMed:15102942, PubMed:15291761, PubMed:15576633, PubMed:17229912, PubMed:18501590, PubMed:26277985, PubMed:28027879). May be responsible for placental absorption of fetal-derived steroid sulfates such as estrone sulfate (E1S) and the steroid hormone precursor dehydroepiandrosterone sulfate (DHEA-S), as well as clearing waste products and xenobiotics from the fetus (PubMed:12409283). Maybe also be involved in placental urate homeostasis (PubMed:17229912). Facilitates the renal reabsorption of organic anions such as urate and derived steroid sulfates (PubMed:15037815, PubMed:17229912). Organic anion glutarate acts as conteranion for E1S renal uptake (PubMed:15037815, PubMed:17229912). Possible transport mode may also include DHEA-S/E1S exchange (PubMed:28027879). Also interacts with inorganic anions such as chloride and hydroxyl ions, therefore possible transport modes may include E1S/Cl(-), E1S/OH(-), urate/Cl(-) and urate/OH(-) (PubMed:17229912). Also mediates the transport of prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) and may be involved in their renal excretion (PubMed:11907186). Also able to uptake anionic drugs, diuretics, bile salts and ochratoxin A (PubMed:10660625, PubMed:26277985). Mediates the unidirectional efflux of glutamate and aspartate (PubMed:28027879). Glutamate efflux down its transmembrane gradient may drive SLC22A11/OAT4-mediated placental uptake of E1S (PubMed:26277985)
- Specific Function
- Organic anion transmembrane transporter activity
- Gene Name
- SLC22A11
- Uniprot ID
- Q9NSA0
- Uniprot Name
- Solute carrier family 22 member 11
- Molecular Weight
- 59970.945 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Functions as a Na(+)-independent bidirectional multispecific transporter (PubMed:11327718, PubMed:18216183, PubMed:21446918, PubMed:28945155). Contributes to the renal and hepatic elimination of endogenous organic compounds from the systemic circulation into the urine and bile, respectively (PubMed:11327718, PubMed:25904762). Capable of transporting a wide range of purine and pyrimidine nucleobases, nucleosides and nucleotides, with cGMP, 2'deoxyguanosine and GMP being the preferred substrates (PubMed:11327718, PubMed:18216183, PubMed:26377792, PubMed:28945155). Functions as a pH- and chloride-independent cGMP bidirectional facilitative transporter that can regulate both intracellular and extracellular levels of cGMP and may be involved in cGMP signaling pathways (PubMed:18216183, PubMed:26377792). Mediates orotate/glutamate bidirectional exchange and most likely display a physiological role in hepatic release of glutamate into the blood (PubMed:21446918). Involved in renal secretion and possible reabsorption of creatinine (PubMed:25904762, PubMed:28945155). Able to uptake prostaglandin E2 (PGE2) and may contribute to PGE2 renal excretion (Probable). Also transports alpha-ketoglutarate and urate (PubMed:11327718, PubMed:26377792). Apart from the orotate/glutamate exchange, the counterions for the uptake of other SLC22A7/OAT2 substrates remain to be identified (PubMed:26377792)
- Specific Function
- Alpha-ketoglutarate transmembrane transporter activity
- Gene Name
- SLC22A7
- Uniprot ID
- Q9Y694
- Uniprot Name
- Solute carrier family 22 member 7
- Molecular Weight
- 60025.025 Da
References
- Khamdang S, Takeda M, Babu E, Noshiro R, Onozato ML, Tojo A, Enomoto A, Huang XL, Narikawa S, Anzai N, Piyachaturawat P, Endou H: Interaction of human and rat organic anion transporter 2 with various cephalosporin antibiotics. Eur J Pharmacol. 2003 Mar 28;465(1-2):1-7. [Article]
- Kobayashi Y, Ohshiro N, Shibusawa A, Sasaki T, Tokuyama S, Sekine T, Endou H, Yamamoto T: Isolation, characterization and differential gene expression of multispecific organic anion transporter 2 in mice. Mol Pharmacol. 2002 Jul;62(1):7-14. [Article]
- Sekine T, Cha SH, Tsuda M, Apiwattanakul N, Nakajima N, Kanai Y, Endou H: Identification of multispecific organic anion transporter 2 expressed predominantly in the liver. FEBS Lett. 1998 Jun 12;429(2):179-82. [Article]
Drug created at June 30, 2007 17:50 / Updated at June 02, 2024 21:58