Identification
- Summary
Cefradine is a first-generation cephalosporin antibiotic used in the treatment of bacterial infections of the respiratory and urinary tracts and of the skin and soft tissues.
- Generic Name
- Cefradine
- DrugBank Accession Number
- DB01333
- Background
A semi-synthetic cephalosporin antibiotic.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Cefradine (DB01333)
- Weight
- Average: 349.405
Monoisotopic: 349.109626801 - Chemical Formula
- C16H19N3O4S
- Synonyms
- (6R,7R)-7-((R)-2-Amino-2-(1,4-cyclohexadien-1-yl)acetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
- (6R,7R)-7-{[(2R)-2-amino-2-cyclohexa-1,4-dien-1-ylacetyl]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- 7-(D-2-Amino-2-(1,4-cyclohexadienyl)acetamide)desacetoxycephalosporanicacid
- CED
- Cefradina
- Cefradine
- Cefradinum
- Cephradin
- Cephradine
Pharmacology
- Indication
Not Available
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.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Bacterial sepsis •••••••••••• Treatment of Bloodstream infections •••••••••••• Treatment of Osteomyelitis •••••••••••• Treatment of Peritonitis •••••••••••• Treatment of Respiratory tract infections (rti) •••••••••••• - 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
Not Available
- Mechanism of action
Cefradine is a first generation cephalosporin antibiotic with a spectrum of activity similar to Cefalexin. Cefradine, like the penicillins, is a beta-lactam antibiotic. 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; it is possible that Cefradine interferes with an autolysin inhibitor.
Target Actions Organism APenicillin-binding protein 1A inhibitorEscherichia coli (strain K12) - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Over 90 percent of the drug is excreted unchanged in the urine within six hours.
- 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
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 Cefradine 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 Cefradine. Abemaciclib The metabolism of Abemaciclib can be increased when combined with Cefradine. Acalabrutinib The metabolism of Acalabrutinib can be increased when combined with Cefradine. Aceclofenac The risk or severity of nephrotoxicity can be increased when Cefradine is combined with Aceclofenac. - Food Interactions
- Take with or without food.
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 Cefradine monohydrate FUC0D71IZN 75975-70-1 VHNPSPMQGXQSET-CYJZLJNKSA-N - International/Other Brands
- Anspor / Eskacef / Intracef (Beximco Pharma) / Lebac (Square pharmaceuticals Ltd.) / Reocef (Rephco Pharmaceuticals Ltd.) / Sefril (ACME laboratories Ltd.)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Velosef Suspension 250 mg/5mL Oral Bristol-Myers Squibb Company 2006-10-23 2006-10-23 US 
Velosef Suspension 125 mg/5mL Oral Bristol-Myers Squibb Company 2006-10-23 2006-10-23 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Velosef Capsule, gelatin coated 500 mg/1 Oral E.R. Squibb & Sons, L.L.C. 1995-01-01 2006-05-31 US Velosef Capsule, gelatin coated 250 mg/1 Oral E.R. Squibb & Sons, L.L.C. 1995-01-01 2006-05-31 US
Categories
- ATC Codes
- J01DB09 — Cefradine
- Drug Categories
- Amides
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- beta-Lactams
- Cephalosporins
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 Enzyme Inducers
- Drugs that are Mainly Renally Excreted
- First-Generation Cephalosporins
- Heterocyclic Compounds, Fused-Ring
- Lactams
- MATE 1 Substrates
- MATE substrates
- Nephrotoxic agents
- OAT1/SLC22A6 inhibitors
- Sulfur Compounds
- Thiazines
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- N-acyl-alpha amino acids and derivatives
- Alternative Parents
- Cephems / 1,3-thiazines / Tertiary carboxylic acid amides / Amino acids / Azetidines / Thiohemiaminal derivatives / Propargyl-type 1,3-dipolar organic compounds / Monocarboxylic acids and derivatives / Azacyclic compounds / Dialkylthioethers show 7 more
- Substituents
- Aliphatic heteropolycyclic compound / Amine / Amino acid / Azacycle / Azetidine / Beta-lactam / Carbonyl group / Carboxamide group / Carboximidic acid / Carboximidic acid derivative show 22 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- cephalosporin (CHEBI:3547)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 9YA6SX5S4D
- CAS number
- 38821-53-3
- InChI Key
- RDLPVSKMFDYCOR-UEKVPHQBSA-N
- InChI
- InChI=1S/C16H19N3O4S/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9/h2-3,6,10-11,15H,4-5,7,17H2,1H3,(H,18,20)(H,22,23)/t10-,11-,15-/m1/s1
- IUPAC Name
- (6R,7R)-7-[(2R)-2-amino-2-(cyclohexa-1,4-dien-1-yl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- SMILES
- [H][C@]12SCC(C)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CCC=CC1)C(O)=O
References
- Synthesis Reference
Dennis Heemskerk, Anja Gerarda Hogenboom, Carlos Lenhardt, Harold Moody, Theodorus Johannes Godfried Maria Dooren, "Process for the preparation of cephradine." U.S. Patent US20060189802, issued August 24, 2006.
US20060189802- General References
- Neiss ES: Cephradine--a summary of preclinical studies and clinical pharmacology. J Ir Med Assoc. 1973 Mar 24;Suppl:1-12. [Article]
- External Links
- Human Metabolome Database
- HMDB0015428
- KEGG Drug
- D00264
- KEGG Compound
- C06897
- PubChem Compound
- 38103
- PubChem Substance
- 46505082
- ChemSpider
- 34933
- BindingDB
- 50370585
- 2239
- ChEBI
- 3547
- ChEMBL
- CHEMBL1604
- ZINC
- ZINC000003830515
- Therapeutic Targets Database
- DAP000454
- PharmGKB
- PA448890
- Wikipedia
- Cefradine
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- E.R. Squibb and Sons LLC
- H.J. Harkins Co. Inc.
- Major Pharmaceuticals
- PD-Rx Pharmaceuticals Inc.
- Pharmedix
- Prepackage Specialists
- Prescription Dispensing Service Inc.
- Teva Pharmaceutical Industries Ltd.
- Dosage Forms
Form Route Strength Capsule Oral 250 mg Capsule Oral 500 mg Tablet Oral 1 G Injection, powder, for solution Intramuscular Injection, powder, for solution Intramuscular; Intravenous 100000 g Injection, powder, for solution Intramuscular; Intravenous 1 g Tablet Oral 1000 mg Capsule, coated Oral 526 mg Tablet, film coated Oral 500 mg Injection, powder, for solution Parenteral 1 g Tablet Oral 100000000 mg Capsule, coated Oral 50000000 mg Capsule Oral Injection, powder, for solution Intramuscular; Intravenous Injection, powder, for solution Parenteral 500 mg Tablet Oral 500 mg Powder, for suspension Oral 5 g Injection, powder, for solution Suspension Oral Syrup Tablet Oral Capsule, gelatin coated Oral 250 mg/1 Capsule, gelatin coated Oral 500 mg/1 Suspension Oral 125 mg/5mL Suspension Oral 250 mg/5mL Powder, for solution Oral 5 g Capsule, coated Oral 500 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 140 °C PhysProp water solubility 2.13E+004 mg/L YALKOWSKY,SH & DANNENFELSER,RM (1992) - Predicted Properties
Property Value Source Water Solubility 0.778 mg/mL ALOGPS logP 0.7 ALOGPS logP -2.4 Chemaxon logS -2.6 ALOGPS pKa (Strongest Acidic) 3.27 Chemaxon pKa (Strongest Basic) 7.6 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 4 Chemaxon Refractivity 92 m3·mol-1 Chemaxon Polarizability 33.19 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 - 0.7238 Blood Brain Barrier - 0.9942 Caco-2 permeable - 0.8957 P-glycoprotein substrate Substrate 0.7962 P-glycoprotein inhibitor I Non-inhibitor 0.8781 P-glycoprotein inhibitor II Non-inhibitor 0.9946 Renal organic cation transporter Non-inhibitor 0.9536 CYP450 2C9 substrate Non-substrate 0.8401 CYP450 2D6 substrate Non-substrate 0.8278 CYP450 3A4 substrate Non-substrate 0.5268 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9254 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8698 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9579 Ames test Non AMES toxic 0.6896 Carcinogenicity Non-carcinogens 0.9204 Biodegradation Not ready biodegradable 0.9857 Rat acute toxicity 1.4329 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9973 hERG inhibition (predictor II) Non-inhibitor 0.8625
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0a4i-2900000000-80091aae9d8fe850aa25 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a5c-0903000000-c4425d102eed49cdad34 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0921000000-84afd1d1b4c57451d435 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-0921000000-c41dcb0c07e3c2f2103c Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0bt9-1935000000-ff94752c208fee57a588 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-052g-5932000000-6cf8fb13e31f563a7358 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-06r6-9730000000-ea9c4fbd2fd27f80692a 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]- 198.9828665 predictedDarkChem Lite v0.1.0 [M-H]- 183.3139665 predictedDarkChem Lite v0.1.0 [M-H]- 180.8333 predictedDeepCCS 1.0 (2019) [M+H]+ 199.6880665 predictedDarkChem Lite v0.1.0 [M+H]+ 183.0020665 predictedDarkChem Lite v0.1.0 [M+H]+ 183.1913 predictedDeepCCS 1.0 (2019) [M+Na]+ 199.4242665 predictedDarkChem Lite v0.1.0 [M+Na]+ 182.9723665 predictedDarkChem Lite v0.1.0 [M+Na]+ 189.90834 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- 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
- Sharma UK, Dwarakanath P, Banerjee N, Town C, Balganesh TS: Expression and characterization of the ponA (ORF I) gene of Haemophilus influenzae: functional complementation in a heterologous system. J Bacteriol. 1995 Dec;177(23):6745-50. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Yasuda K, Ranade A, Venkataramanan R, Strom S, Chupka J, Ekins S, Schuetz E, Bachmann K: A comprehensive in vitro and in silico analysis of antibiotics that activate pregnane X receptor and induce CYP3A4 in liver and intestine. Drug Metab Dispos. 2008 Aug;36(8):1689-97. doi: 10.1124/dmd.108.020701. Epub 2008 May 27. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Symporter activity
- Specific 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. Also transports organic cat...
- Gene Name
- SLC22A5
- Uniprot ID
- O76082
- Uniprot Name
- Solute carrier family 22 member 5
- 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
- SubstrateInhibitor
- General Function
- Proton-dependent oligopeptide secondary active transmembrane transporter activity
- Specific Function
- Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
- Gene Name
- SLC15A1
- Uniprot ID
- P46059
- Uniprot Name
- Solute carrier family 15 member 1
- Molecular Weight
- 78805.265 Da
References
- Han H, de Vrueh RL, Rhie JK, Covitz KM, Smith PL, Lee CP, Oh DM, Sadee W, Amidon GL: 5'-Amino acid esters of antiviral nucleosides, acyclovir, and AZT are absorbed by the intestinal PEPT1 peptide transporter. Pharm Res. 1998 Aug;15(8):1154-9. [Article]
- Han HK, Rhie JK, Oh DM, Saito G, Hsu CP, Stewart BH, Amidon GL: CHO/hPEPT1 cells overexpressing the human peptide transporter (hPEPT1) as an alternative in vitro model for peptidomimetic drugs. J Pharm Sci. 1999 Mar;88(3):347-50. [Article]
- Saito H, Okuda M, Terada T, Sasaki S, Inui K: Cloning and characterization of a rat H+/peptide cotransporter mediating absorption of beta-lactam antibiotics in the intestine and kidney. J Pharmacol Exp Ther. 1995 Dec;275(3):1631-7. [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]
- Terada T, Saito H, Mukai M, Inui K: Characterization of stably transfected kidney epithelial cell line expressing rat H+/peptide cotransporter PEPT1: localization of PEPT1 and transport of beta-lactam antibiotics. J Pharmacol Exp Ther. 1997 Jun;281(3):1415-21. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Peptide:proton symporter activity
- Specific Function
- Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
- Gene Name
- SLC15A2
- Uniprot ID
- Q16348
- Uniprot Name
- Solute carrier family 15 member 2
- Molecular Weight
- 81782.77 Da
References
- 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
- 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
- Cihlar T, Ho ES: Fluorescence-based assay for the interaction of small molecules with the human renal organic anion transporter 1. Anal Biochem. 2000 Jul 15;283(1):49-55. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Monovalent cation:proton antiporter activity
- Specific Function
- Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide (NMN), metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfat...
- Gene Name
- SLC47A1
- Uniprot ID
- Q96FL8
- Uniprot Name
- Multidrug and toxin extrusion protein 1
- Molecular Weight
- 61921.585 Da
References
- Motohashi H, Inui K: Organic cation transporter OCTs (SLC22) and MATEs (SLC47) in the human kidney. AAPS J. 2013 Apr;15(2):581-8. doi: 10.1208/s12248-013-9465-7. Epub 2013 Feb 22. [Article]
- Structure and function of multidrug and toxin extrusion proteins (MATEs) and their relevance to drug therapy and personalized medicine [File]
Drug created at June 30, 2007 18:05 / Updated at April 30, 2021 13:05