Cefradine

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
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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofBacterial sepsis••••••••••••
Treatment ofBloodstream infections••••••••••••
Treatment ofOsteomyelitis••••••••••••
Treatment ofPeritonitis••••••••••••
Treatment ofRespiratory tract infections (rti)••••••••••••
Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
APenicillin-binding protein 1A
inhibitor
Escherichia 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
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Toxicity

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.
DrugInteraction
AbacavirCefradine may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbciximabThe therapeutic efficacy of Abciximab can be decreased when used in combination with Cefradine.
AbemaciclibThe metabolism of Abemaciclib can be increased when combined with Cefradine.
AcalabrutinibThe metabolism of Acalabrutinib can be increased when combined with Cefradine.
AceclofenacThe risk or severity of nephrotoxicity can be increased when Cefradine is combined with Aceclofenac.
Food Interactions
  • Take with or without food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Cefradine monohydrateFUC0D71IZN75975-70-1VHNPSPMQGXQSET-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
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
VelosefSuspension125 mg/5mLOralBristol-Myers Squibb Company2006-10-232006-10-23US flag
VelosefSuspension250 mg/5mLOralBristol-Myers Squibb Company2006-10-232006-10-23US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
VelosefCapsule, gelatin coated250 mg/1OralE.R. Squibb & Sons, L.L.C.1995-01-012006-05-31US flag
VelosefCapsule, gelatin coated500 mg/1OralE.R. Squibb & Sons, L.L.C.1995-01-012006-05-31US flag

Categories

ATC Codes
J01DB09 — Cefradine
Drug Categories
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
  1. Neiss ES: Cephradine--a summary of preclinical studies and clinical pharmacology. J Ir Med Assoc. 1973 Mar 24;Suppl:1-12. [Article]
Human Metabolome Database
HMDB0015428
KEGG Drug
D00264
KEGG Compound
C06897
PubChem Compound
38103
PubChem Substance
46505082
ChemSpider
34933
BindingDB
50370585
RxNav
2239
ChEBI
3547
ChEMBL
CHEMBL1604
ZINC
ZINC000003830515
Therapeutic Targets Database
DAP000454
PharmGKB
PA448890
Wikipedia
Cefradine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableRecruitingNot AvailableSite Infection1

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
FormRouteStrength
CapsuleOral250 mg
CapsuleOral500 mg
TabletOral1 G
Injection, powder, for solutionIntramuscular
Injection, powder, for solutionIntramuscular; Intravenous100000 g
Injection, powder, for solutionIntramuscular; Intravenous1 g
TabletOral1000 mg
Capsule, coatedOral526 mg
Tablet, film coatedOral500 mg
Injection, powder, for solutionParenteral1 g
TabletOral100000000 mg
Capsule, coatedOral50000000 mg
CapsuleOral
Injection, powder, for solutionIntramuscular; Intravenous
Injection, powder, for solutionParenteral500 mg
TabletOral500 mg
Powder, for suspensionOral5 g
Injection, powder, for solution
SuspensionOral
Syrup
TabletOral
Capsule, gelatin coatedOral250 mg/1
Capsule, gelatin coatedOral500 mg/1
SuspensionOral125 mg/5mL
SuspensionOral250 mg/5mL
Powder, for solutionOral5 g
Capsule, coatedOral500 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)140 °CPhysProp
water solubility2.13E+004 mg/LYALKOWSKY,SH & DANNENFELSER,RM (1992)
Predicted Properties
PropertyValueSource
Water Solubility0.778 mg/mLALOGPS
logP0.7ALOGPS
logP-2.4Chemaxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.27Chemaxon
pKa (Strongest Basic)7.6Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area112.73 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity92 m3·mol-1Chemaxon
Polarizability33.19 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.7238
Blood Brain Barrier-0.9942
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.7962
P-glycoprotein inhibitor INon-inhibitor0.8781
P-glycoprotein inhibitor IINon-inhibitor0.9946
Renal organic cation transporterNon-inhibitor0.9536
CYP450 2C9 substrateNon-substrate0.8401
CYP450 2D6 substrateNon-substrate0.8278
CYP450 3A4 substrateNon-substrate0.5268
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9254
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8698
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9579
Ames testNon AMES toxic0.6896
CarcinogenicityNon-carcinogens0.9204
BiodegradationNot ready biodegradable0.9857
Rat acute toxicity1.4329 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9973
hERG inhibition (predictor II)Non-inhibitor0.8625
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0a4i-2900000000-80091aae9d8fe850aa25
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a5c-0903000000-c4425d102eed49cdad34
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0921000000-84afd1d1b4c57451d435
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0921000000-c41dcb0c07e3c2f2103c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0bt9-1935000000-ff94752c208fee57a588
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052g-5932000000-6cf8fb13e31f563a7358
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-06r6-9730000000-ea9c4fbd2fd27f80692a
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-198.9828665
predicted
DarkChem Lite v0.1.0
[M-H]-183.3139665
predicted
DarkChem Lite v0.1.0
[M-H]-180.8333
predicted
DeepCCS 1.0 (2019)
[M+H]+199.6880665
predicted
DarkChem Lite v0.1.0
[M+H]+183.0020665
predicted
DarkChem Lite v0.1.0
[M+H]+183.1913
predicted
DeepCCS 1.0 (2019)
[M+Na]+199.4242665
predicted
DarkChem Lite v0.1.0
[M+Na]+182.9723665
predicted
DarkChem Lite v0.1.0
[M+Na]+189.90834
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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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
  1. 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
  1. 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
  1. 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
Substrate
Inhibitor
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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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
  1. 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
  1. 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
  1. 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]
  2. 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