Details of the Drug

General Information of Drug (ID: DMUNSWV)

Drug Name
Cefradine
Synonyms
Anspor; Cefradin; Cefradina; Cefradinum; Cephradin; Cephradine; Eskacef; Sefril; Velosef; CEPHRADINE SODIUM; SKF D 39304; SQ 11436; VELOSEF 125; VELOSEF 250; VELOSEF 500; Anspor (TN); Cefradina [INN-Spanish]; Cefradinum [INN-Latin]; Cephradine (USP); Cephradine (anhydrous); Cephradine [USAN:BAN]; SQ-11436; SQ-22022; Velosef (TN); Cefradine (JAN/INN); SK&F D-39304; SK-D-39304; (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; (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-cyclohexadien-1-yl)acetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)-oct-2-ene-2-caboxylic acid; 7-(D-2-Amino-2-(1,4-cyclohexadienyl)acetamide)desacetoxycephalosporanicacid; 7beta-[(2R)-2-(cyclohexa-1,4-dienyl)-2-phenylacetamido]-3-methyl-3,4-didehydrocepham-4-carboxylic acid
Indication
Disease Entry ICD 11 Status REF
Acute otitis media AB00 Approved [1]
Bacterial infection 1A00-1C4Z Approved [2]
Pars planitis N.A. Approved [3]
Pneumonia CA40 Approved [4]
Prostatitis N.A. Approved [5]
Respiratory tract infection CA45 Approved [4]
Staphylococcal pneumonia N.A. Approved [4]
Staphylococcus aureus infection N.A. Approved [4]
Urinary tract infection GC08 Approved [6]
⏷ Show the Full List of Indication(s)
Therapeutic Class
Antibiotics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 349.4
Logarithm of the Partition Coefficient (xlogp) 0.4
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 6
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [7]
Bioavailability
94% of drug becomes completely available to its intended biological destination(s) [8]
Clearance
The drug present in the plasma can be removed from the body at the rate of 3.3 mL/min/kg [9]
Elimination
86% of drug is excreted from urine in the unchanged form [7]
Half-life
The concentration or amount of drug in body reduced by one-half in 0.85 hours [9]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 190.89238 micromolar/kg/day [10]
Unbound Fraction
The unbound fraction of drug in plasma is 0.95% [9]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.21 L/kg [9]
Water Solubility
The ability of drug to dissolve in water is measured as 26 mg/mL [7]
Chemical Identifiers
Formula
C16H19N3O4S
IUPAC Name
(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
Canonical SMILES
CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)[C@@H](C3=CCC=CC3)N)SC1)C(=O)O
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
InChIKey
RDLPVSKMFDYCOR-UEKVPHQBSA-N
Cross-matching ID
PubChem CID
38103
ChEBI ID
CHEBI:3547
CAS Number
38821-53-3
DrugBank ID
DB01333
TTD ID
D06KKS
VARIDT ID
DR00544
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Bacterial Penicillin binding protein (Bact PBP) TTJP4SM NOUNIPROTAC Binder [11]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Peptide transporter 2 (SLC15A2) DT8QKNP S15A2_HUMAN Substrate [12]
Peptide transporter 1 (SLC15A1) DT9G7XN S15A1_HUMAN Substrate [13]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Cefradine (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Givosiran DM5PFIJ Moderate Increased risk of nephrotoxicity by the combination of Cefradine and Givosiran. Inborn porphyrin/heme metabolism error [5C58] [14]
Plazomicin DMKMBES Moderate Increased risk of nephrotoxicity by the combination of Cefradine and Plazomicin. Urinary tract infection [GC08] [15]

References

1 [Double-blind comparative trial of cefroxadine and cephalexin in the treatment of acute suppurative otitis media and acute exacerbation of chronic suppurative otitis media]. Jpn J Antibiot. 1983 Sep;36(9):2595-634.
2 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4830).
3 A standard database for drug repositioning. Sci Data. 2017 Mar 14;4:170029.
4 Cefazolin. Ann Intern Med. 1978 Nov;89(5 Pt 1):650-6.
5 Developmental stage and infection status may affect drug distribution in the prostate of rats. Xenobiotica. 2024 Apr 25:1-9.
6 [Bacterial pathogens and resistance patterns in community acquired pediatric urinary tract infection: experience of 152 cases]. Zhongguo Dang Dai Er Ke Za Zhi. 2006 Apr;8(2):115-7.
7 BDDCS applied to over 900 drugs
8 Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
9 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
10 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
11 Staphylococcus aureus PBP4 is essential for beta-lactam resistance in community-acquired methicillin-resistant strains. Antimicrob Agents Chemother. 2008 Nov;52(11):3955-66.
12 Transport characteristics of a novel peptide transporter 1 substrate, antihypotensive drug midodrine, and its amino acid derivatives. J Pharmacol Exp Ther. 2006 Jul;318(1):455-60.
13 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.
14 Cerner Multum, Inc. "Australian Product Information.".
15 Engle JE, Drago J, Carlin B, Schoolwerth AC "Letter: Reversible acute renal failure after cephalothin." Ann Intern Med 83 (1975): 232-3. [PMID: 1147461]