Details of the Drug

General Information of Drug (ID: DMJXDGC)

Drug Name
Cefaclor
Synonyms
Alenfral; Alfacet; Alfatil; CCL; Ceclor; Cefaclorum; Distaclor; Kefolor; Panacef; Panoral; Alfatil Kapseln; Cefaclor anhydrous; Cefaclor hydrate; Cefaclor monohydrate; Dystaclor MR; Kefolor Suspension; Muco Panoral; Lilly 99638 hydrate; Alenfral (TN); Ceclor (TN); Cefaclor (JP15); Cefaclor (USP); Distaclor (TN); Keflor (TN); L-Kefral; Raniclor (TN); S-6472; Cefaclor-1-wasser; Cefaclor [USAN:INN:BAN:JAN]; Ceclor, Distaclor, Keflor, Raniclor, Cefaclor; (6R,7R)-7-((R)-2-Amino-2-phenylacetamido)-3-chloro-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid monohydrate; (6R,7R)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid hydrate; (6R,7R)-7-{[(2R)-2-amino-2-phenylacetyl]amino}-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 3-Chloro-7-D-(2-phenylglycinamido)-3-cephem-4-carboxylic acid; 3-Chloro-7-D-(2-phenylglycinamido)-3-cephem-4-carboxylic acid monohydrate; 7-(2-Amino-2-phenyl-acetylamino)-3-chloro-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 7beta-{[(2R)-2-amino-2-phenylacetyl]amino}-3-chloro-3,4-didehydrocepham-4-carboxylic acid
Indication
Disease Entry ICD 11 Status REF
Bacterial infection 1A00-1C4Z Approved [1]
Pars planitis N.A. Approved [2]
Pneumonia CA40 Approved [2]
Respiratory tract infection CA45 Approved [2]
Staphylococcus aureus infection N.A. Approved [2]
Urinary tract infection GC08 Approved [2]
⏷ 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) 367.8
Logarithm of the Partition Coefficient (xlogp) -1.8
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 [3]
Bioavailability
90% of drug becomes completely available to its intended biological destination(s) [4]
Elimination
52% of drug is excreted from urine in the unchanged form [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 0.6 - 0.9 hours [5]
Metabolism
The drug is metabolized via the liver []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 67.96922 micromolar/kg/day [6]
Water Solubility
The ability of drug to dissolve in water is measured as 8.59 mg/mL [3]
Chemical Identifiers
Formula
C15H14ClN3O4S
IUPAC Name
(6R,7R)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Canonical SMILES
C1C(=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)O)Cl
InChI
InChI=1S/C15H14ClN3O4S/c16-8-6-24-14-10(13(21)19(14)11(8)15(22)23)18-12(20)9(17)7-4-2-1-3-5-7/h1-5,9-10,14H,6,17H2,(H,18,20)(H,22,23)/t9-,10-,14-/m1/s1
InChIKey
QYIYFLOTGYLRGG-GPCCPHFNSA-N
Cross-matching ID
PubChem CID
51039
ChEBI ID
CHEBI:3478
CAS Number
53994-73-3
DrugBank ID
DB00833
TTD ID
D0PW7C
VARIDT ID
DR00259
ACDINA ID
D00104
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
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 [7]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Peptide transporter 2 (SLC15A2) DT8QKNP S15A2_HUMAN Substrate [8]
Peptide transporter 1 (SLC15A1) DT9G7XN S15A1_HUMAN Substrate [9]
Organic anion transporter 1 (SLC22A6) DTQ23VB S22A6_HUMAN Substrate [10]
Organic anion transporter 3 (SLC22A8) DTVP67E S22A8_HUMAN Substrate [11]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Bile salt export pump (ABCB11) OTRU7THO ABCBB_HUMAN Gene/Protein Processing [12]
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Gene/Protein Processing [13]
Organic anion transporter 3 (SLC22A8) OT8BY933 S22A8_HUMAN Regulation of Drug Effects [11]
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 Cefaclor (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Mycophenolic acid DMRBMAU Moderate Altered absorption of Cefaclor due to GI flora changes caused by Mycophenolic acid. Crohn disease [DD70] [14]
Ethacrynic acid DM60QMR Moderate Increased risk of nephrotoxicity by the combination of Cefaclor and Ethacrynic acid. Essential hypertension [BA00] [15]
Bumetanide DMRV7H0 Moderate Increased risk of nephrotoxicity by the combination of Cefaclor and Bumetanide. Heart failure [BD10-BD1Z] [15]
Quinapril DMR8H31 Moderate Decreased absorption of Cefaclor due to formation of complexes caused by Quinapril. Hypertension [BA00-BA04] [16]
Probenecid DMMFWOJ Moderate Decreased elimination of Cefaclor caused by Probenecid mediated competitive inhibition of renal tubular secretion. Inborn purine/pyrimidine/nucleotide metabolism error [5C55] [17]

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Allura red AC dye E00338 33258 Colorant
D&C red no. 28 E00491 6097185 Colorant
FD&C blue no. 1 E00263 19700 Colorant
FD&C blue no. 2 E00446 2723854 Colorant
Isopropyl alcohol E00070 3776 Antimicrobial preservative; Solvent
Mannitol E00103 6251 Diluent; Flavoring agent; Lyophilization aid; Plasticizing agent; Tonicity agent
Quinoline yellow WS E00309 24671 Colorant
Sunset yellow FCF E00255 17730 Colorant
Ammonia E00007 222 Alkalizing agent
Carmellose sodium E00625 Not Available Disintegrant
FD&C red no. 3 E00629 Not Available Colorant
Ferrosoferric oxide E00231 14789 Colorant
Lactose monohydrate E00393 104938 Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate E00208 11177 lubricant
Polyethylene glycol 400 E00653 Not Available Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Potassium hydroxide E00233 14797 Alkalizing agent
Propylene glycol E00040 1030 Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc E00520 16211421 Anticaking agent; Diluent; Glidant; lubricant
Tert-Butyl alcohol E00120 6386 Solvent
Titanium dioxide E00322 26042 Coating agent; Colorant; Opacifying agent
⏷ Show the Full List of 21 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Cefaclor 500 mg capsule 500 mg Oral Capsule Oral
Cefaclor 250 mg capsule 250 mg Oral Capsule Oral
Cefaclor 500 mg tablet 500 mg 12 HR Extended Release Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 062206.
2 Cefaclor FDA Label
3 BDDCS applied to over 900 drugs
4 Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
5 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6 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
7 Antibacterial activity of oral cephems against various clinically isolated strains and evaluation of efficacy based on the pharmacokinetics/pharmacodynamics theory. Jpn J Antibiot. 2004 Dec;57(6):465-74.
8 Interactions of amoxicillin and cefaclor with human renal organic anion and peptide transporters. Drug Metab Dispos. 2006 Apr;34(4):547-55.
9 Protein hydrolysate-induced cholecystokinin secretion from enteroendocrine cells is indirectly mediated by the intestinal oligopeptide transporter PepT1. Am J Physiol Gastrointest Liver Physiol. 2011 May;300(5):G895-902.
10 FDA Drug Development and Drug Interactions
11 Human organic anion transporter hOAT3 is a potent transporter of cephalosporin antibiotics, in comparison with hOAT1. Biochem Pharmacol. 2005 Oct 1;70(7):1104-13.
12 Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43.
13 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.
14 Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ.
15 Chrysos G, Gargalianos P, Lelekis M, Stefanou J, Kosmidis J "Pharmacokinetic interactions of ceftazidime and frusemide." J Chemother 7 Suppl (1995): 107-10. [PMID: 8904125]
16 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
17 Brown G, Zemcov SJ, Clarke AM "Effect of probenecid on cefazolin serum concentrations." J Antimicrob Chemother 31 (1993): 1009-11. [PMID: 8360120]