General Information of Drug (ID: DMJ7A0H)

Drug Name
Cefdinir
Synonyms
CFDN; Cefdinirum; Cefdinyl; Cefdirnir; Cefzon; Omnicef; BMY 28488; FK 482; PD 134393; Cefdinir [USAN:INN]; Cefdinirum [INN-Latin]; Cefzon (TN); FK-482; FR-80482; KS-1038; Omnicef (TN); PD-134393; Cefdinir (JP15/USAN/INN); Omnicef, FK-482, BMY-28488, PD 134393, CI-983, Cefdinir; (-)-(6R,7R)-7-(2-(2-Amino-4-thiazolyl)glyoxylamido)-8-oxo-3-vinyl-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7(sup 2)-(Z)-oxime; (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(hydroxyimino)acetyl]amino}-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 7-(2 (2-aminothiazol-4-yl)-2-hydroxyiminoacetamido)-3-vinyl-3-cephem-4-carboxylic acid; 7beta-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(hydroxyimino)acetamido]-3-ethenyl-3,4-didehydrocepham-4-carboxylic acid
Indication
Disease Entry ICD 11 Status REF
Bacterial infection 1A00-1C4Z Approved [1]
Therapeutic Class
Antibiotics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 395.4
Topological Polar Surface Area (xlogp) 0
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 10
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 4: low solubility and low permeability [2]
Bioavailability
The bioavailability of drug is 25% [3]
Clearance
The renal clearance of drug is 2.0 mL/min/kg [4]
Elimination
Approximately 18.4% of a 300 mg dose of cefdinir was found unchanged in the urine after a 300 mg dose was administered during a pharmacokinetic study of 21 individuals [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 1.7 hours [3]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 25.29 micromolar/kg/day [5]
Vd
The volume of distribution (Vd) of drug is 0.35 L/kg [6]
Chemical Identifiers
Formula
C14H13N5O5S2
IUPAC Name
(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Canonical SMILES
C=CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N\\O)/C3=CSC(=N3)N)SC1)C(=O)O
InChI
InChI=1S/C14H13N5O5S2/c1-2-5-3-25-12-8(11(21)19(12)9(5)13(22)23)17-10(20)7(18-24)6-4-26-14(15)16-6/h2,4,8,12,24H,1,3H2,(H2,15,16)(H,17,20)(H,22,23)/b18-7-/t8-,12-/m1/s1
InChIKey
RTXOFQZKPXMALH-GHXIOONMSA-N
Cross-matching ID
PubChem CID
6915944
ChEBI ID
CHEBI:3485
CAS Number
91832-40-5
DrugBank ID
DB00535
TTD ID
D0WS1X
VARIDT ID
DR00692
ACDINA ID
D00106

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 1 (SLC15A1) DT9G7XN S15A1_HUMAN Substrate [8]
Organic anion transporter 3 (SLC22A8) DTVP67E S22A8_HUMAN Substrate [9]
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 Cefdinir (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Mestranol DMG3F94 Moderate Decreased absorption of Cefdinir due to formation of complexes caused by Mestranol. Contraceptive management [QA21] [36]
Mycophenolic acid DMU65NK Moderate Altered absorption of Cefdinir due to GI flora changes caused by Mycophenolic acid. Crohn disease [DD70] [37]
Ethacrynic acid DM60QMR Moderate Increased risk of nephrotoxicity by the combination of Cefdinir and Ethacrynic acid. Essential hypertension [BA00] [38]
Furosemide DMMQ8ZG Moderate Increased risk of nephrotoxicity by the combination of Cefdinir and Furosemide. Heart failure [BD10-BD1Z] [38]
Bumetanide DMRV7H0 Moderate Increased risk of nephrotoxicity by the combination of Cefdinir and Bumetanide. Heart failure [BD10-BD1Z] [38]
Probenecid DMMFWOJ Moderate Decreased elimination of Cefdinir caused by Probenecid mediated competitive inhibition of renal tubular secretion. Inborn purine/pyrimidine/nucleotide metabolism error [5C55] [39]
Iron DMAP8MV Moderate Decreased absorption of Cefdinir due to formation of complexes caused by Iron. Iron deficiency anaemia [3A00] [40]
Ethinyl estradiol DMODJ40 Moderate Decreased absorption of Cefdinir due to formation of complexes caused by Ethinyl estradiol. Menopausal disorder [GA30] [36]
Mycophenolate mofetil DMPQAGE Moderate Altered absorption of Cefdinir due to GI flora changes caused by Mycophenolate mofetil. Transplant rejection [NE84] [37]
⏷ Show the Full List of 9 DDI Information of This Drug

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
D&C red no. 33 E00261 19116 Colorant
FD&C blue no. 1 E00263 19700 Colorant
FD&C blue no. 2 E00446 2723854 Colorant
Isopropyl alcohol E00070 3776 Antimicrobial preservative; Solvent
Quinoline yellow WS E00309 24671 Colorant
Sodium lauryl sulfate E00464 3423265 Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Ammonia E00007 222 Alkalizing agent
Butyl alcohol E00011 263 Flavoring agent; Solvent
Carmellose sodium E00625 Not Available Disintegrant
Ferrosoferric oxide E00231 14789 Colorant
Magnesium stearate E00208 11177 lubricant
Polyoxyl 40 stearate E00663 Not Available Emulsifying agent; Surfactant
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
Titanium dioxide E00322 26042 Coating agent; Colorant; Opacifying agent
⏷ Show the Full List of 18 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Cefdinir 300 mg capsule 300 mg Oral Capsule Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

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2 BDDCS applied to over 900 drugs
3 FDA Approved Drug Products: Omnicef (cefdinir)
4 DailyMed: Cefdinir oral capsules
5 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
6 Perry CM, Scott LJ: Cefdinir: a review of its use in the management of mild-to-moderate bacterial infections. Drugs. 2004;64(13):1433-64. doi: 10.2165/00003495-200464130-00004.
7 Decreased affinity of mosaic-structure recombinant penicillin-binding protein 2 for oral cephalosporins in Neisseria gonorrhoeae. J Antimicrob Chemother. 2007 Jul;60(1):54-60.
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9 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.
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12 Several hPepT1-transported drugs are substrates of the Escherichia coli proton-coupled oligopeptide transporter YdgR. Res Microbiol. 2017 Jun;168(5):443-449.
13 High-affinity interaction of sartans with H+/peptide transporters. Drug Metab Dispos. 2009 Jan;37(1):143-9.
14 The intestinal H+/peptide symporter PEPT1: structure-affinity relationships. Eur J Pharm Sci. 2004 Jan;21(1):53-60.
15 Three-dimensional quantitative structure-activity relationship analyses of beta-lactam antibiotics and tripeptides as substrates of the mammalian H+/peptide cotransporter PEPT1. J Med Chem. 2005 Jun 30;48(13):4410-9.
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23 Organic anion transporter 3 is involved in the brain-to-blood efflux transport of thiopurine nucleobase analogs. J Neurochem. 2004 Aug;90(4):931-41.
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26 Aspirin and probenecid inhibit organic anion transporter 3-mediated renal uptake of cilostazol and probenecid induces metabolism of cilostazol in the rat. Drug Metab Dispos. 2014 Jun;42(6):996-1007.
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37 Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ.
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