General Information of Drug (ID: DMV2JNY)

Drug Name
Cephapirin
Synonyms
CEPR; Cefa; Cefadyl; Cefapirin; Cefapirina; Cefapirine; Cefapirinum; Cefaprin; Cephapirine; Metricure; CEPHAPIRIN SODIUM; Cefaprinsodium; Cephapirin Monosodium Salt; ANTIBIOTIC BL-P1322; BL-P 1322; Cefa-ak; Cefadyl (TN); Cefapirin (BAN); Cefapirin [INN:BAN]; Cefapirina [INN-Spanish]; Cefapirine [INN-French]; Cefapirinum [INN-Latin]; Metricure (TN); (6R,7R)-3-(Acetoxymethyl)-8-oxo-7-(2-(4-pyridylthio)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-en-2-carbonsaeure; (6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-pyridin-4-ylsulfanylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-{[(pyridin-4-ylthio)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-3-acetoxymethyl-7-[(pyridin-4-ylsulfanyl)acetamido]-3,4-didehydrocepham-4-carboxylic acid; 3-(Hydroxymethyl)-8-oxo-7-(2-(4-pyridylthio)acetamidol-5-thia-1-azabicyclo(4.2.0)oct-2-en-2carbonsaeure acetat; 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-(hydroxymethyl)-8-oxo-7-(2-(4-pyridylthio)acetamido)-, acetate (ester); 7-(2-(4-Pyridylthio)acetamido)cephalosporanic acid
Indication
Disease Entry ICD 11 Status REF
Bacteremia 1A73 Approved [1]
Pneumonia CA40 Approved [1]
Sepsis 1G40-1G41 Approved [2]
Staphylococcal pneumonia N.A. Approved [1]
Staphylococcus aureus infection N.A. Approved [1]
Urinary tract infection GC08 Approved [1]
⏷ 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) 423.5
Logarithm of the Partition Coefficient (xlogp) -1.1
Rotatable Bond Count (rotbonds) 8
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 9
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [3]
Clearance
The drug present in the plasma can be removed from the body at the rate of 2.7 mL/min/kg [4]
Elimination
48% 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 1.2 hours [4]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 236.1445 micromolar/kg/day [5]
Unbound Fraction
The unbound fraction of drug in plasma is 0.55% [4]
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 0.13 L/kg [4]
Chemical Identifiers
Formula
C17H17N3O6S2
IUPAC Name
(6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-pyridin-4-ylsulfanylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Canonical SMILES
CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)CSC3=CC=NC=C3)SC1)C(=O)O
InChI
InChI=1S/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)/t13-,16-/m1/s1
InChIKey
UQLLWWBDSUHNEB-CZUORRHYSA-N
Cross-matching ID
PubChem CID
30699
ChEBI ID
CHEBI:554446
CAS Number
21593-23-7
DrugBank ID
DB01139
TTD ID
D01DSP
VARIDT ID
DR00495
ACDINA ID
D00935
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 [6]
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 Cephapirin (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Kanamycin DM2DMPO Moderate Increased risk of nephrotoxicity by the combination of Cephapirin and Kanamycin. Bacterial infection [1A00-1C4Z] [7]
Plazomicin DMKMBES Moderate Increased risk of nephrotoxicity by the combination of Cephapirin and Plazomicin. Urinary tract infection [GC08] [7]

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

DIG
DIG Name DIG ID PubChem CID Functional Classification
Glyceryl monooleate E00473 5283468 Bioadhesive material; Emollient; Emulsifying agent; Emulsion stabilizing agent; Gelling agent; Modified-release agent; Surfactant
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Cephapirin 200mg/10ml injectable 200mg/10ml Injectable Injection
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 Cephapirin FDA Label
2 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 062720.
3 BDDCS applied to over 900 drugs
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
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 The formation of functional penicillin-binding proteins. J Biol Chem. 1975 Aug 25;250(16):6578-85.
7 Engle JE, Drago J, Carlin B, Schoolwerth AC "Letter: Reversible acute renal failure after cephalothin." Ann Intern Med 83 (1975): 232-3. [PMID: 1147461]