Details of the Drug

General Information of Drug (ID: DM4Y95F)

Drug Name
Cephaloridine
Synonyms
cephaloridine; cefaloridine; Cefaloridin; Cephaloridin; Cephaloridinum; Cepaloridin; Cefalorizin; Cephalomycine; Cefaloridinum; Cepalorin; Cefaloridina; Loridine; Ceflorin; 50-59-9; Kefloridin; Glaxoridin; Ceporin; Vioviantine; Intrasporin; Sefacin; Keflordin; Deflorin; Cilifor; Ceporan; Sasperin; Faredina; Ceporine; Keflodin; Verolgin; Lloncefal; Kefspor; Ampligram; Betaine cephaloridine; CHEBI:3537; UNII-LVZ1VC61HB; Cefaloridinum [INN-Latin]; Cefaloridina [INN-Spanish]; N-(7-(2'-Thienylacetamidoceph-3-ylmethyl))-pyridinium-2-carboxylate; SCH
Indication
Disease Entry ICD 11 Status REF
Gram-positive bacterial infection 1B74-1G40 Withdrawn from market [1]
ATC Code
J01DB02: Cephaloridine
J01DB: First-generation cephalosporins
J01D: OTHER BETA-LACTAM ANTIBACTERIALS
J01: ANTIBACTERIALS FOR SYSTEMIC USE
J: ANTIINFECTIVES FOR SYSTEMIC USE
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 415.5
Logarithm of the Partition Coefficient (xlogp) 1.9
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 6
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [2]
Clearance
The drug present in the plasma can be removed from the body at the rate of 3.3 mL/min/kg [3]
Elimination
The drug is excreted via renal []
Half-life
The concentration or amount of drug in body reduced by one-half in 1.5 hours [3]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 206.3 micromolar/kg/day [4]
Unbound Fraction
The unbound fraction of drug in plasma is 0.8% [3]
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 0.46 L/kg [3]
Chemical Identifiers
Formula
C19H17N3O4S2
IUPAC Name
(6R,7R)-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
Canonical SMILES
C1C(=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)CC3=CC=CS3)C(=O)[O-])C[N+]4=CC=CC=C4
InChI
InChI=1S/C19H17N3O4S2/c23-14(9-13-5-4-8-27-13)20-15-17(24)22-16(19(25)26)12(11-28-18(15)22)10-21-6-2-1-3-7-21/h1-8,15,18H,9-11H2,(H-,20,23,25,26)/t15-,18-/m1/s1
InChIKey
CZTQZXZIADLWOZ-CRAIPNDOSA-N
Cross-matching ID
PubChem CID
5773
ChEBI ID
CHEMBL316157
CAS Number
50-59-9
UNII
LVZ1VC61HB
DrugBank ID
DB09008
TTD ID
D0F8IO
VARIDT ID
DR00612
INTEDE ID
DR0285
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Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Peptide transporter 1 (SLC15A1) DT9G7XN S15A1_HUMAN Substrate [5]
Organic anion transporter 3 (SLC22A8) DTVP67E S22A8_HUMAN Substrate [6]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [7]
Beta-lactamase (blaB) DEKGVS4 PENA_BURM1 Substrate [8]
Beta-lactamase (blaB) DET9I1W BLAC_BACUN Substrate [9]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Organic anion transporter 3 (SLC22A8) OT8BY933 S22A8_HUMAN Regulation of Drug Effects [6]
Solute carrier family 22 member 6 (SLC22A6) OTKRCBVM S22A6_HUMAN Regulation of Drug Effects [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 BDDCS predictions, self-correcting aspects of BDDCS assignments, BDDCS assignment corrections, and classification for more than 175 additional drugs
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4 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
5 Intestinal transport of beta-lactam antibiotics: analysis of the affinity at the H+/peptide symporter (PEPT1), the uptake into Caco-2 cell monolayers and the transepithelial flux. Pharm Res. 1999 Jan;16(1):55-61.
6 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.
7 Gemfibrozil and its glucuronide inhibit the organic anion transporting polypeptide 2 (OATP2/OATP1B1:SLC21A6)-mediated hepatic uptake and CYP2C8-mediated metabolism of cerivastatin: analysis of the mechanism of the clinically relevant drug-drug interaction between cerivastatin and gemfibrozil. J Pharmacol Exp Ther. 2004 Oct;311(1):228-36.
8 Characterization of the penA and penR genes of Burkholderia cepacia 249 which encode the chromosomal class A penicillinase and its LysR-type transcriptional regulator. Antimicrob Agents Chemother. 1997 Nov;41(11):2399-405.
9 Purification and characterization of a new beta-lactamase from Bacteroides uniformis. Antimicrob Agents Chemother. 1995 Jul;39(7):1458-61.