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Gram-positive bacterial infection 1B74-1G40 Withdrawn from market [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 415.5
Topological Polar Surface Area (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 [4]
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 [5]
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
CHEBI:3537
CAS Number
50-59-9
DrugBank ID
DB09008
TTD ID
D0F8IO
VARIDT ID
DR00612
INTEDE ID
DR0285

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 [6]
Organic anion transporter 3 (SLC22A8) DTVP67E S22A8_HUMAN Substrate [7]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [8]
Beta-lactamase (blaB) DEKGVS4 PENA_BURM1 Substrate [9]
Beta-lactamase (blaB) DET9I1W BLAC_BACUN Substrate [10]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

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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
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6 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.
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8 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.
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15 Analysis of human cytochrome P450 2C8 substrate specificity using a substrate pharmacophore and site-directed mutants. Biochemistry. 2004 Dec 14;43(49):15379-92.
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23 Several hPepT1-transported drugs are substrates of the Escherichia coli proton-coupled oligopeptide transporter YdgR. Res Microbiol. 2017 Jun;168(5):443-449.
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