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Gram-positive bacterial infection	1B74-1G40	Withdrawn from market	[1]
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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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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]

Adverse Drug Reaction (ADR)

ADR Term	Variation	Related DOT	DOT ID	REF
Injury	Not Available	GPX1	OTE2O72Q	[5]
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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]

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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]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Glutathione peroxidase 1 (GPX1)	OTE2O72Q	GPX1_HUMAN	Drug Response	[5]
Organic anion transporter 3 (SLC22A8)	OT8BY933	S22A8_HUMAN	Regulation of Drug Effects	[7]
Solute carrier family 22 member 6 (SLC22A6)	OTKRCBVM	S22A6_HUMAN	Regulation of Drug Effects	[7]

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Molecular Interaction Atlas (MIA)

MIA Detail

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	ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
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.
7	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.
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.
9	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.
10	Purification and characterization of a new beta-lactamase from Bacteroides uniformis. Antimicrob Agents Chemother. 1995 Jul;39(7):1458-61.