Details of the Drug

General Information of Drug (ID: DM3VOGS)

Drug Name

Ceftizoxime

Synonyms

Ceftix; Ceftizoxima; Ceftizoximum; Eposerin; Ceftizoxime Monosodium Salt; FK749; FR 13749; Cefizox (TN); Ceftizoxima[INN-Spanish]; Ceftizoxime (INN); Ceftizoxime [INN:BAN]; Ceftizoximum [INN-Latin]; FK-749; FR-13479; FR-13749; SKF-88373; SK&F 88373-2; Syn-7-(2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetamido)-3-cephem-4-carboxylic acid; (6R,7R)-7-(2-(2-Amino-4-thiazolyl)-2Z-(methoxyimino)acetamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-2-carbonsaeure; (6R,7R)-7-(2-(2-Amino-4-thiazolyl)glyoxyamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-carbonsaeure-7-(Z)-(O-methyloxim); (6R,7R)-7-({(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(methyloxy)imino]acetyl}amino)-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-methoxyiminoacetyl]amino]-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-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 7beta-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-2,3-didehydropenam-2-carboxylic acid

Indication

Disease Entry	ICD 11	Status	REF
Acute gonococcal cervicitis	N.A.	Approved	[1]
Bacteremia	1A73	Approved	[1]
Bacterial infection	1A00-1C4Z	Approved	[2]
Peritonitis	N.A.	Approved	[1]
Pneumonia	CA40	Approved	[1]
Staphylococcal pneumonia	N.A.	Approved	[1]
Staphylococcus aureus infection	N.A.	Approved	[1]
Urinary tract infection	GC08	Approved	[1]
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Therapeutic Class

Antibiotics

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

383.4

Logarithm of the Partition Coefficient (xlogp)

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 [3]
Clearance: The drug present in the plasma can be removed from the body at the rate of 2.1 mL/min/kg [4]
Elimination: 93% 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 1.5 hours [4]
Metabolism: The drug is not metabolised []
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 260.8194 micromolar/kg/day [5]
Unbound Fraction: The unbound fraction of drug in plasma is 0.72% [4]
Vd: The volume of distribution (Vd) of drug is 15-28 L [6]

Chemical Identifiers

Formula: C13H13N5O5S2
IUPAC Name: (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Canonical SMILES: CO/N=C(/C1=CSC(=N1)N)\\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=CCS3)C(=O)O
InChI: InChI=1S/C13H13N5O5S2/c1-23-17-7(5-4-25-13(14)15-5)9(19)16-8-10(20)18-6(12(21)22)2-3-24-11(8)18/h2,4,8,11H,3H2,1H3,(H2,14,15)(H,16,19)(H,21,22)/b17-7-/t8-,11-/m1/s1
InChIKey: NNULBSISHYWZJU-LLKWHZGFSA-N

Cross-matching ID

PubChem CID: 6533629
ChEBI ID: CHEBI:553473
CAS Number: 68401-81-0
DrugBank ID: DB01332
TTD ID: D0Y7BD
VARIDT ID: DR00320

Repurposed Drugs (RPD)

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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]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Multidrug resistance-associated protein 4 (ABCC4)	DTCSGPB	MRP4_HUMAN	Substrate	[8]
Organic anion transporter 1 (SLC22A6)	DTQ23VB	S22A6_HUMAN	Substrate	[9]
Organic anion transporter 3 (SLC22A8)	DTVP67E	S22A8_HUMAN	Substrate	[10]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Ceftizoxime (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Plazomicin	DMKMBES	Moderate	Increased risk of nephrotoxicity by the combination of Ceftizoxime and Plazomicin.	Urinary tract infection [GC08]	[11]
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References

1	Ceftizoxime FDA Label
2	Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
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	Richards DM, Heel RC: Ceftizoxime. A review of its antibacterial activity, pharmacokinetic properties and therapeutic use. Drugs. 1985 Apr;29(4):281-329. doi: 10.2165/00003495-198529040-00001.
7	Role of penicillin-binding protein 2 (PBP2) in the antibiotic susceptibility and cell wall cross-linking of Staphylococcus aureus: evidence for the cooperative functioning of PBP2, PBP4, and PBP2A. JBacteriol. 2005 Mar;187(5):1815-24.
8	Oral availability of cefadroxil depends on ABCC3 and ABCC4. Drug Metab Dispos. 2012 Mar;40(3):515-21.
9	FDA Drug Development and Drug Interactions
10	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.
11	Engle JE, Drago J, Carlin B, Schoolwerth AC "Letter: Reversible acute renal failure after cephalothin." Ann Intern Med 83 (1975): 232-3. [PMID: 1147461]