MEZLOCILLIN SODIUM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H24N5O8S2.Na
Molecular Weight	561.564
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](NC(=O)N3CCN(C3=O)S(C)(=O)=O)C4=CC=CC=C4)C([O-])=O

InChI

InChIKey=GTGQRSIMEUWHPA-ZBJAFUORSA-M

InChI=1S/C21H25N5O8S2.Na/c1-21(2)14(18(29)30)26-16(28)13(17(26)35-21)22-15(27)12(11-7-5-4-6-8-11)23-19(31)24-9-10-25(20(24)32)36(3,33)34;/h4-8,12-14,17H,9-10H2,1-3H3,(H,22,27)(H,23,31)(H,29,30);/q;+1/p-1/t12-,13-,14+,17-;/m1./s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6220263

Bayer developed MEZLOCILLIN (previously known as BAYPEN); it is a semisynthetic ampicillin-derived penicillin. Mezlocillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The bactericidal activity of mezlocillin results from the inhibition of cell wall synthesis and is mediated through mezlocillin binding to penicillin binding proteins (PBPs). Mezlocillin is stable against hydrolysis by a variety of beta-lactamases, including penicillinases and cephalosporinases and extended spectrum beta-lactamases. Mezlocillin was poorly absorbed orally and was given either intramuscularly or intravenously. This drug was discontinued in the U.S.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 233 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6220263	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6220263	Curative		Approved 8429	MEZLIN Approved Use Unknown Launch Date 1981

C_max

Value	Dose	Analyte	Population
216.6 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680597	4 g single, intravenous dose: 4 g route of administration: Intravenous experiment type: SINGLE co-administered:	MEZLOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
317 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680597	5 g single, intravenous dose: 5 g route of administration: Intravenous experiment type: SINGLE co-administered:	MEZLOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
138.84 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3818496	3 g single, intravenous dose: 3 g route of administration: Intravenous experiment type: SINGLE co-administered:	MEZLOCILLIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
275 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680597	4 g single, intravenous dose: 4 g route of administration: Intravenous experiment type: SINGLE co-administered:	MEZLOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
403 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680597	5 g single, intravenous dose: 5 g route of administration: Intravenous experiment type: SINGLE co-administered:	MEZLOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
415.2 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3818496	3 g single, intravenous dose: 3 g route of administration: Intravenous experiment type: SINGLE co-administered:	MEZLOCILLIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
1.32 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680597	4 g single, intravenous dose: 4 g route of administration: Intravenous experiment type: SINGLE co-administered:	MEZLOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
1.13 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680597	5 g single, intravenous dose: 5 g route of administration: Intravenous experiment type: SINGLE co-administered:	MEZLOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
2.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3818496	3 g single, intravenous dose: 3 g route of administration: Intravenous experiment type: SINGLE co-administered:	MEZLOCILLIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
6 g 1 times / day multiple, intramuscular Studied dose Dose: 6 g, 1 times / day Route: intramuscular Route: multiple Dose: 6 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6218102	unhealthy, 19-56 years n = 6 Health Status: unhealthy Condition: surgical infections Age Group: 19-56 years Sex: M+F Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/6218102	Sources: https://pubmed.ncbi.nlm.nih.gov/6218102
5 g single, intravenous Highest studied dose Dose: 5 g Route: intravenous Route: single Dose: 5 g Sources: https://pubmed.ncbi.nlm.nih.gov/742869	healthy, 22- 29 years Health Status: healthy Age Group: 22- 29 years Sources: https://pubmed.ncbi.nlm.nih.gov/742869	Sources: https://pubmed.ncbi.nlm.nih.gov/742869
4 g 1 times / day multiple, intramuscular Dose: 4 g, 1 times / day Route: intramuscular Route: multiple Dose: 4 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6218102	unhealthy, 27-74 years n = 4 Health Status: unhealthy Condition: surgical infections Age Group: 27-74 years Sex: M+F Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/6218102	Disc. AE: Nausea, Cephalgia... AEs leading to discontinuation/dose reduction: Nausea (1 patient) Cephalgia (1 patient) Colicky (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/6218102

AEs

AE	Significance	Dose	Population
Cephalgia	1 patient Disc. AE	4 g 1 times / day multiple, intramuscular Dose: 4 g, 1 times / day Route: intramuscular Route: multiple Dose: 4 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6218102	unhealthy, 27-74 years n = 4 Health Status: unhealthy Condition: surgical infections Age Group: 27-74 years Sex: M+F Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/6218102
Colicky	1 patient Disc. AE	4 g 1 times / day multiple, intramuscular Dose: 4 g, 1 times / day Route: intramuscular Route: multiple Dose: 4 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6218102	unhealthy, 27-74 years n = 4 Health Status: unhealthy Condition: surgical infections Age Group: 27-74 years Sex: M+F Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/6218102
Nausea	1 patient Disc. AE	4 g 1 times / day multiple, intramuscular Dose: 4 g, 1 times / day Route: intramuscular Route: multiple Dose: 4 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6218102	unhealthy, 27-74 years n = 4 Health Status: unhealthy Condition: surgical infections Age Group: 27-74 years Sex: M+F Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/6218102

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:6919	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6919
ChemicalBook	CB9268151	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9268151
MolPort	MolPort-006-129-469	https://www.molport.com/shop/molecule-link/MolPort-006-129-469
ZINC	ZINC000003831120	http://zinc15.docking.org/substances/ZINC000003831120
eMolecules	30100390	https://www.emolecules.com/cgi-bin/more?vid=30100390

PubMed

Title	Date	PubMed
Acute interstitial nephritis associated with mezlocillin, nafcillin, and gentamicin treatment for Pseudomonas infection.	1985 Jul	4015267
Severe cholestatic jaundice caused by mezlocillin.	1992 Jul	1617065
Pharmacokinetics of mezlocillin and sulbactam under continuous veno-venous hemodialysis (CVVHD) in intensive care patients with acute renal failure.	1997	9403281
A prospective randomized trial of ceftazidime versus netilmicin plus mezlocillin in the empirical therapy of presumed sepsis in cirrhotic patients.	1997 Apr	9096584
Treatment of accidental high dose intraventricular mezlocillin application by cerebrospinal fluid exchange.	1998 Mar	9527154
An outbreak of Salmonella enteritidis infection in pygmy hogs (Sus salvanius).	2001 Apr	11254078
Neonatal bacteremia: patterns of antibiotic resistance.	2001 Dec	11876455
Efficacy of oral ofloxacin for single-dose perioperative prophylaxis in general surgery--a controlled randomized clinical study.	2001 Nov	11735011
[Analysis of prophylactic antibiotics for cesarean section].	2002 Jan	11953060
[Spectrum of pathogens and resistance to antibiotics in urinary tract infections and the consequences for antibiotic treatment: study of urology inpatients with urinary tract infections (1994-2001)].	2003 Jan	12574879
Clinical, microbiologic, and epidemiologic characteristics of Pseudomonas aeruginosa infections in a University Hospital, Malatya, Turkey.	2006 May	16679175
Wound botulism in injection drug users.	2007 Jun	17582887
Antibiotic prophylaxis in the management of vesicoureteral reflux.	2008	18827896
[Antibiotic susceptibility and occurrence of ESBL, IBL and MBL in Pseudomonas aeruginosa strains].	2008	18819447
Comparative analysis of antibiotic resistance characteristics of Gram-negative bacteria isolated from laying hens and eggs in conventional and organic keeping systems in Bavaria, Germany.	2008 Sep	18667026
Antibiotic susceptibility profile of Aeromonas spp. isolates from food in Abu Dhabi, United Arab Emirates.	2009 Jan	19382665
[Antimicrobial resistance and existence of metallo-beta-lactamase in Acinetobacter species isolated from adult patients].	2009 Jul	19795613
Multiple liver abscesses with isolation of Streptococcus intermedius related to a pyogenic dental infection in an immuno-competent patient.	2010	20696645
Pseudo-template molecularly imprinted polymer for selective screening of trace beta-lactam antibiotics in river and tap water.	2010 Aug 13	20630531
In-vitro efficacy of synergistic antibiotic combinations in multidrug resistant Pseudomonas aeruginosa strains.	2010 Jan	20046523

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Other

In Vitro Use Guide

Unknown

Name

Type

Language

MEZLOCILLIN SODIUM

Common Name

English

Mezlocillin sodium [WHO-DD]

Common Name

English

MEZLOCILLIN SODIUM SALT [MI]

Common Name

English

4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 3,3-DIMETHYL-6-(((((3-(METHYLSULFONYL)-2-OXO-1-IMIDAZOLIDINYL)CARBONYL)AMINO)PHENYLACETYL)AMINO)-7-OXO-, MONOSODIUM SALT, (2S-(2.ALPHA.,5.ALPHA.,6.BETA.(S*)))-

Common Name

English

MEZLOCILLIN SODIUM [USP IMPURITY]

Common Name

English

MEZLOCILLIN SODIUM [VANDF]

Common Name

English

Sodium (2S,5R,6R)-3,3-dimethyl-6-[(R)-2-[3-(methylsulfonyl)-2-oxo-1-imidazolidinecarboxamido]-2-phenylacetamido]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Common Name

English

Code System Code Type Description

ChEMBL

CHEMBL1731