MEZLOCILLIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H25N5O8S2
Molecular Weight	539.582
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](NC(=O)N3CCN(C3=O)S(C)(=O)=O)C4=CC=CC=C4)C(=O)N2[C@H]1C(O)=O

InChI

InChIKey=YPBATNHYBCGSSN-VWPFQQQWSA-N

InChI=1S/C21H25N5O8S2/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)/t12-,13-,14+,17-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C21H25N5O8S2
Molecular Weight	539.582
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 234 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6220263	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6220263	Curative		Approved 8583	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 Health Status: unhealthy Age Group: 19-56 years Sex: M+F 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 Health Status: unhealthy Age Group: 27-74 years Sex: M+F 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 Health Status: unhealthy Age Group: 27-74 years Sex: M+F 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 Health Status: unhealthy Age Group: 27-74 years Sex: M+F 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 Health Status: unhealthy Age Group: 27-74 years Sex: M+F 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
eMolecules	30100390	https://www.emolecules.com/cgi-bin/more?vid=30100390
MolPort	MolPort-006-129-469	https://www.molport.com/shop/molecule-link/MolPort-006-129-469
ZINC	ZINC000003831120	http://zinc15.docking.org/substances/ZINC000003831120

PubMed

Title	Date	PubMed
Pseudo-template molecularly imprinted polymer for selective screening of trace beta-lactam antibiotics in river and tap water.	2010-08-13	20630531
Antibiotics for pre-term pre-labour rupture of membranes: prevention of neonatal deaths due to complications of pre-term birth and infection.	2010-04	20348116
In-vitro efficacy of synergistic antibiotic combinations in multidrug resistant Pseudomonas aeruginosa strains.	2010-01	20046523
Multiple liver abscesses with isolation of Streptococcus intermedius related to a pyogenic dental infection in an immuno-competent patient.	2010	20696645
IVC CLAMP: infrahepatic inferior vena cava clamping during hepatectomy--a randomised controlled trial in an interdisciplinary setting.	2009-10-13	19825186
Prevalence of virulence factors and antimicrobial resistance of uropathogenic Escherichia coli in Jiangsu province (China).	2009-09	19362346
[Antimicrobial resistance and existence of metallo-beta-lactamase in Acinetobacter species isolated from adult patients].	2009-07	19795613
Stenotrophomonas maltophilia induced post-cataract-surgery endophthalmitis: Outbreak investigation and clinical courses of 26 patients.	2009-04	19148575
Antibiotic susceptibility profile of Aeromonas spp. isolates from food in Abu Dhabi, United Arab Emirates.	2009-01	19382665
Isolation of Bordetella avium and novel Bordetella strain from patients with respiratory disease.	2009-01	19116056
Involvement of a phospholipase C in the hemolytic activity of a clinical strain of Pseudomonas fluorescens.	2008-10-30	18973676
[Pneumocephalus caused by neonatal Enterobacter cloacae infection in a case].	2008-09	19099852
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.	2008-09	18667026
Potency of IMP-10 metallo-beta-lactamase in hydrolysing various antipseudomonal beta-lactams.	2008-08	18628498
Lethal pneumatosis coli in a 12-month-old child caused by acute intestinal gas gangrene after prolonged artificial nutrition: a case report.	2008-07-24	18652650
Effects of prophylactic antibiotic therapy with mezlocillin plus sulbactam on the incidence and height of fever after severe acute ischemic stroke: the Mannheim infection in stroke study (MISS).	2008-04	18309164
An RND-type efflux system in Borrelia burgdorferi is involved in virulence and resistance to antimicrobial compounds.	2008-02-29	18389081
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
Wound botulism in injection drug users.	2007-06	17582887
Antimicrobial therapy for acute cholangitis: Tokyo Guidelines.	2007	17252298
Clinical, microbiologic, and epidemiologic characteristics of Pseudomonas aeruginosa infections in a University Hospital, Malatya, Turkey.	2006-05	16679175
Antibiotic therapy for preterm premature rupture of membranes - results of a multicenter study.	2006	16602839
Antibiotic susceptibility of preoperative normal conjunctival bacteria.	2005-04	15808182
Burkholderia cenocepacia vaginal infection in patient with smoldering myeloma and chronic hepatitis C.	2004-11	15550207
Serotypes and anti-microbial susceptibility of Plesiomonas shigelloides isolates from humans, animals and aquatic environments in different countries.	2004-03	14690722
[Nosocomial pseudomonas aeruginosa-associated keratitis in soft contact lens wearer].	2004-01	14745680
Piperacillin induced bone marrow suppression: a case report.	2003-06-05	12791166
[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)].	2003-01	12574879
Clinical determinants for the recovery of fungal and mezlocillin-resistant pathogens from bile specimens.	2002-04-01	11880954
[Analysis of prophylactic antibiotics for cesarean section].	2002-01	11953060
Serotypes, virulence factors, antibiotic sensitivity, beta-lactamase activity and plasmid analysis of Salmonella from children with diarrhea in Tripoli (Libya).	2002	12512253
Neonatal bacteremia: patterns of antibiotic resistance.	2001-12	11876455
Efficacy of oral ofloxacin for single-dose perioperative prophylaxis in general surgery--a controlled randomized clinical study.	2001-11	11735011
Pharmacokinetic basis for oral perioperative prophylaxis with ofloxacin in general surgery.	2001-08	11545485
An outbreak of Salmonella enteritidis infection in pygmy hogs (Sus salvanius).	2001-04	11254078
In vitro activity of mezlocillin, meropenem, aztreonam, vancomycin, teicoplanin, ribostamycin and fusidic acid against Borrelia burgdorferi.	2001-03	11282265
Treatment of accidental high dose intraventricular mezlocillin application by cerebrospinal fluid exchange.	1998-03	9527154
A prospective randomized trial of ceftazidime versus netilmicin plus mezlocillin in the empirical therapy of presumed sepsis in cirrhotic patients.	1997-04	9096584
Pharmacokinetics of mezlocillin and sulbactam under continuous veno-venous hemodialysis (CVVHD) in intensive care patients with acute renal failure.	1997	9403281
Severe cholestatic jaundice caused by mezlocillin.	1992-07	1617065
Identification of penicillin allergenic determinants that bind IgE antibodies in the sera of subjects with penicillin allergy.	1990-11	1701026
A controlled study of the nephrotoxicity of mezlocillin and gentamicin plus ampicillin in the neonate.	1987-12	3316564
Acute interstitial nephritis associated with mezlocillin, nafcillin, and gentamicin treatment for Pseudomonas infection.	1985-07	4015267

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Other

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:27:41 GMT 2025` Edited by `admin` on `Mon Mar 31 18:27:41 GMT 2025`
Record UNII	OH2O403D1G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MEZLOCILLIN

Official Name

English

BAY-F-1353

Preferred Name

English

mezlocillin [INN]

Common Name

English

MEZLOCILLIN [VANDF]

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-, (2S-(2.ALPHA.,5.ALPHA.,6.BETA.(S*)))

Common Name

English

Mezlocillin [WHO-DD]

Common Name

English

MEZLOCILLIN [MI]

Common Name

English

(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-carboxylic acid

Systematic Name

English

MEZLOCILLIN [USAN]

Common Name

English

MEZLOCILLIN [MART.]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QJ01CA10