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

[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=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 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 3.69878401E11

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
A controlled study of the nephrotoxicity of mezlocillin and gentamicin plus ampicillin in the neonate.	1987 Dec	3316564
Severe cholestatic jaundice caused by mezlocillin.	1992 Jul	1617065
Treatment of accidental high dose intraventricular mezlocillin application by cerebrospinal fluid exchange.	1998 Mar	9527154
Neonatal bacteremia: patterns of antibiotic resistance.	2001 Dec	11876455
[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
Burkholderia cenocepacia vaginal infection in patient with smoldering myeloma and chronic hepatitis C.	2004 Nov	15550207
Antibiotic susceptibility of preoperative normal conjunctival bacteria.	2005 Apr	15808182
Antibiotic prophylaxis in the management of vesicoureteral reflux.	2008	18827896
Lethal pneumatosis coli in a 12-month-old child caused by acute intestinal gas gangrene after prolonged artificial nutrition: a case report.	2008 Jul 24	18652650
Antibiotics for pre-term pre-labour rupture of membranes: prevention of neonatal deaths due to complications of pre-term birth and infection.	2010 Apr	20348116

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 `Fri Dec 15 16:25:47 UTC 2023` Edited by `admin` on `Fri Dec 15 16:25:47 UTC 2023`
Record UNII	OH2O403D1G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MEZLOCILLIN

Official 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

BAY-F-1353

Code

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