AZLOCILLIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H23N5O6S
Molecular Weight	461.492
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)N3CCNC3=O)C4=CC=CC=C4)C(O)=O

InChI

InChIKey=JTWOMNBEOCYFNV-NFFDBFGFSA-N

InChI=1S/C20H23N5O6S/c1-20(2)13(17(28)29)25-15(27)12(16(25)32-20)22-14(26)11(10-6-4-3-5-7-10)23-19(31)24-9-8-21-18(24)30/h3-7,11-13,16H,8-9H2,1-2H3,(H,21,30)(H,22,26)(H,23,31)(H,28,29)/t11-,12-,13+,16-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C20H23N5O6S
Molecular Weight	461.492
Charge	0
Count

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

Description
Sources: http://www.antimicrobe.org/new/drugpopup/Azlocillin.pdf | https://www.ncbi.nlm.nih.gov/pubmed/984809

Azlocillin is a semisynthetic penicillin with broad spectrum of anti-bacterial action. The drug is effective against gram-negative and gram-positive infections and acts by inhibition of penicillin-binding protein (PBP)-dependent bacterial cell wall synthesis. Azlocillin was marketed in the USA under the name Azlin (sodium salt), however, its approval was discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 233 Target ID: CHEMBL2354204 Sources: http://www.antimicrobe.org/new/drugpopup/Azlocillin.pdf	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234 Sources: http://www.antimicrobe.org/new/drugpopup/Azlocillin.pdf	Curative		Approved 8429	AZLIN Approved Use Treatment of Gram-positive (Streptococcus spp., Enterococcus, Listeria monocytogenes) and Gram-negative (H. influenzae, E. coli, Proteus mirabilis, Salmonella spp., Shigella spp.) infections. Launch Date 3.99859188E11

C_max

Value	Dose	Co-administered	Analyte	Population
414 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3780161	4 g 4 times / day multiple, intravenous dose: 4 g route of administration: Intravenous experiment type: MULTIPLE co-administered:		AZLOCILLIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
374 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3729353	4 g single, intravenous dose: 4 g route of administration: Intravenous experiment type: SINGLE co-administered:	AZLOCILLIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
592 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2751284	4 g 4 times / day multiple, intravenous dose: 4 g route of administration: Intravenous experiment type: MULTIPLE co-administered:	AZLOCILLIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
772 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2751284	5 g 3 times / day multiple, intravenous dose: 5 g route of administration: Intravenous experiment type: MULTIPLE co-administered:	AZLOCILLIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
1.26 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3729353	4 g single, intravenous dose: 4 g route of administration: Intravenous experiment type: SINGLE co-administered:	AZLOCILLIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.29 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2751284	4 g 4 times / day multiple, intravenous dose: 4 g route of administration: Intravenous experiment type: MULTIPLE co-administered:	AZLOCILLIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.46 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2751284	5 g 3 times / day multiple, intravenous dose: 5 g route of administration: Intravenous experiment type: MULTIPLE co-administered:	AZLOCILLIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3780161	4 g 4 times / day multiple, intravenous dose: 4 g route of administration: Intravenous experiment type: MULTIPLE co-administered:	AZLOCILLIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
17 g 1 times / day multiple, intravenous\|intramuscular Dose: 17 g, 1 times / day Route: intravenous\|intramuscular Route: multiple Dose: 17 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6619026	unhealthy n = 21 Health Status: unhealthy Population Size: 21 Sources: https://pubmed.ncbi.nlm.nih.gov/6619026	Disc. AE: Macular rash, Pruritic rash... AEs leading to discontinuation/dose reduction: Macular rash (4 patients) Pruritic rash (4 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/6619026

AEs

AE	Significance	Dose	Population
Macular rash	4 patients Disc. AE	17 g 1 times / day multiple, intravenous\|intramuscular Dose: 17 g, 1 times / day Route: intravenous\|intramuscular Route: multiple Dose: 17 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6619026	unhealthy n = 21 Health Status: unhealthy Population Size: 21 Sources: https://pubmed.ncbi.nlm.nih.gov/6619026
Pruritic rash	4 patients Disc. AE	17 g 1 times / day multiple, intravenous\|intramuscular Dose: 17 g, 1 times / day Route: intravenous\|intramuscular Route: multiple Dose: 17 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6619026	unhealthy n = 21 Health Status: unhealthy Population Size: 21 Sources: https://pubmed.ncbi.nlm.nih.gov/6619026

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:2956	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2956
ChemicalBook	CB6511850	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6511850
MolPort	MolPort-023-314-370	https://www.molport.com/shop/molecule-link/MolPort-023-314-370
ZINC	ZINC000003830261	http://zinc15.docking.org/substances/ZINC000003830261

PubMed

Title	Date	PubMed
Broth microdilution testing of susceptibilities to 30 antimicrobial agents of Mycobacterium avium strains from patients with acquired immune deficiency syndrome.	1987 Oct	3501698
Evaluation of the immunologic cross-reactivity of aztreonam in patients with cystic fibrosis who are allergic to penicillin and/or cephalosporin antibiotics.	1991 May-Jun	2068466
[Microbiology of open surgical wounds after delivery--episiotomy and cesarean section].	2001	11785348
[Clinical significance of microbiological monitoring of infective agents in an urological hospital in the selection of antibacterial therapy regimens].	2001 Jul-Aug	11569227
[Hoigne syndrome as an acute non-allergic reaction to different drugs: case reports].	2001 Jun	11503262
Natural antibiotic susceptibility of Enterobacter spp., with special reference to Enterobacter aerogenes and Enterobacter intermedius strains.	2002 Oct	12462424
Natural antibiotic susceptibility of Ewingella americana strains.	2003 Oct	14598935
[Bacterial meningitis and Pseudomonas aeruginosa: apropos of a case].	2005 Sep-Dec	17969281
Searching for new antimalarial therapeutics amongst known drugs.	2006 Jun	16882315
How beta-lactam antibiotics enter bacteria: a dialogue with the porins.	2009	19434239
Clinical and ultrasonographic features of abdominal tuberculosis in HIV positive adults in Zambia.	2009 Apr 17	19374757
Detection of Extended Spectrum β-lactamase Production Among Uropathogens.	2009 Jan	21938241
Direct susceptibility testing for multi drug resistant tuberculosis: a meta-analysis.	2009 May 20	19457256
Role of the BACTEC radiometric method in the evaluation of patients with clinically probable tuberculous meningitis.	2010 Apr	20814497
Laboratory diagnosis of tuberculous meningitis - is there a scope for further improvement?	2010 Jan	21814402
In-vitro efficacy of synergistic antibiotic combinations in multidrug resistant Pseudomonas aeruginosa strains.	2010 Jan	20046523

Patents

Sample Use Guides

In Vivo Use Guide

Gram-negative infections: 2 to 5 grams every 8 hours IV. Serious infections: 225 to 300 mg/kg/day IV in 4 to 6 divided doses (usual IV doses 3g q4h or 4g q6h) (up to 18 g/day).

Route of Administration: Intravenous

In Vitro Use Guide

In vitro activity of Azlocillin against different bacterial strains was determined. MIC50 values were 2 ugml (Enterococcus), 8 ug/ml (E. coli), 16 ug/ml (Enterobacter spp.), 64 ug/ml (Klebsiella spp.), 4 ug/ml (P. mirabilis), 16 ug/ml (P. aeruginosa, gentamicin susceptible)).

Substance Class	Chemical Created by `admin` on `Sat Dec 16 18:03:16 UTC 2023` Edited by `admin` on `Sat Dec 16 18:03:16 UTC 2023`
Record UNII	HUM6H389W0
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AZLOCILLIN

Official Name

English

AZLOCILLIN [USAN]

Common Name

English

Azlocillin [WHO-DD]

Common Name

English

AZLOCILLIN [MART.]

Common Name

English

(2S,5R,6R)-3,3-DIMETHYL-7-OXO-6-(((2R)-2-(((2-OXOIMIDAZOLIDIN-1-YL)CARBONYL)AMINO)-2-PHENYLACETYL)AMINO)-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID

Systematic Name

English

(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(R)-2-(2-oxo-1-imidazolidinecarboxamido)-2-phenylacetamido]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Systematic Name

English

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

Common Name

English

NSC-758227

Code

English

AZLOCILLIN [VANDF]

Common Name

English

J01CA09

Code

English

AZLOCILLIN [MI]

Common Name

English

azlocillin [INN]

Common Name

English

Classification Tree Code System Code

WHO-ATC

J01CA09