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

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 1982

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
Sensitization to aztreonam and cross-reactivity with other beta-lactam antibiotics in high-risk patients with cystic fibrosis.	1991 Jan	1991925
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
The penicillins.	1999 Mar	10090000
[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
Effect of beta-estradiol on voltage-gated Ca(2+) channels in rat hippocampal neurons: a comparison with dehydroepiandrosterone.	2001 Mar 30	11290370
Natural antibiotic susceptibility of Enterobacter spp., with special reference to Enterobacter aerogenes and Enterobacter intermedius strains.	2002 Oct	12462424
Evaluation of culture media for the recovery of Mycobacterium avium subsp. paratuberculosis from Cheddar cheese.	2003	12969490
Natural antibiotic susceptibility of Ewingella americana strains.	2003 Oct	14598935
Characterization of the susceptibility of mycobacteria in BACTEC 12B media containing PANTA that had been supplemented with ceftazidime, and characterization of the individual components of PANTA in the presence of C18-carboxypropylbetaine.	2004 Feb	14744453
(-)-Epigallocatechin-3-gallate induces contraction of the rat aorta by a calcium influx-dependent mechanism.	2004 May	15083267
[Azlocillin plus amikacin: an alternative therapy for sepsis caused by resistant staphylococci?].	2004 Nov	15729980
The Malaysian Orthopaedic Association humanitarian mission to Indonesia and Sri Lanka.	2005 Jul	16381273
[Enzyme immunoassay of ampicillin in milk].	2005 Nov-Dec	16358758
[Bacterial meningitis and Pseudomonas aeruginosa: apropos of a case].	2005 Sep-Dec	17969281
Placental transfer of antibiotics administered to the mother: a review.	2006 Feb	16502764
Searching for new antimalarial therapeutics amongst known drugs.	2006 Jun	16882315
Interaction of zwitterionic penicillins with the OmpF channel facilitates their translocation.	2006 Mar 1	16339889
Problematic clinical isolates of Pseudomonas aeruginosa from the university hospitals in Sofia, Bulgaria: current status of antimicrobial resistance and prevailing resistance mechanisms.	2007 Jul	17577062
Human oral drugs absorption is correlated to their in vitro uptake by brush border membrane vesicles.	2007 May 4	17178445
Effects of treatment with antimicrobial agents on the human colonic microflora.	2008 Dec	19337440
Mycobacterium ulcerans disease, Peru.	2008 Mar	18325248
Phylogeography and recolonization of the Swiss Alps by the Valais shrew (Sorex antinorii), inferred with autosomal and sex-specific markers.	2008 Sep	19238709
How beta-lactam antibiotics enter bacteria: a dialogue with the porins.	2009	19434239
Dynamic root exudation of sorgoleone and its in planta mechanism of action.	2009	19357432
A critical role for CD8 T cells in a nonhuman primate model of tuberculosis.	2009 Apr	19381260
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
Data correction pre-processing for electronically stored blood culture results: implications on microbial spectrum and empiric antibiotic therapy.	2009 Jun 7	19500418
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
Pleistocene climatic cycling drives intra-specific diversification in the intermediate horseshoe bat (Rhinolophus affinis) in Southern China.	2010 Jul	20561192
Contrasting patterns of phylogeographic relationships in sympatric sister species of ironclad beetles (Zopheridae: Phloeodes spp.) in California's Transverse Ranges.	2010 Jun 24	20573263
Molecular taxonomy, phylogeny and evolution in the family Stichopodidae (Aspidochirotida: Holothuroidea) based on COI and 16S mitochondrial DNA.	2010 Sep	20399872

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)).

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