Details
| Stereochemistry | EPIMERIC |
| Molecular Formula | C17H16N2O6S.K.H |
| Molecular Weight | 416.49 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H+].[K+].[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C(C([O-])=O)C3=CC=CC=C3)C([O-])=O
InChI
InChIKey=DNAXYSPCMDEAQB-GJUCOGTPSA-M
InChI=1S/C17H18N2O6S.K/c1-17(2)11(16(24)25)19-13(21)10(14(19)26-17)18-12(20)9(15(22)23)8-6-4-3-5-7-8;/h3-7,9-11,14H,1-2H3,(H,18,20)(H,22,23)(H,24,25);/q;+1/p-1/t9?,10-,11+,14-;/m1./s1
| Molecular Formula | H |
| Molecular Weight | 1.0079 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | K |
| Molecular Weight | 39.0983 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C17H16N2O6S |
| Molecular Weight | 376.384 |
| Charge | -2 |
| Count |
|
| Stereochemistry | EPIMERIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: http://link.springer.com/chapter/10.1007%2F978-1-4684-3126-1_11https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050435s009lbl.pdfCurator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/21771 and http://www.ncbi.nlm.nih.gov/pubmed/789326
Sources: http://link.springer.com/chapter/10.1007%2F978-1-4684-3126-1_11https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050435s009lbl.pdf
Curator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/21771 and http://www.ncbi.nlm.nih.gov/pubmed/789326
Geocillin, a trade name is the sodium salt of the indanyl ester of carbenicillin disodium, which used to treat acute and chronic infections of the upper and lower urinary tract and in asymptomatic bacteriuria due to susceptible strains of bacteria. In addition, Geocillin was also indicated in the treatment of prostatitis due to susceptible strains of the following organisms: Escherichia coli; Enterococcus (S. faecalis); Proteus mirabilis; Enterobacter sp. Free carbenicillin is the predominant pharmacologically active fraction of Geocillin. After absorption, Geocillin is rapidly converted to carbenicillin by hydrolysis of the ester linkage. Carbenicillin exerts its antibacterial activity by interference with final cell wall synthesis of susceptible bacteria. Penicillins acylate the penicillin-sensitive transpeptidase C-terminal domain by opening the lactam ring. This inactivation of the enzyme prevents the formation of a cross-link of two linear peptidoglycan strands, inhibiting the third and last stage of bacterial cell wall synthesis. In 2008 Pfizer has decided to discontinue the manufacturing of Geocillin (carbenicillin indanyl sodium)
Originator
Sources: https://books.google.ru/books?id=_J2ti4EkYpkC&pg=PA850&lpg=PA850&dq=CARBENICILLIN+PHENYL+Beecham+Pharmaceuticals&source=bl&ots=N5lxJcAQur&sig=ttx_dwY0skEtBcDySKoDosepBQA&hl=en&sa=X&ved=0ahUKEwiZ8Ljd1YvPAhULlCwKHaO5B38Q6AEIOjAF#v=onepage&q=CARBENICILLIN%20PHENYL%20Beecham%20Pharmaceuticals&f=false Retrieved from Pharmaceutical Manufacturing Encyclopedia, 3rd Edition By William Andrew Publishing, p.851https://www.ncbi.nlm.nih.gov/pubmed/5212169
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1944 |
0.18 µM [Ki] | ||
Target ID: Escherichia coli growth |
|||
Target ID: Staphylococcus aureus growth |
|||
Target ID: Streptococcus pneumoniae growth |
|||
Target ID: Pseudomonas aeruginosa growth |
|||
Target ID: CHEMBL2354204 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | Uticillin Approved UseIndications: urinary tract infections |
|||
| Curative | GEOCILLIN Approved UseGeocillin (carbenicillin indanyl sodium) is indicated in the treatment of acute and chronic infections of the upper and lower urinary tract and in asymptomatic bacteriuria due to susceptible strains of the following organisms: Escherichia coli; Proteus mirabilis; Morganella morganii (formerly Proteus morganii); Providencia rettgeri (formerly Proteus rettgeri); Proteus vulgaris; Pseudomonas
Enterobacter; Enterococci. Geocillin is also indicated in the treatment of prostatitis due to susceptible strains of the following organisms: Escherichia coli; Enterococcus (S. faecalis); Proteus mirabilis; Enterobacter sp. WHEN HIGH AND RAPID BLOOD AND URINE LEVELS OF ANTIBIOTIC ARE INDICATED, THERAPY WITH GEOPEN (CARBENICILLIN DISODIUM) SHOULD BE INITIATED BY PARENTERAL ADMINISTRATION FOLLOWED, AT THE PHYSICIAN’S DISCRETION, BY ORAL THERAPY. To reduce the development of drug-resistant bacteria and maintain effectiveness of Geocillin and other antibacterial drugs, Geocillin should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Launch Date1972 |
|||
| Curative | GEOCILLIN Approved UseGeocillin (carbenicillin indanyl sodium) is indicated in the treatment of acute and chronic infections of the upper and lower urinary tract and in asymptomatic bacteriuria due to susceptible strains of the following organisms: Escherichia coli; Proteus mirabilis; Morganella morganii (formerly Proteus morganii); Providencia rettgeri (formerly Proteus rettgeri); Proteus vulgaris; Pseudomonas
Enterobacter; Enterococci. Geocillin is also indicated in the treatment of prostatitis due to susceptible strains of the following organisms: Escherichia coli; Enterococcus (S. faecalis); Proteus mirabilis; Enterobacter sp. WHEN HIGH AND RAPID BLOOD AND URINE LEVELS OF ANTIBIOTIC ARE INDICATED, THERAPY WITH GEOPEN (CARBENICILLIN DISODIUM) SHOULD BE INITIATED BY PARENTERAL ADMINISTRATION FOLLOWED, AT THE PHYSICIAN’S DISCRETION, BY ORAL THERAPY. To reduce the development of drug-resistant bacteria and maintain effectiveness of Geocillin and other antibacterial drugs, Geocillin should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Launch Date1972 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
6.5 μg/mL |
382 mg single, oral dose: 382 mg route of administration: Oral experiment type: SINGLE co-administered: |
CARBENICILLIN serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
16 μg × h/mL |
382 mg single, oral dose: 382 mg route of administration: Oral experiment type: SINGLE co-administered: |
CARBENICILLIN serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2 h |
382 mg single, oral dose: 382 mg route of administration: Oral experiment type: SINGLE co-administered: |
CARBENICILLIN serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
5 g 4 times / day steady, intravenous Dose: 5 g, 4 times / day Route: intravenous Route: steady Dose: 5 g, 4 times / day Sources: |
unhealthy, 57 years Health Status: unhealthy Condition: interstitial nephritis Age Group: 57 years Sex: M Sources: |
Other AEs: Nephrotoxicity... |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Nephrotoxicity | 1 patient | 5 g 4 times / day steady, intravenous Dose: 5 g, 4 times / day Route: intravenous Route: steady Dose: 5 g, 4 times / day Sources: |
unhealthy, 57 years Health Status: unhealthy Condition: interstitial nephritis Age Group: 57 years Sex: M Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes | yes (co-administration study) Comment: When coadministrated with Probenecid (OAT inhibitor), Carbenicillin CLr was significantlly reduced. |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Carbenicillin prodrugs: stability kinetics of alpha-phenyl and alpha-indanyl esters in aqueous solution. | 1979 Oct |
|
| Val-237 for Ala substitution in the TEM-2 beta-lactamase dramatically alters the catalytic efficiencies towards carbenicillin and ticarcillin. | 1994 Apr 15 |
|
| [Optimization of T-dNA insertional mutagenesis and analysis of mutants of Magnaporthe grisea]. | 2003 Jul |
|
| Antimicrobial susceptibility pattern of clinical isolates of non-fermentative bacteria. | 2003 Jul |
|
| Intravenous colistin in the treatment of sepsis from multiresistant Gram-negative bacilli in critically ill patients. | 2003 Oct |
|
| The susceptibility of ionophore-resistant Clostridium aminophilum F to other antibiotics. | 2003 Oct |
|
| Shewanella waksmanii sp. nov., isolated from a sipuncula (Phascolosoma japonicum). | 2003 Sep |
|
| Serovar determination, drug resistance patterns and plasmid profiles of Pseudomonas aeruginosa isolated from burn patients at two hospitals of Tehran (IRAN). | 2003 Sep |
|
| Thermophile-specific proteins: the gene product of aq_1292 from Aquifex aeolicus is an NTPase. | 2003 Sep 23 |
|
| Evaluation of a simple carrier molecule to enhance drug penetration of dermal layers by utilizing multivariate methods, structure property correlations, and continuous system modeling. | 2004 |
|
| [Pseudomonas aeruginosa--a significant hospital pathogen and resistance to carbapenem]. | 2004 |
|
| Genome-wide mutagenesis of Zea mays L. using RescueMu transposons. | 2004 |
|
| Investigation of Burkholderia cepacia nosocomial outbreak with high fatality in patients suffering from diseases other than cystic fibrosis. | 2004 |
|
| Self-transmissible antibiotic resistance to ampicillin, streptomycin, and tetracyclin found in Escherichia coli isolates from contaminated drinking water. | 2004 |
|
| Penicillin derivatives induce chemical structure-dependent root development, and application for plant transformation. | 2004 Apr |
|
| Vibrio vulnificus in Taiwan. | 2004 Aug |
|
| Interaction studies on proteins encoded by the phthiocerol dimycocerosate locus of Mycobacterium tuberculosis. | 2004 Dec |
|
| Distribution and characterization of Campylobacter spp. from Russian poultry. | 2004 Feb |
|
| Staphylococcus aureus and Escherichia hermanii in diabetes patient. | 2004 Jul |
|
| Molecular dissection of the human antibody response to the structural repeat epitope of Plasmodium falciparum sporozoite from a protected donor. | 2004 Jul 29 |
|
| Prevalence, antibiotic susceptibility, and virulence factors of Yersinia enterocolitica and related species from ready-to-eat vegetables available in Korea. | 2004 Jun |
|
| Serratia marcescens internalization and replication in human bladder epithelial cells. | 2004 Jun 9 |
|
| Bacterial variations on the methionine salvage pathway. | 2004 Mar 4 |
|
| Xylella fastidiosa subspecies: X. fastidiosa subsp. [correction] fastidiosa [correction] subsp. nov., X. fastidiosa subsp. multiplex subsp. nov., and X. fastidiosa subsp. pauca subsp. nov. | 2004 May |
|
| Symbiotic innovation in the oxymonad Streblomastix strix. | 2004 May-Jun |
|
| Dictyostelium myosin bipolar thick filament formation: importance of charge and specific domains of the myosin rod. | 2004 Nov |
|
| Mycobacterium tuberculosis from chronic murine infections that grows in liquid but not on solid medium. | 2004 Nov 17 |
|
| Functional characterization in Caenorhabditis elegans of transmembrane worm-human orthologs. | 2004 Nov 8 |
|
| Resistance to beta-lactam antibiotics in Aeromonas hydrophila isolated from rainbow trout (Oncorhynchus mykiss). | 2004 Sep |
|
| Incorporation of different antibiotics into carbonated hydroxyapatite coatings on titanium implants, release and antibiotic efficacy. | 2004 Sep 14 |
|
| Early detection of breast cancer based on gene-expression patterns in peripheral blood cells. | 2005 |
|
| Common antimicrobial resistance patterns, biotypes and serotypes found among Pseudomonas aeruginosa isolates from patient's stools and drinking water sources in Jordan. | 2005 Apr |
|
| Efficient genetic transformation of Sorghum using a visual screening marker. | 2005 Apr |
|
| Nuclear hormone receptor NHR-49 controls fat consumption and fatty acid composition in C. elegans. | 2005 Feb |
|
| New genes tied to endocrine, metabolic, and dietary regulation of lifespan from a Caenorhabditis elegans genomic RNAi screen. | 2005 Jul |
|
| Characterization of Pseudomonas aeruginosa isolated from chronically infected children with cystic fibrosis in India. | 2005 Jul 21 |
|
| Development of ERK Activity Sensor, an in vitro, FRET-based sensor of Extracellular Regulated Kinase activity. | 2005 Jul 5 |
|
| Epidemic strain Shigella dysenteriae Type 1 Dt66 encodes several drug resistances by chromosome. | 2005 Jul-Aug |
|
| Cognate peptide-receptor ligand mapping by directed phage display. | 2005 Jun 17 |
|
| Selectivity of ertapenem for Pseudomonas aeruginosa mutants cross-resistant to other carbapenems. | 2005 Mar |
|
| [Antibiotic resistance of shigellae and rationale for etiotropic therapy of Shigella infections]. | 2005 Mar-Apr |
|
| Antimicrobial responses of Yersinia enterocolitica isolates in comparison to other commonly encountered bacteria that causes diarrhoea. | 2005 May |
|
| Infrared and Raman microspectroscopy of foreign materials in tissue specimens. | 2005 May |
|
| Characterization of antimicrobial resistance and class 1 integrons found in Escherichia coli isolates from humans and animals in Korea. | 2005 May |
|
| Occurrence of antibiotic and metal resistance in bacteria from organs of river fish. | 2005 May |
|
| An improved method for rapid generation of unmarked Pseudomonas aeruginosa deletion mutants. | 2005 May 23 |
|
| A combined approach exploring gene function based on worm-human orthology. | 2005 May 6 |
|
| Functional genomic analysis of C. elegans molting. | 2005 Oct |
|
| Uncoupling of longevity and telomere length in C. elegans. | 2005 Sep |
|
| Changes in patterns of antimicrobial susceptibility and class 1 integron carriage among Escherichia coli isolates. | 2005 Sep |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 14:59:55 GMT 2023
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on
Fri Dec 15 14:59:55 GMT 2023
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| Record UNII |
3UX6B304L3
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| Record Status |
Validated (UNII)
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| Record Version |
|
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Download
| Name | Type | Language | ||
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Official Name | English | ||
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Code | English | ||
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Systematic Name | English | ||
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Common Name | English |
| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C1500
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3UX6B304L3
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23684326
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C76220
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DTXSID70938124
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CHEMBL1214
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17230-86-3
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241-269-6
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