carbenicillin

Trade name: pyopen

Small moleculeapproved

Approved

Jun 1, 1966

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) — NCATS

Clinical trial activity

2 trials · 4 clinical orgs · 3 marketing orgs

Phase 1

Phase 2

Phase 3

Phase 4

Earliest trial started Aug 1, 2013 (NCT01931150)

Timeline

1960s

Jun 1, 1966
Earliest FDA Approval

1970s

Oct 26, 1972
Beecham — First NDA Organization
Oct 26, 1972
Pfizer — NDA Secondary Org
Oct 26, 1972
Beecham — NDA Organization

2010s

Jan 1, 2013
Earliest Phase 3 Sponsor(trial)
Jan 1, 2014
Earliest Phase 1 Sponsor(trial)

Indications

Approved for

Studied for

Mechanism of action

Bacterial penicillin-binding proteinINHIBITOR
Bacterial penicillin-binding protein inhibitor

Approval history

approvedJun 1, 1966

Chemistry & pharmacology

Loading structure…

SMILES

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

Mol. weight: 378.4 g/mol
Lipinski Ro5: Pass
Rule of 3: No
Chirality: Racemic Mixture
Inorganic: No
Polymer: No
Delivery: Oral
Availability: Discontinued

Oral

Yes

Parenteral

Topical

Prodrug

Sources

Also known as

(2s,5r,6r)-6-{[carboxy(phenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(2s,5r,6r)-6-{[carboxy(phenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
alpha-carboxybenzylpencillin
alpha-carboxybenzylpencillin
alpha-phenyl(carboxymethylpenicillin)
alpha-phenyl(carboxymethylpenicillin)
brl-2064
brl-2064
carbenicilina
carbenicilina
carbenicillin
carbenicillin
carbenicillin
carbenicillin
carbenicillin
carbenicillin
carbenicillin
carbenicillin
carbenicillin
carbenicillin
carbenicillin disodium
carbenicillin disodium
carbenicillin disodium
carbenicillin disodium
carbenicilline
carbenicilline
carbenicillin indanyl
carbenicillin indanyl
carbenicillin indanyl
carbenicillin indanyl
carbenicillin indanyl
carbenicillin indanyl
carbenicillin indanyl, 2s-(2alpha,5alpha,6beta)-isomer
carbenicillin indanyl ester
carbenicillin indanyl sodium
carbenicillin indanyl sodium
carbenicillin indanyl sodium
carbenicillin indanyl sodium
carbenicillin indanyl sodium
carbenicillin potassium
carbenicillin sodium
carbenicillin sodium
carbenicillin sodium
carbenicillinum
carbenicillinum
carboxybenzylpenicillin
carboxybenzylpenicillin
carboxybenzylpenicillin
carboxybenzylpenicillin acid
cardinacillin
carindacillin
carindacillin
carindacillin
carindacillin
carindacillin
carindacillin
carindacillin sodium
carindacillin sodium
carindacillin sodium
carindacillin sodium
carindapen
cbpc
cbpc
cp 15464
cp-15464
cp 15,464-2
cp-154642
cp-154642
cp-15,464-2
cp-15464-2
cp-15464-2
cp-15464-2
cp-15-639-2
cp-15-639-2
geocillin
geocillin
geocillin
geopen
geopen
indanyl carbenicillin
indanyl carbenicillin
n-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)hept-6-yl)-2-phenylmalonamate
n-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)hept-6-yl)-2-phenylmalonamic acid
n-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)hept-6-yl)-2-phenylmalonamic acid
pyopen
pyopen
pyopen
sodium carindacillin

Clinical trials

NCT ID	Phase	Start date	Sponsor(s)
NCT02099240	Early Phase 1 (Phase 1)	Apr 1, 2014	James Graham Brown Cancer Center, University of Louisville
NCT01931150	Phase 3	Aug 1, 2013	Bristol-Myers Squibb, Cornell University

Showing 2 of 2 trials

Page 1 / 1

Organizations

Research & Development (4)

Organization	Org type	Trials	As lead sponsor	Phases	Earliest year
Bristol-Myers Squibb	For profit	1	0	1	2013
Cornell University	Academic/Hospital	1	1	1	2013
James Graham Brown Cancer Center	Academic/Hospital	1	0	1	2014
University of Louisville	Academic/Hospital	1	1	1	2014

4 organizations

Page 1 / 1

Marketing (3)

Organization	Org type	Relationship	Date
Beecham	For profit	NDA	Oct 26, 1972
GlaxoSmithKline	For profit	NDA2	—
Pfizer	For profit	NDA2	Oct 26, 1972