DrugBank: Carbenicillin (DB00578)

targets (1) transporters (1)

Identification

Name

Carbenicillin

Accession Number

DB00578 (APRD00846)

Type

small molecule

Groups

approved

Description

Broad-spectrum semisynthetic penicillin derivative used parenterally. It is susceptible to gastric juice and penicillinase and may damage platelet function. [PubChem]

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

alpha-Carboxybenzylpencillin
Carbenicilina [INN-Spanish]
Carbenicillina [DCIT]
Carbenicilline [INN-French]
Carbenicillinum [INN-Latin]
Carboxybenzylpenicillin
Carboxybenzylpenicillin acid

Brand names

Geopen
Pyopen

Brand name mixtures

Not Available

Categories

Anti-Bacterial Agents
Penicillins

CAS number

4697-36-3

Weight

Average: 378.4
Monoisotopic: 378.088557008

Chemical Formula

C₁₇H₁₈N₂O₆S

InChI Key

InChIKey=FPPNZSSZRUTDAP-UWFZAAFLSA-N

InChI

InChI=1S/C17H18N2O6S/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)/t9?,10-,11+,14-/m1/s1

Plain Text

IUPAC Name

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

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C(C(O)=O)C1=CC=CC=C1)C(O)=O

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Phenylacetates
Penicillins
Phenethylamines

Substructures

Hydroxy Compounds
Acetates
Keto-Acids
Amino Ketones
Carboxylic Acids and Derivatives
Phenylacetates
Benzene and Derivatives
Aliphatic and Aryl Amines
Beta Lactams
Penicillins
Thiazoles
Phenethylamines
Heterocyclic compounds
Aromatic compounds
Carboxamides and Derivatives
Lactams
Azetidines
Thiazolidines

Pharmacology

Indication

For the treatment of acute and chronic infections of the upper and lower urinary tract and in asymptomatic bacteriuria due to susceptible strains of bacteria.

Pharmacodynamics

Carbenicillin is a semisynthetic penicillin. Though carbenicillin provides substantial in vitro activity against a variety of both gram-positive and gram-negative microorganisms, the most important aspect of its profile is in its antipseudomonal and antiproteal activity. Because of the high urine levels obtained following administration, carbenicillin has demonstrated clinical efficacy in urinary infections due to susceptible strains of: Escherichia coli, Proteus mirabilis, Proteus vulgaris, Morganella morganii, Pseudomonas species, Providencia rettgeri, Enterobacter species, and Enterococci (S. faecalis).

Mechanism of action

Free carbenicillin is the predominant pharmacologically active fraction of the salt. 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. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that carbenicillin interferes with an autolysin inhibitor.

Absorption

Rapidly absorbed from the small intestine following oral administration. Oral bioavailability is 30 to 40%.

Volume of distribution

Not Available

Protein binding

30 to 60%

Metabolism

Minimal.

Route of elimination

Not Available

Half life

1 hour

Clearance

Not Available

Toxicity

Carbenicillin blood levels achievable are very low, and toxic reactions as a function of overdosage should not occur systematically. The oral LD₅₀ in mice is 3,600 mg/kg, in rats 2,000 mg/kg, and in dogs is in excess of 500 mg/kg. The lethal human dose is not known. Symptoms of overdose include diarrhea, nausea, stomach upset, and vomiting.

Affected organisms

Enteric bacteria and other eubacteria

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Roerig div pfizer inc
Glaxosmithkline

Packagers

Pfizer Inc.
Pharmaceutical Utilization Management Program VA Inc.

Dosage forms

Form	Route	Strength
Tablet, film coated	Oral

Prices

Not Available

Patents

Not Available

Properties

State

solid

Melting point

Not Available

Experimental Properties

Property	Value	Source
water solubility	451 mg/L	PhysProp
logP	1.8	PhysProp

Predicted Properties

Property	Value	Source
water solubility	3.90e-01 g/l	ALOGPS
logP	1.13	ALOGPS
logP	0.82	ChemAxon Molconvert
logS	-2.99	ALOGPS
pKa	3.86	ChemAxon Molconvert
hydrogen acceptor count	6	ChemAxon Molconvert
hydrogen donor count	3	ChemAxon Molconvert
polar surface area	124.01	ChemAxon Molconvert
rotatable bond count	5	ChemAxon Molconvert
refractivity	90.82	ChemAxon Molconvert
polarizability	36.39	ChemAxon Molconvert

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
KEGG Compound	C06869
PubChem Compound	20824
PubChem Substance	46505653
ChemSpider	19599
ChEBI	3393
ChEMBL	3393
Therapeutic Targets Database	DAP000438
PharmGKB	PA448788
Drug Product Database	0
RxList	http://www.rxlist.com/cgi/generic3/geocillin.htm
Drugs.com	http://www.drugs.com/cdi/carbenicillin-indanyl.html
Wikipedia	http://en.wikipedia.org/wiki/Carbenicillin

ATC Codes

J01CA03

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

show (72 KB)

Interactions

Drug Interactions

Not Available

Food Interactions

Take on an empty stomach.

Targets
1. Pencillin Binding Protein 3, P. aeruginosa Pharmacological action: yes Actions: inhibitor References: Sainsbury S, Bird L, Rao V, Shepherd SM, Stuart DI, Hunter WN, Owens RJ, Ren J: Crystal structures of penicillin-binding protein 3 from Pseudomonas aeruginosa: Comparison of native and antibiotic-bound forms. J Mol Biol. 2010 Oct 22. Pubmed*

Transporters
1. Solute carrier family 22 member 6 Actions: inhibitor UniProt ID: Q4U2R8 Gene: hROAT1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. Pubmed

Transporters

1. Solute carrier family 22 member 6

Actions: inhibitor
UniProt ID: Q4U2R8 Link_out

Gene: hROAT1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. Pubmed

Comments

Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:04

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.