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Identification
- Generic Name
- Carbenicillin
- DrugBank Accession Number
- DB00578
- Background
Broad-spectrum semisynthetic penicillin derivative used parenterally. It is susceptible to gastric juice and penicillinase and may damage platelet function.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Carbenicillin (DB00578)
- Weight
- Average: 378.4
Monoisotopic: 378.088557008 - Chemical Formula
- C17H18N2O6S
- Synonyms
- (2S,5R,6R)-6-{[carboxy(phenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- Carbenicilina
- Carbenicillin
- Carbenicilline
- Carbenicillinum
- Carboxybenzylpenicillin
- CBPC
- N-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)hept-6-yl)-2-phenylmalonamic acid
- α-carboxybenzylpencillin
- α-phenyl(carboxymethylpenicillin)
- External IDs
- BRL 2064
- CP 15639-2
- NSC 111071
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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism APenicillin-binding protein inhibitorGram positive and gram negative bacteria UBeta-lactamase Toho-1 substrateEscherichia coli - 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
- Adverse Effects
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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.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcamprosate The excretion of Acamprosate can be decreased when combined with Carbenicillin. Acemetacin Acemetacin may decrease the excretion rate of Carbenicillin which could result in a higher serum level. Acenocoumarol Carbenicillin may increase the anticoagulant activities of Acenocoumarol. Acyclovir The excretion of Acyclovir can be decreased when combined with Carbenicillin. Adefovir dipivoxil The excretion of Adefovir dipivoxil can be decreased when combined with Carbenicillin. - Food Interactions
- Take on an empty stomach.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Carbenicillin disodium 9TS4B3H261 4800-94-6 RTYJTGSCYUUYAL-YCAHSCEMSA-L - International/Other Brands
- Carbenicillin (Polfa Tarchomin) / Pyopen (GlaxoSmithKline)
Categories
- ATC Codes
- J01CR50 — Combinations of penicillins
- J01CR — Combinations of penicillins, incl. beta-lactamase inhibitors
- J01C — BETA-LACTAM ANTIBACTERIALS, PENICILLINS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Dipeptides
- Alternative Parents
- Penicillins / N-acyl-alpha amino acids and derivatives / Phenylacetamides / 1,3-dicarbonyl compounds / Dicarboxylic acids and derivatives / Thiazolidines / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Azetidines / Thiohemiaminal derivatives show 7 more
- Substituents
- 1,3-dicarbonyl compound / Alpha-amino acid or derivatives / Alpha-dipeptide / Aromatic heteropolycyclic compound / Azacycle / Azetidine / Benzenoid / Beta-lactam / Carbonyl group / Carboxamide group show 22 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- penicillin (CHEBI:3393)
- Affected organisms
- Enteric bacteria and other eubacteria
- Gram-negative Bacteria
- Pseudomonas aeruginosa
- Escherichia coli
- Proteus mirabilis
Chemical Identifiers
- UNII
- G42ZU72N5G
- CAS number
- 4697-36-3
- InChI Key
- 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
- 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
References
- Synthesis Reference
Brain, E.G. and Nayler, J.H.C.; US. Patents 3,282,926; November 1,1966 and 3,492,291; January 27,1970; both assigned to Beecham Group Limited, England.
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014717
- KEGG Drug
- D07614
- KEGG Compound
- C06869
- PubChem Compound
- 20824
- PubChem Substance
- 46505653
- ChemSpider
- 19599
- 2015
- ChEBI
- 3393
- ChEMBL
- CHEMBL1214
- Therapeutic Targets Database
- DAP000438
- PharmGKB
- PA448788
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Carbenicillin
- MSDS
- Download (72 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data0 Terminated Treatment Osteomyelitis 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Roerig div pfizer inc
- Glaxosmithkline
- Packagers
- Pfizer Inc.
- Pharmaceutical Utilization Management Program VA Inc.
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility 451 mg/L Not Available logP 1.13 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.39 mg/mL ALOGPS logP 1.13 ALOGPS logP 0.82 Chemaxon logS -3 ALOGPS pKa (Strongest Acidic) 3.11 Chemaxon pKa (Strongest Basic) -6.3 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 124.01 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 90.82 m3·mol-1 Chemaxon Polarizability 36.39 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9112 Blood Brain Barrier - 0.9954 Caco-2 permeable - 0.7812 P-glycoprotein substrate Substrate 0.5274 P-glycoprotein inhibitor I Non-inhibitor 0.9447 P-glycoprotein inhibitor II Non-inhibitor 0.9872 Renal organic cation transporter Non-inhibitor 0.962 CYP450 2C9 substrate Non-substrate 0.7684 CYP450 2D6 substrate Non-substrate 0.8611 CYP450 3A4 substrate Non-substrate 0.5946 CYP450 1A2 substrate Non-inhibitor 0.8778 CYP450 2C9 inhibitor Non-inhibitor 0.9259 CYP450 2D6 inhibitor Non-inhibitor 0.935 CYP450 2C19 inhibitor Non-inhibitor 0.9206 CYP450 3A4 inhibitor Non-inhibitor 0.8921 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9761 Ames test Non AMES toxic 0.8884 Carcinogenicity Non-carcinogens 0.6178 Biodegradation Not ready biodegradable 0.976 Rat acute toxicity 1.4599 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9997 hERG inhibition (predictor II) Non-inhibitor 0.9091
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-000f-9648000000-75c4ae9c8d8548759c79 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-08ml-0941000000-dd04761aba676e737365 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-0093000000-2481d8576e383313ecfa Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0910000000-5e16937a715baee100d2 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0016-9774000000-fce5db20fc35ce747364 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-014l-1900000000-9fcde5d9a40519e2fca4 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9626000000-3b8a7fd71c7606208706 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 190.0361556 predictedDarkChem Lite v0.1.0 [M-H]- 182.77989 predictedDeepCCS 1.0 (2019) [M+H]+ 191.4709556 predictedDarkChem Lite v0.1.0 [M+H]+ 185.17546 predictedDeepCCS 1.0 (2019) [M+Na]+ 190.5526556 predictedDarkChem Lite v0.1.0 [M+Na]+ 191.08798 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein group
- Organism
- Gram positive and gram negative bacteria
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Serine-type d-ala-d-ala carboxypeptidase activity
- Specific Function
- Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors.
Components:
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. 2011 Jan 7;405(1):173-84. doi: 10.1016/j.jmb.2010.10.024. Epub 2010 Oct 23. [Article]
- Kind
- Protein
- Organism
- Escherichia coli
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Beta-lactamase activity
- Specific Function
- Has strong cefotaxime-hydrolyzing activity.
- Gene Name
- bla
- Uniprot ID
- Q47066
- Uniprot Name
- Beta-lactamase Toho-1
- Molecular Weight
- 31446.6 Da
References
- Ishii Y, Ohno A, Taguchi H, Imajo S, Ishiguro M, Matsuzawa H: Cloning and sequence of the gene encoding a cefotaxime-hydrolyzing class A beta-lactamase isolated from Escherichia coli. Antimicrob Agents Chemother. 1995 Oct;39(10):2269-75. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Has primarily calcium-dependent phospholipase and lysophospholipase activities, with a major role in membrane lipid remodeling and biosynthesis of lipid mediators of the inflammatory response (PubMed:10358058, PubMed:14709560, PubMed:16617059, PubMed:17472963, PubMed:18451993, PubMed:27642067, PubMed:7794891, PubMed:8619991, PubMed:8702602, PubMed:9425121). Plays an important role in embryo implantation and parturition through its ability to trigger prostanoid production (By similarity). Preferentially hydrolyzes the ester bond of the fatty acyl group attached at sn-2 position of phospholipids (phospholipase A2 activity) (PubMed:10358058, PubMed:17472963, PubMed:18451993, PubMed:7794891, PubMed:8619991, PubMed:9425121). Selectively hydrolyzes sn-2 arachidonoyl group from membrane phospholipids, providing the precursor for eicosanoid biosynthesis via the cyclooxygenase pathway (PubMed:10358058, PubMed:17472963, PubMed:18451993, PubMed:7794891, PubMed:9425121). In an alternative pathway of eicosanoid biosynthesis, hydrolyzes sn-2 fatty acyl chain of eicosanoid lysophopholipids to release free bioactive eicosanoids (PubMed:27642067). Hydrolyzes the ester bond of the fatty acyl group attached at sn-1 position of phospholipids (phospholipase A1 activity) only if an ether linkage rather than an ester linkage is present at the sn-2 position. This hydrolysis is not stereospecific (PubMed:7794891). Has calcium-independent phospholipase A2 and lysophospholipase activities in the presence of phosphoinositides (PubMed:12672805). Has O-acyltransferase activity. Catalyzes the transfer of fatty acyl chains from phospholipids to a primary hydroxyl group of glycerol (sn-1 or sn-3), potentially contributing to monoacylglycerol synthesis (PubMed:7794891)
- Specific Function
- Calcium ion binding
- Gene Name
- PLA2G4A
- Uniprot ID
- P47712
- Uniprot Name
- Cytosolic phospholipase A2
- Molecular Weight
- 85238.2 Da
References
- Sugatani J, Saito K, Honjo I: In vitro actions of some antibiotics on phospholipases. J Antibiot (Tokyo). 1979 Jul;32(7):734-9. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Secondary active transporter that functions as a Na(+)-independent organic anion (OA)/dicarboxylate antiporter where the uptake of one molecule of OA into the cell is coupled with an efflux of one molecule of intracellular dicarboxylate such as 2-oxoglutarate or glutarate (PubMed:11669456, PubMed:11907186, PubMed:14675047, PubMed:22108572, PubMed:23832370, PubMed:28534121, PubMed:9950961). Mediates the uptake of OA across the basolateral side of proximal tubule epithelial cells, thereby contributing to the renal elimination of endogenous OA from the systemic circulation into the urine (PubMed:9887087). Functions as a biopterin transporters involved in the uptake and the secretion of coenzymes tetrahydrobiopterin (BH4), dihydrobiopterin (BH2) and sepiapterin to urine, thereby determining baseline levels of blood biopterins (PubMed:28534121). Transports prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) and may contribute to their renal excretion (PubMed:11907186). Also mediates the uptake of cyclic nucleotides such as cAMP and cGMP (PubMed:26377792). Involved in the transport of neuroactive tryptophan metabolites kynurenate (KYNA) and xanthurenate (XA) and may contribute to their secretion from the brain (PubMed:22108572, PubMed:23832370). May transport glutamate (PubMed:26377792). Also involved in the disposition of uremic toxins and potentially toxic xenobiotics by the renal organic anion secretory pathway, helping reduce their undesired toxicological effects on the body (PubMed:11669456, PubMed:14675047). Uremic toxins include the indoxyl sulfate (IS), hippurate/N-benzoylglycine (HA), indole acetate (IA), 3-carboxy-4- methyl-5-propyl-2-furanpropionate (CMPF) and urate (PubMed:14675047, PubMed:26377792). Xenobiotics include the mycotoxin ochratoxin (OTA) (PubMed:11669456). May also contribute to the transport of organic compounds in testes across the blood-testis-barrier (PubMed:35307651)
- Specific Function
- Alpha-ketoglutarate transmembrane transporter activity
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
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. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 02, 2024 21:55