Details of the Drug

General Information of Drug (ID: DMLEDNK)

Drug Name
Carbenicillin
Synonyms
CBPC; Carbenicilina; Carbenicillina; Carbenicilline; Carbenicillinum; Carboxybenzylpenicillin; Pyopen; Carbenicillina [DCIT]; Carboxybenzyl Penicillin; Carboxybenzylpenicillin acid; Alpha-Carboxybenzylpencillin; Alpha-Carboxybenzylpenicillin solution; Carbenicilina [INN-Spanish]; Carbenicillin (INN); Carbenicillin [INN:BAN]; Carbenicilline [INN-French]; Carbenicillinum [INN-Latin]; Alpha-Phenyl(carboxymethylpenicillin); N-(2-Carboxy-3,3-dimethyl-7-oxo-4-thia-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; (2S,5R,6R)-6-[(3-hydroxy-3-oxo-2-phenylpropanoyl)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; 6-(alpha-Carboxyphenylacetamido)penicillanic acid; 6beta-(2-carboxy-2-phenylacetamido)-2,2-dimethylpenam-3alpha-carboxylic acid
Indication
Disease Entry ICD 11 Status REF
Infection of the upper and lower urinary tract GC08 Approved [1]
Prostatitis N.A. Approved [2]
Urinary tract infection GC08 Approved [2]
Therapeutic Class
Antibiotics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 378.4
Logarithm of the Partition Coefficient (xlogp) 1.1
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 7
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [3]
Bioavailability
The bioavailability of drug is 30-40% []
Clearance
The drug present in the plasma can be removed from the body at the rate of 1.9 mL/min/kg [4]
Elimination
82% of drug is excreted from urine in the unchanged form [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 1 hours [4]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 115.37 micromolar/kg/day [5]
Unbound Fraction
The unbound fraction of drug in plasma is 0.52% [4]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.17 L/kg [4]
Water Solubility
The ability of drug to dissolve in water is measured as 50 mg/mL [3]
Chemical Identifiers
Formula
C17H18N2O6S
IUPAC Name
(2S,5R,6R)-6-[(2-carboxy-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Canonical SMILES
CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)C(C3=CC=CC=C3)C(=O)O)C(=O)O)C
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
InChIKey
FPPNZSSZRUTDAP-UWFZAAFLSA-N
Cross-matching ID
PubChem CID
20824
ChEBI ID
CHEBI:3393
CAS Number
4697-36-3
DrugBank ID
DB00578
TTD ID
D02TBI
VARIDT ID
DR00995
INTEDE ID
DR2390
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Bacterial Penicillin binding protein (Bact PBP) TTJP4SM NOUNIPROTAC Binder [6]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
N-acylhomoserine lactone acylase (lacA) DEIU0XN A0A0A1VBK6_9BURK Substrate [7]
PenA beta-lactamase (penA1) DE2ARDZ O08350_BURCE Substrate [8]
Beta-lactamase (blaB) DEF01WC A0A3S4HKA9_CHRVL Substrate [9]
Beta-lactamase (blaB) DEXB2A9 A0A379CPC3_PLESH Substrate [10], [11]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Carbenicillin (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Anisindione DM2C48U Moderate Increased risk of bleeding by the combination of Carbenicillin and Anisindione. Coagulation defect [3B10] [12]
Mycophenolic acid DMRBMAU Moderate Altered absorption of Carbenicillin due to GI flora changes caused by Mycophenolic acid. Crohn disease [DD70] [13]
Probenecid DMMFWOJ Minor Decreased elimination of Carbenicillin caused by Probenecid mediated competitive inhibition of renal tubular secretion. Inborn purine/pyrimidine/nucleotide metabolism error [5C55] [14]
Warfarin DMJYCVW Moderate Increased risk of bleeding by the combination of Carbenicillin and Warfarin. Supraventricular tachyarrhythmia [BC81] [12]
Mycophenolate mofetil DMPQAGE Moderate Altered absorption of Carbenicillin due to GI flora changes caused by Mycophenolate mofetil. Transplant rejection [NE84] [13]

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Carbenicillin FDA Label
3 BDDCS applied to over 900 drugs
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
6 Resistance of Pseudomonas aeruginosa to cefsulodin: modification of penicillin-binding protein 3 and mapping of its chromosomal gene. J Antimicrob Chemother. 1990 Apr;25(4):513-23.
7 A novel quorum-quenching N-acylhomoserine lactone acylase from Acidovorax sp. strain MR-S7 mediates antibiotic resistance. Appl Environ Microbiol. 2017 Jun 16;83(13). pii: e00080-17.
8 Characterization of the penA and penR genes of Burkholderia cepacia 249 which encode the chromosomal class A penicillinase and its LysR-type transcriptional regulator. Antimicrob Agents Chemother. 1997 Nov;41(11):2399-405.
9 Beta-lactamase activity in Chromobacterium violaceum. J Infect Dis. 1976 Sep;134(3):290-3.
10 Beta-lactamase expression in Plesiomonas shigelloides. J Antimicrob Chemother. 2000 Jun;45(6):877-80.
11 Identification and functional characterization of arylamine N-acetyltransferases in eubacteria: evidence for highly selective acetylation of 5-aminosalicylic acid. J Bacteriol. 2001 Jun;183(11):3417-27.
12 Alexander DP, Russo ME, Fohrman DE, Rothstein G "Nafcillin-induced platelet dysfunction and bleeding." Antimicrob Agents Chemother 23 (1983): 59-62. [PMID: 6830209]
13 Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ.
14 Allen MB, Fitzpatrick RW, Barratt A, Cole RB "The use of probenecid to increase the serum amoxycillin levels in patients with bronchiectasis." Respir Med 84 (1990): 143-6. [PMID: 2371437]