Carindacillin

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Summary

Carindacillin is a penicillin antibiotic used to treat a variety of infections, but is no longer marketed in the USA.

Generic Name
Carindacillin
DrugBank Accession Number
DB09319
Background

Carindacillin or Carbenicillin isdanyl was an oral penicillin prodrug of carbenicillin marketed by Pfizer as Geocillin. It is no longer marketed in the United States.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 494.56
Monoisotopic: 494.151157739
Chemical Formula
C26H26N2O6S
Synonyms
  • 6β-{2-[(2,3-dihydro-1H-inden-5-yloxy)carbonyl]-2-phenylacetamido}-2,2-dimethylpenam-3α-carboxylic acid
  • Carbenicillin indanyl
  • Carindacilina
  • Carindacillin
  • Carindacilline
  • Carindacillinum
  • Indanyl carbenicillin

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 Escherichia coli, Proteus mirabilis, Morganella morganii, Providencia rettgeri, Proteus vulgaris, Pseudomonas, Enterobacter, and Enterococci.). Also indicated in the treatment of prostatitis (due to susceptible strains Escherichia coli Enterococcus (S. faecalis), Proteus mirabilis Enterobacter sp.).

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
APenicillin-binding protein
inhibitor
Gram positive and gram negative bacteria
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

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.
DrugInteraction
AcemetacinAcemetacin may decrease the excretion rate of Carindacillin which could result in a higher serum level.
AcenocoumarolCarindacillin may increase the anticoagulant activities of Acenocoumarol.
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Carindacillin.
AtracuriumThe therapeutic efficacy of Atracurium can be increased when used in combination with Carindacillin.
Atracurium besylateThe therapeutic efficacy of Atracurium besylate can be increased when used in combination with Carindacillin.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Carindacillin.
CapreomycinThe serum concentration of Capreomycin can be decreased when it is combined with Carindacillin.
CinoxacinThe serum concentration of Cinoxacin can be increased when it is combined with Carindacillin.
CiprofloxacinThe serum concentration of Ciprofloxacin can be increased when it is combined with Carindacillin.
CisatracuriumThe therapeutic efficacy of Cisatracurium can be increased when used in combination with Carindacillin.
Interactions
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Carbenicillin indanyl sodium4OUL81K2RT26605-69-6QFWPXOXWAUAYAB-XZVIDJSISA-M
Active Moieties
NameKindUNIICASInChI Key
CarbenicillinprodrugG42ZU72N5G4697-36-3FPPNZSSZRUTDAP-UWFZAAFLSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
GeocillinTablet, film coated382 mg/1OralRoerig1972-10-262007-09-30US flag

Categories

ATC Codes
J01CR50 — Combinations of penicillinsJ01CA05 — Carindacillin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
N-acyl-alpha amino acids and derivatives
Alternative Parents
Indanes / Penams / Benzene and substituted derivatives / Dicarboxylic acids and derivatives / Thiazolidines / Tertiary carboxylic acid amides / Azetidines / Carboxylic acid esters / Thiohemiaminal derivatives / Propargyl-type 1,3-dipolar organic compounds
show 9 more
Substituents
Aromatic heteropolycyclic compound / Azacycle / Azetidine / Benzenoid / Beta-lactam / Carbonyl group / Carboxamide group / Carboximidic acid / Carboximidic acid derivative / Carboxylic acid
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
penicillin (CHEBI:52015)
Affected organisms
Not Available

Chemical Identifiers

UNII
5V278481KE
CAS number
35531-88-5
InChI Key
JIRBAUWICKGBFE-MNRDOXJOSA-N
InChI
InChI=1S/C26H26N2O6S/c1-26(2)20(24(31)32)28-22(30)19(23(28)35-26)27-21(29)18(15-7-4-3-5-8-15)25(33)34-17-12-11-14-9-6-10-16(14)13-17/h3-5,7-8,11-13,18-20,23H,6,9-10H2,1-2H3,(H,27,29)(H,31,32)/t18?,19-,20+,23-/m1/s1
IUPAC Name
(2S,5R,6R)-6-[3-(2,3-dihydro-1H-inden-5-yloxy)-3-oxo-2-phenylpropanamido]-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)OC1=CC2=C(CCC2)C=C1)C1=CC=CC=C1)C(O)=O

References

General References
  1. English AR, Retsema JA, Ray VA, Lynch JE: Carbenicillin indanyl sodium, an orally active derivative of carbenicillin. Antimicrob Agents Chemother. 1972 Mar;1(3):185-91. [Article]
ChemSpider
84127
ChEBI
52015
ChEMBL
CHEMBL1596
Wikipedia
Carindacillin
FDA label
Download (63.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0TerminatedTreatmentOsteomyelitis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, film coatedOral382 mg/1
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00491 mg/mLALOGPS
logP3.57ALOGPS
logP3.63ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)3.29ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area113.01 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity128.25 m3·mol-1ChemAxon
Polarizability50.52 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
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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
  1. 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]
  2. Gotoh N, Nunomura K, Nishino T: 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. [Article]
  3. Rodriguez-Tebar A, Rojo F, Damaso D, Vazquez D: Carbenicillin resistance of Pseudomonas aeruginosa. Antimicrob Agents Chemother. 1982 Aug;22(2):255-61. [Article]

Drug created on November 17, 2015 17:22 / Updated on May 07, 2021 21:41