Carindacillin
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
- 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.).
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism APenicillin-binding protein inhibitorGram 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcemetacin Acemetacin may decrease the excretion rate of Carindacillin which could result in a higher serum level. Acenocoumarol Carindacillin may increase the anticoagulant activities of Acenocoumarol. Ambroxol The risk or severity of methemoglobinemia can be increased when Carindacillin is combined with Ambroxol. Amikacin The serum concentration of Amikacin can be decreased when it is combined with Carindacillin. Articaine The risk or severity of methemoglobinemia can be increased when Carindacillin is combined with Articaine. - Food Interactions
- Not Available
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 indanyl sodium 4OUL81K2RT 26605-69-6 QFWPXOXWAUAYAB-XZVIDJSISA-M - Active Moieties
Name Kind UNII CAS InChI Key Carbenicillin prodrug G42ZU72N5G 4697-36-3 FPPNZSSZRUTDAP-UWFZAAFLSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Geocillin Tablet, film coated 382 mg/1 Oral Roerig 1972-10-26 2007-09-30 US
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 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
- 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]
- External Links
- ChemSpider
- 84127
- ChEBI
- 52015
- ChEMBL
- CHEMBL1596
- Wikipedia
- Carindacillin
- FDA label
- Download (63.7 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 0 Terminated Treatment Osteomyelitis 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, film coated Oral 382 mg/1 - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00491 mg/mL ALOGPS logP 3.57 ALOGPS logP 3.63 Chemaxon logS -5 ALOGPS pKa (Strongest Acidic) 3.29 Chemaxon pKa (Strongest Basic) -6.3 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 113.01 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 128.25 m3·mol-1 Chemaxon Polarizability 50.52 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0bti-0429100000-40abe7e1eae2fd3d0962 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0gb9-0008900000-f946af6baf11bedccbb3 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0fw9-1619300000-fc80d380e7c88d953db9 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-0539100000-0f868457fd61c17d95c3 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0292-0911000000-2ad590d494c1e8250dd5 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-000x-6916200000-58c1a37276d450896d00 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]- 231.4504003 predictedDarkChem Lite v0.1.0 [M-H]- 203.19629 predictedDeepCCS 1.0 (2019) [M+H]+ 229.7946003 predictedDarkChem Lite v0.1.0 [M+H]+ 205.09169 predictedDeepCCS 1.0 (2019) [M+Na]+ 230.1479003 predictedDarkChem Lite v0.1.0 [M+Na]+ 210.88762 predictedDeepCCS 1.0 (2019)
Targets
- 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]
- 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]
- 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 at November 17, 2015 17:22 / Updated at February 02, 2024 22:53