carindacillin   Click here for help

GtoPdb Ligand ID: 12276

Synonyms: carbenicillin indanyl | CP-15,464-2 | CP-15464-2 | Geocillin®
Approved drug
carindacillin is an approved drug (FDA (1972))
Compound class: Synthetic organic
Comment: Carindacillin is a semisynthetic carboxypenicillin belonging to the β-lactam class of antibacterial compounds. It is an orally bioavailable prodrug that is hydrolysed into carbenicillin [1-2].
2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 138.31
Molecular weight 494.15
XLogP 4.62
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
Canonical SMILES O=C(C(C(=O)Oc1ccc2c(c1)CCC2)c1ccccc1)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C
Isomeric SMILES CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)C(c1ccccc1)C(=O)Oc1cc2c(CCC2)cc1)C(=O)O)C
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
InChI Key JIRBAUWICKGBFE-MNRDOXJOSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. FDA (1972)
Withdrawn drug? Yes
Is prodrug? Yes
Active form carbenicillin
IUPAC Name Click here for help
(2S,5R,6R)-6-[[3-(2,3-dihydro-1H-inden-5-yloxy)-3-oxo-2-phenylpropanoyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
3405 carindacillin
Synonyms Click here for help
carbenicillin indanyl | CP-15,464-2 | CP-15464-2 | Geocillin®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Carindacillin
Other databases
CAS Registry No. 35531-88-5 (source: Scifinder)
ChEBI CHEBI:52015
ChEMBL Ligand CHEMBL1596
DrugBank Ligand DB09319
DrugCentral Ligand 508
GtoPdb PubChem SID 473153864
PubChem CID 93184
Search Google for chemical match using the InChIKey JIRBAUWICKGBFE-MNRDOXJOSA-N
Search Google for chemicals with the same backbone JIRBAUWICKGBFE
Search PubMed clinical trials carindacillin
Search PubMed titles carindacillin
Search PubMed titles/abstracts carindacillin
UniChem Compound Search for chemical match using the InChIKey JIRBAUWICKGBFE-MNRDOXJOSA-N
UniChem Connectivity Search for chemical match using the InChIKey JIRBAUWICKGBFE-MNRDOXJOSA-N