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carfecillin   Click here for help

GtoPdb Ligand ID: 12288

Synonyms: BRL 3475 | carbenicillin phenyl | Uticillin®
Approved drug
carfecillin is an approved drug
Compound class: Synthetic organic
Comment: Carfecillin is a semisynthetic carboxypenicillin (β-lactam) antibacterial compound. It is an orally delivered phenyl ester of carbenicillin [2].
2D Structure
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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.

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Physico-chemical Properties
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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.

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Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 138.31
Molecular weight 454.12
XLogP 3.73
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
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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/)

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Canonical SMILES O=C(C(C(=O)Oc1ccccc1)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)Oc1ccccc1)C(=O)O)C
InChI InChI=1S/C23H22N2O6S/c1-23(2)17(21(28)29)25-19(27)16(20(25)32-23)24-18(26)15(13-9-5-3-6-10-13)22(30)31-14-11-7-4-8-12-14/h3-12,15-17,20H,1-2H3,(H,24,26)(H,28,29)/t15?,16-,17+,20-/m1/s1
InChI Key NZDASSHFKWDBBU-KVMCETHSSA-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.
Is prodrug? Yes
Active form carbenicillin
IUPAC Name Click here for help
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[[3-oxo-3-(phenoxy)-2-phenylpropanoyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
3487 carfecillin
Synonyms Click here for help
BRL 3475 | carbenicillin phenyl | Uticillin®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Carfecillin
Other databases
CAS Registry No. 27025-49-6 (source: Scifinder)
ChEBI CHEBI:3414
ChEMBL Ligand CHEMBL1095283
DrugBank Ligand DB13506
DrugCentral Ligand 507
GtoPdb PubChem SID 479821079
PubChem CID 33672
Search Google for chemical match using the InChIKey NZDASSHFKWDBBU-KVMCETHSSA-N
Search Google for chemicals with the same backbone NZDASSHFKWDBBU
Search PubMed clinical trials carfecillin
Search PubMed titles carfecillin
Search PubMed titles/abstracts carfecillin
UniChem Compound Search for chemical match using the InChIKey NZDASSHFKWDBBU-KVMCETHSSA-N
UniChem Connectivity Search for chemical match using the InChIKey NZDASSHFKWDBBU-KVMCETHSSA-N