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
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Physico-chemical Properties
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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
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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
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Withdrawn drug?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, indanyl carbenicillin
Other databases
CAS Registry No. 35531-88-5 (source: Scifinder)
ChEMBL Ligand CHEMBL1596
DrugBank Ligand DB09319
DrugCentral Ligand 508
GtoPdb PubChem SID 473153864
PubChem CID 93184
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