pivmecillinam   Click here for help

GtoPdb Ligand ID: 10922

Synonyms: amdinocillin pivoxil | pivmecillinam hydrochloride | RO-10-9071 | RO-109071 | Selexid®
Approved drug
pivmecillinam is an approved drug (UK (1977))
Compound class: Synthetic organic
Comment: Pivmecillinam is a penicillanic acid ester prodrug of mecillinam, and is a semisynthetic, broad spectrum β-lactam penicillin antibacterial. It is considered to be active only against Gram-negative bacteria.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 0
Rotatable bonds 8
Topological polar surface area 113.81
Molecular weight 439.21
XLogP 2.67
No. Lipinski's rules broken 0
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Canonical SMILES O=C([C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)N=CN1CCCCCC1)OCOC(=O)C(C)(C)C
Isomeric SMILES O=C([C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)N=CN1CCCCCC1)OCOC(=O)C(C)(C)C
InChI InChI=1S/C21H33N3O5S/c1-20(2,3)19(27)29-13-28-18(26)15-21(4,5)30-17-14(16(25)24(15)17)22-12-23-10-8-6-7-9-11-23/h12,14-15,17H,6-11,13H2,1-5H3/t14-,15+,17-/m1/s1
1. Graninger W. (2003)
Pivmecillinam--therapy of choice for lower urinary tract infection.
Int J Antimicrob Agents, 22 Suppl 2: 73-8. [PMID:14527775]
2. Tanphaichitra D, Srimuang S, Chiaprasittigul P, Menday P, Christensen OE. (1984)
The combination of pivmecillinam and pivampicillin in the treatment of enteric fever.
Infection, 12 (6): 381-3. [PMID:6569851]