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pivmecillinam   Click here for help

GtoPdb Ligand ID: 10922

Synonyms: amdinocillin pivoxil | pivmecillinam hydrochloride | Pivya® | RO-10-9071 | RO-109071 | Selexid®
Approved drug
pivmecillinam is an approved drug (UK (1977), FDA (2024))
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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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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Click here for structure editor
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 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

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@@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
InChI Key NPGNOVNWUSPMDP-HLLBOEOZSA-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. UK MHRA (1977)
Is prodrug? Yes
Active form mecillinam
International Nonproprietary Names Click here for help
INN number INN
3499 pivmecillinam
Synonyms Click here for help
amdinocillin pivoxil | pivmecillinam hydrochloride | Pivya® | RO-10-9071 | RO-109071 | Selexid®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Pivmecillinam (Prodrug of Amdinocillin)
Other databases
CAS Registry No. 32886-97-8 (source: WHO INN record)
ChEMBL Ligand CHEMBL1650818
DrugBank Ligand DB01605
GtoPdb PubChem SID 405560363
PubChem CID 115163
Search Google for chemical match using the InChIKey NPGNOVNWUSPMDP-HLLBOEOZSA-N
Search Google for chemicals with the same backbone NPGNOVNWUSPMDP
Search PubMed clinical trials pivmecillinam
Search PubMed titles pivmecillinam
Search PubMed titles/abstracts pivmecillinam
UniChem Compound Search for chemical match using the InChIKey NPGNOVNWUSPMDP-HLLBOEOZSA-N
UniChem Connectivity Search for chemical match using the InChIKey NPGNOVNWUSPMDP-HLLBOEOZSA-N