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cefpiramide   Click here for help

GtoPdb Ligand ID: 12027

Synonyms: SM-1652 | WY-44635
Approved drug
cefpiramide is an approved drug (FDA (1989))
Compound class: Synthetic organic
Comment: Cefpiramide is a semisynthetic, third generation cephalosporin and belongs to the β-lactam class of antibacterial compounds.

cefpiramide is commercially available from our sponsors

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 11
Hydrogen bond donors 5
Rotatable bonds 11
Topological polar surface area 263.1
Molecular weight 612.12
XLogP 2.24
No. Lipinski's rules broken 1

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 Oc1ccc(cc1)[C@H](C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nnnn1C)NC(=O)c1c[nH]c(cc1=O)C
Isomeric SMILES Cc1cc(=O)c(c[nH]1)C(=O)N[C@H](c1ccc(cc1)O)C(=O)N[C@H]1[C@@H]2N(C1=O)C(=C(CS2)CSc1nnnn1C)C(=O)O
InChI InChI=1S/C25H24N8O7S2/c1-11-7-16(35)15(8-26-11)20(36)27-17(12-3-5-14(34)6-4-12)21(37)28-18-22(38)33-19(24(39)40)13(9-41-23(18)33)10-42-25-29-30-31-32(25)2/h3-8,17-18,23,34H,9-10H2,1-2H3,(H,26,35)(H,27,36)(H,28,37)(H,39,40)/t17-,18-,23-/m1/s1
InChI Key PWAUCHMQEXVFJR-PMAPCBKXSA-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. US FDA (1989)
IUPAC Name Click here for help
(6R,7R)-7-[[(2R)-2-(4-hydroxyphenyl)-2-[(6-methyl-4-oxo-1H-pyridine-3-carbonyl)amino]acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
5152 cefpiramide
Synonyms Click here for help
SM-1652 | WY-44635
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Cefpiramide
Other databases
CAS Registry No. 70797-11-4 (source: Scifinder)
ChEBI CHEBI:59213
ChEMBL Ligand CHEMBL1201204
DrugBank Ligand DB00430
DrugCentral Ligand 552
GtoPdb PubChem SID 464244168
PubChem CID 636405
Search Google for chemical match using the InChIKey PWAUCHMQEXVFJR-PMAPCBKXSA-N
Search Google for chemicals with the same backbone PWAUCHMQEXVFJR
Search PubMed clinical trials cefpiramide
Search PubMed titles cefpiramide
Search PubMed titles/abstracts cefpiramide
UniChem Compound Search for chemical match using the InChIKey PWAUCHMQEXVFJR-PMAPCBKXSA-N
UniChem Connectivity Search for chemical match using the InChIKey PWAUCHMQEXVFJR-PMAPCBKXSA-N

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MedChemExpress
Cefpiramide (links to external site)
Cat. No. HY-B1354