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sultamicillin   Click here for help

GtoPdb Ligand ID: 12290

Synonyms: CP-49,952 | Unasyn®
Approved drug
sultamicillin is an approved drug (FDA (1986))
Compound class: Synthetic organic
Comment: Sultamicillin is a prodrug of ampicillin and sulbactam linked as a double ester. This orally bioavailable molecule has similar antibacterial activity and clinical efficacy to that of the parenteral formulation of ampicillin and sulbactam [1].

sultamicillin 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 13
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 216.16
Molecular weight 594.15
XLogP -0.13
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 O=C([C@@H](c1ccccc1)N)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)OCOC(=O)[C@@H]1N2C(=O)C[C@H]2S(=O)(=O)C1(C)C)(C)C
Isomeric SMILES CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](c1ccccc1)N)C(=O)OCOC(=O)[C@H]1C(S(=O)(=O)[C@H]2N1C(=O)C2)(C)C)C
InChI InChI=1S/C25H30N4O9S2/c1-24(2)17(29-20(32)16(21(29)39-24)27-19(31)15(26)12-8-6-5-7-9-12)22(33)37-11-38-23(34)18-25(3,4)40(35,36)14-10-13(30)28(14)18/h5-9,14-18,21H,10-11,26H2,1-4H3,(H,27,31)/t14-,15-,16-,17+,18+,21-/m1/s1
InChI Key OPYGFNJSCUDTBT-PMLPCWDUSA-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 (1986)
Is prodrug? Yes
Active form ampicillin, sulbactam
IUPAC Name Click here for help
[(2S,5R)-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carbonyl]oxymethyl (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
International Nonproprietary Names Click here for help
INN number INN
5151 sultamicillin
Synonyms Click here for help
CP-49,952 | Unasyn®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Sultamicillin
Other databases
CAS Registry No. 76497-13-7 (source: Scifinder)
ChEBI CHEBI:51770
ChEMBL Ligand CHEMBL506110
DrugBank Ligand DB12127
DrugCentral Ligand 2539
GtoPdb PubChem SID 479821081
PubChem CID 444022
Search Google for chemical match using the InChIKey OPYGFNJSCUDTBT-PMLPCWDUSA-N
Search Google for chemicals with the same backbone OPYGFNJSCUDTBT
Search PubMed clinical trials sultamicillin
Search PubMed titles sultamicillin
Search PubMed titles/abstracts sultamicillin
UniChem Compound Search for chemical match using the InChIKey OPYGFNJSCUDTBT-PMLPCWDUSA-N
UniChem Connectivity Search for chemical match using the InChIKey OPYGFNJSCUDTBT-PMLPCWDUSA-N

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MedChemExpress
Sultamicillin (links to external site)
Cat. No. HY-N7115