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].
2D Structure
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Physico-chemical Properties
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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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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 (FDA (1986))
Approved drug? Yes. FDA (1986)
Is prodrug? Yes
Active form ampicillinsulbactam
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
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UniChem Compound Search for chemical match using the InChIKey OPYGFNJSCUDTBT-PMLPCWDUSA-N
UniChem Connectivity Search for chemical match using the InChIKey OPYGFNJSCUDTBT-PMLPCWDUSA-N