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zifanocycline   Click here for help

GtoPdb Ligand ID: 12794

Synonyms: KBP-7072
Compound class: Synthetic organic
Comment: Zifanocycline is an aminomethylcycline (tetracycline derivative) with broad-spectrum antibacterial activity [3]. We show the chemical structure provided by PubChem, but note that this is not an exact match for the CAS number assigned in the WHO INN record for this drug.
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 5
Topological polar surface area 167.87
Molecular weight 552.62
XLogP 0.55
No. Lipinski's rules broken 2

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 CN(C)C1=C2C[C@H]3C[C@H]4[C@@H](C(=O)C(=C([C@]4(C(=O)C3=C(C2=C(C(=C1)CN5CC6CC6C5)O)O)O)O)C(=O)N)N(C)C
Isomeric SMILES CN(C)[C@H]1[C@@H]2C[C@@H]3CC4=C(C=C(C(=C4C(=C3C(=O)[C@@]2(C(=C(C1=O)C(=O)N)O)O)O)O)CN5CC6CC6C5)N(C)C
InChI InChI=1S/C29H36N4O7/c1-31(2)18-8-15(11-33-9-13-5-14(13)10-33)23(34)20-16(18)6-12-7-17-22(32(3)4)25(36)21(28(30)39)27(38)29(17,40)26(37)19(12)24(20)35/h8,12-14,17,22,34-35,38,40H,5-7,9-11H2,1-4H3,(H2,30,39)/t12-,13?,14?,17-,22-,29-/m0/s1
InChI Key LBKXOQRVWDAQSX-OMBSCLNISA-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/)
No information available.
Summary of Clinical Use Click here for help
Zifanocycline is being developed by KBP Biosciences as an intravenous or oral treatment for community-acquired bacterial pneumonia (CABP) and acute bacterial skin and skin structure infections (ABSSSI). It has completed several Phase 1 clinical trials (NCT02454361, NCT02654626, and NCT04532957) and recruitment has commenced for a further Phase 1 trial (NCT05507463).
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT04532957 A Multiple Ascending Dose Study to Investigate Safety of KBP-7072 in Healthy Subjects Phase 1 Interventional KBP Biosciences
NCT02454361 Safety, Tolerability and Pharmacokinetics of KBP-7072 Phase 1 Interventional KBP Biosciences
NCT02654626 A Multiple Ascending Dose Study of KBP-7072 in Healthy Subjects Phase 1 Interventional KBP Biosciences
NCT05507463 Study of KBP-7072 in Healthy Male and Female Subjects Phase 1 Interventional KBP Biosciences