metacycline   Click here for help

GtoPdb Ligand ID: 13618

Synonyms: GS-2876 | methacycline | methylenecycline | Physiomycine® | Rondomycin®
Approved drug
metacycline is an approved drug (France)
Compound class: Synthetic organic
Comment: Metacycline is a tetracycline antibacterial compound, derived from oxytetracycline [1]. Note that the structure shown here matches the CAS-assigned structure. The PubChem link, provided in the table below, is to their standardized chemical structure (CID 54675785), although this is not an exact structural match.
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 10
Hydrogen bond donors 6
Rotatable bonds 2
Topological polar surface area 181.62
Molecular weight 442.42
XLogP -0.56
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 C=C1C2=CC=CC(=C2C(=O)C3=C([C@]4([C@]([H])([C@@H](C(=C(C4=O)C(=O)N)O)N(C)C)[C@H]([C@]13[H])O)O)O)O
Isomeric SMILES O[C@]12[C@]([C@H](N(C)C)C(O)=C(C(N)=O)C1=O)([C@@H](O)[C@]3(C(=C2O)C(=O)C=4C(C3=C)=CC=CC4O)[H])[H]
InChI InChI=1S/C22H22N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-6,10,14-15,17,25,27-29,32H,1H2,2-3H3,(H2,23,31)/t10-,14-,15+,17+,22+/m1/s1
InChI Key MHIGBKBJSQVXNH-IWVLMIASSA-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
Metacycline hydrochloride is authourised by the French national medicine agency (ANSM) and marketed under the trade name Physiomycine®. It is indicated as an oral treatment for acne and for a wide range of bacterial infections including those of the respiratory and genitourinary systems. Metacycline hydrochloride was also marketed in the US (trade name Rondomycin®) but has since been discontinued.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Tetracyclines inhibit bacterial protein synthesis by binding reversibly to the bacterial 30S ribosomal subunit and preventing the aminoacyl tRNA from binding to the acceptor (A) site on the mRNA-ribosome complex (reviewed in [2-3]).