methacycline

Also known as GS-2876, 6-demethyl-6-deoxy-5-hydroxy-6-methylenetetracycline, 6-deoxy-6-demethyl-6-methylene-5-oxytetracycline, 6-methylene-5-hydroxytetracycline, 6-methylene-5-oxytetracycline, 6-methyleneoxytetracycline, methylenecycline

Metacycline or methacycline is a tetracycline antibiotic. It is used as a precursor in the industrial synthesis of doxycycline hyclate.

Chemical data

Formula: C22H22N2O8
Molecular weight: 442.4 g/mol
IUPAC name: (2Z,4S,4aR,5S,5aR,12aS)-2-[amino(hydroxy)methylidene]-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methylidene-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione
SMILES: CN(C)[C@H]1[C@@H]2[C@H]([C@@H]3C(=C)C4=C(C(=CC=C4)O)C(=C3C(=O)[C@@]2(C(=O)/C(=C(/N)\O)/C1=O)O)O)O
InChIKey: GLFJCEVWKWQSJP-ISFNZQQKSA-N
XLogP: -0.2
Polar surface area: 182 Å²
H-bond donors: 6
H-bond acceptors: 10
Formal charge: 0

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Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1982
Admin. routes: oral
Indications: bacterial disease, osteomyelitis

via ChEMBL · EBI

Research

431 papers

Methacycline displays a strong efficacy in reducing toxicity in a SCA3 Caenorhabditis elegans model.Biochimica et biophysica acta. General subjects · 2019
Pharmacokinetics and pharmacodynamics of the tetracyclines including glycylcyclines.The Journal of antimicrobial chemotherapy · 2006
The tetracyclines.The Medical clinics of North America · 1970
Tetracyclines.Zentralblatt fur Bakteriologie, Parasitenkunde, Infektionskrankheiten und Hygiene. Zweite naturwissenschaftliche Abt.: Allgemeine, landwirtschaftliche und technische Mikrobiologie · 1973
Inhibition of epithelial-to-mesenchymal transition and pulmonary fibrosis by methacycline.American journal of respiratory cell and molecular biology · 2014

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Wikidata facts

Subclass of: chemical compound
Mass: 442.1376
Has use: medication

Show 8 more facts

chemical formula: C₂₂H₂₂N₂O₈
defined daily dose: 0.6
World Health Organisation international non-proprietary name: metacycline
isomeric SMILES: CN(C)[C@H]1[C@@H]2[C@H]([C@@H]3C(=C)C4=CC=CC(=C4C(=O)C3=C([C@@]2(C(=O)C(=C1O)C(=O)N)O)O)O)O
canonical SMILES: CN(C)C1C2C(C3C(=C)C4=CC=CC(=C4C(=O)C3=C(C2(C(=O)C(=C1O)C(=O)N)O)O)O)O
subject has role: bactericide
medical condition treated: bronchitis
Commons category: Metacycline

Sources (7)

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Encyclopedic overview

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Contents

References

Metacycline or methacycline is a tetracycline antibiotic. It is used as a precursor in the industrial synthesis of doxycycline hyclate.

It has been found to act as an agonist of the human pregnane X receptor ligand-binding domain and to induce CYP3A4 expression in vitro.

Excerpted from Wikipedia’s “methacycline” article, available under the CC BY-SA 4.0 licence.

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