Drug/Small Molecule:

minocycline

Overview

Generic Names:	minocycline
IUPAC Name:	(2Z,4S,4aS,5aR,12aS)-2-(amino-hydroxymethylidene)-4,7-bis(dimethylamino)-10,11,12a-trihydroxy-4a,5,5a,6-tetrahydro-4H-tetracene-1,3,12-trione
Trade Names:	Alti-Minocycline; Apo-Minocycline; Arestin; Dynacin; Gen-Minocycline; Klinomycin; Minociclina [INN-Spanish]; Minocin; Minocyclin; Minocycline HCl; Minocyclinum [INN-Latin]; Minocyn; Minomycin; Novo-Minocycline; Solodyn; Vectrin
PharmGKB Accession Id:	PA450519

Description

A tetracycline analog, having a 7-dimethylamino and lacking the 5 methyl and hydroxyl groups, which is effective against tetracycline-resistant staphylococcus infections. [PubChem]

Indication

For the treatment of infections caused by susceptible strains of microorganisms, such as Rocky Mountain spotted fever, typhus fever and the typhus group, Q fever, rickettsial pox and tick fevers caused by Rickettsiae, upper respiratory tract infections caused by Streptococcus pneumoniae and for the treatment of asymptomatic carriers of Neisseria meningitidis.

ATC Therapeutic Categories

• A01AB:Antiinfectives and antiseptics for local oral treatment
• J01AA:Tetracyclines

Pharmacology and Interactions

Mechanism Of Action

Minocycline passes directly through the lipid bilayer or passively diffuses through porin channels in the bacterial membrane. Tetracyclines like minocycline bind to the 30S ribosomal subunit, preventing the binding of tRNA to the mRNA-ribosome complex and interfering with protein synthesis.

Pharmacology

Minocycline, the most lipid soluble and most active tetracycline antibiotic, is, like doxycycline, a long-acting tetracycline. Minocycline's effects are related to the inhibition of protein synthesis. Although minocycline's broader spectrum of activity, compared to other members of the group, includes activity against Neisseria meningitidis, its use as a prophylaxis is no longer recomended because of side effects (dizziness and vertigo). Current research is examining the possible neuroprotective effects of minocycline against progression of Huntington's Disease, an inherited neurodegenerative disorder. The neuroprotective action of minocycline may include its inhibitory effect on 5-lipoxygenase, an inflammatory enzyme associated with brain aging.

Food Interactions

Calcium and iron needs increased with long term use. Do not take Aluminum or magnesium antacids or supplements while on this medication. Take with food.

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Hepatic.

Protein Binding

55% to 76%

Absorption

Rapidly absorbed from the gastrointestinal tract and absorption is not significantly impaired by ingestion of food or milk. Oral bioavailability is 100%.

Half Life

11-22 hours

Toxicity

Minocycline has been observed to cause a dark discoloration of the thyroid in experimental animals (rats, minipigs, dogs and monkeys). In the rat, chronic treatment with minocycline has resulted in goiter accompanied by elevated radioactive iodine uptake and evidence of thyroid tumor production. Minocycline has also been found to produce thyroid hyperplasia in rats and dogs. LD₅₀=2380 mg/kg (rat, oral), LD₅₀=3600 mg/kg (mouse, oral)

Chemical Properties

Chemical Formula:

C₂₃H₂₇N₃O₇

SMILES Code:

CN(C)c1ccc(c2c1C[C@H]3C[C@H]4[C@@H](C(=C(C(=O)[C@]4(C(=C3C2=O)O)O)C(=O)N)O)N(C)C)O

(Format: OpenEye Isomeric)

Molecular Weight ( average / monoisotopic )

457.4764 / 457.1849

Non-Curated Information

A list of non-curated publications that mention this drug along with other genes is available.

Drug Targets

• ALOX5
• VEGFA
• MMP9
• CASP1
• IL1B
• CYCS
• CASP3

Non-Curated Information

A list of non-curated publications that mention this drug along with other drugs is available.

Drug Interactions

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

Additional Datasets

These datasets are minimally curated and are sorted alphabetically by title.

1. The Connectivity Map: using gene-expression signatures to connect small molecules, genes, and disease

LinkOuts

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Non-Curated Publications

A list of non-curated publications that mention this drug is available.