Minocycline

IUPAC: 4β ,7- bis (dimethylamino) -1,4,4 a, 5,5 a, 6,11,12 a- octahydro - 3,10,12,12 a- tetrahydroxy -1, 11 - dioxo -2- naphthacenecarboxamide

J01AA08, A01AB23

Yellow crystalline powder ( monohydrochloride )

Tetracycline

> 175 ° C ( decomposition) ( monohydrochloride )

Attention

140 mg · kg -1 ( LD50, mouse, i.v.)

Template: Infobox chemical / molecular formula search available

Minocycline is an antibiotic in the class of tetracyclines. It has a broad spectrum of activity and shows a bacteriostatic activity against gram- positive, gram- negative cell wall and germs. Minocycline is used to treat infections of the respiratory and ear, nose and throat area, certain forms of pneumonia, infections of the urinary tract and the reproductive organs, the gastrointestinal tract as well as skin diseases, severe forms of acne, conjunctivitis and Lyme disease.

Regardless of the antibacterial action of minocycline also protective effects on nerve cells have been detected since 2000 and for the kidney in diabetes mellitus.

Production

The multi-stage synthesis of the active agent is described in the literature. Here, a benzylic hydroxy group is prepared starting from fermentation and partially synthetically derived 6- demethyltetracycline first cleaved by hydrogenolysis. Subsequently, a nitro group is introduced by reaction with potassium nitrate / hydrofluoric acid in the ortho position to the phenolic hydroxy group. Obtained as the corresponding aniline derivative by reduction of this nitro group. Nitrating with a nitro group on the aromatic ring in para-position is introduced to the phenolic hydroxy group. The diazotisation of the aniline derivative yields the diazonium salt. By catalytic reduction of the nitrogen of the diazonium salt is cleaved and at the same time reduces the second nitro group ( in the para position of the phenol ) to the amino group. This amino group is now doubly methylated with formaldehyde so that minocycline results. The drug thus contains two dimethylamino functions (see box).

Anti-inflammatory and neuroprotective properties

The current research examined the possible neuroprotective and anti-inflammatory effects of minocycline against progression of a group of neurodegenerative diseases such as multiple sclerosis, rheumatoid arthritis, Huntington's disease, Parkinson 's disease and other of this kind, as well as in stroke.

However, a study on the use of minocycline in amyotrophic lateral sclerosis and was disappointed, however, that the drug in this disease may well show destructive, krankheitsbeschleunigende effect.

In an animal model of orofacial pain minocycline has shown a significant weakening effect at low inflammation-related hyperalgesia of masseter muscle, but not in the hyperalgesia of the skin. It is believed that the neuroprotective action of minocycline is independent of the anti-inflammatory properties.

Trade names

Aknefug Mino (D), Aknoral (CH), Aknosan (D), Minakne (D), Skid (D), Skinocyclin (D), Udima (D, A ), numerous generics (D, A, CH), cyclin ( Taiwan)