Lymecycline

Lymecycline

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Systematic (IUPAC) name
(2S)-6-[[[(Z)-[(4S,4aS,5aS,6S,12aS) -4-(dimethylamino)-6,10,11,12a-tetrahydroxy-6-methyl-1,3,12-trioxo-4,4a,5,5a-tetrahydrotetracen-2-ylidene]-hydroxymethyl]amino]methylamino]-2-aminohexanoic acid
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy category	?
Legal status	Schedule 4 (Aust)
Routes of administration	oral
Pharmacokinetic data
Bioavailability	100% (oral)
Metabolism	?
Biological half-life	10 h
Excretion	renal
Identifiers
CAS Number	992-21-2 Y
ATC code	J01AA04 (WHO)
PubChem	CID: 24757945
DrugBank	DB00256 Y
ChemSpider	20121315
UNII	7D6EM3S13P Y
KEGG	D06884 Y
Chemical data
Formula	C29H38N4O10
Molecular mass	602.63
SMILES C[C@@]1([C@H]2C[C@H]3[C@@H](C(=C(C(=O)[C@]3(C(=C2C(=O)C4=C1C=CC=C4O)O)O)C(=O)NCNCCCC[C@@H](C(=O)O)N)O)N(C)C)O
InChI InChI=1S/C29H38N4O10/c1-28(42)13-7-6-9-17(34)18(13)22(35)19-14(28)11-15-21(33(2)3)23(36)20(25(38)29(15,43)24(19)37)26(39)32-12-31-10-5-4-8-16(30)27(40)41/h6-7,9,14-16,21,31,34,36-37,42-43H,4-5,8,10-12,30H2,1-3H3,(H,32,39)(H,40,41)/t14-,15-,16-,21-,28+,29-/m0/s1 Key:AHEVKYYGXVEWNO-UEPZRUIBSA-N
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Lymecycline is a tetracycline broad-spectrum antibiotic marketed by the pharmaceutical company Galderma. It is approximately 5,000 times more soluble than tetracycline base and is unique amongst tetracyclines in that it is absorbed by an active transport process across the intestinal wall, making use of the same fast and efficient mechanism by which carbohydrates are absorbed.

The greater absorption of lymecycline allows for lower dosages to be used; the standard dose of 408 mg is equivalent to 300 mg tetracycline base and, in its action, to 500 mg tetracycline hydrochloride. Lymecycline, unlike tetracycline hydrochloride, is soluble at all physiological pH values.

History

Lymecycline was released into the pharmaceutical market in 1963.

Indications

Lymecycline, like other tetracyclines, is used to treat a range of infections. Its better absorption profile makes it preferable to tetracycline for moderately severe acne and typically prescribed for 8 weeks at a time, but alternatives should be sought if no improvement occurs by 3 months.

File:Tetralysal tablets with packaging in background.jpg

Lymecycline capsules

Side effects

Lymecycline's side effects can include rash, headache, diarrhoea, ulcerative colitis, nausea, vomiting, dermatitis, dysphasia, inflammation of the liver, hypersensitive reactions, and visual disturbances. When taken for a long period of time, it can cause reflux oesophagitis.

Recent studies found a possible link between Inflammatory Bowel Disease (IBD) and Lymecycline, particularly Ulcerative Colitis.

See also

• Timeline of antibiotics