Lymecycline

Lymecycline
Clinical data
Trade names	Tetralysal
AHFS/Drugs.com	International Drug Names
Routes of; administration	By mouth
ATC code	J01AA04 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only);
Pharmacokinetic data
Bioavailability	100% (oral)
Elimination half-life	10 hours
Excretion	Kidney
Identifiers
	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;
CAS Number	992-21-2 ;
PubChem CID	54707177;
DrugBank	DB00256 ;
ChemSpider	20121315 ;
UNII	7D6EM3S13P;
KEGG	D06884 ;
CompTox Dashboard (EPA)	DTXSID9045344 ;
ECHA InfoCard	100.012.357
Chemical and physical data
Formula	C29H38N4O10
Molar mass	602.641 g·mol−1
3D model (JSmol)	Interactive image;
	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. 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.^[1]

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.^{[citation needed]}

History

Lymecycline was introduced by Farmitalia in 1963.^{[citation needed]}

Indications

Lymecycline, like other tetracyclines, is used to treat a range of infections.

Acne

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.^[2]

Lymecycline capsules

Side effects

Lymecycline's side effects can include rash, headache, diarrhoea, nausea, vomiting, dermatitis, inflammation of the liver, hypersensitive reactions, and visual disturbances. When taken for a long period of time, it can cause reflux oesophagitis.^[3] Recently, the family of tetracycline antibiotics has been associated with thyroid dysfunction in youth.^[4]

References

^ New Zealand Datasheet Archived 2006-03-03 at the Wayback Machine August 2003
^ British National Formulary 45 March 2003
^ Wang P. "Side effects of Tetralysal". Retrieved 23 March 2011.
^ Pollock AJ, Seibert T, Allen DB (June 2016). "Severe and Persistent Thyroid Dysfunction Associated with Tetracycline-Antibiotic Treatment in Youth". The Journal of Pediatrics. 173: 232–4. doi:10.1016/j.jpeds.2016.03.034. PMC 4884496. PMID 27059913.

[1] New Zealand Datasheet Archived 2006-03-03 at the Wayback Machine August 2003

[2] British National Formulary 45 March 2003

[3] Wang P. "Side effects of Tetralysal". Retrieved 23 March 2011.

[4] Pollock AJ, Seibert T, Allen DB (June 2016). "Severe and Persistent Thyroid Dysfunction Associated with Tetracycline-Antibiotic Treatment in Youth". The Journal of Pediatrics. 173: 232–4. doi:10.1016/j.jpeds.2016.03.034. PMC 4884496. PMID 27059913.

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