Lymecycline

Lymecycline

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 cat.	?
Legal status	Schedule 4 (Aust)
Routes	oral
Pharmacokinetic data
Bioavailability	100% (oral)
Metabolism	?
Half-life	10 h
Excretion	renal
Identifiers
CAS number	992-21-2 Y
ATC code	J01AA04
PubChem	CID 24757945
DrugBank	APRD00565
ChemSpider	16736147 Y
UNII	7D6EM3S13P N
KEGG	D06884 Y
Chemical data
Formula	C29H38N4O10
Mol. mass	602.63
SMILES	eMolecules & PubChem
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)32-12-31-16(27(40)41)8-4-5-10-30/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 Y Key:WLQCPSFWJHLZAY-CCZWQWCCSA-N Y
N(what is this?)  (verify)

Lymecycline is a tetracycline broad-spectrum antibiotic marketed by the pharmeceutical company Galderma. It is approximately 5000 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.

History

Lymecycline was released onto 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.^[2]

Dosage

The standard dose is 408 mg (one capsule) daily by mouth. In particularly severe infections this dose may be increased to 1224–1632 mg (three or four capsules) daily.

The 408 mg once daily dosage for acne aids good drug compliance.^{[clarification needed]}

Lymecycline capsules

Side effects

Lymecycline's side effects can include rash, headache, diarrhoea, 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.^[3]

References

1. ^ New Zealand Datasheet August 2003
2. ^ British National Formulary 45 March 2003
3. ^ Dr Wang, Peter. "Side effects of Tetralysal". http://www.steadyhealth.com/about/side_effects_of_tetralysal.html. Retrieved 23 March 2011. 

See also

• Timeline of antibiotics