Lymecycline

Chemical compound
  • J01AA04 (WHO)
Legal statusLegal status
  • AU: S4 (Prescription only)
Pharmacokinetic dataBioavailability100% (oral)Elimination half-life10 hoursExcretionKidneyIdentifiers
  • (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 checkY
PubChem CID
  • 54707177
DrugBank
  • DB00256 checkY
ChemSpider
  • 20121315 ☒N
UNII
  • 7D6EM3S13P
KEGG
  • D06884 checkY
CompTox Dashboard (EPA)
  • DTXSID9045344 Edit this at Wikidata
ECHA InfoCard100.012.357 Edit this at WikidataChemical and physical dataFormulaC29H38N4O10Molar mass602.641 g·mol−13D model (JSmol)
  • Interactive image
  • 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 ☒N
  • Key:AHEVKYYGXVEWNO-UEPZRUIBSA-N ☒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]

See also

References

  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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