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Lymecycline

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Lymecycline
Clinical data
Trade namesTetralysal
AHFS/DrugsInternational Drug Names
Routes of
administration
By mouth
ATC code
Legal status
Legal status
  • AU:S4(Prescription only)
Pharmacokineticdata
Bioavailability100% (oral)
Eliminationhalf-life10 hours
ExcretionKidney
Identifiers
  • (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
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
CompTox Dashboard(EPA)
ECHA InfoCard100.012.357Edit this at Wikidata
Chemical and physical data
FormulaC29H38N4O10
Molar mass602.641g·mol−1
3D model (JSmol)
  • 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=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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Lymecyclineis atetracyclinebroad-spectrum antibiotic.It is approximately 5,000 times moresolublethantetracyclinebase and is unique amongst tetracyclines in that it isabsorbedby anactive transportprocess across the intestinal wall, making use of the same fast and efficient mechanism by whichcarbohydratesare 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 allphysiologicalpHvalues.[citation needed]

History

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Lymecycline was introduced byFarmitaliain 1963.[citation needed]

Indications

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

Acne

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Its better absorption profile makes it preferable to tetracycline for moderately severeacneand 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

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

See also

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References

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  1. ^New ZealandDatasheetArchived2006-03-03 at theWayback MachineAugust 2003
  2. ^British National Formulary45March 2003
  3. ^Wang P."Side effects of Tetralysal".Retrieved23 March2011.
  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.PMC4884496.PMID27059913.