Lymecycline

Last updated
Lymecycline
Lymecycline.svg
Clinical data
Trade names Tetralysal
AHFS/Drugs.com International Drug Names
Routes of
administration
By mouth
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
Pharmacokinetic data
Bioavailability 100% (oral)
Elimination half-life 10 hours
Excretion Kidney
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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard 100.012.357 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C29H38N4O10
Molar mass 602.63 g·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 X mark.svgN
  • Key:AHEVKYYGXVEWNO-UEPZRUIBSA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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]

Contents

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 Tetralysal tablets with packaging in background.jpg
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

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Thyroid disease in pregnancy can affect the health of the mother as well as the child before and after delivery. Thyroid disorders are prevalent in women of child-bearing age and for this reason commonly present as a pre-existing disease in pregnancy, or after childbirth. Uncorrected thyroid dysfunction in pregnancy has adverse effects on fetal and maternal well-being. The deleterious effects of thyroid dysfunction can also extend beyond pregnancy and delivery to affect neurointellectual development in the early life of the child. Due to an increase in thyroxine binding globulin, an increase in placental type 3 deioidinase and the placental transfer of maternal thyroxine to the fetus, the demand for thyroid hormones is increased during pregnancy. The necessary increase in thyroid hormone production is facilitated by high human chorionic gonadotropin (hCG) concentrations, which bind the TSH receptor and stimulate the maternal thyroid to increase maternal thyroid hormone concentrations by roughly 50%. If the necessary increase in thyroid function cannot be met, this may cause a previously unnoticed (mild) thyroid disorder to worsen and become evident as gestational thyroid disease. Currently, there is not enough evidence to suggest that screening for thyroid dysfunction is beneficial, especially since treatment thyroid hormone supplementation may come with a risk of overtreatment. After women give birth, about 5% develop postpartum thyroiditis which can occur up to nine months afterwards. This is characterized by a short period of hyperthyroidism followed by a period of hypothyroidism; 20–40% remain permanently hypothyroid.

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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.