Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Lymecycline: Difference between pages

{{Short description|Chemical compound}}

| verifiedrevid = 462094956

| IUPAC_name = (2''S'')-6-<nowiki>[[[</nowiki>(''Z'')-[(4''S'',4a''S'',5a''S'',6''S'',12a''S'') -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

| image = Lymecycline.svg

| width = 300

| tradename = Tetralysal

| pregnancy_category =

| legal_status =

| legal_AU = Schedule 4

| routes_of_administration = [[Oral administration|By mouth]]

| metabolism =

| elimination_half-life = 10 hours

| excretion = [[Kidney]]

| PubChem = 54707177

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 20121315

| UNII_Ref = {{fdacite|correct|FDA}}

| 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

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = AHEVKYYGXVEWNO-UEPZRUIBSA-N

'''Lymecycline''' is a [[tetracycline antibiotics|tetracycline]] [[broad-spectrum antibiotic]]. It is approximately 5,000 times more [[soluble]] than [[tetracycline]] base and is unique amongst tetracyclines in that it is [[Absorption (chemistry)|absorbed]] by an [[active transport]] process across the intestinal wall, making use of the same fast and efficient mechanism by which [[carbohydrate]]s are absorbed.<ref>[[New Zealand]] [http://www.medsafe.govt.nz/profs/Datasheet/t/Tetralysalcap.htm Datasheet] {{webarchive|url=https://web.archive.org/web/20060303205705/http://www.medsafe.govt.nz/profs/datasheet/t/Tetralysalcap.htm |date=2006-03-03 }} August 2003</ref>

The greater absorption of lymecycline allows for lower dosages to be used; the standard dose of 408&nbsp;mg is equivalent to 300&nbsp;mg tetracycline base and, in its action, to 500&nbsp;mg tetracycline hydrochloride. Lymecycline, unlike tetracycline hydrochloride, is soluble at all [[physiological]] [[pH]] values.{{cn|date=March 2023}}

==History==

Lymecycline was introduced by [[Farmitalia]] in 1963.{{cn|date=March 2023}}

==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 vulgaris|acne]] and typically prescribed for 8 weeks at a time, but alternatives should be sought if no improvement occurs by 3 months.<ref>[[British National Formulary]] ''45'' March 2003</ref>

[[File:Tetralysal tablets with packaging in background.jpg|thumb|250px|Lymecycline capsules]]

== Side effects ==

Lymecycline's side effects can include [[rash]], [[headache]], [[Diarrhea|diarrhoea]], [[nausea]], [[vomiting]], [[dermatitis]], inflammation of the liver, [[Hypersensitive response|hypersensitive reactions]], and [[Vision disorder|visual disturbances]]. When taken for a long period of time, it can cause [[reflux oesophagitis]].<ref>{{cite web| vauthors = Wang P |title=Side effects of Tetralysal|url=http://www.steadyhealth.com/about/side_effects_of_tetralysal.html|access-date=23 March 2011}}</ref> Recently, the family of tetracycline antibiotics has been associated with thyroid dysfunction in youth.<ref>{{cite journal | vauthors = Pollock AJ, Seibert T, Allen DB | title = Severe and Persistent Thyroid Dysfunction Associated with Tetracycline-Antibiotic Treatment in Youth | journal = The Journal of Pediatrics | volume = 173 | pages = 232–4 | date = June 2016 | pmid = 27059913 | pmc = 4884496 | doi = 10.1016/j.jpeds.2016.03.034 }}</ref>

== See also ==

* [[Timeline of antibiotics]]

== References ==

{{Reflist}}

{{TetracyclineAntiBiotics}}

[[Category:Alpha-Amino acids]]

[[Category:Amino acid derivatives]]

[[Category:Anti-acne preparations]]

[[Category:Tetracycline antibiotics]]