lymecycline

Also known as N6-((4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamido)methyl)lysine, N-Lysinomethyltetracycline, Limeciclina, Tetracycline-L-methylene lysine, Tetracycline-L-methylenelysine, N(2)-(((+)-5-Amino-5-carboxypentylamino)methyl)tetracycline, (+)-N-(5-Amino-5-carboxypentylaminomethyl)-4-dimethylamino-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxonaphthacene-2-carboxamide, Lymecyclinum

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.

Chemical data

Formula: C29H38N4O10
Molecular weight: 602.6 g/mol
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
SMILES: C[C@@]1([C@H]2C[C@H]3[C@@H](C(=O)/C(=C(\NCNCCCC[C@@H](C(=O)O)N)/O)/C(=O)[C@]3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)N(C)C)O
InChIKey: UVGVZMXVTBRRTB-VLSZFCQSSA-N
XLogP: -3.5
Polar surface area: 243 Å²
H-bond donors: 9
H-bond acceptors: 14
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
Indications: bacterial disease, acne

via ChEMBL · EBI

Research

201 papers

LYMECYCLINE.British medical journal · 1965
Lymecycline reverses acquired EGFR-TKI resistance in non-small-cell lung cancer by targeting GRB2.Pharmacological research · 2020
Pharmacokinetics and pharmacodynamics of the tetracyclines including glycylcyclines.The Journal of antimicrobial chemotherapy · 2006
Pseudotumor cerebri syndrome secondary to lymecycline therapy.European journal of ophthalmology · 2022
Lymecycline in the treatment of acne: an efficacious, safe and cost-effective alternative to minocycline.European journal of dermatology : EJD · 2003

via PubMed

Wikidata facts

Subclass of: chemical compound
Mass: 602.2588
Has use: medication

Show 7 more facts

significant drug interaction: isotretinoin
chemical formula: C₂₉H₃₈N₄O₁₀
World Health Organisation international non-proprietary name: lymecycline
canonical SMILES: CC1(C2=CC=CC(=C2C(=O)C3=C(C4(C(CC31)C(C(=C(C4=O)C(=O)NCNCCCCC(C(=O)O)N)O)N(C)C)O)O)O)O
subject has role: bactericide
isomeric SMILES: C[C@@]1([C@H]2C[C@H]3[C@@H](C(=O)C(=C([C@]3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)NCNCCCC[C@@H](C(=O)O)N)N(C)C)O
Commons category: Lymecycline

Sources (1)

wikidata.org

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~2 min read

Encyclopedic overview

6 sections

Contents

History
Indications
Acne
Side effects
See also
References

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.

Excerpted from Wikipedia’s “lymecycline” article, available under the CC BY-SA 4.0 licence.

Gallery (2)

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