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Identification
- Summary
Lymecycline is a tetracycline antibiotic used for the treatment of acne vulgaris and other susceptible infections.
- Generic Name
- Lymecycline
- DrugBank Accession Number
- DB00256
- Background
Lymecycline is a broad-spectrum second-generation tetracycline antibiotic used for the treatment of acne and other susceptible bacterial infections.8,9 It has been proven a cost-effective alternative to treatment with minocycline with comparable safety and efficacy.2 Lymecycline was initially discovered in 1961. It is marketed by Galderma and used in the UK as well as New Zealand in addition to other countries. Lymecycline is not marketed in the USA, however, equivalent drugs are available, such as minocycline and tetracycline.5,8
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Lymecycline (DB00256)
- Weight
- Average: 602.6328
Monoisotopic: 602.258793456 - Chemical Formula
- C29H38N4O10
- Synonyms
- (+)-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
- Limeciclina
- Lymecycline
- Lymecyclinum
- N-Lysinomethyltetracycline
- N2-(((+)-5-Amino-5-carboxypentylamino)methyl)tetracycline
- 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
- Tetracycline-L-methylene lysine
- Tetracycline-L-methylenelysine
Pharmacology
- Indication
Lymecycline is used for the treatment of acne in addition to other susceptible infections; propionibacterium is often the cause of acne.8 Some of the infections that can be treated with lymecycline include upper respiratory tract infections, urinary tract infections, bronchitis, chlamydial infections, and rickettsial infections.9
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Acne vulgaris •••••••••••• ••••••• Treatment of Susceptible bacterial infections •••••••••••• ••••••• - Contraindications & Blackbox Warnings
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Lymecycline, like other tetracyclines, exerts bacteriostatic actions on intracellular and extracellular bacteria, treating susceptible bacterial infections.9 It has been shown to be safe and effective in the treatment of moderate to severe acne.1
It is important to note that like other tetracyclines, lymecycline may cause esophageal irritation and ulceration, which can be prevented by drinking adequate fluids during administration. It also has the potential to cause photosensitivity. Lymecycline can lead to renal tubular acidosis or hepatic toxicity. It is not recommended to administer this drug in patients with renal disease or severe hepatic disease.8,9
- Mechanism of action
Normally, the ribosome synthesizes proteins through the binding of aminoacyl-tRNA to the mRNA-ribosome complex. Lymecycline binds to the 30S ribosomal subunit, preventing amino-acyl tRNA from binding to the A site of the ribosome, which prevents the elongation of polypeptide chains.5,6,8 This results in bacteriostatic actions, treating various infections.
Target Actions Organism A30S ribosomal protein S4 inhibitorEscherichia coli (strain K12) - Absorption
Lymecycline is 77-88% absorbed after oral administration with a relative bioavailability of 70%.4 The Cmax of lymecycline is 2.1 mg/L and is achieved about 3 hours after administration.3 The AUC is 21.9 ± 4.3 mg·h/L.3
- Volume of distribution
Lymecycline is lipophilic and easily crosses the cell membrane and passively diffuses through bacterial porin channels.3,5 As a second-generation tetracycline, the concentration in the bile ranges from 10 to 25 times higher than plasma concentration.3,7 In general, the volume of distribution of tetracyclines ranges from 1.3–1.7 L/kg or 100–130 L.3
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Lymecycline is 25% eliminated in the urine.3 Based on being a member of the tetracycline drug class, fecal elimination is likely another route of elimination.7
- Half-life
The half-life of lymecycline is approximately 8 hours.3
- Clearance
Lymecycline is partially cleared by the kidneys, like other tetracyclines.7
- Adverse Effects
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The oral LD50 of lymecycline in rats is 3200 mg/kg.10 Overdoses with lymecycline are rare. In the case of an overdose, gastric lavage should be performed immediately. Provide supportive treatment and maintain fluid balance.9
- Pathways
Pathway Category Lymecycline Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcenocoumarol Lymecycline may increase the anticoagulant activities of Acenocoumarol. Acitretin The risk or severity of pseudotumor cerebri can be increased when Lymecycline is combined with Acitretin. Alitretinoin The risk or severity of pseudotumor cerebri can be increased when Lymecycline is combined with Alitretinoin. Almasilate Almasilate can cause a decrease in the absorption of Lymecycline resulting in a reduced serum concentration and potentially a decrease in efficacy. Aluminium Aluminium can cause a decrease in the absorption of Lymecycline resulting in a reduced serum concentration and potentially a decrease in efficacy. - Food Interactions
- Take with or without food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Eficiclina / Tetralisal / Tetralysal
Categories
- ATC Codes
- J01AA04 — Lymecycline
- J01AA — Tetracyclines
- J01A — TETRACYCLINES
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as tetracyclines. These are polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Tetracyclines
- Sub Class
- Not Available
- Direct Parent
- Tetracyclines
- Alternative Parents
- Naphthacenes / Anthracenecarboxylic acids and derivatives / L-alpha-amino acids / Tetralins / Aryl ketones / Medium-chain fatty acids / Amino fatty acids / 1-hydroxy-4-unsubstituted benzenoids / Hydroxy fatty acids / Aralkylamines show 16 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Alcohol / Alpha-amino acid / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Amino fatty acid / Anthracene carboxylic acid or derivatives show 37 more
- Molecular Framework
- Aromatic homopolycyclic compounds
- External Descriptors
- tetracyclines (CHEBI:59040)
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- 7D6EM3S13P
- CAS number
- 992-21-2
- InChI Key
- AHEVKYYGXVEWNO-UEPZRUIBSA-N
- 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
- IUPAC Name
- (2S)-6-[({[(4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracen-2-yl]formamido}methyl)amino]-2-aminohexanoic acid
- SMILES
- [H][C@@]12C[C@@]3([H])C(C(=O)C4=C(O)C=CC=C4[C@@]3(C)O)=C(O)[C@]1(O)C(=O)C(C(=O)NCNCCCC[C@H](N)C(O)=O)=C(O)[C@H]2N(C)C
References
- Synthesis Reference
Willis L. Winstrom, "Process and apparatus for the preparation of chlortetracycline-containing animal feed compositions." U.S. Patent US06844006, issued January 18, 2005.
US06844006- General References
- Dubertret L, Alirezai M, Rostain G, Lahfa M, Forsea D, Niculae BD, Simola M, Horvath A, Mizzi F: The use of lymecycline in the treatment of moderate to severe acne vulgaris: a comparison of the efficacy and safety of two dosing regimens. Eur J Dermatol. 2003 Jan-Feb;13(1):44-8. [Article]
- Bossuyt L, Bosschaert J, Richert B, Cromphaut P, Mitchell T, Al Abadie M, Henry I, Bewley A, Poyner T, Mann N, Czernielewski J: Lymecycline in the treatment of acne: an efficacious, safe and cost-effective alternative to minocycline. Eur J Dermatol. 2003 Mar-Apr;13(2):130-5. [Article]
- Agwuh KN, MacGowan A: Pharmacokinetics and pharmacodynamics of the tetracyclines including glycylcyclines. J Antimicrob Chemother. 2006 Aug;58(2):256-65. Epub 2006 Jul 1. [Article]
- Sjolin-Forsberg G, Hermansson J: Comparative bioavailability of tetracycline and lymecycline. Br J Clin Pharmacol. 1984 Oct;18(4):529-33. doi: 10.1111/j.1365-2125.1984.tb02500.x. [Article]
- Chopra I, Roberts M: Tetracycline antibiotics: mode of action, applications, molecular biology, and epidemiology of bacterial resistance. Microbiol Mol Biol Rev. 2001 Jun;65(2):232-60 ; second page, table of contents. [Article]
- Chukwudi CU: rRNA Binding Sites and the Molecular Mechanism of Action of the Tetracyclines. Antimicrob Agents Chemother. 2016 Jul 22;60(8):4433-41. doi: 10.1128/AAC.00594-16. Print 2016 Aug. [Article]
- Vojtova V, Urbanek K: [Pharmacokinetics of tetracyclines and glycylcyclines]. Klin Mikrobiol Infekc Lek. 2009 Feb;15(1):17-21. [Article]
- EMC: Tetralysal 300mg Hard Capsules [Link]
- New Zealand data sheet: Tetralysal (lymecycline) oral capsules [Link]
- ClearSynth: Lymecycline MSDS [Link]
- External Links
- Human Metabolome Database
- HMDB0014401
- KEGG Drug
- D06884
- PubChem Compound
- 54707177
- PubChem Substance
- 46505518
- ChemSpider
- 20121315
- 6513
- ChEBI
- 59040
- ChEMBL
- CHEMBL2103929
- ZINC
- ZINC000053682936
- Therapeutic Targets Database
- DAP000881
- PharmGKB
- PA164747190
- Wikipedia
- Lymecycline
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data4 Unknown Status Treatment Cervicitis / Chlamydia Trachomatis / Genital Mycoplasma Infection / Urethritis 1 somestatus stop reason just information to hide 4 Unknown Status Treatment Mild to Moderate Acne 1 somestatus stop reason just information to hide 3 Completed Treatment Acne Vulgaris 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Lederle laboratories div american cyanamid co
- Packagers
- Galderma Laboratories
- Proter SPA
- Dosage Forms
Form Route Strength Capsule Oral 150.00 mg Capsule Oral Capsule Oral 150 MG Injection Intramuscular 100 MG Capsule, coated Oral 300 mg Capsule, coated Oral 30000000 mg Capsule Oral 300.000 mg Capsule Oral 300 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 192.5 https://m.chemicalbook.com/ProductChemicalPropertiesCB2891297_EN.htm boiling point (°C) 928.1±65.0 http://www.chemspider.com/Chemical-Structure.20121315.html logP -1.70 http://www.chemspider.com/Chemical-Structure.20121315.html pKa 2.50±0.24 https://m.chemicalbook.com/ProductChemicalPropertiesCB2891297_EN.htm - Predicted Properties
Property Value Source Water Solubility 1.31 mg/mL ALOGPS logP -0.27 ALOGPS logP -7.1 Chemaxon logS -2.7 ALOGPS pKa (Strongest Acidic) 2.51 Chemaxon pKa (Strongest Basic) 9.77 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 13 Chemaxon Hydrogen Donor Count 9 Chemaxon Polar Surface Area 242.98 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 154.51 m3·mol-1 Chemaxon Polarizability 62.48 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.7376 Blood Brain Barrier - 0.9893 Caco-2 permeable - 0.6208 P-glycoprotein substrate Substrate 0.9292 P-glycoprotein inhibitor I Non-inhibitor 0.9211 P-glycoprotein inhibitor II Non-inhibitor 0.6582 Renal organic cation transporter Non-inhibitor 0.8738 CYP450 2C9 substrate Non-substrate 0.7747 CYP450 2D6 substrate Non-substrate 0.8136 CYP450 3A4 substrate Substrate 0.6766 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9123 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8593 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9265 Ames test Non AMES toxic 0.6718 Carcinogenicity Non-carcinogens 0.9182 Biodegradation Not ready biodegradable 0.8673 Rat acute toxicity 2.5422 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9699 hERG inhibition (predictor II) Inhibitor 0.5732
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 263.3754598 predictedDarkChem Lite v0.1.0 [M-H]- 227.81355 predictedDeepCCS 1.0 (2019) [M+H]+ 265.0168598 predictedDarkChem Lite v0.1.0 [M+H]+ 229.9655 predictedDeepCCS 1.0 (2019) [M+Na]+ 264.7337598 predictedDarkChem Lite v0.1.0 [M+Na]+ 236.04247 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- Curator comments
- A representative organism has been selected for this target. Lymecycline inhibits the 30S ribosomal subunit of various bacteria.
- General Function
- Translation repressor activity, nucleic acid binding
- Specific Function
- One of two assembly initiator proteins for the 30S subunit, it binds directly to 16S rRNA where it nucleates assembly of the body of the 30S subunit.With S5 and S12 plays an important role in trans...
- Gene Name
- rpsD
- Uniprot ID
- P0A7V8
- Uniprot Name
- 30S ribosomal protein S4
- Molecular Weight
- 23468.915 Da
References
- Chopra I, Roberts M: Tetracycline antibiotics: mode of action, applications, molecular biology, and epidemiology of bacterial resistance. Microbiol Mol Biol Rev. 2001 Jun;65(2):232-60 ; second page, table of contents. [Article]
- Chukwudi CU: rRNA Binding Sites and the Molecular Mechanism of Action of the Tetracyclines. Antimicrob Agents Chemother. 2016 Jul 22;60(8):4433-41. doi: 10.1128/AAC.00594-16. Print 2016 Aug. [Article]
- New Zealand data sheet: Tetralysal (lymecycline) oral capsules [Link]
Drug created at June 13, 2005 13:24 / Updated at August 02, 2024 07:24