From August 18th 2026, GtoPdb will require users to register to use the website. Please see our blog post for more information.

lymecycline   Click here for help

GtoPdb Ligand ID: 10912

Synonyms: N-Lysinomethyltetracycline | tetracycline-L Methylene-Lysine | Tetralysal®
Approved drug
lymecycline is an approved drug (UK (1995))
Compound class: Synthetic organic
Comment: Lymecycline is a tetracycline-based broad-spectrum antibacterial [3]. It is substantially more soluble than tetracycline, so can be used at lower doses. Lymecycline also has anti-protozoal activity.

lymecycline is commercially available from our sponsors

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 13
Hydrogen bond donors 9
Rotatable bonds 11
Topological polar surface area 242.98
Molecular weight 602.26
XLogP -1.85
No. Lipinski's rules broken 2

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
Canonical SMILES N[C@H](C(=O)O)CCCCNCNC(=O)C1=C(O)[C@@]2([C@H]([C@@H](C1=O)N(C)C)C[C@H]1C(=C(O)c3c([C@@]1(C)O)cccc3O)C2=O)O
Isomeric SMILES N[C@H](C(=O)O)CCCCNCNC(=O)C1=C(O)[C@@]2([C@H]([C@@H](C1=O)N(C)C)C[C@H]1C(=C(O)c3c([C@@]1(C)O)cccc3O)C2=O)O
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/h6-7,9,14-16,21,31,34-35,38,42-43H,4-5,8,10-12,30H2,1-3H3,(H,32,39)(H,40,41)/t14-,15-,16-,21-,28+,29-/m0/s1
InChI Key PZTCVADFMACKLU-UEPZRUIBSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Dréno B, Kaufmann R, Talarico S, Torres Lozada V, Rodríguez-Castellanos MA, Gómez-Flores M, De Maubeuge J, Berg M, Foley P, Sysa-Jedrzejowska A et al.. (2011)
Combination therapy with adapalene-benzoyl peroxide and oral lymecycline in the treatment of moderate to severe acne vulgaris: a multicentre, randomized, double-blind controlled study.
Br J Dermatol, 165 (2): 383-90. [PMID:21495995]
2. Dubertret L, Alirezai M, Rostain G, Lahfa M, Forsea D, Niculae BD, Simola M, Horvath A, Mizzi F. (2003)
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, 13 (1): 44-8. [PMID:12609781]
3. STRATFORD BC. (1965)
LYMECYCLINE.
Br Med J, 1 (5439): 922. [PMID:14257415]