Page last updated: 2024-11-12

lymecycline

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

Lymecycline: A semisynthetic antibiotic related to TETRACYCLINE. It is more readily absorbed than TETRACYCLINE and can be used in lower doses. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

lymecycline : A tetracycline-based broad-spectrum antibiotic. It is approximately 5000 times more soluble than tetracycline base and is unique amongst tetracyclines in that it is absorbed by the "active transport" process across the intestinal wall. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID54707177
CHEMBL ID2103929
CHEBI ID59040
SCHEMBL ID149162
SCHEMBL ID23248015
MeSH IDM0012776

Synonyms (62)

Synonym
n(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]carbonyl}amino)methyl]-l-lysine
n(2)-(((+)-5-amino-5-carboxypentylamino)methyl)tetracycline
limeciclina
CHEBI:59040 ,
lymecyclinum
unii-7d6em3s13p
7d6em3s13p ,
2-naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, lysinemethylene deriv.
l-lysine, n6-(((((4s,4as,5as,6s,12as)-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenyl)carbonyl)amino)methyl)-
armyl
vebicyclysal
infaciclina
ciclisin
einecs 213-592-2
limeciclina [inn-spanish]
n(sup 2)-(((+)-5-amino-5-carboxypentylamino)methyl)tetracycline
tetraciclina-l-metilenlisina [italian]
mucomycin
tetralisal
lymecycline [inn:ban]
tetracycline, lysinomethyl-
lisinbiotic
lysine, n(sup 6)-((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)-, (+)-
lymecyclinum [inn-latin]
ciclolysal
l-lysine, n6-((((4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenyl)carbonyl)amino)methyl)-, (4s-(4alpha,4aalpha,6beta,12aalpha))-
tetralysal
992-21-2
lymecycline
tetracycline-l-methylene lysine
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
DB00256
(+)-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
tetracycline-l-methylenelysine
n-lysinomethyltetracycline
n2-(((+)-5-amino-5-carboxypentylamino)methyl)tetracycline
D06884
lymecycline (inn)
tetraciclina-l-metilenlisina
ciclolysine
tetracyclinemethylenelysine
CHEMBL2103929
AKOS016340328
lymecycline [who-dd]
lymecycline [mart.]
lymecycline [inn]
lymecycline [ep monograph]
lymecycline [mi]
AHEVKYYGXVEWNO-UEPZRUIBSA-N
SCHEMBL149162
KS-1366
l-lysine,n6-[[[[(4s,4as,5as,6s,12as)-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenyl]carbonyl]amino]methyl]-
Q897051
tetracycline-l methylene-lysine
(2s)-6-[[[(4s,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carbonyl]amino]methylamino]-2-aminohexanoic acid
gtpl10912
SCHEMBL23248015
lymecycline (85%)
(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
EN300-19790903
HY-106339
CS-0025613

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Clinical and microbiological evaluations were performed and adverse effects monitored at check-ups after 15-35 and 40-65 days."( Efficacy and safety of azithromycin versus lymecyline in the treatment of genital chlamydial infections in women.
Brihmer, C; Kallings, I; Mårdh, PA; Osser, S; Röbech, M; Sikström, B; Wanger, L, 1996
)
0.29
"1% of minocycline recipients experienced treatment-related adverse events, the majority of which were mild in nature."( A comparison of the efficacy and safety of lymecycline and minocycline in patients with moderately severe acne vulgaris.
Alirezai, M; Belaïch, S; Grosshans, E; Meynadier, J; Thomas, L,
)
0.13
" Reduction in inflammatory lesion counts at week 12 was the primary efficacy variable (global improvement was a primary efficacy parameter vs placebo) and safety was assessed by adverse events."( The use of lymecycline in the treatment of moderate to severe acne vulgaris: a comparison of the efficacy and safety of two dosing regimens.
Alirezai, M; Dubertret, L; Forsea, D; Horvath, A; Lahfa, M; Mizzi, F; Niculae, BD; Rostain, G; Simola, M,
)
0.13
"9%) patients receiving minocycline suffered 55 adverse events (22 of them gastrointestinal), while 28 (33."( Safety and efficacy comparison of minocycline microgranules vs lymecycline in the treatment of mild to moderate acne: randomized, evaluator-blinded, parallel, and prospective clinical trial for 8 weeks.
Berber, A; de la Fuente-Garcia, A; Ocampo-Candiani, J; Trevino-Gomezharper, C; Velazquez-Arenas, LL, 2014
)
0.4

Bioavailability

ExcerptReferenceRelevance
"The relative bioavailability of lymecycline and tetracycline hydrochloride was compared in 12 healthy volunteers in a double-blind cross-over study using a high performance liquid chromatographic method for plasma and urine analyses."( Comparative bioavailability of tetracycline and lymecycline.
Hermansson, J; Sjölin-Forsberg, G, 1984
)
0.27
"The dissimilar bioavailability and antimicrobial efficacy between the two bacteriostatic agents may impart different clinical efficacy."( A pilot study on bacterial viability in acne. Assessment using dual flow cytometry on microbials present in follicular casts and comedones.
Arrese, JE; Avila-Camacho, M; Goffin, V; Greimers, R; Piérard, GE, 1998
)
0.3

Dosage Studied

Lymecycline and doxycycline should be regarded as 'intermediate-acting' tetracyclines. Each should consequently be dosed twice daily.

ExcerptRelevanceReference
" It is concluded that doxycycline is the most potent photosensitizer at the dosage tested."( Double blind cross-over studies on phototoxicity to three tetracycline derivatives in human volunteers.
Bjellerup, M; Ljunggren, B, 1987
)
0.27
" According to our results, both lymecycline and doxycycline should be regarded as 'intermediate-acting' tetracyclines, and each should consequently be dosed twice daily."( Pharmacokinetics of lymecycline and doxycycline in serum and suction blister fluid.
Digranes, A; Schreiner, A, 1985
)
0.27
" The relative bioavailability of lymecycline was only 70% compared with tetracycline in multiple dosing (19."( Comparative bioavailability of tetracycline and lymecycline.
Hermansson, J; Sjölin-Forsberg, G, 1984
)
0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Pathways (1)

PathwayProteinsCompounds
Lymecycline Action Pathway14

Bioassays (20)

Assay IDTitleYearJournalArticle
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1871982Antimycobacterial activity against Mycobacterium tuberculosis2022European journal of medicinal chemistry, Feb-05, Volume: 229Tuberculosis drug discovery: Progression and future interventions in the wake of emerging resistance.
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (119)

TimeframeStudies, This Drug (%)All Drugs %
pre-199076 (63.87)18.7374
1990's15 (12.61)18.2507
2000's4 (3.36)29.6817
2010's15 (12.61)24.3611
2020's9 (7.56)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials30 (22.56%)5.53%
Reviews5 (3.76%)6.00%
Case Studies15 (11.28%)4.05%
Observational0 (0.00%)0.25%
Other83 (62.41%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (3)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Efficacy and Safety Comparison of Epiduo Gel Associated With Lymecycline 300 mg Capsules Versus Epiduo Vehicle Gel Associated With Lymecycline 300 mg Capsules in the Treatment of Moderate to Severe Acne Vulgaris [NCT01014689]Phase 3378 participants (Actual)Interventional2009-08-31Completed
Safety and Efficacy Comparison of Minocycline Microgranules vs Lymecycline in the Treatment of Mild to Moderate Acne. Randomized, Double Blind, Parallel and Prospective Clinical Trial for 8 Weeks [NCT00988026]Phase 4168 participants (Anticipated)Interventional2009-06-30Recruiting
Study of Time to Eradication of Mycoplasma Genitalium and Chlamydia Trachomatis After Antibiotic Treatment [NCT01661985]Phase 4160 participants (Anticipated)Interventional2010-02-28Recruiting
[information is prepared from clinicaltrials.gov, extracted Sep-2024]

Trial Outcomes

TrialOutcome
NCT01014689 (2) [back to overview]Percent Change From Baseline in Total Lesion Count
NCT01014689 (2) [back to overview]Success Rate on the Investigator's Global Assessment (IGA) at Week 12

Percent Change From Baseline in Total Lesion Count

Percent change from Baseline in Total Lesion count (sum of Non-Inflammatory and Inflammatory lesions) at Week 12. (NCT01014689)
Timeframe: Baseline and Week 12

Interventionpercent of change (Median)
Adapalene 0.1% / BPO 2.5% Gel + Lymecycline-74.1
Adapalene 0.1% / BPO 2.5% Vehicle Gel + Lymecycline-56.8

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Success Rate on the Investigator's Global Assessment (IGA) at Week 12

"Percentage of Subjects Clear or Almost Clear on 6-point IGA scale(0=clear, 1=almost clear, 2=mild, 3=moderate, 4=severe and 5=very severe) at Week 12." (NCT01014689)
Timeframe: Baseline and Week 12

Interventionpercent of subjects (Number)
Adapalene 0.1% / BPO 2.5% Gel + Lymecycline47.6
Adapalene 0.1% / BPO 2.5% Vehicle Gel + Lymecycline33.7

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