U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C29H38N4O10
Molecular Weight 602.6328
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LYMECYCLINE

SMILES

[H][C@@]12C[C@@]3([H])C(C(=O)C4=C(C=CC=C4O)[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

InChI

InChIKey=AHEVKYYGXVEWNO-UEPZRUIBSA-N
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

HIDE SMILES / InChI

Molecular Formula C29H38N4O10
Molecular Weight 602.6328
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.drugs.com/international/lymecycline.html | https://www.medicines.org.uk/emc/medicine/702 | https://clinicaltrials.gov/ct2/show/NCT00988026 | https://clinicaltrials.gov/ct2/show/NCT01661985 | https://www.ncbi.nlm.nih.gov/pubmed/28275291 | https://www.ncbi.nlm.nih.gov/pubmed/14257415

Lymecycline is a tetracycline broad-spectrum antibiotic marketed by the pharmaceutical company Galderma. 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. Lymecycline's side effects can include rash, headache, diarrhoea, ulcerative colitis, nausea, vomiting, dermatitis, dysphasia, inflammation of the liver, hypersensitive reactions, and visual disturbances. When taken for a long period of time, it can cause reflux oesophagitis.

Originator

Sources: Gazzetta Sanitaria, Volume 32, Pages 662-6, Journal, 1961

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Tetralysal

Approved Use

Unknown
Curative
Tetralysal

Approved Use

Unknown
Primary
Tetralysal

Approved Use

Unknown
Primary
Tetralysal

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Systemic antibiotics for acne.
1998
Patents

Sample Use Guides

The usual dosage for the chronic treatment of acne is 1 capsule (300 mg) daily: treatment should be continued for at least 8 weeks. For other infections, the usual dosage is 1 capsule b.d. If higher doses are required, 3-4 capsules may be given over 24 hours. Lower doses may be given for prophylaxis.
Route of Administration: Oral
In Vitro Use Guide
The concentration of lymecycline in serum, extracts or tissue pieces was determined by using a microbiological assay for tetracycline. A spore suspension of Bacillus cereus ATCC 11778 incorporated in PDM agar, pH 6.6 (AB Biodisk, Stockholm) was used. The analyses of solid tissue pieces (”punch method”) were performed on the same type of plate. They were rinsed for excess of blood in phosphate-buffered saline and gently blotted between filter papers. The tubal tissue was sectioned longitudinally, thus allowing separation of the serosa from the mucosa with its muscular coat. Some 6- 10 pieces of each tissue were punched out using a metal cylinder 5 mm in diameter. The pieces were weighed on a microbalance and pieces weighing 10- 30 mg were chosen for the analyses. These were applied directly on the preseeded agar plates which were left at room temperature, allowing prediffusion from the tissues for 60 min. After 16 hours of incubation at + 30°C the diameter of the inhibition zones was registered with a vernier caliper and curves were plotted on semilogarithmic paper.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:46:37 UTC 2023
Edited
by admin
on Fri Dec 15 15:46:37 UTC 2023
Record UNII
7D6EM3S13P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LYMECYCLINE
EP   INN   MART.   MI   WHO-DD  
INN  
Official Name English
CICLOLYSINE
Common Name English
LYMECYCLINE [MI]
Common Name English
TETRACYCLINE-L-METHYLENELYSINE
Common Name English
(+)-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
Common Name English
CICLOLYSAL
Common Name English
LYMECYCLINE [EP MONOGRAPH]
Common Name English
LYMECYCLINE [MART.]
Common Name English
Lymecycline [WHO-DD]
Common Name English
TETRALYSAL
Brand Name English
TETRACYCLINEMETHYLENELYSINE
Common Name English
lymecycline [INN]
Common Name English
MUCOMYCIN
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C1595
Created by admin on Fri Dec 15 15:46:37 UTC 2023 , Edited by admin on Fri Dec 15 15:46:37 UTC 2023
WHO-ATC J01AA04
Created by admin on Fri Dec 15 15:46:37 UTC 2023 , Edited by admin on Fri Dec 15 15:46:37 UTC 2023
WHO-VATC QJ01AA04
Created by admin on Fri Dec 15 15:46:37 UTC 2023 , Edited by admin on Fri Dec 15 15:46:37 UTC 2023
Code System Code Type Description
MESH
D008194
Created by admin on Fri Dec 15 15:46:37 UTC 2023 , Edited by admin on Fri Dec 15 15:46:37 UTC 2023
PRIMARY
ChEMBL
CHEMBL2103929
Created by admin on Fri Dec 15 15:46:37 UTC 2023 , Edited by admin on Fri Dec 15 15:46:37 UTC 2023
PRIMARY
DRUG CENTRAL
1619
Created by admin on Fri Dec 15 15:46:37 UTC 2023 , Edited by admin on Fri Dec 15 15:46:37 UTC 2023
PRIMARY
FDA UNII
7D6EM3S13P
Created by admin on Fri Dec 15 15:46:37 UTC 2023 , Edited by admin on Fri Dec 15 15:46:37 UTC 2023
PRIMARY
NCI_THESAURUS
C76991
Created by admin on Fri Dec 15 15:46:37 UTC 2023 , Edited by admin on Fri Dec 15 15:46:37 UTC 2023
PRIMARY
CAS
992-21-2
Created by admin on Fri Dec 15 15:46:37 UTC 2023 , Edited by admin on Fri Dec 15 15:46:37 UTC 2023
PRIMARY
EPA CompTox
DTXSID9045344
Created by admin on Fri Dec 15 15:46:37 UTC 2023 , Edited by admin on Fri Dec 15 15:46:37 UTC 2023
PRIMARY
DRUG BANK
DB00256
Created by admin on Fri Dec 15 15:46:37 UTC 2023 , Edited by admin on Fri Dec 15 15:46:37 UTC 2023
PRIMARY
CHEBI
59040
Created by admin on Fri Dec 15 15:46:37 UTC 2023 , Edited by admin on Fri Dec 15 15:46:37 UTC 2023
PRIMARY
INN
1679
Created by admin on Fri Dec 15 15:46:37 UTC 2023 , Edited by admin on Fri Dec 15 15:46:37 UTC 2023
PRIMARY
SMS_ID
100000081734
Created by admin on Fri Dec 15 15:46:37 UTC 2023 , Edited by admin on Fri Dec 15 15:46:37 UTC 2023
PRIMARY
ECHA (EC/EINECS)
213-592-2
Created by admin on Fri Dec 15 15:46:37 UTC 2023 , Edited by admin on Fri Dec 15 15:46:37 UTC 2023
PRIMARY
EVMPD
SUB08625MIG
Created by admin on Fri Dec 15 15:46:37 UTC 2023 , Edited by admin on Fri Dec 15 15:46:37 UTC 2023
PRIMARY
WIKIPEDIA
LYMECYCLINE
Created by admin on Fri Dec 15 15:46:37 UTC 2023 , Edited by admin on Fri Dec 15 15:46:37 UTC 2023
PRIMARY
MERCK INDEX
m6959
Created by admin on Fri Dec 15 15:46:37 UTC 2023 , Edited by admin on Fri Dec 15 15:46:37 UTC 2023
PRIMARY Merck Index
RXCUI
6513
Created by admin on Fri Dec 15 15:46:37 UTC 2023 , Edited by admin on Fri Dec 15 15:46:37 UTC 2023
PRIMARY RxNorm
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
sum of impurities D and G: not more than the area of the corresponding peak in the chromatogram obtained with reference solution (f) (0.5 per cent)
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
sum of impurities D and G: not more than the area of the corresponding peak in the chromatogram obtained with reference solution (f) (0.5 per cent)
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY