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Lymecycline

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Also known as: Tetralysal, N-lysinomethyltetracycline, Limeciclina, Lymecyclinum, Tetracycline-l-methylenelysine, Ciclolysal

Molecular Formula

C₂₉H₃₈N₄O₁₀

Molecular Weight

602.6 g/mol

InChI Key

PZTCVADFMACKLU-UEPZRUIBSA-N

FDA UNII

7D6EM3S13P

A semisynthetic antibiotic related to TETRACYCLINE. It is more readily absorbed than TETRACYCLINE and can be used in lower doses.

1 2D Structure

Lymecycline

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(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

2.1.2 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

2.1.3 InChI Key

PZTCVADFMACKLU-UEPZRUIBSA-N

2.1.4 Canonical SMILES

CC1(C2CC3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)NCNCCCCC(C(=O)O)N)N(C)C)O

2.1.5 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

2.2 Other Identifiers

2.2.1 UNII

7D6EM3S13P

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Hydrochloride, Lymecycline

2. Lymecycline Hydrochloride

3. Lysine, Tetracycline-l-methylene

4. Lysine, Tetracyclinemethylene

5. N Lysinomethyltetracycline

6. N-lysinomethyltetracycline

7. Tetracycline L Methylene Lysine

8. Tetracycline-l-methylene Lysine

9. Tetracyclinemethylene Lysine

2.3.2 Depositor-Supplied Synonyms

1. Tetralysal

2. N-lysinomethyltetracycline

3. Limeciclina

4. Lymecyclinum

5. Tetracycline-l-methylenelysine

6. Ciclolysal

7. Mucomycin

8. 992-21-2

9. Tetracycline-l-methylene Lysine

10. Ciclolysine

11. Tetracyclinemethylenelysine

12. Lymecycline (inn)

13. (+)-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

14. Tetralisal

15. 7d6em3s13p

16. 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

17. Chebi:59040

18. N(2)-(((+)-5-amino-5-carboxypentylamino)methyl)tetracycline

19. Lymecycline [inn]

20. 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]-

21. 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

22. Infaciclina

23. Lisinbiotic

24. Vebicyclysal

25. Ciclisin

26. Armyl

27. Tetraciclina-l-metilenlisina

28. (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

29. Lymecycline [inn:ban]

30. Lymecyclinum [inn-latin]

31. Limeciclina [inn-spanish]

32. Tetracycline, Lysinomethyl-

33. Unii-7d6em3s13p

34. Einecs 213-592-2

35. Tetraciclina-l-metilenlisina [italian]

36. Lymecycline (85%)

37. Lymecycline [mi]

38. Lymecycline [mart.]

39. Lymecycline [who-dd]

40. Schembl149162

41. Tetracycline-l Methylene-lysine

42. Chembl2103929

43. Schembl23248015

44. Gtpl10912

45. Lymecycline [ep Monograph]

46. N(sup 2)-(((+)-5-amino-5-carboxypentylamino)methyl)tetracycline

47. Zinc53682936

48. Akos016340328

49. Db00256

50. Ks-1366

51. 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.

52. D06884

53. Q897051

54. N2-(((+)-5-amino-5-carboxypentylamino)methyl)tetracycline

55. 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)-

56. 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))-

57. 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)-, (+)-

2.4 Create Date

2011-12-26

3 Chemical and Physical Properties

Molecular Formula	C₂₉H₃₈N₄O₁₀
Molecular Weight	602.6 g/mol
XLogP3	-4.4
Hydrogen Bond Donor Count	9
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	10
Exact Mass	602.25879342 g/mol
Monoisotopic Mass	602.25879342 g/mol
Topological Polar Surface Area	243 Å²
Heavy Atom Count	43
Formal Charge	0
Complexity	1230
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Lymecycline is used for the treatment of acne in addition to other susceptible infections; propionibacterium is often the cause of acne. Some of the infections that can be treated with lymecycline include upper respiratory tract infections, urinary tract infections, bronchitis, chlamydial infections, and rickettsial infections.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Lymecycline, like other tetracyclines, exerts bacteriostatic actions on intracellular and extracellular bacteria, treating susceptible bacterial infections. It has been shown to be safe and effective in the treatment of moderate to severe acne. 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.

5.2 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

5.3 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01A - Tetracyclines

J01AA - Tetracyclines

J01AA04 - Lymecycline

5.4 Absorption, Distribution and Excretion

Absorption

Lymecycline is 77-88% absorbed after oral administration with a relative bioavailability of 70%. The Cmax of lymecycline is 2.1 mg/L and is achieved about 3 hours after administration. The AUC is 21.9 4.3 mgh/L.

Route of Elimination

Lymecycline is 25% eliminated in the urine. Based on being a member of the tetracycline drug class, fecal elimination is likely another route of elimination.

Volume of Distribution

Lymecycline is lipophilic and easily crosses the cell membrane and passively diffuses through bacterial porin channels. As a second-generation tetracycline, the concentration in the bile ranges from 10 to 25 times higher than plasma concentration. In general, the volume of distribution of tetracyclines ranges from 1.31.7 L/kg or 100130 L.

Clearance

Lymecycline is partially cleared by the kidneys, like other tetracyclines.

5.5 Biological Half-Life

The half-life of lymecycline is approximately 8 hours.

5.6 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. This results in bacteriostatic actions, treating various infections.