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Substance Name: Lymecycline [INN:BAN]
RN: 992-21-2
UNII: 7D6EM3S13P
InChIKey: AHEVKYYGXVEWNO-UEPZRUIBSA-N

Note

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

Molecular Formula

  • C29-H38-N4-O10

Molecular Weight

  • 602.6372
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Drug / Therapeutic Agent
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Names and Synonyms

Name of Substance

  • Lymecycline
  • Lymecycline [INN:BAN]

MeSH Heading

  • Lymecycline

Synonyms

  • 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.
  • Armyl
  • Ciclisin
  • Ciclolysal
  • EINECS 213-592-2
  • Infaciclina
  • Limeciclina
  • Limeciclina [INN-Spanish]
  • Lisinbiotic
  • Lymecycline
  • Lymecyclinum
  • Lymecyclinum [INN-Latin]
  • Mucomycin
  • N(sup 2)-(((+)-5-Amino-5-carboxypentylamino)methyl)tetracycline
  • N-Lysinomethyltetracycline
  • 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
  • Tetraciclina-L-metilenlisina
  • Tetraciclina-L-metilenlisina [Italian]
  • Tetracycline, lysinomethyl-
  • Tetracycline-L-methylene lysine
  • Tetracycline-L-methylenelysine
  • Tetralisal
  • Tetralysal
  • UNII-7D6EM3S13P
  • Vebicyclysal

Systematic Names

  • (+)-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
  • 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)-
  • 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))-
  • Lymecycline
  • 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)-, (+)-

Registry Numbers

CAS Registry Number

  • 992-21-2

FDA UNII

  • 7D6EM3S13P

Other Registry Numbers

  • 15302-19-9
  • 31041-50-6
  • 8059-91-4

System Generated Number

  • 0000992212

Structure Descriptors

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

InChIKey

AHEVKYYGXVEWNO-UEPZRUIBSA-N

Smiles

CN(C)[C@H]1[C@@H]2C[C@H]3C(=C(O)[C@]2(O)C(=O)C(=C1O)C(=O)NCNCCCC[C@H](N)C(=O)O)C(=O)c4c(O)cccc4[C@@]3(C)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LD50 unreported 253mg/kg (253mg/kg)   British Medical Journal. Vol. 2, Pg. 106, 1964.
mouse LD50 intravenous 181mg/kg (181mg/kg)   Research Progress in Organic-Biological and Medicinal Chemistry. Vol. 2, Pg. 333, 1970.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -3.220 (none)   EST
Atmospheric OH Rate Constant 4.11E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.