CAS 992-21-2

Lymecycline

Description:

Lymecycline is a semi-synthetic antibiotic belonging to the tetracycline class, primarily used to treat various bacterial infections. It exhibits broad-spectrum antibacterial activity against both Gram-positive and Gram-negative bacteria by inhibiting protein synthesis through binding to the 30S ribosomal subunit. This action prevents the growth and reproduction of bacteria. Lymecycline is characterized by its stability in acidic environments, which enhances its bioavailability when administered orally. It is often prescribed for conditions such as acne, respiratory tract infections, and certain skin infections. The compound is generally well-tolerated, although it may cause side effects such as gastrointestinal disturbances, photosensitivity, and potential effects on bone and teeth development in children. As with other tetracyclines, it is contraindicated in pregnant women and young children due to the risk of tooth discoloration and skeletal effects. Lymecycline's pharmacokinetics involve absorption in the gastrointestinal tract, with distribution to various tissues, and it is primarily excreted through the kidneys.

Formula: C₂₉H₃₈N₄O₁₀

InChI: InChI=1/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)32-12-31-16(27(40)41)8-4-5-10-30/h6-7,9,14-16,21,31-32,34-35,39,42-43H,4-5,8,10-12,30H2,1-3H3,(H,40,41)/b26-20+/t14?,15-,16?,21-,28+,29-/m0/s1

InChI key: InChIKey=AHEVKYYGXVEWNO-UEPZRUIBSA-N

SMILES: O[C@@]12[C@@](C[C@]3(C(=C1O)C(=O)C=4C([C@@]3(C)O)=CC=CC4O)[H])([C@H](N(C)C)C(O)=C(C(NCNCCCC[C@@H](C(O)=O)N)=O)C2=O)[H]

Synonyms:

• (+)-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
• 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.
• <span class="text-smallcaps">L</span>-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]-
• <span class="text-smallcaps">L</span>-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-(4α,4aα,5aα,6β,12aα)]-
• Armyl
• Ciclisin
• Ciclolysal
• Ciclolysine
• Infaciclina
• 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-(4α,4aα,5aα,6β,12aα)]-
• Limeciclina
• Lisinbiotic
• Lisinciclina
• Lymecyclin
• Lymecycline
• 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, 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]-, 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-naphthacenecarboxamido]methyl]-
• 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]-, <span class="text-smallcaps">L</span>-
• Mucomycin
• N-Lysinomethyltetracycline
• N2-[[(+)-5-Amino-5-carboxypentylamino]methyl]tetracycline
• 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
• N6-[[[[4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-oxtahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenyl]carbonyl]amino]methyl]-L-lysine
• N²-[[(+)-5-Amino-5-carboxypentylamino]methyl]tetracycline
• 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
• 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]-<span class="text-smallcaps">L</span>-lysine
• Tertamyl
• Tetracycline-<span class="text-smallcaps">L</span>-methylenelysine
• Tetracycline-L-methylenelysine
• Tetracyclinemethylenelysine
• Tetralisal
• Tetralysal
• Tetramyl
• Vebicyclysal
• 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]-
• N~2~-({[(Z)-[(4aS,6S,12aS)-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-6-methyl-1,3,12-trioxo-3,4,4a,5,5a,6,12,12a-octahydrotetracen-2(1H)-ylidene](hydroxy)methyl]amino}methyl)lysine
• (2Z,4S,4aS,5aS,6S,12aS)-2-[amino(hydroxy)methylidene]-7-chloro-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-6-methyl-4a,5a,6,12a-tetrahydrotetracene-1,3,12(2H,4H,5H)-trione
• N~2~-({[(E)-[(4S,4aS,6S,12aS)-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-6-methyl-1,3,12-trioxo-3,4,4a,5,5a,6,12,12a-octahydrotetracen-2(1H)-ylidene](hydroxy)methyl]amino}methyl)lysine
• N-(N2-lysinomethyl)tetracycline
• 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
• lymecycline USP/EP/BP
• Lymecycline (85%)
• N6-[[(4S)-4β-(Dimethylamino)-1,4,4aβ,5,5aβ,6,11,12a-octahydro-3,6α,10,12,12aβ-pentahydroxy-6-methyl-1,11-dioxonaphthacen-2-yl]carbonylaminomethyl]-L-lysine
• Tetracyclinemethylene lysine

Lymecycline

CAS: 992-21-2

Lymecycline

Formula: C₂₂H₂₃ClN₂O₈

Color and Shape: Dark Yellow

Molecular weight: 478.8796

Ref: 47-218

Lymecycline

CAS: 992-21-2

Lymecycline is a semisynthetic antibiotic. It is related to TETRACYCLINE.

Formula: C₂₉H₃₈N₄O₁₀

Color and Shape: Solid

Molecular weight: 602.64

Ref: TM-T20164

Lymecycline

CAS: 992-21-2

Formula: C₂₉H₃₈N₄O₁₀

Molecular weight: 602.64

Ref: 4Z-L-237001

Lymecycline-d8 (>80%)

Controlled Product

CAS: 992-21-2

Stability Light Sensitive, Temperature Sensitive
Applications Labelled Lymecycline. A semi-synthetic antibiotic related to Tetracycline (T291400). Antibacterial.
References Andrews, C., et al.: Pharm. Res., 17, 639 (2000), Votano, J., et al.: J. Med. Chem., 49, 7169 (2006), Davis, A., et al.: Curr. Opin. Chem. Biol., 8, 378 (2004),

Formula: C₂₉H₃₀D₈N₄O₁₀

Purity: >80%

Color and Shape: Neat

Molecular weight: 610.68

Ref: TR-L487802

Lymecycline (85%)

CAS: 992-21-2

Stability Temperature sensitive
Applications A semi-synthetic antibiotic related to Tetracycline (T291400). Antibacterial.
References Andrews, C., et al.: Pharm. Res., 17, 639 (2000), Votano, J., et al.: J. Med. Chem., 49, 7169 (2006), Davis, A., et al.: Curr. Opin. Chem. Biol., 8, 378 (2004),

Formula: C₂₉H₃₈N₄O₁₀

Purity: 85%

Color and Shape: Yellow To Dark Brown

Molecular weight: 602.63

Ref: TR-L487800

Lymecycline

CAS: 992-21-2

Lymecycline is a tetracycline antibiotic that has been shown to be effective in the treatment of inflammatory bowel disease, chronic arthritis, and experimental models of inflammatory reactions. Lymecycline inhibits epidermal growth factor (EGF) and its receptor EGF-R. This inhibition leads to reduced inflammation in the bowel. Lymecycline also has an anti-inflammatory effect on the skin, inhibiting reactive oxygen species (ROS) production from neutrophils and macrophages. It also reduces the symptoms of toxic epidermal necrolysis by preventing ROS production and reducing cytokines such as TNF-α and IL-1β. Lymecycline binds to magnesium ions, which are necessary for bacterial growth and replication. This binding leads to bacteriostatic activity against bacteria that are sensitive to lymecycline, including Mycobacterium tuberculosis and other infectious diseases. The histological

Formula: C₂₉H₃₈N₄O₁₀

Purity: Min. 85 Area-%

Color and Shape: Powder

Molecular weight: 602.63 g/mol

Ref: 3D-FL164019

Lymecycline

CAS: 992-21-2

Formula: C₂₉H₃₈N₄O₁₀

Molecular weight: 602.64

Ref: 4Z-T-405

Lymecycline-d8

CAS: 992-21-2

Formula: C₂₉H₃₀D₈N₄O₁₀

Molecular weight: 610.69

Ref: 4Z-T-406