CAS 914-00-1

Methacycline

Description:

Methacycline is a semi-synthetic antibiotic belonging to the tetracycline class, characterized by its broad-spectrum antibacterial activity. It is primarily effective against a variety of Gram-positive and Gram-negative bacteria, as well as certain protozoa. Methacycline is known for its ability to inhibit bacterial protein synthesis by binding to the 30S ribosomal subunit, thereby preventing the translation of mRNA. This compound is typically administered orally and is utilized in the treatment of various infections, including respiratory tract infections and skin infections. Methacycline exhibits a relatively stable structure, which allows it to maintain efficacy in the presence of certain bacterial resistance mechanisms. Additionally, it has a moderate solubility in water and is often formulated in various dosage forms for clinical use. As with other tetracyclines, it may cause side effects such as gastrointestinal disturbances and photosensitivity. Due to its potential for resistance development, careful consideration is necessary when prescribing methacycline, and it is often used in conjunction with other therapeutic agents.

Formula: C₂₂H₂₂N₂O₈

InChI: InChI=1/C22H22N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-6,10,14-15,17,25-27,31-32H,1,23H2,2-3H3/b21-13+/t10-,14-,15+,17+,22+/m1/s1

InChI key: InChIKey=MHIGBKBJSQVXNH-IWVLMIASSA-N

SMILES: O[C@]12[C@]([C@H](N(C)C)C(O)=C(C(N)=O)C1=O)([C@@H](O)[C@]3(C(=C2O)C(=O)C=4C(C3=C)=CC=CC4O)[H])[H]

Synonyms:

• (4S,4aR,5S,5aR,12aS)-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-2-naphthacenecarboxamide
• 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-
• 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-, [4S-(4α,4aα,5α,5aα,12aα)]-
• 4-Dimethylamino-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-2-naphthacenecarboxamide
• 6-Demethyl-6-deoxy-5-hydroxy-6-methylenetetracycline
• 6-Deoxy-6-methylene-6-demethyl-5-hydroxytetracycline
• 6-Methylene-5-hydroxy-tetracycline
• 6-Methylene-5-hydroxytetracycline
• 6-Methyleneoxytetracycline
• Bialatan
• Gs 2876
• Metaciclina
• Metacyclin
• Metacycline
• Methacycline
• Oxytetracycline, 6-methylene-
• Rondomycin
• Tri-methacycline
• 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-, (4S,4aR,5S,5aR,12aS)-
• (2Z,4S,4aR,5S,5aR,12aS)-2-[amino(hydroxy)methylidene]-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methylidene-4a,5a,6,12a-tetrahydrotetracene-1,3,12(2H,4H,5H)-trione
• (2E,4S,4aR,5S,5aR,12aS)-2-[amino(hydroxy)methylidene]-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methylidene-4a,5a,6,12a-tetrahydrotetracene-1,3,12(2H,4H,5H)-trione
• ,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-
• 6-Methyleneoxytetracycline, Metacycline, RondoMycin
• Doxycycline Impurity 2(Doxycycline EP Impurity B)
• 12aalpha))-ph
• 6-methylene-oxytetracyclin
• 10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-,(4s-(4alpha,4aalpha,5alpha,5aal
• methacyclinebase
• 6-deoxy-6-demethyl-6-methylene-5-oxytetracycline
• 6-methylene-5-oxytetracycline
• methacyclineamphoteric
• METHACYCLINE USP/EP/BP

(4S,4aR,5S,5aR,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methylidene-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

CAS: 914-00-1

Formula: C₂₂H₂₂N₂O₈

Purity: 90%

Color and Shape: Solid

Molecular weight: 442.4187

Ref: IN-DA01DN9X

Doxycycline EP Impurity B

CAS: 914-00-1

Formula: C₂₂H₂₂N₂O₈

Molecular weight: 442.42

Ref: 4Z-D-1812

Methacycline

CAS: 914-00-1

Impurity Doxycycline EP Impurity B
Applications Methacycline is a tetracycline with broad range antibacterial and antiprotozoal properties. Potential veterinary drug.
References Li, J. et al: J. Sep. Sci., 41, 4115 (2018); Tejada-Casado, C. et al.: Anal. Chim. Act, 1043 (52 (2018);

Formula: C₂₂H₂₂N₂O₈

Color and Shape: Off-White

Molecular weight: 442.42

Ref: TR-M258788

Methacycline

CAS: 914-00-1

Methacycline, a tetracycline antibiotic, inhibits bacterial protein synthesis and effectively suppresses epithelial-mesenchymal transition (EMT). It blocks EMT in vitro and inhibits fibrogenesis in vivo without directly affecting the TGF-β1Smad signaling pathway. As an antimicrobial agent, Methacycline holds potential for research in pulmonary fibrosis.

Formula: C₂₂H₂₂N₂O₈

Color and Shape: Solid

Molecular weight: 442.42

Ref: TM-T201726