CAS 2013-58-3

meclocycline

Description:

Meclocycline is a semi-synthetic antibiotic belonging to the tetracycline class, primarily used for its broad-spectrum antibacterial properties. It is effective against a variety of gram-positive and gram-negative bacteria, as well as certain protozoa. The chemical structure of meclocycline features a naphthacene core, which is characteristic of tetracyclines, and it contains specific functional groups that enhance its antimicrobial activity. Meclocycline works by inhibiting bacterial protein synthesis through binding to the 30S ribosomal subunit, thereby preventing the translation of mRNA. This antibiotic is typically administered orally and is used to treat various infections, including respiratory tract infections, skin infections, and some sexually transmitted diseases. However, like other tetracyclines, meclocycline may cause side effects such as gastrointestinal disturbances, photosensitivity, and potential effects on bone and teeth development in children. It is important to use this antibiotic judiciously to minimize the risk of antibiotic resistance.

Formula: C₂₂H₂₁ClN₂O₈

InChI: InChI=1S/C22H21ClN2O8/c1-6-9-7(23)4-5-8(26)11(9)16(27)12-10(6)17(28)14-15(25(2)3)18(29)13(21(24)32)20(31)22(14,33)19(12)30/h4-5,10,14-15,17,26,28-30,33H,1H2,2-3H3,(H2,24,32)/t10-,14-,15+,17+,22+/m1/s1

InChI key: InChIKey=GGQJXCQBBONZFX-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)=C(Cl)C=CC4O)[H])[H]

Synonyms:

• (2E,4S,4aR,5S,5aR,12aS)-2-[amino(hydroxy)methylidene]-7-chloro-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methylidene-4a,5a,6,12a-tetrahydrotetracene-1,3,12(2H,4H,5H)-trione
• (2E,4aR,5S,5aS,12aS)-2-[amino(hydroxy)methylidene]-7-chloro-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methylidene-4a,5a,6,12a-tetrahydrotetracene-1,3,12(2H,4H,5H)-trione
• (2Z)-2-[amino(hydroxy)methylidene]-7-chloro-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methylidene-4a,5a,6,12a-tetrahydrotetracene-1,3,12(2H,4H,5H)-trione
• (2Z,4S,4aR,5S,5aR,12aS)-2-[amino(hydroxy)methylidene]-7-chloro-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methylidene-4a,5a,6,12a-tetrahydrotetracene-1,3,12(2H,4H,5H)-trione
• (4S,4aR,5S,5aR,12aS)-7-Chloro-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, 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-
• 2-Naphthacenecarboxamide, 7-chloro-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)-
• 2-Naphthacenecarboxamide, 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-, (4S-(4alpha,4aalpha,5alpha,5aalpha,12aalpha))-
• 2-Naphthacenecarboxamide, 7-chloro-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)]-
• 2-hydroxy-5-sulfobenzoic acid - (4S,4aR,5S,5aR,12aS)-7-chloro-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methylidene-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide (1:1)
• 7-Chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-2-naphthacenecarboxamide
• 7-Chloro-6-methylene-5-oxytetracycline
• 7-Cloro-6-metilene-5-ossitetraciclina
• 7-Cloro-6-metilene-5-ossitetraciclina [Italian]
• Gs 2989
• Meclociclina
• Meclociclina [INN-Spanish]
• Meclociclina [Italian]
• Meclocycline [USAN:INN:BAN]
• Meclocyclinum
• Meclocyclinum [INN-Latin]
• Nsc 78502
• Unii-23Q8M2He6S
• Meclocycline
• 7-Chloro-6-Methylene-oxytetracycline, GS 2989, NCS 78502
• GGQJXCQBBONZFX-IWVLMIASSA-N
• MECLOCYLINE
• meclocycline USP/EP/BP
• Meclocycline(usan)
• Meclocycline base
• Chlormethylenecycline
• (4S)-4β-(Dimethylamino)-1,4,4aβ,5,5aβ,6,11,12a-octahydro-3,5β,10,12,12aβ-pentahydroxy-6-methylene-7-chloro-1,11-dioxo-2-naphthacenecarboxamide
• Aids-043973
• Meclocycline (1.0mg/ml in DMSO)
• Aids043973

Meclocycline

Controlled Product

CAS: 2013-58-3

Stability Light Sensitive
Applications Meclocycline is a close structural analogue of methacycline which shows antibacterial and antiprotozoan activity.

Formula: C₂₂H₂₁ClN₂O₈

Color and Shape: Neat

Molecular weight: 476.86

Ref: TR-M202723

Meclocycline

CAS: 2013-58-3

Meclocycline: a tetracycline antibiotic, inhibits LDH, reduces cell toxicity from mutant huntingtin, doesn't change protein levels in PC12 cells.

Formula: C₂₂H₂₁ClN₂O₈

Color and Shape: Solid

Molecular weight: 476.86

Ref: TM-T71903