CAS 751-97-3

Rolitetracycline

Description:

Rolitetracycline is a broad-spectrum antibiotic belonging to the tetracycline class, characterized by its ability to inhibit bacterial protein synthesis. It is derived from the natural product chlortetracycline and exhibits a similar mechanism of action by binding to the 30S ribosomal subunit, thereby preventing the attachment of aminoacyl-tRNA to the ribosome. This antibiotic is effective against a variety of gram-positive and gram-negative bacteria, making it useful in treating various infections. Rolitetracycline is typically administered orally and is known for its relatively good absorption and distribution in the body. Its chemical structure features a naphthacene core with multiple hydroxyl and dimethylamino groups, contributing to its solubility and biological activity. However, like other tetracyclines, it may cause side effects such as gastrointestinal disturbances and photosensitivity. Additionally, its use is limited in certain populations, such as pregnant women and young children, due to potential adverse effects on bone and teeth development. Overall, Rolitetracycline remains an important agent in the arsenal against bacterial infections, particularly in cases where resistance to other antibiotics is a concern.

Formula: C₂₇H₃₃N₃O₈

InChI: InChI=1S/C27H33N3O8/c1-26(37)13-7-6-8-16(31)17(13)21(32)18-14(26)11-15-20(29(2)3)22(33)19(24(35)27(15,38)23(18)34)25(36)28-12-30-9-4-5-10-30/h6-8,14-15,20,31,33-34,37-38H,4-5,9-12H2,1-3H3,(H,28,36)/t14-,15-,20-,26+,27-/m0/s1

InChI key: InChIKey=HMEYVGGHISAPJR-IAHYZSEUSA-N

SMILES: O[C@]12[C@]([C@H](N(C)C)C(O)=C(C(NCN3CCCC3)=O)C1=O)(C[C@]4(C(=C2O)C(=O)C=5C([C@@]4(C)O)=CC=CC5O)[H])[H]

Synonyms:

• (2Z,4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-2-{hydroxy[(pyrrolidin-1-ylmethyl)amino]methylidene}-6-methyl-4a,5a,6,12a-tetrahydrotetracene-1,3,12(2H,4H,5H)-trione
• (2Z,4S,6S,12aS)-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-2-{hydroxy[(pyrrolidin-1-ylmethyl)amino]methylidene}-6-methyl-4a,5a,6,12a-tetrahydrotetracene-1,3,12(2H,4H,5H)-trione
• (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-N-(1-pyrrolidinylmethyl)-2-naphthacenecarboxamide
• (4S,4aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-N-(pyrrolidin-1-ylmethyl)-1,4,4a,5,5a,6,11,12a-octahydrotetracene-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-N-(1-pyrrolidinylmethyl)-
• 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-N-(1-pyrrolidinylmethyl)-, (4S,4aS,5aS,6S,12aS)-
• 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-N-(1-pyrrolidinylmethyl)-, [4S-(4α,4aα,5aα,6β,12aα)]-
• 4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-N-(1-pyrrolidinylmethyl)-2-naphthacenecarboxamide
• 4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-N-(pyrrolidin-1-ylmethyl)-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
• Abricycline
• Bristacin
• N-(1-Pyrrolidinylmethyl)tetracycline
• N-(Pyrrolidinomethyl)tetracycline
• N-(pyrrolidin-1-ylmethyl)tetracycline
• Pyrrolidinylmethyltetracycline
• Reverin
• Rolitetraciclina
• Rolitetracyclin
• Sq 15659
• Superciclin
• Synotodecin
• Syntetrin
• Tetraverin
• Transcycline

Rolitetracycline Trifluoroacetate

CAS: 751-97-3

Formula: C₂₇H₃₃N₃O₈·C₂HF₃O₂

Color and Shape: Yellow Solid

Molecular weight: 527.57 114.02

Ref: 4Z-T-4013

Rolitetracycline

CAS: 751-97-3

Formula: C₂₇H₃₃N₃O₈

Purity: ≥ 98.0%

Color and Shape: Yellow to orange or red solid

Molecular weight: 527.57

Ref: 7W-GA0375

Rolitetracycline (Technical Grade)

Controlled Product

CAS: 751-97-3

Applications Rolitetracycline is a tetracycline antibiotic that may be given intravenously or intramuscularly in serious bacterial infections when oral administration is not practicable.
References Choudhary, S., et al.: Chem. Biol. Drug. Des., 80, 693 (2012); Ejim, L., et al.: Nature. Chem. Biol., 7, 348 (2011); Giorgetti, S., et al.: J. Biol. Chem., 286, 2121 (2011);

Formula: C₂₇H₃₃N₃O₈

Color and Shape: Dark Red To Dark Brown

Molecular weight: 527.57

Ref: TR-R640030

Rolitetracycline

CAS: 751-97-3

Rolitetracycline is a semi-synthetic tetracycline antibiotic, which is derived from the natural compound tetracycline. It functions primarily by inhibiting protein synthesis in susceptible bacteria. This is achieved through the binding to the 30S ribosomal subunit, effectively blocking the attachment of aminoacyl-tRNA to the mRNA-ribosome complex, thereby preventing the addition of new amino acids to the nascent peptide chain. As a result, bacterial cell growth is inhibited, leading to bacteriostatic effects.

Formula: C₂₇H₃₃N₃O₈

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 527.57 g/mol

Ref: 3D-AR29566