CAS 7518-17-4

4-Epianhydrotetracycline

Description:

4-Epianhydrotetracycline is a semi-synthetic derivative of tetracycline, a broad-spectrum antibiotic. It is characterized by its tetracyclic structure, which is essential for its biological activity. This compound exhibits antibacterial properties by inhibiting protein synthesis in bacteria, making it effective against a variety of gram-positive and gram-negative organisms. The chemical formula of 4-Epianhydrotetracycline includes multiple functional groups, contributing to its solubility and reactivity. It is typically administered in its hydrochloride salt form to enhance stability and bioavailability. The substance is known for its moderate to high stability under acidic conditions but may degrade in alkaline environments. Additionally, it has been studied for its potential applications beyond antibiotic use, including anti-inflammatory and anticancer properties. As with other tetracyclines, it may cause side effects such as gastrointestinal disturbances and photosensitivity. Proper handling and storage conditions are essential to maintain its efficacy and safety profile.

Formula: C₂₂H₂₂N₂O₇

InChI: InChI=1S/C22H22N2O7/c1-8-9-5-4-6-12(25)13(9)17(26)14-10(8)7-11-16(24(2)3)18(27)15(21(23)30)20(29)22(11,31)19(14)28/h4-6,11,16,25-27,31H,7H2,1-3H3,(H2,23,30)/t11-,16+,22-/m0/s1

InChI key: InChIKey=CXCVEERYMJZMMM-WPINSWFRSA-N

SMILES: O[C@]12[C@]([C@@H](N(C)C)C(O)=C(C(N)=O)C1=O)(CC=3C(C2=O)=C(O)C=4C(C3C)=CC=CC4O)[H]

Synonyms:

• (4R)-Anhydrotetracycline
• (4R,4aS,12aS)-4-(Dimethylamino)-1,4,4a,5,12,12a-hexahydro-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-2-naphthacenecarboxamide
• (4R,4aS,12aS)-4-(Dimethylamino)-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-1,4,4a,5,12,12a-hexahydrotetracene-2-carboxamide
• (4R,4aS,12aS)-4-(dimethylamino)-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-4a,5-dihydro-4H-tetracene-2-carboxamide
• 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,12,12a-hexahydro-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-, 4-epimer
• 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,12,12a-hexahydro-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-, [4R-(4α,4aβ,12aβ)]-
• 2-naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,12,12a-hexahydro-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-, (4R,4aS,12aS)-
• 4-Epianhydrotetracycline
• 4-epi-5a,6-Anhydrotetracycline
• 4-epi-Anhydrotetracycline
• Anhydro-4-epitetracycline
• Anhydroepitetracycline
• Epianhydrotetracycline

Tetracycline EP Impurity D (Chlortetracycline EP Impurity I, Lymecycline EP Impurity D, 4-Epianhydrotetracycline)

CAS: 7518-17-4

Formula: C₂₂H₂₂N₂O₇

Molecular weight: 426.43

Ref: 4Z-T-404

4-Epianhydrotetracycline

CAS: 7518-17-4

4-Epianhydrotetracycline is a chemical compound that is a derivative of tetracycline, a well-known antibiotic. It is primarily a byproduct arising from the chemical degradation of tetracycline antibiotics, occurring under acidic or basic conditions. The source of this compound is the structural transformation of tetracycline, resulting in an altered molecular configuration.

Formula: C₂₂H₂₂N₂O₇

Purity: Min. 95%

Molecular weight: 426.4 g/mol

Ref: 3D-HAA51817

Lymecycline EP Impurity D

CAS: 7518-17-4

Formula: C₂₂H₂₂N₂O₇

Molecular weight: 426.42

Ref: ST-EA-CP-L64004

4-Epianhydrotetracycline hydrochloride hydrate

CAS: 4465-65-0, 7518-17-4

4-Epianhydrotetracycline hydrochloride hydrate is a chemical compound that inhibits the activation of protein kinase C (PKC) and blocks the apoptosis pathway. It has been shown to induce apoptosis in prostate cancer cells and also inhibits the proliferation of human microvessel endothelial cells. 4-Epianhydrotetracycline hydrochloride hydrate is stable in both human serum and wastewater, which makes it an ideal drug for treating many types of cancers. It is also used in pharmaceutical drugs as a cytochalasin, which are used to treat angina pectoris by reducing oxygen uptake by erythrocytes, thereby inhibiting oxidative phosphorylation. 4-Epianhydrotetracycline hydrochloride hydrate prevents mitochondrial cytochrome c release, thus blocking the apoptotic pathway in cells. This chemical compound may act as a regulatory molecule that affects energy metabolism and epidermal growth factor (EGF)

Formula: C₂₂H₂₃ClN₂O₇

Purity: Min. 95%

Molecular weight: 462.88 g/mol

Ref: 3D-FE22716