808-26-4

Basic information

• Product Name: Sancycline
• Synonyms: SANCYCLINE;(4S,4aS,5aR,12aS)-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1-11-dioxo-2-naphthacenecarboxamide;6-Demethyl-6-deoxytetracycline;Bonomycin;GS 2147;Norcycline;Sancycline Hydrochloride;(4S,4aS,5aR,12aS)-4-(Dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-2-naphthacenecarboxamide
• CAS NO: 808-26-4
• Molecular Formula: C₂₁H₂₂N₂O₇
• Molecular Weight: 414.41
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 808-26-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 224-2280C (dec)
• Boiling Point: 750.9 °C at 760 mmHg
• Flash Point: 407.9 °C
• Appearance: /
• Density: 1.61 g/cm³
• Vapor Pressure: 3E-17mmHg at 25°C
• Refractive Index: 1.734
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Aqueous Acid (Slightly), Chloroform (Slightly), Methanol (Slightly), Water (Slig
• PKA: 4.50±1.00(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: Sancycline(CAS DataBase Reference)
• NIST Chemistry Reference: Sancycline(808-26-4)
• EPA Substance Registry System: Sancycline(808-26-4)

Safety Data

• Hazardous Substances Data: 808-26-4(Hazardous Substances Data)

Usage

Description

Sancycline is a semisynthetic tetracycline antibiotic that is more active than tetracycline against 339 strains of anaerobic bacteria (average MIC90s = 1 and 32 μg/ml, respectively). Sancycline is active against tetracycline-resistant E. coli, S. aureus, and E. faecalis strains with MICs ranging from 0.06 to 1 μg/ml. In vivo, sancycline is active against S. aureus in mice with ED50 values of 0.46 and 0.6 mg/kg for intravenous and subcutaneous administration, respectively.

Chemical Properties

Yellow Solid

Uses

Different sources of media describe the Uses of 808-26-4 differently. You can refer to the following data:
1. A semi-synthetic antibiotic related to tetracycline
2. Sancycline is a rare semi-synthetic tetracycline prepared by hydrogenolysis of the chloro and benzylic hydroxy moieties of declomycin, first reported in 1962. As the simplest of the early tetracyclines, sancycline was the first to be totally synthesised by Conover and co-workers. Like other tetracyclines, sancycline acts by reversibly binding to the 30S ribosomal subunit and inhibiting protein translation by blocking entry of aminoacyl-tRNA into the ribosome A site.
3. Sancycline is a tetracycline bacteriostatic antibiotic which also binds to the Tet repressor protein (TetR).

Brand name

Bonomycin (Pfizer).

InChI:InChI=1/C21H22N2O7/c1-23(2)15-10-7-9-6-8-4-3-5-11(24)12(8)16(25)13(9)18(27)21(10,30)19(28)14(17(15)26)20(22)29/h3-5,9-10,15,24-25,29-30H,6-7,22H2,1-2H3/b20-14+/t9-,10-,15-,21-/m0/s1

Upstream product

• 987-02-0 6-demethyltetracycline 
• 64-73-3 demeclocycline hydrochloride 
• 127-33-3 Demeclocycline 
• 64-19-7 acetic acid 
• 5679-00-5 7-amino-6-desmethyl-6-deoxytetracycline 

Downstream Products

• 13614-98-7 minocycline Hydrochloride 
• 5679-00-5 7-amino-6-desmethyl-6-deoxytetracycline 
• 5585-59-1 [4S-(4a,12aα)]-7-nitro-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a octahydro-naphthacene-2-carboxylic acid amide 

Relevant articles and documents

Preparation process of 6-demethyl-6-deoxytetracycline

The invention discloses a preparation process of 6-demethyl-6-deoxytetracycline. The preparation process comprises the following steps: sequentially adding demethylchlortetracycline and urea into softwater, uniformly mixing, reacting in a hydrogen environment by taking Pd/C as a catalyst, filtering the catalyst to obtain a compound I; dissolving the obtained compound I in alcohol, adding an acid,stirring until the compound I is completely dissolved, adding DMF, reacting in a hydrogen environment by taking Pd/C as a catalyst, filtering the catalyst to obtain a compound II; concentrating the compound II under a reduced pressure, recovering alcohol, drying, adding into soft water, adding urea for dissolving, filtering to obtain double salt; adding the double salt into alcohol, stirring for2 hours at a low temperature, and filtering to obtain a high-purity compound II. The preparation process has the beneficial effects that an isomer with a lactone structure is prevented from being generated by ring opening; the yield and the purity are improved; not only is the safety coefficient of production improved, but also the cost loss caused by the loss of an organic solvent is reduced; thereaction temperature is reduced, the product purity is improved; and the epimers are reduced.

SEMI-SYNTHESIS PROCEDURES

Provided herein are improved processes tor convening C7-amino-substituted tetracyclines to C7-fluoro-substituted tetracyclines, as well as intermediates produced by or used in these processes. In one embodiment, a thermal fluorination method is provided in which a suspension comprising a non-polar organic solvent and a C7-diazo-substituted tetracycline hexafluorophosphate, hexafluoarsenate or hexafluorosilicate salt, or a salt, solvate or combination thereof, is healed to provide a C7-fluoro-substituted tetracycline, or salt, solvate or combination thereof. In another embodiment, a photolytic fluorination is provided in which a solution comprising an ionic liquid and a C-7diazo-substituted tetracycline tetrafluoroborate, hexafluorophosphate, hexafluoroarsenate or hexafluorosilicate salt, or a salt, solvate or combination thereof, is irradiated to provide a C7-fluoro-substituted tetracycline, or salt, solvate or combination thereof.

TETRACYCLINE COMPOUNDS FOR THE TREATMENT OF RHEUMATOID ARTHRITIS AND RELATED METHODS OF TREATMENT

The present invention pertains, at least in part, to substituted tetracycline compounds. The present invention also pertains to methods for treating rheumatoid arthritis in a subject, comprising administering to the subject a tetracycline compound of the invention.