Oxytetracycline

Base Information

• Chemical Name: Oxytetracycline
• CAS No.: 79-57-2
• Molecular Formula: C22H24N2O9
• Molecular Weight: 460.441
• Hs Code.: 30029090
• Mol file: 79-57-2.mol

Synonyms:2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-(7CI,8CI);5-Hydroxytetracycline;Abbocin;Antibiotic TM 25;Biostat;2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-,(4S,4aR,5S,5aR,6S,12aS)-;Dabicycline;Geomycin;Geomycin (Streptomyces vimosus);Geotilin;LA 200;Lenocycline;Liquamycin LA 200;Mycoshield TMQTHC 20;NSC 9169;Oxiter 200;Oxitetracyclin;Oxycline;Oxydon;Oxylim;Oxymykoin;Oxysentin 100;Oxyterracin;Oxyterracine;Oxytetracycline amphoteric;Oxytetral;Ryomycin;Stevacin;Stevasin;Tarosin;Terrafungine;Terralon LA;Terramycin343;Terramycin Q 50;Tetran;Ursocyclin;Ursocycline;Vendarcin;

Chemical Property of Oxytetracycline

Chemical Property:

• Appearance/Colour: beige to light yellow crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 183 °C
• Refractive Index: 1.749
• Boiling Point: 727.8 °C at 760 mmHg
• PKA: pKa 3.27/7.32/9.11(H2O,t =25,I<0.01)(Approximate)
• Flash Point: 394 °C
• PSA: 201.85000
• Density: 1.71 g/cm³
• LogP: -0.54330
• Storage Temp.: -20°C
• Solubility.: Sparingly soluble in aqueous solution at 0.6 mg/mL
• Water Solubility.: 0.2 g/L

Purity/Quality:

99% ^*data from raw suppliers

Oxytetracycline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 63-36-36/37/38
• Safety Statements: 22-24/25-36/37/39-26-36

MSDS Files:

SDS file from LookChem

Useful:

• description: Oxytetracycline (PC Code 006304) is a broad-spectrum antibiotic produced from the actinomycete Streptomyces rimosus. Two related compounds, hydroxytetracycline monohydrochloride (PC Code 006308) and oxytetracycline calcium (PC Code 006321), are registered as pesticides, for use in preventing the growth of or killing bacteria, fungi and mycoplasma-like organisms; there is no active product for PC Code 006304. Oxytetracycline is also approved by the Food and Drug Administration (FDA) for use as a human and animal drug to treat a variety of bacterial infections. Specifically, oxytetracycline is used to treat infections caused by chlamydia, mycoplasma organisms, propionebacterium acnes, haemophilus influenzae, and rickettsiae. It acts by inhibiting protein synthesis by binding to the 30S ribosomal subunit of the bacteria. In conjunction with the FDA-approved animal drug uses, food-additive tolerances are established for residues of tetracyclines in commodities of beef cattle, dairy cattle, calves, swine, sheep, chickens, turkeys, finfish, and lobster (21 CFR §556.500).
• Description: Oxytetracycline also is one of the classic tetracyclines. It is produced by fermentation of Streptomyces rimosis and other soil microorganisms. The most hydrophilic tetracycline on the market, it has largely now been replaced by its semisynthetic descendants. It is primarily used today for IM injections.
• Uses: Oxytetracycline, which has seen significant usage in plant disease control, does not contain the Cl atom but has an additional -OH group at the C5 position on the tetracycline molecule (4). Tetracyclines are widely used therapeutic agents in clinical medicine [second to penicillins in total tons used each year (5)] for bacterial respiratory, periodontal, and urogenital tract diseases (6). Oxytetracycline is also used as a feed amendment for growth promotion and as a therapeutic agent for curing diseases of agricultural animals including fish. Oxytetracycline(Terramycin) was the second of the broad-spectrum tetracycline group of antibiotics to be discovered. Oxytetracycline works by interfering with the ability of bacteria to produce proteins that are essential to them. Without these proteins t Oxytetracycline (terramycin) is a linear, tetracyclic broad spectrum antibiotic originally isolated from Streptomyces rimosus in 1949. Like all tetracyclines, oxytetracycline shows broad spectrum antibacterial and antiprotozoan activity and acts by binding to the 30S and 50S ribosomal sub-units, blocking protein synthesis. Oxytetracycline, although less coloured than other tetracyclines, is still a pigment and is thus sensitive to environmental and storage conditions. Commercial oxytetracycline may contain significant levels of degradation products.
• Therapeutic Function: Antibiotic
• Clinical Use: It offers no unique therapeutic advantages, although it is one of the cheaper preparations.
• Drug interactions: Potentially hazardous interactions with other drugs Anticoagulants: possibly enhanced anticoagulant effect of coumarins and phenindione. Oestrogens: possibly reduced contraceptive effects of oestrogens (risk probably small). Retinoids: possible increased risk of benign intracranial hypertension with tetracyclines and retinoids - avoid.

Technology Process of Oxytetracycline

There total 5 articles about Oxytetracycline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

TETRACYCLINE (60-54-8) → Oxytetracycline (79-57-2) + anhydrotetracycline (1665-56-1,7518-17-4,4907-76-0)

Guidance literature:

With laccase from Trametes versicolor; In water; at 25 ℃; for 24h; pH=6; Reagent/catalyst; pH-value; Catalytic behavior; Kinetics; Enzymatic reaction;

DOI:10.1016/j.cattod.2014.02.051

Reference yield:

TETRACYCLINE (60-54-8) → Oxytetracycline (79-57-2)

Guidance literature:

With laccase from Pycnoporus sp. SYBC-L₁₀; 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt; In aq. phosphate buffer; at 25 ℃; for 0.0666667h; pH=6; Reagent/catalyst; Temperature; pH-value; Catalytic behavior; Enzymatic reaction;

DOI:10.1016/j.jhazmat.2019.121084

Reference yield:

→ Oxytetracycline (79-57-2)

Guidance literature:

Verb. III, Triphenylphosphin;

upstream raw materials:

TETRACYCLINE

Downstream raw materials:

tyrosine*oxytetracycline

(3S)-4t-[(R)-4,5-dihydroxy-9-methyl-3-oxo-1,3-dihydro-naphtho[2,3-c]furan-1-yl)-3r-dimethylamino-2,5ξ-dihydroxy-6-oxo-cyclohex-1-enecarboxylic acid amide

terrinolide

carbon dioxide

Refernces

• 1、 De Cazes,Belleville,Petit,Llorca,Rodríguez-Mozaz,De Gunzburg,Barceló,Sanchez-Marcano. "Design and optimization of an enzymatic membrane reactor for tetracycline degradation". . p. 146 - 152. Retrieved 2014/12/09.
• 2、 -. "Biodegradable ionic matrix of variable internal polarity with grafted polymer". . . Retrieved 2008/06/13.