Doxycycline monohydrate Chemical Properties

Melting point:

167-168℃

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

DMSO: soluble1mg/mL

form 

powder or crystals

color 

Light Yellow

Water Solubility 

Soluble in ethanol or methanol. Sparingly soluble in water.Soluble in dilute acids, alkali hydroxides and dimethyl sulfoxide.

Major Application

pharmaceutical (small molecule)

InChIKey

XQTWDDCIUJNLTR-PGTYNCOMNA-N

SMILES

[C@@]12([H])[C@@H](O)[C@@]3([H])C(C(=O)C4C(O)=CC=CC=4[C@@H]3C)=C(O)[C@]1(O)C(=O)C(C(=O)N)=C(O)[C@H]2N(C)C.O |&1:0,2,4,16,20,30,r|

CAS DataBase Reference

17086-28-1

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22-63

Safety Statements 

26-36/37

WGK Germany 

3

HS Code 

29413000

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral

Doxycycline monohydrate Usage And Synthesis

Description

Doxycycline is a broad-spectrum antibiotic synthetically derived from oxytetracycline. It is a semi-synthetic tetracycline. Doxycycline penetrates the bacterial cell and interferes with the protein biosynthesis, stopping the process. Other microorganisms are also sensitive to the antibiotic activity of Doxycycline, such as Mycoplasma, Chlamydia and Ricketsiae. Resistance to antibiotics of the tetracycline family is primarily due to inhibition of transport of the drug into the cell or by increasing antibiotic efflux. The biological mechanism is mainly through plasmid mediation but it may also occur by chromossomal alteration.

Chemical Properties

Doxycycline monohydrate is a Yellow, crystalline powder. It is soluble in ethanol or methanol. It has a high degree of lipid solubility and a low affinity for calcium binding. It is highly stable in normal human serum. It is very slightly soluble in water.

Uses

Doxycycline Monohydrate is used to treat bacterial infections, Lyme disease, chlamydia, Rocky Mountain Spotted Fever, and other susceptible bacterial infections. It is an antibiotic with bacteriostatic properties.
Tetracycline antibacterial.

Uses

An antimicrobial. Inhibits angiogenesis and reduces lung metastases by inhibiting matrix metalloproteinasesDoxycycline monohydrate acts as an antibiotic, antimicrobial agent and a matrix metalloproteinase inhibitor. It is also used for the treatment of chloroquine-resistant falciparum malaria. Further, it is used to treat a wide variety of bacterial infections, including those that cause acne. In addition to this, it inhibits the bacterial protein synthesis by preventing the interaction of aminoacyl-tRNA and the bacterial ribosome.

Application

In yeast cells, doxycycline has been used in doxycycline-inducible system for overexpression of methyltransferase Hmt1 (hnRNP methyltransferase 1).
It has been used in the doxycycline-inducible IFITM (interferon-induced transmembrane) cell lines.
It has also been used as an antimicrobial agent.

Indications

Doxycycline monohydrate (Vibramycin Monohydrate, Monodox, Mondoxyne NL) is a moderately priced drug used to treat many kinds of infections, like dental, skin, respiratory, and urinary tract infections. It also treats acne, Lyme disease, malaria, and certain sexually transmitted infections. This drug is more popular than comparable drugs. It is available in multiple brand and generic versions. Generic doxycycline monohydrate is covered by most Medicare and insurance plans, but some pharmacy coupons or cash prices may be lower. The lowest GoodRx price for the most common version of doxycycline monohydrate is around $6.02, 80% off the average retail price of $30.66. Compare tetracycline antibiotics.

Definition

ChEBI: The monohydrate form of doxycycline. A semi-synthetic tetracycline antibiotic, it is used to inhibit bacterial protein synthesis and treat non-gonococcal urethritis and cervicitis, exacerbations of bronchitis in patients with chronic obstructive pulmonary isease (COPD), and adult periodontitis.

brand name

Doxychel (Rachelle); Monodox (Oclassen); Oracea (CollaGenex); Vibramycin (Pfizer).

General Description

Doxycycline was synthesized by Pfizer starting with either tetracycline or oxytetracycline in 1958. It shows about fourfold higher antibacterial activity than tetracycline against a variety of pathogens. Doxycycline shows higher oral absorption than tetracycline, and its concentration in tissue is higher and maintained longer. Hyclate is a preparation of doxycycline containing one mole of hydrochloric acid and one-half mole each of ethanol and water per mole of doxycycline.

Biological Activity

Doxycycline is a semisynthetic tetracycline that is active against bacteria, mycoplasma and protozoan parasites. It inhibits the bacterial protein synthesis by inhibiting the interaction of aminoacyl-tRNA and the bacterial ribosome.

Synthesis

(1) 100g of hydrogenated salts (??-6-deoxy hygromycin 5-sulfosalicylate crude) was added to 200mL, 15??, 70% (v/v) ethanol aqueous solution, stirred for 10min, started to add ammonia dropwise, when the pH value reaches 5.8, stop dropping ammonia, at this time, the temperature is 18??, stirred for 10min, until the alkaloid dissolved clear, filtered, and the filtrate was heated to 45 ??, keep warm for 30min, cool to 25 ?? out of the material, centrifugal separation, get the first alkalizer tide 65g. (2) take 60g of the tide of step 1), add to 180mL, 60% (v/v) ethanol aqueous solution, add 10% hydrochloric acid to adjust the pH to 3.5, heating to 55 ??, making the material all dissolved, and then add 60g of sulfosalicylic acid, stirring for 10min, and then cooled down to 25 ??, the second salts precipitation, centrifugal separation, to get the second salts tide of 85g._ x000D_. x000D_ 3) Take 80g of the tide obtained in step 2), add it to 240mL of 70% (v/v) ethanol at 15??C, stir fully for 30min, start adding ammonia dropwise, control the process of adding ammonia dropwise, the temperature does not exceed 18??C, when the pH value reaches 6.0, stop adding ammonia dropwise, after the ammonia dropwise is completed, the temperature is 6??C, stir for 10min, until the alkaloid dissolves and clears, filter, and the The filtrate was heated to 45??, kept warm for 30min, cooled until the product was precipitated, cooled down to 15?? and discharged, centrifuged and separated, obtaining the second alkalizer tide 50g. 4) The tide product of step 3) was dried by vacuum drying oven at 0.08MPa and 70 degrees Celsius, and 42g of finished product of doxycycline monohydrate was obtained, the purity of which was 98.8%.

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