Doxycycline

Base Information

• Chemical Name: Doxycycline
• CAS No.: 564-25-0
• Molecular Formula: C22H24N2O8
• Molecular Weight: 444.441
• Hs Code.: 3004909090
• Mol file: 564-25-0.mol

Synonyms:2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-(6CI,8CI);2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-,[4S-(4a,4aa,5a,5aa,6a,12aa)]-;4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide;5-Hydroxy-a-6-deoxytetracycline;6-Deoxy-5-hydroxytetracycline;6-Deoxyoxytetracycline;Dentistar;Deoxymykoin;Dotur;Doximal;Doxinyl;Doxivetin;Doxy RW;Doxy-Gel;Doxycen;Doxycycline;GS 3065;Hydramycin;Liviatin;Medeomycin;Monodox;Oxytetracycline, 6-deoxy-;Pulmodox;Ronaxan;Tolexine;Unidox;Vibramycin;Vibramycine;Vibraveineuse;a-6-Deoxy-5-hydroxytetracycline;a-Doxycycline;

Chemical Property of Doxycycline

Chemical Property:

• Appearance/Colour: yellow solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 206-209 °C
• Refractive Index: 1.737
• Boiling Point: 685.2 °C at 760 mmHg
• PKA: pKa 3.5 (Uncertain);7.7 (Uncertain);9.5 (Uncertain)
• Flash Point: 368.2 °C
• PSA: 181.62000
• Density: 1.63 g/cm³
• LogP: 0.35270
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility.: 0.63g/L(25 oC)

Purity/Quality:

99.9% ^*data from raw suppliers

Doxycycline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: tetracycline antibiotics Doxycycline is a semi-synthetic tetracycline prepared by hydrogenolysis of oxytetracycline to remove the 6-hydroxy group. Although the synthesis was reported in 1958, it was not released for use until 1967. Doxycycline, together with minocycline, is regarded as a ‘third generation’ tetracycline largely replacing the analogues and pro-drugs produced in the early 1960s for mainstream antibiotic applications. Like all tetracyclines, doxycycline shows broad spectrum antibacterial and antiprotozoan activity and acts by binding to the 30S and 50S ribosomal subunits, blocking protein synthesis. Doxycycline has been extensively cited in the literature with over 10,000 references. Doxycycline is used for the same indications as other antibiotics of the tetracycline series; however, it belongs to the group of long-lasting tetracyclines. In some cases it is more active with respect to a number of organisms, and is better tolerated than other tetracyclines. Synonyms of this drug are azudoxat, codidoxal, eftapan, vibramycin, and others.
• Indications: Doxycycline (Vibramycin, Monodox) has similar absorption and durationof- activity characteristics. Its effectiveness in acne approaches that of minocycline, when used in the same fashion with similar dosages. Early data suggests that subantimicrobial doses of doxycycline, 20 mg (Periostat), may play a therapeutic role in acne by reducing inflammation through anticollagenolytic, antimatrix-degrading metalloproteinase, and cytokine downregulating properties.
• Therapeutic Function: Antibiotic
• Clinical Use: Its once-daily administration and safety in renal insufficiency make it one of the most widely used tetracyclines. It is used in the prophylaxis and treatment of malaria in areas in which resistance to conventional antimalarial agents is common. Like the other tetracyclines, doxycycline inhibits the pathogen’s protein synthesisby reversibly inhibiting the 30S ribosomal subunit.Bacteria and Plasmodium ribosomal subunits differ significantlyfrom mammalian ribosomes such that this group ofantibiotics do not readily bind to mammalian ribosomesand, therefore, show good selective toxicity. Althoughdoxycycline is a good antibacterial, its use for malaria islimited to prophylaxis against strains of P. falciparumn resistantto chloroquine and sulfadoxine–pyrimethamine.This use normally should not exceed 4 months. Becausethe tetracyclines chelate calcium, they can interfere withdevelopment of the permanent teeth in children. Therefore,their use in children definitely should be short term. Also, tetracycline photosensitivity must be kept in mind, particularlybecause areas where malaria is endemic are also theareas with the greatest sunlight.
• Drug interactions: Potentially hazardous interactions with other drugsAnticoagulants: possibly enhanced anticoagulant effect of coumarins and phenindione.Ciclosporin: possibly increases plasma-ciclosporin concentration.Oestrogens: possibly reduced contraceptive effects of oestrogens (risk probably small) Retinoids: possible increased risk of benign intracranial hypertension - avoid.

Technology Process of Doxycycline

There total 22 articles about Doxycycline 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: 90.0%

C37H34N2O10 → doxycycline hydrochloride (10592-13-9,41411-66-9,564-25-0,61281-03-6)

Guidance literature:

C₃₇H₃₄N₂O₁₀; With hydrogen; palladium; In tetrahydrofuran; methanol; at 23 ℃; for 2h; under 760.051 Torr;

With hydrogenchloride; In methanol; water; HPLC;

DOI:10.1021/ja806629e

Reference yield: 90.0%

doxycycline (564-25-0,10597-92-9,7164-70-7,7264-10-0) → doxycycline hydrochloride (10592-13-9,41411-66-9,564-25-0,61281-03-6)

Guidance literature:

With hydrogenchloride; In methanol; water;

Reference yield: 41.0%

methacycline hydrochloride (3963-95-9) → doxycycline (564-25-0,10597-92-9,7164-70-7,7264-10-0) + 6-epidoxycycline (3219-99-6,10597-92-9,7164-70-7,7264-10-0)

Guidance literature:

With hydrogen; closo-3,3-(η²,η³-C7H7CH2)-3,1,2-RhC2B9H11; In methanol; at 43 ℃; for 4h; under 76000 Torr;

DOI:10.1016/S0040-4039(00)60321-0

upstream raw materials:

methacycline hydrochloride

doxycycline hydrochloride

doxycycline

(1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid

Downstream raw materials:

doxycycline hydrochloride

doxycycline

C₂₂H₂₄N₂O₈*C₇H₆O₆S

(4S,4aR,5S,5aR,6R,12aS)-3,5,10,12,12a-pentahydroxy-6-methyl-4-(methylamino)-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

Refernces

• 1、 -. "Preparation method of doxycycline hydrochloride intermediate hydride". Paragraph 0026; 0029; 0031; 0034. . Retrieved 2017/07/19.
• 2、 Sun, Cuixiang,Wang, Qiu,Brubaker, Jason D.,Wright, Peter M.,Lerner, Christian D.,Noson, Kevin,Charest, Mark,Siegel, Dionicio R.,Wang, Yi-Ming,Myers, Andrew G.. "A robust platform for the synthesis of new tetracycline antibiotics". supporting information; experimental part. p. 17913 - 17927. Retrieved 2009/07/18.