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독시싸이클린 구조식 이미지
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독시싸이클린 속성

206-209°C (dec.)
끓는 점
554.44°C (rough estimate)
1.3809 (rough estimate)
1.6500 (estimate)
산도 계수 (pKa)
pKa 3.5 (Uncertain);7.7 (Uncertain);9.5 (Uncertain)
CAS 데이터베이스
564-25-0(CAS DataBase Reference)
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,4aR,5S,5aR,6R,12aS)-(564-25-0)


유해 물질 데이터 564-25-0(Hazardous Substances Data)

독시싸이클린 MSDS


독시싸이클린 C화학적 특성, 용도, 생산

화학적 성질

Yellow Solid


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.


ChEBI: Tetracycline in which the 5beta-hydrogen is replaced by a hydroxy group, while the 6alpha-hydroxy group is replaced by hydrogen. A semi-synthetic tetracycline antibiotic, it is used to inhibit bacterial protein synthesis a d treat non-gonococcal urethritis and cervicitis, exacerbations of bronchitis in patients with chronic obstructive pulmonary disease (COPD), and adult periodontitis.


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

Antimicrobial activity

It is active against some tetracycline-resistant Staph. aureus and is more active than other tetracyclines against Str. pyogenes, enterococci and Nocardia spp. Mor. catarrhalis (MIC 0.5 mg/L), Legionella pneumophila and most strains of Ureaplasma urealyticum (MIC 0.5 mg/L) are susceptible.

일반 설명

A more recent addition to the tetracycline group of antibioticsavailable for antibacterial therapy is doxycycline,α-6-deoxy-5-oxytetracycline (Vibramycin), first reportedby Stephens et al. in 1958. It was obtained first in smallyields by a chemical transformation of oxytetracycline, butit is now produced by catalytic hydrogenation of methacyclineor by reduction of a benzyl mercaptan derivative ofmethacycline with Raney nickel. The latter processproduces a nearly pure form of the 6α-methyl epimer. The6α-methyl epimer is more than 3 times as active as itsβ-epimer.169 Apparently, the difference in orientation of themethyl groups, which slightly affects the shapes of the molecules,causes a substantial difference in biological effect. Also, absence of the 6-hydroxyl group produces acompound that is very stable in acids and bases and that hasa long biological half-life. In addition, it is absorbed verywell from the GI tract, thus allowing a smaller dose to be administered.High tissue levels are obtained with it, and unlikeother tetracyclines, doxycycline apparently does not accumulatein patients with impaired renal function.Therefore, it is preferred for uremic patients with infectionsoutside the urinary tract. Its low renal clearance may limit itseffectiveness, however, in urinary tract infections.
Doxycycline is available as a hydrate salt, a hydrochloridesalt solvated as the hemiethanolate hemihydrate, and amonohydrate. The hydrate form is sparingly soluble in waterand is used in a capsule; the monohydrate is water insolubleand is used for aqueous suspensions, which are stable for upto 2 weeks when kept in a cool place.

Pharmaceutical Applications

6-Deoxy-5β-hydroxytetracycline. A semisynthetic product supplied as the hyclate, calcium salt or the hydrochloride for oral and intravenous administration.


Oral absorption: 90%
Cmax 100–200 mg oral: 1.7–5.7 mg/L after 2–3.5 h
100 mg intravenous infusion (1 h): 2.5 mg/L end infusion
Plasma half-life:18 h
Volume of distribution: 0.9–1.8 L/kg
Plasma protein binding: 90%
Doxycycline is rapidly absorbed from the upper gastrointestinal tract and absorption appears to be linearly related to the administered dose. Food, especially dairy products, reduces peak serum concentrations by 20%. Alcohol also delays absorption. As with other tetracyclines, divalent and trivalent cations, as in antacids and ferrous sulfate, form chelates which reduce absorption.
The greater lipophilicity of doxycycline is responsible for its widespread tissue distribution. Concentrations in liver, biliary system, kidneys and the digestive tract are approximately twice those in plasma. Within the respiratory tract, it achieves concentrations of 2.3–6.7 mg/kg in tonsils and 2.3–7.5 mg/kg in maxillary sinus mucosa. In bronchial secretions concentrations are about 20% of plasma levels, increasing to 25–35% in the presence of pleurisy. Gallbladder concentrations are approximately 75% those of plasma, and prostate concentrations are 60–100%. It penetrates well into the aqueous humor. CSF concentrations range from 11% to 56% of plasma levels and are not affected by inflammation. In the elderly, tissue concentrations are 50–100% higher than in young adults. The half-life remains unaltered and one explanation is reduced fecal elimination.
Metabolism and excretion
Doxycycline is largely excreted unchanged. Around 35% is eliminated through the kidneys and the remainder through the digestive tract. Renal clearance ranges from 1.8 to 2.1 L/h, and is largely via glomerular filtration, with approximately 70% tubular reabsorption. Alkalinization enhances renal clearance. Fecal elimination partly reflects biliary excretion but also includes diffusion across the intestinal wall. Provided the drug is not chelated, reabsorption occurs with enterohepatic recycling. The elimination half-life is long (15–25 h).
The half-life and the area under the concentration–time curve (AUC) are little altered in renal insufficiency, with no evidence of accumulation after repeat dosing, even in anuric patients, evidently as a result of increased clearance through the liver or gastrointestinal tract, since biliary and fecal concentrations increase in renal failure. Although the plasma elimination half-life is unchanged, the drug appears to accumulate in tissues with increasing renal failure, and it has been suggested that less drug is bound to plasma protein and red cells through competition with other metabolites, which in turn increases hepatic elimination. Pharmacokinetics are unaltered by hemodialysis or peritoneal dialysis. Clearance is decreased by about half in patients with type IIa and type IV hyperlipidemia.
The plasma elimination half-life is shortened by various antiepileptic agents including phenytoin, barbiturates and carbamazepine, presumably as a result of liver enzyme induction, although there is also evidence for some interference with the protein binding of doxycycline.

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.

Clinical Use

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.


Untoward reactions are generally those typical of the group but gastrointestinal side effects are less common than with other tetracyclines due to the lower total dosage and the ability to administer the drug with meals. Esophageal ulceration as a result of capsule impaction has been reported. Dental and bone deposition appear to be less common than with other tetracycline derivatives. Other adverse phenomena include occasional vestibular toxicity.
Hypersensitivity reactions include photosensitivity and eosinophilia, but rarely anaphylaxis. In common with demeclocycline and chlortetracycline it may be a more powerful sensitizer than other tetracyclines. It is contraindicated in patients with acute porphyria because it has been demonstrated to be porphyrinogenic in animals.

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