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What Is The Chemical Makeup Of Doxycycline Hyclate

Written By Saturday, May 28, 2022 Add Comment Edit

Tetracycline-class antibiotic

Doxycycline
Doxycycline structure.svg
Doxycycline 3D ball.png
Clinical information
Pronunciation
DOKS-iss-EYE-kleen
Trade names Doxy, Doryx, Vibramycin, others
AHFS/Drugs.com Monograph
MedlinePlus a682063
License data
  • U.s.a.  DailyMed:Doxycycline
  • Usa FDA: Doxycycline
Pregnancy
category
  • AU: D
Routes of
assistants		 Past mouth, intravenous[i]
ATC code
  • J01AA02 (WHO) A01AB22 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • United kingdom: POM (Prescription only)
  • US: ℞-simply
Pharmacokinetic data
Bioavailability ~100%
Protein binding fourscore–90%
Metabolism Negligible
Emptying half-life 10–22 hours
Excretion Mainly faeces, twoscore% urine
Identifiers

IUPAC name

  • (fourS,4aR,5S,5aR,sixR,12aS)-4-(Dimethylamino)-three,5,ten,12,12a-pentahydroxy-6-methyl-1,xi-dioxo-1,iv,4a,5,5a,6,11,12a-octahydrotetracene-two-carboxamide
CAS Number
  • 564-25-0 check Y
PubChem CID
  • Doxycycline
DrugBank
  • DB00254 check Y
ChemSpider
  • 10482106 check Y
UNII
  • 334895S862
KEGG
  • D00307 ☒ N
ChEBI
  • CHEBI:60648 check Y
ChEMBL
  • ChEMBL1433 ☒ N
CompTox Dashboard (EPA)
  • DTXSID0037653 Edit this at Wikidata
ECHA InfoCard 100.008.429 Edit this at Wikidata
Chemical and physical data
Formula C 22 H 24 N 2 O 8
Molar mass 444.440 m·mol−1
3D model (JSmol)
  • Interactive prototype

SMILES

  • CN(C)[C@@H]3C(\O)=C(\C(Due north)=O)C(=O)[C@@]4(O)C(/O)=C2/C(=O)c1c(cccc1O)[C@H](C)[C@H]2[C@H](O)[C@@H]34

InChI

  • InChI=1S/C22H24N2O8.Water/c1-7-viii-5-iv-6-9(25)xi(8)sixteen(26)12-ten(7)17(27)14-15(24(2)iii)18(28)xiii(21(23)31)20(30)22(fourteen,32)nineteen(12)29;/h4-seven,10,xiv-15,17,25,27-29,32H,one-3H3,(H2,23,31);1H2/t7-,10+,14+,15-,17-,22-;/m0./s1check Y

  • Key:XQTWDDCIUJNLTR-CVHRZJFOSA-Northcheck Y

☒ N check Y  (what is this?) (verify)

Doxycycline is a broad-spectrum tetracycline-form antibody used in the treatment of infections acquired past leaner and certain parasites.[1] It is used to care for bacterial pneumonia, acne, chlamydia infections, Lyme disease, cholera, typhus, and syphilis.[1] It is besides used to foreclose malaria in combination with quinine.[1] Doxycycline may be taken by mouth or past injection into a vein.[i]

Mutual side effects include diarrhea, nausea, airsickness, and an increased risk of sunburn.[1] Use during pregnancy is not recommended.[one] Doxycycline is a broad-spectrum antibiotic, of the tetracycline class.[1] Similar other agents of the tetracycline course, it either slows or kills bacteria by inhibiting protein production.[ane] [2] It kills malaria by targeting a plastid organelle, the apicoplast.[3] [four]

Doxycycline was patented in 1957 and came into commercial use in 1967.[5] [6] It is on the World Health Arrangement's List of Essential Medicines.[7] Doxycycline is available as a generic medicine.[1] [8] In 2019, it was the 90th near ordinarily prescribed medication in the Usa, with more than eightmillion prescriptions.[ix] [x]

Medical use [edit]

Generic 100 mg doxycycline capsules

In improver to the general indications for all members of the tetracycline antibiotics group, doxycycline is ofttimes used to care for Lyme disease, chronic prostatitis, sinusitis, pelvic inflammatory illness,[11] [12] acne, rosacea,[13] [14] and rickettsial infections.[xv]

In Canada, in 2004, doxycycline was considered a commencement-line treatment for chlamydia and non-gonococcal urethritis and with cefixime for uncomplicated gonorrhea.[16]

Antibacterial [edit]

Moraxella catarrhalis, Brucella melitensis, Chlamydia pneumoniae, and Mycoplasma pneumoniae are generally susceptible to doxycycline, while some Haemophilus spp., Mycoplasma hominis, and Pseudomonas aeruginosa accept developed resistance to varying degrees.[17]

It is used in the handling and prophylaxis of anthrax and Leptospirosis.[18] It is also effective against Yersinia pestis (the infectious agent of bubonic plague), and is prescribed for the treatment of Lyme illness,[19] [20] [21] [22] ehrlichiosis,[23] [24] and Rocky Mountain spotted fever.[25]

Doxycycline is indicated for treatment of:[25] [26]

  • Rocky Mountain spotted fever, typhus fever and the typhus grouping, Q fever,[27] rickettsialpox, and tick fevers acquired past Rickettsia
  • Respiratory tract infections caused by Mycoplasma pneumoniae [28]
  • Lymphogranuloma venereum, trachoma, inclusion conjunctivitis, and uncomplicated urethral, endocervical, or rectal infections in adults acquired past Chlamydia trachomatis
  • Psittacosis
  • Nongonococcal urethritis caused by Ureaplasma urealyticum
  • Relapsing fever due to Borrelia recurrentis
  • Chancroid caused past Haemophilus ducreyi
  • Plague due to Yersinia pestis
  • Tularemia
  • Cholera
  • Campylobacter fetus infections
  • Brucellosis caused by Brucella species (in conjunction with streptomycin)
  • Bartonellosis
  • Granuloma inguinale (Klebsiella species)
  • Lyme disease[29]

When bacteriologic testing indicates appropriate susceptibility to the drug, doxycycline may be used to care for these infections caused past Gram-negative bacteria:[25] [26]

  • Escherichia coli infections
  • Enterobacter aerogenes (formerly Aerobacter aerogenes) infections
  • Shigella species infections
  • Acinetobacter species (formerly Mima species and Herellea species) infections
  • Respiratory tract infections acquired past Haemophilus influenzae
  • Respiratory tract and urinary tract infections caused by Klebsiella species

Some Gram-positive bacteria have developed resistance to doxycycline. Upwards to 44% of Streptococcus pyogenes and upwardly to 74% of Due south. faecalis specimens take developed resistance to the tetracycline group of antibiotics. Upwards to 57% of P. acnes strains developed resistance to doxycycline.[thirty] When bacteriologic testing indicates appropriate susceptibility to the drug, doxycycline may be used to treat these infections caused by Gram-positive leaner:[25] [26]

  • Upper respiratory infections acquired by Streptococcus pneumoniae (formerly Diplococcus pneumoniae)
  • Skin and soft tissue infections caused by Staphylococcus aureus, including methicillin-resistant Staphylococcus aureus infections
  • Anthrax caused by Bacillus anthracis infection

When penicillin is contraindicated, doxycycline can be used to treat:[25] [26]

  • Syphilis caused past Treponema pallidum
  • Yaws caused by Treponema pertenue
  • Listeriosis due to Listeria monocytogenes
  • Vincent'southward infection caused by Fusobacterium fusiforme
  • Actinomycosis caused past Actinomyces israelii
  • Infections acquired by Clostridium species

Doxycycline may also exist used as adjunctive therapy for severe acne.[25] [26]

The beginning-line handling for brucellosis is a combination of doxycycline and streptomycin and the 2nd-line is a combination of doxycycline and rifampicin (rifampin).[31]

Antimalarial [edit]

Doxycycline is active confronting the erythrocytic stages of Plasmodium falciparum but not against the gametocytes of P. falciparum.[32] Information technology is used to prevent malaria.[33] It is not recommended lonely for initial treatment of malaria, even when the parasite is doxycycline-sensitive, because the antimalarial event of doxycycline is delayed.[34]

The World Health Arrangement (WHO) guidelines country that the combination of doxycycline with either artesunate or quinine may be used for the treatment of unproblematic malaria due to P. falciparum or following intravenous treatment of severe malaria.[35]

Antihelminthic [edit]

Doxycycline kills the symbiotic Wolbachia bacteria in the reproductive tracts of parasitic filarial nematodes, making the nematodes sterile, and thus reducing transmission of diseases such as onchocerciasis and elephantiasis.[36] Field trials in 2005 showed an eight-week grade of doxycycline almost completely eliminates the release of microfilariae.[37]

Spectrum of susceptibility [edit]

Doxycycline has been used successfully to care for sexually transmitted, respiratory, and ophthalmic infections. Representative pathogenic genera include Chlamydia, Streptococcus, Ureaplasma, Mycoplasma, and others. The following represents MIC susceptibility data for a few medically significant microorganisms.[38]

  • Chlamydia psittaci: 0.03 μg/mL
  • Mycoplasma pneumoniae: 0.016 μgrand/mL — 2 μgrand/mL
  • Streptococcus pneumoniae: 0.06 μg/mL — 32 μg/mL

Sclerotherapy [edit]

Doxycycline is also used for sclerotherapy in deadening-menstruum vascular malformations, namely venous and lymphatic malformations, too every bit post-operative lymphoceles.[39]

Others [edit]

Subantimicrobial-dose doxycycline (SDD) is widely used as an adjunctive handling to scaling and root planing for periodontitis. Significant differences were observed for all investigated clinical parameters of periodontitis in favor of the scaling and root planing + SDD grouping where SDD dosage regimens is 20 mg twice daily for 3 months in a meta-assay published in 2011.[forty]

Contraindications [edit]

Pregnancy and lactation [edit]

Doxycycline is categorized past the FDA every bit a class D drug in pregnancy. Doxycycline crosses into breastmilk.[41] Other tetracycline antibiotics are contraindicated in pregnancy and upwardly to viii years of age, due to the potential for disrupting bone and tooth evolution.[42] They include a class alarm almost staining of teeth and decreased evolution of dental enamel in children exposed to tetracyclines in utero, during breastfeeding or during young childhood.[43] However, the FDA has acknowledged that the actual adventure of dental staining of chief teeth is undetermined for doxycycline specifically. The best available evidence indicates that doxycycline has trivial or no effect on hypoplasia of dental enamel or on staining of teeth and the CDC recommends the use of doxycycline for treatment of Q fever and besides for tick-borne rickettsial diseases in young children and others abet for its use in malaria.[44]

Other [edit]

Other contraindications are severe liver affliction and concomitant apply of isotretinoin or other retinoids, as both tetracyclines and retinoids tin can cause intracranial hypertension (increased pressure around the brain) in rare cases.[45]

Adverse effects [edit]

Adverse effects are similar to those of other members of the tetracycline antibiotic grouping. Doxycycline can cause gastrointestinal upset.[46] [47] Oral doxycycline can cause pill esophagitis, particularly when it is swallowed without adequate fluid, or by persons with difficulty swallowing or impaired mobility.[48] Doxycycline is less likely than other antibiotic drugs to crusade Clostridium difficile colitis.[49]

An erythematous rash in sun-exposed parts of the body has been reported to occur in 7.3–21.ii% of persons taking doxycycline for malaria prophylaxis. One written report examined the tolerability of diverse malaria prophylactic regimens and establish doxycycline did not cause a significantly higher percent of all skin events (photosensitivity not specified) when compared with other antimalarials. The rash resolves upon discontinuation of the drug.[50]

Different another members of the tetracycline group, it may be used in those with renal impairment.[51]

Doxycycline use has been associated with increased take chances of inflammatory bowel disease.[52] In i large retrospective written report, patients who were prescribed doxycycline for their acne had a 2.25-fold greater risk of developing Crohn's disease.[53]

Interactions [edit]

The combination of doxycycline with dairy, antacids, calcium supplements, iron products, laxatives containing magnesium, or bile acid sequestrants is not inherently dangerous, but any of these foods and supplements may subtract doxycycline'southward effectiveness.[45] [54]

Breakfast was observed to reduce doxycycline assimilation significantly. Assimilation of tetracycline occurs in the stomach and the upper modest intestine. Assimilation of tetracyclines has been reported to be impaired by milk products, aluminum hydroxide gels, sodium bicarbonate, calcium and magnesium salts, laxatives containing magnesium and iron preparations. The mechanisms responsible for decreased assimilation appear to be chelation and an increment in gastric pH. ... In view of these results, it is advisable to instruct the patients to take doxycycline on an empty stomach.[55]

Previously, doxycycline was believed to impair the effectiveness of many types of hormonal contraception due to CYP450 induction. Enquiry has shown no pregnant loss of effectiveness in oral contraceptives while using most tetracycline antibiotics (including doxycycline), although many physicians notwithstanding recommend the use of barrier contraception for people taking the drug to foreclose unwanted pregnancy.[56] [57] [58]

Pharmacology [edit]

Doxycycline, similar other tetracycline antibiotics, is bacteriostatic. Information technology works past preventing bacteria from reproducing through the inhibition of poly peptide synthesis.[59]

Doxycycline is highly lipophilic so tin easily enter cells, pregnant the drug is easily absorbed afterward oral administration and has a large volume of distribution. Information technology can likewise exist re-absorbed in the renal tubules and gastrointestinal tract due to its high lipophillicity then has a long elimination half life, and does not accumulate in the kidneys of patients with kidney failure due to the compensatory excretion in faeces.[47] [60] Doxycycline–metal ion complexes are unstable at acid pH, therefore more doxycycline enters the duodenum for absorption than the earlier tetracycline compounds. In addition, nutrient has less effect on absorption than on assimilation of earlier drugs with doxycycline serum concentrations beingness reduced by about 20% by exam meals compared with l% for tetracycline.[61]

Mechanism of activity [edit]

Doxycycline is a broad-spectrum antibiotic. It inhibits the synthesis of bacterial proteins by binding to the 30S ribosomal subunit, which is only establish in bacteria.[46] [sixty] This prevents the binding of transfer RNA to messenger RNA at the ribosomal subunit significant amino acids cannot be added to polypeptide chains and new proteins cannot be made. This stops bacterial growth giving the immune organization time to kill and remove the leaner.[62]

Pharmacokinetics [edit]

The substance is about completely absorbed from the upper part of the pocket-size intestine. It reaches highest concentrations in the claret plasma after 1 to two hours and has a high plasma protein binding rate of about lxxx–xc%. Doxycycline penetrates into about all tissues and body fluids. Very loftier concentrations are constitute in the gallbladder, liver, kidneys, lung, breast milk, bone and genitals; low ones in saliva, aqueous sense of humor, cerebrospinal fluid (CSF), and especially in inflamed meninges.[45] [63] [64] Past comparing, the tetracycline antibody minocycline penetrates significantly better into the CSF and meninges.[65]

Doxycycline metabolism is negligible. Information technology is actively excreted into the gut (in part via the gallbladder, in part directly from blood vessels), where some of information technology is inactivated by forming chelates. Virtually 40% are eliminated via the kidneys, much less in people with end-stage kidney affliction. The biological half-life is 18 to 22 hours (16±six hours co-ordinate to some other source[63]) in healthy people, slightly longer in those with end-stage kidney disease, and significantly longer in those with liver disease.[45] [63] [64]

Chemistry [edit]

Expired tetracyclines or tetracyclines allowed to stand at a pH less than ii are reported to be nephrotoxic due to the germination of a degradation product, anhydro-four-epitetracycline[66] [67] causing Fanconi syndrome.[68] In the case of doxycycline, the absence of a hydroxyl group in C-6 prevents the formation of the nephrotoxic compound.[67] Nonetheless, tetracyclines and doxycycline itself have to be taken with circumspection in patients with kidney injury, every bit they tin can worsen azotemia due to catabolic effects.[68]

Chemic properties [edit]

Doxycycline, doxycycline monohydrate and doxycycline hyclate are xanthous, crystalline powders with a bitter taste. The latter smells faintly of ethanol; a ane% aqueous solution has a pH of two–3; and the specific rotation is [ α ] D 25 {\displaystyle [\alpha ]_{D}^{25}} −110° cm³/dm·g in 0.01 N methanolic hydrochloric acid.[63]

Solubility[63]
Solubility in Doxycycline Doxycycline monohydrate Doxycycline Hyclate
H2o very slightly very slightly freely
Ethanol very slightly very slightly sparingly
Aqueous acids freely freely
Alkali hydroxyde solutions freely freely
Chloroform very slightly practically insoluble practically insoluble
Diethyl ether insoluble practically insoluble practically insoluble

History [edit]

After penicillin revolutionized the handling of bacterial infections in WWII, many chemic companies moved into the field of discovering antibiotics past bioprospecting. American Cyanamid was one of these, and in the late 1940s chemists at that place discovered chlortetracycline, the starting time member of the tetracycline grade of antibiotics.[2] Shortly thereafter, scientists at Pfizer discovered terramycin and it was brought to marketplace. Both compounds, like penicillin, were natural products and information technology was ordinarily believed that nature had perfected them, and further chemical changes could only degrade their effectiveness. Scientists at Pfizer led by Lloyd Conover modified these compounds, which led to the invention of tetracycline itself, the start semi-synthetic antibiotic. Charlie Stephens' group at Pfizer worked on further analogs and created one with greatly improved stability and pharmacological efficacy: doxycycline. It was clinically developed in the early 1960s and approved by the FDA in 1967.[2]

As its patent grew most to expiring in the early on 1970s, the patent became the subject of lawsuit between Pfizer and International Rectifier[69] that was not resolved until 1983; at the fourth dimension it was the largest litigated patent case in The states history.[70] Instead of a cash payment for infringement, Pfizer took the veterinary and feed-additive businesses of International Rectifier'south subsidiary, Rachelle Laboratories.[70]

In Jan 2013, the FDA reported shortages of some, but not all, forms of doxycycline "acquired by increased need and manufacturing issues".[71] Companies involved included an unnamed major generics manufacturer that ceased production in February 2013, Teva (which ceased production in May 2013), Mylan, Actavis, and Hikma Pharmaceuticals.[72] [73] The shortage came at a specially bad time, since at that place were also shortages of an culling antibiotic, tetracycline, at the same time.[74] The market cost for doxycycline dramatically increased in the United States in 2013 and early on 2014 (from $xx to over $1800 for a canteen of 500 tablets),[75] [76] [77] earlier decreasing over again.[78] [79]

Order and culture [edit]

Doxycycline is available worldwide under many brand names.[80] Doxycycline is available equally a generic medicine.[1] [8]

Enquiry [edit]

Research areas have included:

  • Macular degeneration[81]
  • Rheumatoid arthritis instead of minocycline (both of which have demonstrated modest efficacy for this illness)[82]

Tet-ON inducible shRNA arrangement

Enquiry reagent [edit]

Doxycycline and other members of the tetracycline course of antibiotics are often used equally inquiry reagents in in vitro and in vivo biomedical research experiments involving bacteria besides in experiments in eukaryotic cells and organisms with inducible protein expression systems using tetracycline-controlled transcriptional activation. The mechanism of action for the antibacterial event of tetracyclines relies on disrupting protein translation in bacteria, thereby damaging the ability of microbes to grow and repair; however poly peptide translation is also disrupted in eukaryotic mitochondria impairing metabolism and leading to furnishings that tin can confound experimental results.[83] [84] Doxycycline is also used in "tet-on" (factor expression activated past doxycycline) and "tet-off" (cistron expression inactivated past doxycycline) tetracycline-controlled transcriptional activation to regulate transgene expression in organisms and cell cultures.[85] Doxycycline is more stable than tetracycline for this purpose.[85] At subantimicrobial doses, doxycycline is an inhibitor of matrix metalloproteases, and has been used in various experimental systems for this purpose, such as for recalcitrant recurrent corneal erosions.[86]

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External links [edit]

  • "Doxycycline". Drug Information Portal. U.S. National Library of Medicine.

Source: https://en.wikipedia.org/wiki/Doxycycline

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