Doxycycline
Identification
- Name
- Doxycycline
- Accession Number
- DB00254
- Description
Doxycycline is a broad-spectrum antibiotic synthetically derived from oxytetracycline Label. This drug is a second-generation tetracycline, exhibiting lesser toxicity than first-generation tetracyclines 7. Doxycycline may be used to treat a wide range of bacterial infections, depending on the results of antibiotic susceptibility testing.
- Type
- Small Molecule
- Groups
- Approved, Investigational, Vet approved
- Structure
- Weight
- Average: 444.4346
Monoisotopic: 444.153265754 - Chemical Formula
- C22H24N2O8
- Synonyms
- 5-hydroxy-α-6-deoxytetracycline
- 6-alpha-deoxy-5-oxytetracycline
- 6alpha-deoxy-5-oxytetracycline
- 6α-deoxy-5-oxytetracycline
- Anhydrous doxycycline
- Doxiciclina
- Doxycyclin
- Doxycycline
- Doxycycline (anhydrous)
- Doxycycline anhydrous
- Doxycyclinum
Pharmacology
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- Indication
Doxycycline is indicated for the treatment of various infections by gram-positive and gram-negative bacteria, aerobes and anaerobes, as well other types of bacteria. A complete list of organisms is available in the FDA label and in the "indications" section of this drug entry Label.
The following are some of the major infections that may be treated with doxycycline Label:
Rocky mountain spotted fever, typhus fever and the typhus group, Q fever, rickettsialpox, and tick fevers caused by Rickettsiae
Respiratory tract infections caused by Mycoplasma pneumoniae
Lymphogranuloma venereum caused by Chlamydia trachomatis
Psittacosis (ornithosis) caused by Chlamydia psittaci
Trachoma caused by Chlamydia trachomatis, although the infectious agent is not always eliminated as judged by immunofluorescence
Inclusion conjunctivitis caused by Chlamydia trachomatis
Uncomplicated urethral, endocervical or rectal infections in adults caused by Chlamydia trachomatis
Nongonococcal urethritis caused by Ureaplasma urealyticum
Relapsing fever due to Borrelia recurrentis
A note regarding anti-microbial resistance
It is important to note that doxycycline is not the drug of choice in the treatment of any type of staphylococcal infection. Up to 44 percent of strains of Streptococcus pyogenes and 74 percent of Streptococcus faecalis have been found to be resistant to tetracyclines. Therefore, tetracyclines such as doxycycline should not be used to treat streptococcal infections unless the microorganism has been demonstrated to be susceptible Label.
- Associated Conditions
- Acinetobacter infection
- Acne Rosacea
- Actinomycosis
- Acute epididymo-orchitis caused by Chlamydia Trachomatis
- Anal chlamydia infection
- Bacterial Infection caused by Enterobacter aerogenes
- Bartonellosis
- Brucellosis
- Campylobacter Infection
- Chancroid
- Chlamydial Urethritis
- Chlamydial cervicitis
- Cholera
- Clostridium Infections
- Epididymo-orchitis gonococcal
- Gonorrhea
- Granuloma Inguinale
- Infection Due to Escherichia Coli
- Intestinal Amebiasis
- Listeria infection
- Lymphogranuloma Venereum
- Necrotizing ulcerative gingivostomatitis
- Plague
- Plasmodium Infections
- Primary Syphilis
- Psittacosis
- Q Fever
- Rectal infection
- Rectal infection caused by Chlamydia Trachomatis
- Recurring fever caused by Borrelia recurrentis
- Relapsing fever caused by Borrelia recurrentis
- Respiratory Tract Infections (RTI)
- Rickettsialpox
- Rocky Mountain Spotted Fever
- Secondary Syphilis
- Severe Acne
- Shigella Infection
- Skin Infections
- Tick-borne fever
- Trachoma
- Trachoma inclusion conjunctivitis
- Tularemia
- Typhus Fever
- Upper Respiratory Tract Infection
- Ureaplasma urethritis
- Urinary Tract Infection
- Yaws
- Inhaled anthrax caused by Bacillus anthracis
- Contraindications & Blackbox Warnings
- Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects
- Pharmacodynamics
The tetracyclines, including doxycycline, are mainly bacteriostatic and are thought to exert antimicrobial effects by the inhibition of protein synthesis. Bacteriostatic antibiotics suppress the growth of bacteria, or keep them in the stationary phase of growth 4. The tetracyclines, including doxycycline, have a similar antimicrobial spectrum of activity against a variety of gram-positive and gram-negative microorganisms, treating numerous infectious diseases. Cross-resistance of these microorganisms to tetracyclines is a common occurrence Label. Doxycycline shows favorable intra-cellular penetration, with bacteriostatic activity on a wide range of bacteria 5. Doxycycline has antiparasitic effects 2, 3, 4. In addition to the above effects, this drug has demonstrated anti-inflammatory actions, which may help to manage inflammatory conditions such as rosacea 6.
- Mechanism of action
In bacterial replication, an interaction that is important for translation initiation of proteins occurs at the 3′ end of the 16S rRNA, found on the ribosome on the 30S subunit 12, 11, 13. The 30S subunit is the smaller subunit of the ribosome of prokaryotes, including bacteria16.
Tetracyclines such as doxycycline are thought to inhibit translation by binding to the 16S rRNA portion of the ribosome 9, preventing binding of tRNA to the RNA-30S bacterial ribosomal subunit, which is necessary for the delivery of amino acids for protein synthesis. As a result of the above actions, the initiation of protein synthesis by polyribosome formation is blocked. This stops the replication of bacteria and produces a bacteriostatic effect 14.
Target Actions Organism A16S ribosomal RNA binderEnteric bacteria and other eubacteria - Absorption
Tetracyclines, such as doxycycline, are readily absorbed and are bound to plasma proteins by varying degrees. Doxycycline is almost completely absorbed after oral administration. This drug is highly lipid soluble and has a low affinity for calcium binding Label. Absorption is not significantly affected by the concomitant ingestion of food or milk 14. Peak serum levels of approximately 2.6 mcg/ml are reached at 2 hours following a 200 mg tablet oral dose 14.
- Volume of distribution
Doxycycline diffuses readily into most body tissues, fluid and/or cavities and the volume of distribution has been measured as 0.7 L/kg 14.
- Protein binding
- Metabolism
Doxycycline is metabolized in the liver and gastrointestinal tract and concentrated in bile Label, 15. Major metabolic pathways of doxycycline have not been identified, however, enzyme inducers have been found to decrease the half-life of doxycycline 15.
- Route of elimination
Mainly the urine and feces as active and unchanged drug Label. Between 40% and 60% of an administered dose can be accounted for in the urine by 92 hours, and approximately 30% can be accounted for in the feces 15.
- Half-life
16.33 hr (± 4.53 sd) Label.
- Clearance
The excretion of doxycycline by the kidney is about 40% over 72 hours in individuals with normal kidney function (creatinine clearance approximately 75 mL/min). This rate may fall as low as 1-5% over 72 hours in individuals with severe renal insufficiency (creatinine clearance below 10 mL/min). Some clinical studies have shown no major difference in serum half-life of doxycycline (range 18-22 hours) in patients with normal and severely impaired renal function. Hemodialysis does not affect serum half-life of doxycycline Label.
- Adverse Effects
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- Toxicity
There are various precautions to be undertaken while doxycyline is administered 14. A full list of adverse events is included in the "Adverse Effects" section of this drug entry.
A note on tooth development and tetracycline use
The use of tetracyclines, including doxycycline, during tooth development (i.e. the last half of pregnancy, throughout infancy, and in childhood up to 8 years of age) may lead to tooth enamel hypoplasia and yellow-gray discoloration of teeth. It is advisable not to administer doxycycline in this age group according to the FDA label, except for in cases of post-exposure cases of anthrax (including inhalational anthrax) Label. Other sources state that doxycycline should not be administered in children under 12 years 14.
A note on Clostridium difficile Clostridium difficile associated diarrhea (CDAD) and antibiotic associated pseudomembranous colitis may result from doxycycline use. Administering antibacterial agents changes the normal flora of the colon leading to an overgrowth of C. difficile. This bacteria produces toxins A and B, which contribute to the development of CDAD 14. in moderate to severe cases, therapy with a suitable oral antibacterial agent effective against Clostridium difficile should be considered. Fluids, electrolytes and protein replacement should be provided when warranted 14.
A note on gastrointestinal irritation Gastrointestinal irritation may also occur. Rarely, esophagitis and esophageal ulcers have been reported in patients receiving doxycycline. Most of these patients took medication immediately before going to bed. Administration of appropriate amounts of fluid with the tablets is recommended to reduce the risk of esophageal irritation and ulceration, and late evening ingestion of the dose should be avoided 14. To decrease the risk of gastric irritation, it is recommended that doxycycline is taken with food or milk. The absorption of doxycycline is not significantly influenced by simultaneous ingestion of food or milk 14.
Pregnancy Results of animal research indicate that tetracyclines cross the placenta, are found in fetal tissues and exert toxic effects on the developing fetus, manifested by retardation of skeletal development. The importance of this in humans is not known, however, doxycycline should not be used in pregnant women unless the benefit significantly outweighs the risk 14.
Carcinogenicity In vivo studies conducted in rats and mice have not provided conclusive evidence that tetracyclines may be carcinogenic or that they affect fertility. In two mammalian cell lines, positive tests for mutagenicity occurred at concentrations of 60 and 10 mcg/ml respectively. In humans, no association between tetracyclines and these effects have been established 14.
- Affected organisms
- Humans and other mammals
- Pathways
Pathway Category Doxycycline Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Doxycycline may decrease the excretion rate of Abacavir which could result in a higher serum level. Abametapir The serum concentration of Doxycycline can be increased when it is combined with Abametapir. Abciximab The risk or severity of bleeding can be increased when Doxycycline is combined with Abciximab. Abemaciclib The metabolism of Abemaciclib can be decreased when combined with Doxycycline. Acalabrutinib The metabolism of Acalabrutinib can be decreased when combined with Doxycycline. Aceclofenac Aceclofenac may decrease the excretion rate of Doxycycline which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Doxycycline which could result in a higher serum level. Acenocoumarol The risk or severity of bleeding can be increased when Doxycycline is combined with Acenocoumarol. Acetaminophen Doxycycline may decrease the excretion rate of Acetaminophen which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Doxycycline which could result in a lower serum level and potentially a reduction in efficacy. Improve patient outcomesBuild effective decision support tools with the industry’s most comprehensive drug-drug interaction checker.Learn more - Food Interactions
- Avoid alcohol.
- Avoid multivalent ions. Calcium, iron, and aluminum containing products taken up to 2 hours before and 6 hours after administration can decrease drug concentrations.
- Take with a full glass of water.
Products
- Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets
- Product Ingredients
Ingredient UNII CAS InChI Key Doxycycline calcium 8ZL07I20SB 94088-85-4 IYECPECUTCOMMD-QFWOMMJSSA-N Doxycycline hyclate 19XTS3T51U 24390-14-5 HALQELOKLVRWRI-VDBOFHIQSA-N Doxycycline hydrochloride 4182Z6T2ET 10592-13-9 RUYHIJHUVHIMIR-CVHRZJFOSA-N Doxycycline monohydrate N12000U13O 17086-28-1 XQTWDDCIUJNLTR-CVHRZJFOSA-N - Product Images
- International/Other Brands
- Doxy (Galpharma) / Doxycin (Laboratoire Riva) / Doxylin (Actavis) / Jenacyclin / Microdox (Micro Labs) / NicAzelDoxyKit / Nu-Doxycycline (Nu-Pharm) / Supracyclin (Grünenthal) / Vibramycin (Pfizer)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Acticlate Tablet, coated 75 mg/1 Oral Almirall, LLC 2014-07-28 Not applicable US Acticlate Tablet, coated 150 mg/1 Oral Almirall, LLC 2014-07-28 Not applicable US Acticlate CAP Capsule 75 mg/1 Oral Aqua Pharmaceuticals 2018-05-31 Not applicable US Apprilon 40 mg Oral Galderma 2012-11-29 Not applicable Canada Atridox Kit 50 mg/1 Oral Den-mat Holdings, Llc 2016-12-01 2021-12-31 US Atridox 8.8 % Oral Den Mat Holdings, Llc 2001-01-31 Not applicable Canada Atridox Kit 50 mg/500mg Oral TOLMAR Inc. 1998-09-03 2018-10-01 US Doryx Tablet, delayed release 100 mg/1 Oral Allergan 2005-09-01 2011-08-01 US Doryx Tablet, delayed release 200 mg/1 Oral Mayne Pharma Inc. 2015-04-13 Not applicable US Doryx Capsule, delayed release pellets 100 mg/1 Oral Physicians Total Care, Inc. 1985-07-22 2000-09-19 US - Generic Prescription Products
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image BenoxylDoxy 30 Kit Doxycycline monohydrate (100 mg/1) + Benzoyl peroxide (44 mg/1mL) Kit Oral; Topical Elorac, Inc. 2014-07-01 2014-08-07 US BenoxylDoxy 60 Kit Doxycycline monohydrate (100 mg/1) + Benzoyl peroxide (44 mg/1mL) Kit Oral; Topical Elorac, Inc. 2014-07-01 2015-07-18 US BenzoDox 30 Kit Doxycycline monohydrate (100 mg/1) + Benzoyl peroxide (44 mg/1mL) Kit Oral; Topical Elorac, Inc. 2015-10-01 Not applicable US BenzoDox 60 Kit Doxycycline monohydrate (100 mg/1) + Benzoyl peroxide (44 mg/1mL) Kit Oral; Topical Elorac, Inc. 2015-09-22 Not applicable US NicAzel Doxy Kit Doxycycline monohydrate (100 mg/1) + Cupric oxide (2 mg/1) + Folic acid (500 ug/1) + Pyridoxine (8 mg/1) + Zinc oxide (12 mg/1) Kit Oral Elorac, Inc. 2014-06-30 2015-07-30 US
Categories
- ATC Codes
- J01AA02 — Doxycycline
- J01AA — Tetracyclines
- J01A — TETRACYCLINES
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- A01AB — Antiinfectives and antiseptics for local oral treatment
- A01A — STOMATOLOGICAL PREPARATIONS
- A01 — STOMATOLOGICAL PREPARATIONS
- A — ALIMENTARY TRACT AND METABOLISM
- Drug Categories
- Agents that produce neuromuscular block (indirect)
- Alimentary Tract and Metabolism
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives and Antiseptics for Local Oral Treatment
- Antiinfectives for Systemic Use
- Antiparasitic Agents
- Antiprotozoals
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Drugs causing inadvertant photosensitivity
- Drugs that are Mainly Renally Excreted
- Naphthacenes
- OAT1/SLC22A6 inhibitors
- Photosensitizing Agents
- Stomatological Preparations
- Tetracyclines
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as tetracyclines. These are polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Tetracyclines
- Sub Class
- Not Available
- Direct Parent
- Tetracyclines
- Alternative Parents
- Naphthacenes / Anthracenecarboxylic acids and derivatives / Tetralins / Aryl ketones / 1-hydroxy-2-unsubstituted benzenoids / 1-hydroxy-4-unsubstituted benzenoids / Aralkylamines / Cyclohexenones / Tertiary alcohols / Vinylogous acids show 9 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Alcohol / Amine / Amino acid or derivatives / Anthracene carboxylic acid or derivatives / Aralkylamine / Aromatic homopolycyclic compound / Aryl ketone / Benzenoid show 24 more
- Molecular Framework
- Aromatic homopolycyclic compounds
- External Descriptors
- tetracyclines (CHEBI:50845) / Linear tetracyclines (C06973) / Linear tetracyclines (LMPK07000001)
Chemical Identifiers
- UNII
- 334895S862
- CAS number
- 564-25-0
- InChI Key
- JBIWCJUYHHGXTC-AKNGSSGZSA-N
- InChI
- InChI=1S/C22H24N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-7,10,14-15,17,25,27-29,32H,1-3H3,(H2,23,31)/t7-,10+,14+,15-,17-,22-/m0/s1
- IUPAC Name
- (4S,4aR,5S,5aR,6R,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
- SMILES
- [H][C@@]12[C@@H](C)C3=CC=CC(O)=C3C(=O)C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]1([H])[C@H]2O
References
- Synthesis Reference
Dai-Wu Seol, "DNA cassette for the production of secretable recombinant trimeric TRAIL proteins, tetracycline/ doxycycline-inducible adeno-associated virus vector, their combination and use in gene therapy." U.S. Patent US20020128438, issued September 12, 2002.
US20020128438- General References
- Dahl EL, Shock JL, Shenai BR, Gut J, DeRisi JL, Rosenthal PJ: Tetracyclines specifically target the apicoplast of the malaria parasite Plasmodium falciparum. Antimicrob Agents Chemother. 2006 Sep;50(9):3124-31. [PubMed:16940111]
- Hoerauf A, Mand S, Fischer K, Kruppa T, Marfo-Debrekyei Y, Debrah AY, Pfarr KM, Adjei O, Buttner DW: Doxycycline as a novel strategy against bancroftian filariasis-depletion of Wolbachia endosymbionts from Wuchereria bancrofti and stop of microfilaria production. Med Microbiol Immunol. 2003 Nov;192(4):211-6. Epub 2003 Mar 5. [PubMed:12684759]
- Taylor MJ, Makunde WH, McGarry HF, Turner JD, Mand S, Hoerauf A: Macrofilaricidal activity after doxycycline treatment of Wuchereria bancrofti: a double-blind, randomised placebo-controlled trial. Lancet. 2005 Jun 18-24;365(9477):2116-21. [PubMed:15964448]
- Bernatova S, Samek O, Pilat Z, Sery M, Jezek J, Jakl P, Siler M, Krzyzanek V, Zemanek P, Hola V, Dvorackova M, Ruzicka F: Following the mechanisms of bacteriostatic versus bactericidal action using Raman spectroscopy. Molecules. 2013 Oct 24;18(11):13188-99. doi: 10.3390/molecules181113188. [PubMed:24284484]
- Bonnetblanc JM: [Doxycycline]. Ann Dermatol Venereol. 2002 Jun-Jul;129(6-7):874-82. [PubMed:12218915]
- Valentin S, Morales A, Sanchez JL, Rivera A: Safety and efficacy of doxycycline in the treatment of rosacea. Clin Cosmet Investig Dermatol. 2009 Aug 12;2:129-40. [PubMed:21436975]
- Smilack JD: The tetracyclines. Mayo Clin Proc. 1999 Jul;74(7):727-9. doi: 10.4065/74.7.727. [PubMed:10405705]
- Weinberg JM: The anti-inflammatory effects of tetracyclines. Cutis. 2005 Apr;75(4 Suppl):6-11. [PubMed:15916224]
- Chukwudi CU: rRNA Binding Sites and the Molecular Mechanism of Action of the Tetracyclines. Antimicrob Agents Chemother. 2016 Jul 22;60(8):4433-41. doi: 10.1128/AAC.00594-16. Print 2016 Aug. [PubMed:27246781]
- Nguyen F, Starosta AL, Arenz S, Sohmen D, Donhofer A, Wilson DN: Tetracycline antibiotics and resistance mechanisms. Biol Chem. 2014 May;395(5):559-75. doi: 10.1515/hsz-2013-0292. [PubMed:24497223]
- Chopra I, Roberts M: Tetracycline antibiotics: mode of action, applications, molecular biology, and epidemiology of bacterial resistance. Microbiol Mol Biol Rev. 2001 Jun;65(2):232-60 ; second page, table of contents. [PubMed:11381101]
- Laursen BS, Sorensen HP, Mortensen KK, Sperling-Petersen HU: Initiation of protein synthesis in bacteria. Microbiol Mol Biol Rev. 2005 Mar;69(1):101-23. doi: 10.1128/MMBR.69.1.101-123.2005. [PubMed:15755955]
- Xu Z, Culver GM: Differential assembly of 16S rRNA domains during 30S subunit formation. RNA. 2010 Oct;16(10):1990-2001. doi: 10.1261/rna.2246710. Epub 2010 Aug 24. [PubMed:20736336]
- Doxycycline MedSafe NZ [File]
- Doxycycline EMA label [File]
- Antibiotics that affect the ribosome [File]
- External Links
- Human Metabolome Database
- HMDB0014399
- KEGG Drug
- D07876
- KEGG Compound
- C06973
- PubChem Compound
- 54671203
- PubChem Substance
- 46506491
- ChemSpider
- 10469369
- BindingDB
- 50041429
- 1545992
- ChEBI
- 50845
- ChEMBL
- CHEMBL1433
- ZINC
- ZINC000016052277
- Therapeutic Targets Database
- DAP001371
- PharmGKB
- PA449415
- PDBe Ligand
- DXT
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Doxycycline
- AHFS Codes
- 52:04.04 — Antibacterials
- 08:12.24 — Tetracyclines
- PDB Entries
- 2o7o / 2xrl / 5om2 / 5om3 / 6rbl / 6rcr / 6rgx
- FDA label
- Download (157 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Prevention Human Immunodeficiency Virus (HIV) Infections / Syphilis 1 4 Active Not Recruiting Treatment Epistaxis 1 4 Active Not Recruiting Treatment Exacerbation of Ulcerative Colitis / Granulomatous Colitis / Ulcerative Colitis, Active Severe 1 4 Completed Basic Science Bacterial Infections 1 4 Completed Basic Science Rabies 1 4 Completed Prevention Endometritis 1 4 Completed Prevention Medically induced abortion / Pregnancy Termination / Vomiting 1 4 Completed Supportive Care Acne Rosacea 1 4 Completed Treatment Acne 2 4 Completed Treatment Acne Rosacea 4
Pharmacoeconomics
- Manufacturers
- Mylan pharmaceuticals inc
- Par pharmaceutical inc
- Ranbaxy laboratories ltd
- Sandoz inc
- Watson laboratories inc
- Watson pharmaceuticals inc
- Galderma laboratories lp
- Rachelle laboratories inc
- Ivax pharmaceuticals inc sub teva pharmaceuticals usa
- Pfizer laboratories div pfizer inc
- Lannett holdings inc
- Mutual pharmaceutical co inc
- Pliva inc
- Mayne pharma international faulding pharm
- Warner chilcott bermuda ltd
- Medicis pharmaceutical corp
- Halsey drug co inc
- Heather drug co inc
- Interpharm inc
- Private formulations inc
- Ranbaxy pharmaceuticals inc
- Superpharm corp
- Warner chilcott div warner lambert co
- West ward pharmaceutical corp
- Teva pharmaceuticals usa inc
- Collagenex inc
- App pharmaceuticals llc
- Baxter healthcare corp anesthesia and critical care
- Bedford laboratories div ben venue laboratories inc
- Tolmar inc
- Corepharma llc
- Larken laboratories inc
- Mutual pharmacal co
- Truxton inc
- Vintage pharmaceuticals inc
- Packagers
- Actavis Group
- Acura Pharmaceutical Technologies Inc.
- Advanced Pharmaceutical Services Inc.
- Advanced Vision Research
- Aidarex Pharmacuticals LLC
- Amerisource Health Services Corp.
- Amneal Pharmaceuticals
- Apace Packaging
- Apical Pharmaceutical Corporation
- Apotheca Inc.
- Apothecon
- APP Pharmaceuticals
- Aqua Pharmaceuticals
- A-S Medication Solutions LLC
- Avidas Pharmaceuticals
- Bedford Labs
- Belgomex Sprl
- Ben Venue Laboratories Inc.
- Bioglan Pharmaceuticals Co.
- Blenheim Pharmacal
- Block Drug Corp.
- Blu Pharmaceuticals LLC
- Bryant Ranch Prepack
- Bv Pharbita
- Cardinal Health
- Carlisle Laboratories Inc.
- Catalent Pharma Solutions
- Collagenex Pharmaceuticals Inc.
- Community Action Inc. Community Health Services
- Comprehensive Consultant Services Inc.
- Corepharma LLC
- Coupler Enterprises Inc.
- Darby Dental Supply Co. Inc.
- Dept Health Central Pharmacy
- DHHS Program Support Center Supply Service Center
- Direct Dispensing Inc.
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- DSM Corp.
- Eon Labs
- Galderma Laboratories
- Golden State Medical Supply Inc.
- Goldline Laboratories Inc.
- H and H Laboratories
- H.J. Harkins Co. Inc.
- Hikma Pharmaceuticals
- Innoviant Pharmacy Inc.
- Ivax Pharmaceuticals
- Kaiser Foundation Hospital
- Keltman Pharmaceuticals Inc.
- Lake Erie Medical and Surgical Supply
- Lannett Co. Inc.
- Liberty Pharmaceuticals
- Major Pharmaceuticals
- Mayne Pharma International Pty Ltd.
- Mckesson Corp.
- Medisca Inc.
- Medvantx Inc.
- Mississippi State Dept Health
- Murfreesboro Pharmaceutical Nursing Supply
- Mutual Pharmaceutical Co.
- Mylan
- Nucare Pharmaceuticals Inc.
- Oclassen Pharmaceuticals Inc.
- Ohm Laboratories Inc.
- Palmetto Pharmaceuticals Inc.
- Par Pharmaceuticals
- Patheon Inc.
- Patient First Corp.
- PCA LLC
- PD-Rx Pharmaceuticals Inc.
- Pfizer Inc.
- Pharmaceutical Manufacturing Research Services Inc.
- Pharmaceutical Utilization Management Program VA Inc.
- Pharmaderm
- Pharmedix
- Pharmpak Inc.
- Physicians Total Care Inc.
- Pliva Inc.
- Preferred Pharmaceuticals Inc.
- Prepackage Specialists
- Prepak Systems Inc.
- Qualitest
- Ranbaxy Laboratories
- Rebel Distributors Corp.
- Redpharm Drug
- Remedy Repack
- Sandhills Packaging Inc.
- Sandoz
- Southwood Pharmaceuticals
- St Mary's Medical Park Pharmacy
- Stat Rx Usa
- Teva Pharmaceutical Industries Ltd.
- Tolmar Inc.
- Tya Pharmaceuticals
- Universal Laboratories Inc.
- Veratex Corp.
- Versapharm Inc.
- Warner Chilcott Co. Inc.
- Watson Pharmaceuticals
- WC Pharmaceuticals
- West-Ward Pharmaceuticals
- Dosage Forms
Form Route Strength Capsule Oral 150 mg/1 Kit Oral 50 mg/1 Kit Oral 50 mg/500mg Kit Oral; Topical Capsule, delayed release pellets Oral 100 mg/1 Capsule, delayed release pellets Oral 75 mg/1 Tablet, delayed release Oral 150 mg/1 Tablet, delayed release Oral 80 mg/1 Capsule, extended release Oral Tablet, delayed release Oral 120 mg/1 Tablet, delayed release Oral 60 mg/1 Capsule Oral Capsule, coated Oral 100 mg Tablet Oral 100 mg Tablet, soluble Oral Tablet Oral For suspension Oral 25 mg/5mL Injection, powder, for solution Intravenous 100 mg/1 Injection, powder, lyophilized, for solution Intravenous 100 mg/10mL Injection, powder, lyophilized, for solution Intravenous 200 mg/20mL Powder, for suspension Oral 25 mg/5mL Tablet, coated Oral 100 mg/1 Tablet, film coated Oral 150 mg/1 Tablet, film coated Oral 50 mg/1 Tablet, film coated Oral 75 mg/1 Capsule Oral 100 mg/1 Capsule Oral 50 mg/1 Capsule, gelatin coated Oral 100 mg/1 Capsule, gelatin coated Oral 50 mg/1 Powder Not applicable 1 g/1g Tablet Oral 100 mg/1 Tablet, coated Oral 150 mg/1 Tablet, coated Oral 75 mg/1 Tablet, delayed release Oral 100 mg/1 Tablet, delayed release Oral 200 mg/1 Tablet, delayed release Oral 50 mg/1 Tablet, delayed release Oral 75 mg/100mg Tablet, delayed release Oral 75 mg/1 Tablet, film coated Oral 100 1/1 Tablet, film coated Oral 100 mg/1 Tablet, film coated Oral 20 mg/1 Tablet Oral 150 mg/1 Tablet Oral 50 mg/1 Tablet Oral 75 mg/1 Tablet, film coated Oral Tablet, coated Oral Capsule, coated Oral Gel Periodontal Capsule Oral 50 mg/50mg Capsule Oral 100 mg/100mg Capsule Oral 75 mg/1 Capsule Oral; Topical 50 mg/1 Kit Oral Capsule Oral 40 mg/1 Capsule, delayed release pellets Oral 40 mg/1 Capsule, extended release Oral 40 mg Capsule, delayed release Oral Capsule Oral 20 mg Tablet Oral 20 mg/1 Capsule Oral 100 MG Syrup Oral 50 mg/5mL Powder Intravenous Solution Intravenous Tablet, delayed release Oral Tablet, film coated Oral 100 mg - Prices
Unit description Cost Unit Vibramycin 25 mg/5ml Suspension 60ml Bottle 36.29USD bottle Adoxa pak 1-150 mg tablet 19.93USD tablet Doryx 150 mg Enteric Coated Tabs 17.51USD tab Doryx dr 150 mg tablet 16.83USD tablet Doxycycline hyc 100 mg vial 14.16USD vial Adoxa 100 mg tablet 13.86USD tablet Monodox 100 mg capsule 13.46USD capsule Adoxa 75 mg tablet 12.77USD tablet Oracea 40 mg Delayed Release Capsule 12.44USD capsule Oracea 40 mg capsule 11.96USD capsule Avidoxy 100 mg tablet 11.52USD tablet Monodox 75 mg capsule 11.02USD capsule Doryx 100 mg Enteric Coated Tabs 10.31USD tab Doryx dr 100 mg tablet 9.91USD tablet Adoxa pak 1-100 mg tablet 9.88USD tablet Doxycycline Monohydrate 150 mg tablet 9.51USD tablet Adoxa 50 mg tablet 9.29USD tablet Doxycycline mono 150 mg tablet 9.13USD tablet Doryx 75 mg Enteric Coated Tabs 8.76USD tab Doryx dr 75 mg tablet 8.42USD tablet Vibramycin 100 mg capsule 6.67USD capsule Vibra-tabs 100 mg tablet 6.67USD tablet Monodox 50 mg capsule 6.0USD capsule Doxycycline mono 100 mg tablet 5.98USD tablet Periostat 20 mg tablet 5.75USD tablet Doxycycline mono 75 mg tablet 5.74USD tablet Doxycycline Monohydrate 100 mg tablet 5.12USD tablet Doxycycline mono 50 mg tablet 4.17USD tablet Doxycycline Monohydrate 50 mg tablet 3.0USD tablet Doxycycline hyclate powder 2.56USD g Vibramycin 50 mg capsule 2.41USD capsule Doxycycline Monohydrate 100 mg capsule 2.22USD capsule Vibramycin 100 mg Capsule 1.91USD capsule Doxycycline Monohydrate 50 mg capsule 1.51USD capsule Doxycycline hyclate 100 mg tablet 1.28USD tablet Doxycycline hyclate 20 mg tablet 1.28USD tablet Doxycycline Hyclate 100 mg capsule 1.18USD capsule Doxycycline Hyclate 50 mg capsule 0.76USD capsule Vibramycin 50 mg/5ml Syrup 0.67USD ml Vibramycin 50 mg/5 ml syrup 0.64USD ml Apo-Doxy 100 mg Capsule 0.61USD capsule Apo-Doxy 100 mg Tablet 0.61USD tablet Doxycin 100 mg Capsule 0.61USD capsule Doxycin 100 mg Tablet 0.61USD tablet Novo-Doxylin 100 mg Capsule 0.61USD capsule Novo-Doxylin 100 mg Tablet 0.61USD tablet Nu-Doxycycline 100 mg Capsule 0.61USD capsule Pms-Doxycycline 100 mg Capsule 0.61USD capsule Pms-Doxycycline 100 mg Tablet 0.61USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US6958161 No 2005-10-25 2022-12-15 US US8715724 No 2014-05-06 2028-02-03 US US7211267 No 2007-05-01 2022-04-05 US US7232572 No 2007-06-19 2022-04-05 US US7749532 No 2010-07-06 2027-12-19 US US8206740 No 2012-06-26 2025-12-24 US US8394405 No 2013-03-12 2024-04-07 US US8394406 No 2013-03-12 2024-04-07 US US8470364 No 2013-06-25 2024-04-07 US US8603506 No 2013-12-10 2022-04-05 US US5789395 No 1998-08-04 2016-08-30 US US5919775 No 1999-07-06 2016-08-30 US US8709478 No 2014-04-29 2024-04-07 US US9241946 No 2016-01-26 2022-04-05 US US9511031 No 2016-12-06 2034-10-23 US US9446057 No 2016-09-20 2034-12-23 US US9295652 No 2016-03-29 2034-10-23 US US10058564 No 2018-08-28 2022-04-05 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 201 °C https://www.sigmaaldrich.com/content/dam/sigma-aldrich/docs/Sigma/Product_Information_Sheet/d9891pis.pdf water solubility 50 mg/mL https://www.sigmaaldrich.com/content/dam/sigma-aldrich/docs/Sigma/Product_Information_Sheet/d9891pis.pdf logP 0.63 https://deepblue.lib.umich.edu/bitstream/handle/2027.42/64911/21954_ftp.pdf?sequence=1 pKa 3.09 https://www.ncbi.nlm.nih.gov/pubmed/34018 - Predicted Properties
Property Value Source Water Solubility 0.63 mg/mL ALOGPS logP -0.72 ALOGPS logP -3.3 ChemAxon logS -2.8 ALOGPS pKa (Strongest Acidic) 3.27 ChemAxon pKa (Strongest Basic) 8.33 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 9 ChemAxon Hydrogen Donor Count 6 ChemAxon Polar Surface Area 181.62 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 113.89 m3·mol-1 ChemAxon Polarizability 43.65 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.85 Blood Brain Barrier - 0.9881 Caco-2 permeable - 0.8706 P-glycoprotein substrate Substrate 0.699 P-glycoprotein inhibitor I Non-inhibitor 0.8038 P-glycoprotein inhibitor II Non-inhibitor 0.8628 Renal organic cation transporter Non-inhibitor 0.9562 CYP450 2C9 substrate Non-substrate 0.8008 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Substrate 0.6551 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9144 CYP450 2D6 inhibitor Non-inhibitor 0.9293 CYP450 2C19 inhibitor Non-inhibitor 0.9099 CYP450 3A4 inhibitor Non-inhibitor 0.8567 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8086 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.8632 Biodegradation Not ready biodegradable 0.9941 Rat acute toxicity 2.3159 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9946 hERG inhibition (predictor II) Non-inhibitor 0.7466
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets

References
- Pringle M, Fellstrom C, Johansson KE: Decreased susceptibility to doxycycline associated with a 16S rRNA gene mutation in Brachyspira hyodysenteriae. Vet Microbiol. 2007 Jul 20;123(1-3):245-8. Epub 2007 Feb 25. [PubMed:17428623]
- Kumar S, Kutlin A, Roblin P, Kohlhoff S, Bodetti T, Timms P, Hammerschlag MR: Isolation and antimicrobial susceptibilities of Chlamydial isolates from Western barred bandicoots. J Clin Microbiol. 2007 Feb;45(2):392-4. Epub 2006 Nov 22. [PubMed:17122017]
- Ross JI, Eady EA, Cove JH, Cunliffe WJ: 16S rRNA mutation associated with tetracycline resistance in a gram-positive bacterium. Antimicrob Agents Chemother. 1998 Jul;42(7):1702-5. [PubMed:9661007]
- Chukwudi CU: rRNA Binding Sites and the Molecular Mechanism of Action of the Tetracyclines. Antimicrob Agents Chemother. 2016 Jul 22;60(8):4433-41. doi: 10.1128/AAC.00594-16. Print 2016 Aug. [PubMed:27246781]
- Valentin S, Morales A, Sanchez JL, Rivera A: Safety and efficacy of doxycycline in the treatment of rosacea. Clin Cosmet Investig Dermatol. 2009 Aug 12;2:129-40. [PubMed:21436975]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Zhao XJ, Ishizaki T: A further interaction study of quinine with clinically important drugs by human liver microsomes: determinations of inhibition constant (Ki) and type of inhibition. Eur J Drug Metab Pharmacokinet. 1999 Jul-Sep;24(3):272-8. [PubMed:10716067]
- Zhao XJ, Ishizaki T: The In vitro hepatic metabolism of quinine in mice, rats and dogs: comparison with human liver microsomes. J Pharmacol Exp Ther. 1997 Dec;283(3):1168-76. [PubMed:9399990]
- Tan KR, Magill AJ, Parise ME, Arguin PM: Doxycycline for malaria chemoprophylaxis and treatment: report from the CDC expert meeting on malaria chemoprophylaxis. Am J Trop Med Hyg. 2011 Apr;84(4):517-31. doi: 10.4269/ajtmh.2011.10-0285. [PubMed:21460003]
- CYP3A4 document, CTEP [File]
- MEDICATIONS METABOLIZED BY CYTOCHROME P450 3A4 [File]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- Babu E, Takeda M, Narikawa S, Kobayashi Y, Yamamoto T, Cha SH, Sekine T, Sakthisekaran D, Endou H: Human organic anion transporters mediate the transport of tetracycline. Jpn J Pharmacol. 2002 Jan;88(1):69-76. [PubMed:11855680]
- In Vitro and In Vivo Evidence of the Importance of Organic Anion Transporters (OATs) in Drug Therapy [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Efflux transmembrane transporter activity
- Specific Function
- Drug efflux transporter present in a number of stem cells that acts as a regulator of cellular differentiation. Able to mediate efflux from cells of the rhodamine dye and of the therapeutic drug do...
- Gene Name
- ABCB5
- Uniprot ID
- Q2M3G0
- Uniprot Name
- ATP-binding cassette sub-family B member 5
- Molecular Weight
- 138639.48 Da
References
- Mealey KL, Barhoumi R, Burghardt RC, Safe S, Kochevar DT: Doxycycline induces expression of P glycoprotein in MCF-7 breast carcinoma cells. Antimicrob Agents Chemother. 2002 Mar;46(3):755-61. [PubMed:11850258]
- A ROLE OF P-GLYCOPROTEIN IN MODULATION OF ANTIBIOTIC PHARMACOKINETICS [File]
Drug created on June 13, 2005 13:24 / Updated on April 13, 2021 00:29