Identification

Summary

Doxycycline is a tetracycline antibiotic used to treat a wide variety of bacterial infections.

Brand Names
Acticlate, Adoxa, Apprilon, Atridox, Doryx, Doxy, Doxycin, Lymepak, Mondoxyne, Monodox, Morgidox, Okebo, Oracea, Periostat, Targadox, Vibramycin
Generic Name
Doxycycline
DrugBank Accession Number
DB00254
Background

Doxycycline is a broad-spectrum antibiotic synthetically derived from oxytetracycline.13 It is a second-generation tetracycline that was first discovered in 1967.6 Second-generation tetracyclines exhibit lesser toxicity than first-generation tetracyclines.5 Doxycycline is used to treat a wide variety of gram-positive and gram-negative bacterial infections. It is also used to treat acne and malaria.8

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

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, including:

  • Early Lyme disease (as evidenced by erythema migraines) due to Borrelia burgdorferi in adults and pediatric patients 8 years of age and older weighing 45 kg and above 12
  • Rickettsial infections,11 such as Rocky Mountain spotted fever, typhus fever and the typhus group, Q fever, rickettsialpox, and tick fevers 13
  • Sexually transmitted infections 11
  • Respiratory tract infections 11 caused by Mycoplasma pneumoniae and Haemophilus influenzae 13
  • Specific bacterial infections 11 after indicative bacteriologic testing. These include infections caused by Escherichia coli, Enterobacter aerogenes, Shigella species, Acinetobacter species, and Klebsiella species 13
  • Ophthalmic infections,11 such as inclusion conjunctivitis caused by Chlamydia trachomatis 13
  • Anthrax, including inhalational anthrax (post-exposure) 11
  • Alternative treatment for selected infections when penicillin is contraindicated 11
  • Adjunctive therapy in acute intestinal amebiasis and severe acne 11,13
  • Lymphogranuloma venereum caused by Chlamydia trachomatis 13
  • Psittacosis (ornithosis) caused by Chlamydophila psittaci 13
  • Trachoma caused by Chlamydia trachomatis, although the infectious agent is not always eliminated, as judged by immunofluorescence 13
  • Uncomplicated urethral, endocervical, or rectal infections in adults caused by Chlamydia trachomatis 13
  • Nongonococcal urethritis caused by Ureaplasma urealyticum 13
  • Relapsing fever due to Borrelia recurrentis 13
  • Prophylaxis of malaria due to Plasmodium falciparum in short-term travelers (<4 months) to areas with chloroquine and/or pyrimethamine-sulfadoxine resistant strains 11,13

It is also used to treat infections caused by the following gram-negative microorganisms:

  • Chancroid caused by Haemophilus ducreyi 13
  • Plague due to Yersinia pestis 13
  • Tularemia due to Francisella tularensis 13
  • Cholera caused by Vibrio cholerae 13
  • Campylobacter fetus infections caused by Campylobacter fetus 13
  • Brucellosis due to Brucella species (in conjunction with streptomycin) 13
  • Bartonellosis due to Bartonella bacilliformis 13
  • Granuloma inguinale caused by Klebsiella granulomatis 13
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Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Doxycycline and other tetracyclines are mainly bacteriostatic and are thought to exert antimicrobial effects by the inhibition of protein synthesis. They suppress the growth of bacteria or keep them in the stationary phase of growth.3 Tetracyclines have antimicrobial spectrum of activity against a variety of gram-positive and gram-negative microorganisms.11 Cross-resistance of these microorganisms to tetracyclines is a common occurrence.11

As it is a highly lipophilic drug, doxycycline crosses multiple membranes of target molecules.8 Doxycycline shows favorable intra-cellular penetration, with bacteriostatic activity against a wide range of bacteria.9 Doxycycline also exhibits antiparasitic properties 1,2,3 and anti-inflammatory actions.4,8 Its anti-inflammatory effects were investigated in various inflammatory skin conditions, such as bullous dermatoses 8 and rosacea.4,8

Mechanism of action

Protein synthesis is essential for survival and functioning of cells, including bacteria.7 Doxycycline inhibits bacterial protein synthesis by allosterically binding to the 30S prokaryotic ribosomal subunit.8,11 The drug blocks the association charged aminoacyl-tRNA (aa-tRNA) with the ribosomal A site, which is the acceptor site on the mRNA-ribosome complex. Doxycycline ultimately impedes the elongation phase of protein synthesis and halts the production of essential proteins for bacterial survival and functioning.7,8

Doxycycline mediates anti-inflammatory actions by preventing calcium-dependent microtubular assembly and lymphocytic proliferation, thereby inhibiting leukocyte movement during inflammation.8 It also inhibits nitric oxide synthase, which is an enzyme that produces nitric oxide, an inflammatory signaling molecule.8

TargetActionsOrganism
A30S ribosomal protein
inhibitor
Absorption

Doxycycline is virtually completely absorbed after oral administration 11 with a bioavailability of ranging from 73-95%.10 Following an oral dose of 500 mg, the Cmax of 15.3 mg/L was reached in four hours.10

Following a 200 mg dose, normal adult volunteers averaged peak serum levels of 2.6 mcg/mL of doxycycline at 2 hours, decreasing to 1.45 mcg/mL at 24 hours.13 While a high-fat meal lowers Cmax and the rate of absorption, the effect is not clinically significant.11

Volume of distribution

There is limited information available.

Protein binding

While there is limited information available, tetracyclines bound to plasma proteins in varying degree.13

Metabolism

There is limited information available.

Route of elimination

Tetracyclines, including doxycycline, are concentrated in bile by the liver and excreted in the urine and feces at high concentrations and in a biologically active form.11 Excretion of doxycycline by the kidney is about 40%/72 hours in individuals with a creatinine clearance of about 75 mL/min. This percentage may fall as low as 1-5%/72 hours in individuals with a creatinine clearance below 10 mL/min.11

Half-life

There is limited information available.

Clearance

Population pharmacokinetic analysis of sparse concentration-time data of doxycycline following standard of care intravenous and oral dosing in 44 pediatric patients two to 18 years of age showed allometrically -scaled clearance (CL) ranging from 3.27 to 3.58 L/h/70 kg.13

Adverse Effects
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Toxicity

Oral LD50 is 2000 mg/kg in rats, 1870 mg/kg in mice, and 500 mg/kg in dog.14

In case of overdosage, doxycycline should be discontinued and symptomatic and supportive treatment should be initiated. Dialysis does not alter serum half-life and thus would not be of benefit in treating cases of overdosage.11

Pathways
PathwayCategory
Doxycycline Action PathwayDrug 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.
DrugInteraction
AbacavirDoxycycline may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbciximabThe risk or severity of bleeding can be increased when Doxycycline is combined with Abciximab.
AceclofenacAceclofenac may decrease the excretion rate of Doxycycline which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Doxycycline which could result in a higher serum level.
AcenocoumarolThe risk or severity of bleeding can be increased when Doxycycline is combined with Acenocoumarol.
AcetaminophenDoxycycline may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Doxycycline which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Doxycycline which could result in a higher serum level.
AcitretinThe risk or severity of pseudotumor cerebri can be increased when Acitretin is combined with Doxycycline.
AclidiniumDoxycycline may decrease the excretion rate of Aclidinium which could result in a higher serum level.
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Food Interactions
  • Avoid multivalent ions. The absorption of tetracyclines is reduced when taken with foods, especially those which contain calcium.
  • Take with or without food. The absorption of tetracyclines is reduced when taken with foods, but not to a significant extent. If gastric irritation occurs, it is recommended that doxycycline be given with food or milk.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Doxycycline calcium8ZL07I20SB94088-85-4IYECPECUTCOMMD-QFWOMMJSSA-N
Doxycycline hyclate19XTS3T51U24390-14-5HALQELOKLVRWRI-VDBOFHIQSA-N
Doxycycline hydrochloride4182Z6T2ET10592-13-9RUYHIJHUVHIMIR-CVHRZJFOSA-N
Doxycycline monohydrateN12000U13O17086-28-1XQTWDDCIUJNLTR-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
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ActiclateTablet, coated75 mg/1OralAlmirall, LLC2014-07-28Not applicableUS flag
ActiclateTablet, coated150 mg/1OralAlmirall, LLC2014-07-28Not applicableUS flag
Acticlate CAPCapsule75 mg/1OralAqua Pharmaceuticals2018-05-31Not applicableUS flag
Apprilon40 mgOralGalderma2012-11-29Not applicableCanada flag
AtridoxKit50 mg/1OralDen-mat Holdings, Llc2016-12-012021-12-31US flag
AtridoxKit50 mg/500mgOralTOLMAR Inc.1998-09-032018-10-01US flag
Atridox8.8 % w/wOralDen Mat Holdings, Llc2001-01-31Not applicableCanada flag
DoryxCapsule, delayed release pellets100 mg/1OralAllergan1985-09-012007-08-30US flag
DoryxTablet, delayed release150 mg/1OralWarner Chilcott (US), LLC2008-07-012009-08-01US flag
DoryxTablet, delayed release200 mg/1OralMayne Pharma Inc.2015-04-13Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AdoxaCapsule150 mg/1OralPharma Derm, A Division Of Fougera Pharmaceuticals Inc.2011-06-01Not applicableUS flag
AlodoxTablet20 mg/1OralOCuSOFT Inc.2008-10-012015-06-30US flag
Alti-doxycycline - Tab 100mgTablet100 mg / tabOralAltimed Pharma Inc.1995-12-312001-09-05Canada flag
Alti-doxycycline-cap 100mgCapsule100 mg / capOralAltimed Pharma Inc.1995-12-312001-09-05Canada flag
Apo-doxy Cap 100mgCapsule100 mgOralApotex Corporation1987-12-31Not applicableCanada flag
Apo-doxy Tabs 100mgTablet100 mgOralApotex Corporation1990-12-31Not applicableCanada flag
Apo-doxycycline Mr40 mgOralApotex Corporation2021-09-01Not applicableCanada flag
Dom-doxycyclineTablet100 mgOralDominion Pharmacal2008-04-162016-10-25Canada flag
Dom-doxycyclineCapsule100 mgOralDominion Pharmacal2008-04-162016-10-25Canada flag
Doxy 100Injection, powder, lyophilized, for solution100 mg/10mLIntravenousFresenius Kabi USA, LLC2000-10-17Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
BenoxylDoxy 30 KitDoxycycline monohydrate (100 mg/1) + Benzoyl peroxide (44 mg/1mL)KitOral; TopicalElorac, Inc.2014-07-012014-08-07US flag
BenoxylDoxy 60 KitDoxycycline monohydrate (100 mg/1) + Benzoyl peroxide (44 mg/1mL)KitOral; TopicalElorac, Inc.2014-07-012015-07-18US flag
BenzoDox 30 KitDoxycycline monohydrate (100 mg/1) + Benzoyl peroxide (44 mg/1mL)KitOral; TopicalElorac, Inc.2015-10-01Not applicableUS flag
BenzoDox 60 KitDoxycycline monohydrate (100 mg/1) + Benzoyl peroxide (44 mg/1mL)KitOral; TopicalElorac, Inc.2015-09-22Not applicableUS flag
NicAzel Doxy KitDoxycycline monohydrate (100 mg/1) + Cupric oxide (2 mg/1) + Folic acid (500 ug/1) + Pyridoxine (8 mg/1) + Zinc oxide (12 mg/1)KitOralElorac, Inc.2014-06-302015-07-30US flag

Categories

ATC Codes
J01AA02 — DoxycyclineA01AB22 — DoxycyclineJ01AA20 — Combinations of tetracyclines
Drug Categories
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)
Affected organisms
  • Gram negative and gram positive bacteria
  • Various aerobic and anaerobic microorganisms
  • Plasmodium falciparum

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
  1. 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. [Article]
  2. 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. [Article]
  3. 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. [Article]
  4. 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. [Article]
  5. Smilack JD: The tetracyclines. Mayo Clin Proc. 1999 Jul;74(7):727-9. doi: 10.4065/74.7.727. [Article]
  6. 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. [Article]
  7. Shutter MC, Akhondi H: Tetracycline . [Article]
  8. Patel RS, Parmar M: Doxycycline Hyclate . [Article]
  9. Bonnetblanc JM: [Doxycycline]. Ann Dermatol Venereol. 2002 Jun-Jul;129(6-7):874-82. [Article]
  10. Agwuh KN, MacGowan A: Pharmacokinetics and pharmacodynamics of the tetracyclines including glycylcyclines. J Antimicrob Chemother. 2006 Aug;58(2):256-65. Epub 2006 Jul 1. [Article]
  11. FDA Approved Drug Products: DORYX (doxycycline hyclate) delayed-release tablets, for oral use [Link]
  12. DailyMed Label: LYMEPAK (doxycycline hyclate) tablets, for oral use [Link]
  13. DailyMed Label: VIBRAMYCIN and VIBRA-TABS (doxycycline), for oral use [Link]
  14. Merck: Doxycycline MSDS [Link]
Human Metabolome Database
HMDB0014399
KEGG Drug
D07876
KEGG Compound
C06973
PubChem Compound
54671203
PubChem Substance
46506491
ChemSpider
10469369
BindingDB
50041429
RxNav
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
PDB Entries
2o7o / 2xrl / 5om2 / 5om3 / 6rbl / 6rcr / 6rgx / 7b8r

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingPreventionChlamydia Trachomatis Infection / Human Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS) / Neisseria Gonorrheae Infection / Syphilis Infection1
4Active Not RecruitingPreventionChlamydial Infections / Neisseria Gonorrhoeae Infection / Syphilis1
4Active Not RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections / Syphilis1
4CompletedBasic ScienceBacterial Infections1
4CompletedBasic ScienceRabies1
4CompletedPreventionEndometritis1
4CompletedPreventionMedically induced abortion / Vomiting1
4CompletedSupportive CareRosacea1
4CompletedTreatmentAcne2
4CompletedTreatmentAcne Vulgaris4

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
FormRouteStrength
CapsuleOral150 mg/1
KitOral50 mg/500mg
KitOral50 mg/1
KitOral; Topical
Capsule, delayed release pelletsOral100 mg/1
Capsule, delayed release pelletsOral75 mg/1
Tablet, delayed releaseOral150 mg/1
Tablet, delayed releaseOral80 mg/1
Capsule, extended releaseOral100 mg / cap
Tablet, delayed releaseOral120 mg/1
Tablet, delayed releaseOral60 mg/1
CapsuleOral
Capsule, coatedOral40 mg
TabletOral100 mg
TabletOral200 MG
Tablet, solubleOral
TabletOral200 mg/1
CapsuleOral200 mg/1
TabletOral
For suspensionOral25 mg/5mL
Injection, powder, for solutionIntravenous100 mg/1
Injection, powder, lyophilized, for solutionIntravenous100 mg/10mL
Injection, powder, lyophilized, for solutionIntravenous200 mg/20mL
Powder, for suspensionOral25 mg/5mL
Tablet, coatedOral100 mg/1
Tablet, film coatedOral150 mg/1
Tablet, film coatedOral50 mg/1
Tablet, film coatedOral75 mg/1
CapsuleOral100 mg/1
CapsuleOral50 mg/1
Capsule, gelatin coatedOral100 mg/1
Capsule, gelatin coatedOral50 mg/1
PowderNot applicable1 g/1g
TabletOral100 mg/1
Tablet, coatedOral150 mg/1
Tablet, coatedOral75 mg/1
Tablet, delayed releaseOral100 mg/1
Tablet, delayed releaseOral200 mg/1
Tablet, delayed releaseOral50 mg/1
Tablet, delayed releaseOral75 mg/100mg
Tablet, delayed releaseOral75 mg/1
Tablet, film coatedOral100 mg/1
Tablet, film coatedOral100 1/1
Tablet, film coatedOral20 mg/1
TabletOral150 mg/1
TabletOral50 mg/1
TabletOral75 mg/1
Tablet, film coatedOral
Tablet, coatedOral
CapsuleOral40 MG
Capsule, coatedOral100 mg
GelPeriodontal
GelPeriodontal140 mg/g
CapsuleOral50 mg/50mg
CapsuleOral100 mg/100mg
CapsuleOral75 mg/1
CapsuleOral; Topical50 mg/1
KitOral
CapsuleOral40 mg/1
Capsule, delayed release pelletsOral40 mg/1
Capsule, extended releaseOral40 mg
Capsule, delayed releaseOral
CapsuleOral20 mg
TabletOral20 mg/1
CapsuleOral100 mg / cap
TabletOral100 mg / tab
CapsuleOral100 MG
SyrupOral50 mg/5mL
PowderIntravenous100 mg / vial
SolutionIntravenous100 mg/5ml
Tablet, delayed releaseOral100 mg
Tablet, film coatedOral100 mg
Prices
Unit descriptionCostUnit
Vibramycin 25 mg/5ml Suspension 60ml Bottle36.29USD bottle
Adoxa pak 1-150 mg tablet19.93USD tablet
Doryx 150 mg Enteric Coated Tabs17.51USD tab
Doryx dr 150 mg tablet16.83USD tablet
Doxycycline hyc 100 mg vial14.16USD vial
Adoxa 100 mg tablet13.86USD tablet
Monodox 100 mg capsule13.46USD capsule
Adoxa 75 mg tablet12.77USD tablet
Oracea 40 mg Delayed Release Capsule12.44USD capsule
Oracea 40 mg capsule11.96USD capsule
Avidoxy 100 mg tablet11.52USD tablet
Monodox 75 mg capsule11.02USD capsule
Doryx 100 mg Enteric Coated Tabs10.31USD tab
Doryx dr 100 mg tablet9.91USD tablet
Adoxa pak 1-100 mg tablet9.88USD tablet
Doxycycline Monohydrate 150 mg tablet9.51USD tablet
Adoxa 50 mg tablet9.29USD tablet
Doxycycline mono 150 mg tablet9.13USD tablet
Doryx 75 mg Enteric Coated Tabs8.76USD tab
Doryx dr 75 mg tablet8.42USD tablet
Vibramycin 100 mg capsule6.67USD capsule
Vibra-tabs 100 mg tablet6.67USD tablet
Monodox 50 mg capsule6.0USD capsule
Doxycycline mono 100 mg tablet5.98USD tablet
Periostat 20 mg tablet5.75USD tablet
Doxycycline mono 75 mg tablet5.74USD tablet
Doxycycline Monohydrate 100 mg tablet5.12USD tablet
Doxycycline mono 50 mg tablet4.17USD tablet
Doxycycline Monohydrate 50 mg tablet3.0USD tablet
Doxycycline hyclate powder2.56USD g
Vibramycin 50 mg capsule2.41USD capsule
Doxycycline Monohydrate 100 mg capsule2.22USD capsule
Vibramycin 100 mg Capsule1.91USD capsule
Doxycycline Monohydrate 50 mg capsule1.51USD capsule
Doxycycline hyclate 100 mg tablet1.28USD tablet
Doxycycline hyclate 20 mg tablet1.28USD tablet
Doxycycline Hyclate 100 mg capsule1.18USD capsule
Doxycycline Hyclate 50 mg capsule0.76USD capsule
Vibramycin 50 mg/5ml Syrup0.67USD ml
Vibramycin 50 mg/5 ml syrup0.64USD ml
Apo-Doxy 100 mg Capsule0.61USD capsule
Apo-Doxy 100 mg Tablet0.61USD tablet
Doxycin 100 mg Capsule0.61USD capsule
Doxycin 100 mg Tablet0.61USD tablet
Novo-Doxylin 100 mg Capsule0.61USD capsule
Novo-Doxylin 100 mg Tablet0.61USD tablet
Nu-Doxycycline 100 mg Capsule0.61USD capsule
Pms-Doxycycline 100 mg Capsule0.61USD capsule
Pms-Doxycycline 100 mg Tablet0.61USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US6958161No2005-10-252022-12-15US flag
US8715724No2014-05-062028-02-03US flag
US7211267No2007-05-012022-04-05US flag
US7232572No2007-06-192022-04-05US flag
US7749532No2010-07-062027-12-19US flag
US8206740No2012-06-262025-12-24US flag
US8394405No2013-03-122024-04-07US flag
US8394406No2013-03-122024-04-07US flag
US8470364No2013-06-252024-04-07US flag
US8603506No2013-12-102022-04-05US flag
US5789395No1998-08-042016-08-30US flag
US5919775No1999-07-062016-08-30US flag
US8709478No2014-04-292024-04-07US flag
US9241946No2016-01-262022-04-05US flag
US9511031No2016-12-062034-10-23US flag
US9446057No2016-09-202034-12-23US flag
US9295652No2016-03-292034-10-23US flag
US10058564No2018-08-282022-04-05US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)201 °Chttps://www.sigmaaldrich.com/content/dam/sigma-aldrich/docs/Sigma/Product_Information_Sheet/d9891pis.pdf
water solubility50 mg/mLhttps://www.sigmaaldrich.com/content/dam/sigma-aldrich/docs/Sigma/Product_Information_Sheet/d9891pis.pdf
logP0.63https://deepblue.lib.umich.edu/bitstream/handle/2027.42/64911/21954_ftp.pdf?sequence=1
pKa3.09https://www.ncbi.nlm.nih.gov/pubmed/34018
Predicted Properties
PropertyValueSource
Water Solubility0.63 mg/mLALOGPS
logP-0.72ALOGPS
logP-3.3ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.27ChemAxon
pKa (Strongest Basic)8.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area181.62 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity113.89 m3·mol-1ChemAxon
Polarizability43.65 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.85
Blood Brain Barrier-0.9881
Caco-2 permeable-0.8706
P-glycoprotein substrateSubstrate0.699
P-glycoprotein inhibitor INon-inhibitor0.8038
P-glycoprotein inhibitor IINon-inhibitor0.8628
Renal organic cation transporterNon-inhibitor0.9562
CYP450 2C9 substrateNon-substrate0.8008
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.6551
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9144
CYP450 2D6 inhibitorNon-inhibitor0.9293
CYP450 2C19 inhibitorNon-inhibitor0.9099
CYP450 3A4 inhibitorNon-inhibitor0.8567
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8086
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.8632
BiodegradationNot ready biodegradable0.9941
Rat acute toxicity2.3159 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9946
hERG inhibition (predictor II)Non-inhibitor0.7466
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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1. 30S ribosomal protein
Kind
Group
Organism
Not Available
Pharmacological action
Yes
Actions
Inhibitor
Group which encompasses the subunits of the 30S ribosomal protein not specific to any organism.
References
  1. Patel RS, Parmar M: Doxycycline Hyclate . [Article]
  2. FDA Approved Drug Products: DORYX (doxycycline hyclate) delayed-release tablets, for oral use [Link]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
CYP3A4 inhibition was demonstrated in a single in vitro study, where doxycycline inhibited CYP3A4-mediated metabolism of quinine to 3-hydroxyquinine.
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
  1. 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. [Article]
  2. 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. [Article]
  3. 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. [Article]
  4. CYP3A4 document, CTEP [File]
  5. MEDICATIONS METABOLIZED BY CYTOCHROME P450 3A4 [File]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Aver'eva EV, Kivman GIa, Markovich MN, Shraiber NF, Pognoevskii OT: [Competition of antibacterial drugs for binding sites of human serum albumin]. Antibiot Khimioter. 1988 Jun;33(6):444-8. [Article]

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
  1. 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. [Article]
  2. 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
  1. 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. [Article]
  2. A ROLE OF P-GLYCOPROTEIN IN MODULATION OF ANTIBIOTIC PHARMACOKINETICS [File]

Drug created at June 13, 2005 13:24 / Updated at August 19, 2022 08:38