Doxycycline

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

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MOLSDFPDBSMILESInChI

Similar Structures

Structure for Doxycycline (DB00254)

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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

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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

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Treatment of	Acinetobacter infections		••••••••••••
Treatment of	Anthrax		••••••••••••
Treatment of	Bacterial infection caused by enterobacter aerogenes		••••••••••••
Treatment of	Bartonellosis		••••••••••••
Used in combination to treat	Brucellosis	Regimen in combination with: Streptomycin (DB01082)	••••••••••••

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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

Target	Actions	Organism
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 C_max 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 C_max 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

Pathway	Category
Doxycycline Action Pathway	Drug action

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Not Available

Interactions

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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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abacavir	Doxycycline may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abciximab	The risk or severity of bleeding can be increased when Doxycycline is combined with Abciximab.
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.

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

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

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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
Acticlate	Tablet, coated	150 mg/1	Oral	Almirall, LLC	2014-07-28	Not applicable
Acticlate CAP	Capsule	75 mg/1	Oral	Aqua Pharmaceuticals	2018-05-31	Not applicable
Apprilon		40 mg	Oral	Galderma	2012-11-29	Not applicable
Atridox	Kit	50 mg/1	Oral	Den-mat Holdings, Llc	2016-12-01	2021-12-31

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Adoxa	Capsule	150 mg/1	Oral	Pharma Derm, A Division Of Fougera Pharmaceuticals Inc.	2011-06-01	Not applicable
Alodox	Tablet	20 mg/1	Oral	OCuSOFT Inc.	2008-10-01	2015-06-30
Alti-doxycycline - Tab 100mg	Tablet	100 mg / tab	Oral	Altimed Pharma Inc.	1995-12-31	2001-09-05
Alti-doxycycline-cap 100mg	Capsule	100 mg / cap	Oral	Altimed Pharma Inc.	1995-12-31	2001-09-05
Apo-doxy Cap 100mg	Capsule	100 mg	Oral	Apotex Corporation	1987-12-31	Not applicable

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
BenoxylDoxy 60 Kit	Doxycycline monohydrate (100 mg/1) + Benzoyl peroxide (44 mg/1mL)	Kit	Oral; Topical	Elorac, Inc.	2014-07-01	2015-07-18
BenzoDox 30 Kit	Doxycycline monohydrate (100 mg/1) + Benzoyl peroxide (44 mg/1mL)	Kit	Oral; Topical	Elorac, Inc.	2015-10-01	Not applicable
BenzoDox 60 Kit	Doxycycline monohydrate (100 mg/1) + Benzoyl peroxide (44 mg/1mL)	Kit	Oral; Topical	Elorac, Inc.	2015-09-22	Not applicable
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

Categories

ATC Codes

J01AA02 — Doxycycline

• J01AA — Tetracyclines
• J01A — TETRACYCLINES
• J01 — ANTIBACTERIALS FOR SYSTEMIC USE
• J — ANTIINFECTIVES FOR SYSTEMIC USE

A01AB22 — Doxycycline

• A01AB — Antiinfectives and antiseptics for local oral treatment
• A01A — STOMATOLOGICAL PREPARATIONS
• A01 — STOMATOLOGICAL PREPARATIONS
• A — ALIMENTARY TRACT AND METABOLISM

J01AA20 — Combinations of tetracyclines

• J01AA — Tetracyclines
• J01A — TETRACYCLINES
• J01 — ANTIBACTERIALS FOR SYSTEMIC USE
• J — ANTIINFECTIVES FOR SYSTEMIC USE

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 CYP3A4 Inhibitors
• Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
• Cytochrome P-450 Enzyme Inhibitors
• 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 / Trialkylamines / Amino acids and derivatives / Primary carboxylic acid amides / Secondary alcohols / Enols / Polyols / Organic oxides / Hydrocarbon derivatives / Organopnictogen compounds

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 / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Cyclohexenone / Enol / Hydrocarbon derivative / Ketone / Naphthacene / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Polyol / Primary carboxylic acid amide / Secondary alcohol / Tertiary alcohol / Tertiary aliphatic amine / Tertiary amine / Tetracene / Tetracycline / Tetralin / Vinylogous acid

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]

External Links

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 / 7x5p

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Prevention	Chlamydia Trachomatis Infection / Human Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS) / Neisseria Gonorrheae Infection / Syphilis Infection	1
4	Active Not Recruiting	Prevention	Chlamydial Infections / Neisseria Gonorrhoeae Infection / Syphilis	1
4	Active Not Recruiting	Prevention	Sexually Transmitted Infections (STIs) / Syphilis	1
4	Completed	Basic Science	Bacterial Infections	1
4	Completed	Basic Science	Rabies	1

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	100 mg / cap
Tablet, delayed release	Oral	120 mg/1
Tablet, delayed release	Oral	60 mg/1
Tablet, film coated	Oral
Capsule, coated	Oral	40 mg
Capsule, coated	Oral	10000000 mg
Tablet	Oral	100 mg
Tablet	Oral	200 MG
Tablet, soluble	Oral
Tablet	Oral	200 mg/1
Capsule	Oral	200 mg/1
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/1
Tablet, delayed release	Oral	75 mg/100mg
Tablet, film coated	Oral	100 mg/1
Tablet, film coated	Oral	100 1/1
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	50 mg
Tablet, film coated	Oral	200 mg
Tablet, coated	Oral
Tablet	Oral
Capsule	Oral	40 MG
Capsule, coated	Oral	100 mg
Capsule	Oral
Capsule	Oral	50.000 mg
Gel	Periodontal	140 mg/g
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	40 mg
Capsule	Oral	20 mg
Tablet	Oral	20 mg/1
Capsule	Oral	100 mg / cap
Tablet	Oral	100 mg / tab
Capsule	Oral	100.000 mg
Capsule	Oral	100 MG
Solution	Intravenous	25.370 mg
Syrup	Oral	50 mg/5mL
Powder	Intravenous	100 mg / vial
Solution	Intravenous	100 mg/5ml
Tablet, delayed release	Oral	100 mg
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
US8715724	No	2014-05-06	2028-02-03
US7211267	No	2007-05-01	2022-04-05
US7232572	No	2007-06-19	2022-04-05
US7749532	No	2010-07-06	2027-12-19
US8206740	No	2012-06-26	2025-12-24
US8394405	No	2013-03-12	2024-04-07
US8394406	No	2013-03-12	2024-04-07
US8470364	No	2013-06-25	2024-04-07
US8603506	No	2013-12-10	2022-04-05
US5789395	No	1998-08-04	2016-08-30
US5919775	No	1999-07-06	2016-08-30
US8709478	No	2014-04-29	2024-04-07
US9241946	No	2016-01-26	2022-04-05
US9511031	No	2016-12-06	2034-10-23
US9446057	No	2016-09-20	2034-12-23
US9295652	No	2016-03-29	2034-10-23
US10058564	No	2018-08-28	2022-04-05

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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0zfr-5392300000-04bc3e193569d5361cd9
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-004j-0000900000-935048b8d3cfe4303be1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-004l-0001900000-6ec51b6c9a3b8ec21d1e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-004i-0000900000-0b59d411d391a9e10b5b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-004l-0044900000-b17186c06c8d328522e0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0f6x-5796200000-66f53c607488d1a33712
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0g59-1292200000-ddc4c8c94295c8f4b0cc
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	209.2471399	predicted	DarkChem Lite v0.1.0
[M-H]-	209.6925399	predicted	DarkChem Lite v0.1.0
[M-H]-	197.94159	predicted	DeepCCS 1.0 (2019)
[M+H]+	212.1786399	predicted	DarkChem Lite v0.1.0
[M+H]+	212.9159399	predicted	DarkChem Lite v0.1.0
[M+H]+	200.33716	predicted	DeepCCS 1.0 (2019)
[M+Na]+	212.2655399	predicted	DarkChem Lite v0.1.0
[M+Na]+	212.5330399	predicted	DarkChem Lite v0.1.0
[M+Na]+	206.24968	predicted	DeepCCS 1.0 (2019)

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]

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Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54