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

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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

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

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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	binder	Enteric 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

>90% ^Label, ¹⁵.

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.

• 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.
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.

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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

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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
Atridox		8.8 %	Oral	Den Mat Holdings, Llc	2001-01-31	Not applicable
Atridox	Kit	50 mg/500mg	Oral	TOLMAR Inc.	1998-09-03	2018-10-01
Doryx	Tablet, delayed release	100 mg/1	Oral	Allergan	2005-09-01	2011-08-01
Doryx	Tablet, delayed release	200 mg/1	Oral	Mayne Pharma Inc.	2015-04-13	Not applicable
Doryx	Capsule, delayed release pellets	100 mg/1	Oral	Physicians Total Care, Inc.	1985-07-22	2000-09-19

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		Oral	Altimed Pharma Inc.	1995-12-31	2001-09-05
Alti-doxycycline-cap 100mg	Capsule		Oral	Altimed Pharma Inc.	1995-12-31	2001-09-05
Apo-doxy Cap 100mg	Capsule		Oral	Apotex Corporation	1987-12-31	Not applicable
Apo-doxy Tabs 100mg	Tablet		Oral	Apotex Corporation	1990-12-31	Not applicable
Dom-doxycycline	Capsule		Oral	Dominion Pharmacal	2008-04-16	2016-10-25
Dom-doxycycline	Tablet		Oral	Dominion Pharmacal	2008-04-16	2016-10-25
Doxy 100	Injection, powder, lyophilized, for solution	100 mg/10mL	Intravenous	Fresenius Kabi USA, LLC	2000-10-17	Not applicable
Doxy 100	Injection, powder, lyophilized, for solution	100 mg/10mL	Intravenous	General Injectables & Vaccines, Inc	2012-02-22	2021-09-30

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 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 / 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)

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. 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]
2. 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]
3. 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]
4. 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]
5. Bonnetblanc JM: [Doxycycline]. Ann Dermatol Venereol. 2002 Jun-Jul;129(6-7):874-82. [PubMed:12218915]
6. 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]
7. Smilack JD: The tetracyclines. Mayo Clin Proc. 1999 Jul;74(7):727-9. doi: 10.4065/74.7.727. [PubMed:10405705]
8. Weinberg JM: The anti-inflammatory effects of tetracyclines. Cutis. 2005 Apr;75(4 Suppl):6-11. [PubMed:15916224]
9. 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]
10. 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]
11. 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]
12. 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]
13. 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]
14. Doxycycline MedSafe NZ [File]
15. Doxycycline EMA label [File]
16. 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

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

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
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	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

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with our fully connected ADMET & drug target dataset.

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Accelerate your drug discovery research with our ADMET & drug target dataset

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Details1. 16S ribosomal RNA

Kind

Nucleotide

Organism

Enteric bacteria and other eubacteria

Pharmacological action

Yes

Actions

Binder

In prokaryotes, the 16S rRNA is essential for recognizing the 5' end of mRNA and hence positioning it correctly on the ribosome. The 16S rRNA has a characteristic secondary structure in which half of the nucleotides are base-paired. The 16S rRNA sequence has been highly conserved and is often used for evolutionary and species comparative analysis.

References

1. 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]
2. 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]
3. 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]
4. 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]
5. 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]

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Drug created on June 13, 2005 13:24 / Updated on April 13, 2021 00:29