Identification

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Name
Doxycycline
Accession Number
DB00254  (APRD00597)
Type
Small Molecule
Groups
Approved, Investigational, Vet approved
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.

Structure
Thumb
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
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
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ActiclateTablet, coated150 mg/1OralAlmirall, LLC2014-07-28Not applicableUs
ActiclateTablet, coated75 mg/1OralAlmirall, LLC2014-07-28Not applicableUs
Acticlate CAPCapsule75 mg/1OralAqua Pharmaceuticals2018-05-31Not applicableUs
Apprilon40 mgOralGalderma2012-11-29Not applicableCanada
AtridoxKit50 mg/500mgOralTOLMAR Inc.1998-09-03Not applicableUs
Atridox8.8 %OralTolmar Inc2001-01-31Not applicableCanada
AtridoxKit50 mg/1OralDen-mat Holdings, Llc2016-12-01Not applicableUs
DoryxCapsule, delayed release pellets75 mg/1OralAllergan1985-09-012006-09-30Us
DoryxTablet, delayed release200 mg/1OralAllergan2013-07-012016-04-30Us00430 0114 20 nlmimage10 1a3a0d30
DoryxCapsule, delayed release pellets100 mg/1OralPhysicians Total Care, Inc.1985-07-222000-09-19Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AdoxaCapsule150 mg/1OralPharma Derm, A Division Of Fougera Pharmaceuticals Inc.2011-06-01Not applicableUs10337 0815 06 nlmimage10 7203b95d
AlodoxTablet20 mg/1OralOCuSOFT Inc.2008-10-01Not applicableUs
Alti-doxycycline - Tab 100mgTablet100 mgOralAltimed Pharma Inc.1995-12-312001-09-05Canada
Alti-doxycycline-cap 100mgCapsule100 mgOralAltimed Pharma Inc.1995-12-312001-09-05Canada
Apo-doxy Cap 100mgCapsule100 mgOralApotex Corporation1987-12-31Not applicableCanada
Apo-doxy Tabs 100mgTablet100 mgOralApotex Corporation1990-12-31Not applicableCanada
Dom-doxycyclineCapsule100 mgOralDominion Pharmacal2008-04-162016-10-25Canada
Dom-doxycyclineTablet100 mgOralDominion Pharmacal2008-04-162016-10-25Canada
Doxy 100Injection, powder, lyophilized, for solution100 mg/10mLIntravenousGeneral Injectables & Vaccines, Inc2012-02-22Not applicableUs
Doxy 100Injection, powder, lyophilized, for solution100 mg/10mLIntravenousFresenius Kabi2000-10-17Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
BenoxylDoxy 30 KitDoxycycline monohydrate (100 mg/1) + Benzoyl peroxide (44 mg/1mL)KitTopicalElorac, Inc.2014-07-012014-08-07Us
BenoxylDoxy 60 KitDoxycycline monohydrate (100 mg/1) + Benzoyl peroxide (44 mg/1mL)KitTopicalElorac, Inc.2014-07-012015-07-18Us
BenzoDox 30 KitDoxycycline monohydrate (100 mg/1) + Benzoyl peroxide (44 mg/1mL)KitTopicalElorac, Inc.2015-10-01Not applicableUs
BenzoDox 60 KitDoxycycline monohydrate (100 mg/1) + Benzoyl peroxide (44 mg/1mL)KitTopicalElorac, Inc.2015-09-22Not applicableUs
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
International/Other Brands
Doxy (Galpharma) / Doxycin (Laboratoire Riva) / Doxylin (Actavis) / Jenacyclin / Microdox (Micro Labs) / NicAzelDoxyKit / Nu-Doxycycline (Nu-Pharm) / Supracyclin (Grünenthal) / Vibramycin (Pfizer)
Categories
UNII
334895S862
CAS number
564-25-0
Weight
Average: 444.4346
Monoisotopic: 444.153265754
Chemical Formula
C22H24N2O8
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=C(C(O)=CC=C3)C(=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

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. 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
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.

TargetActionsOrganism
A16S rRNA
binder
Enteric bacteria and other eubacteria
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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.

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, such as doxycycline during the first half of pregnancy as well as during certain periods in childhood up to 8 years 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
PathwayCategory
Doxycycline Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Doxycycline is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Doxycycline is combined with (S)-Warfarin.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Doxycycline.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Doxycycline is combined with 4-hydroxycoumarin.
4-OxoretinolThe risk or severity of pseudotumor cerebri and elevated intracranial pressure can be increased when 4-Oxoretinol is combined with Doxycycline.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Doxycycline.
6-Deoxyerythronolide BThe metabolism of Doxycycline can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Doxycycline.
7-ethyl-10-hydroxycamptothecinThe metabolism of 7-ethyl-10-hydroxycamptothecin can be decreased when combined with Doxycycline.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be decreased when combined with Doxycycline.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

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Food Interactions
  • Avoid alcohol.
  • Avoid milk, calcium containing dairy products, iron, antacids, or aluminum salts 2 hours before or 6 hours after using antacids while on this medication.
  • Take with a full glass of water Do not take calcium, aluminum, magnesium or Iron supplements within 2 hours of taking this medication.

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
ChEBI
50845
ChEMBL
CHEMBL1433
Therapeutic Targets Database
DAP001371
PharmGKB
PA449415
HET
DXT
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Doxycycline
ATC Codes
J01AA02 — DoxycyclineA01AB22 — DoxycyclineJ01AA20 — Combinations of tetracyclines
AHFS Codes
  • 52:04.04 — Antibacterials
  • 08:12.24 — Tetracyclines
PDB Entries
2o7o / 2xrl / 5om2 / 5om3
FDA label
Download (157 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingOtherAcne Rosacea / Cutaneous Rosacea / Ocular Rosacea1
0RecruitingTreatmentLymphoma, T-Cell, Cutaneous1
0RecruitingTreatmentMalignant Neoplasms of Respiratory and Intrathoracic Organs / Malignant Pleural Effusions1
0RecruitingTreatmentOsteomyelitis1
1Active Not RecruitingPreventionCardiorenal Syndrome / Chronic Kidney Disease (CKD)1
1CompletedNot AvailableHealthy Volunteers4
1CompletedNot AvailableTo Determine Bioequivalence Under Fasting Conditions3
1CompletedBasic ScienceBacterial Infections / Healthy Volunteers / Infections, Fungal1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedOtherTo Determine Bioequivalence Under Fed Conditions2
1CompletedPreventionArteriovenous Malformations / Brain Aneurysms / Cavernous Angiomas1
1CompletedTreatmentAneurysms / Arteriovenous Malformations1
1RecruitingTreatmentMalignant Neoplasm of Breast / Malignant Neoplasms of Digestive Organs / Malignant Neoplasms of Eye Brain and Other Parts of Central Nervous System / Malignant Neoplasms of Female Genital Organs / Malignant Neoplasms of Ill-defined Secondary and Unspecified Sites / Malignant Neoplasms of Independent (Primary) Multiple Sites / Malignant Neoplasms of Lip Oral Cavity and Pharynx / Malignant Neoplasms of Male Genital Organs / Malignant Neoplasms of Mesothelial and Soft Tissue / Malignant Neoplasms of Respiratory and Intrathoracic Organs / Malignant Neoplasms of Thyroid and Other Endocrine Glands / Malignant Neoplasms of Urinary Tract1
1TerminatedTreatmentAnthrax1
1, 2Active Not RecruitingHealth Services ResearchAcne Vulgaris1
1, 2CompletedTreatmentAmyloidosis; Heart (Manifestation) / Senile Cardiac Amyloidosis1
1, 2CompletedTreatmentAutoimmune Diseases / Endocrine System Diseases / Eye Diseases / Eye Diseases, Hereditary / Graves Diseases / Graves Ophthalmopathy / Hyperthyroidism / Immune System Diseases / Thyroid Diseases1
1, 2CompletedTreatmentPeriodontitis, Aggressive1
1, 2TerminatedTreatmentDiabetic Foot Ulcers (DFU)1
1, 2TerminatedTreatmentMelanoma1
1, 2Unknown StatusTreatmentAcne Vulgaris1
2Active Not RecruitingTreatmentAneurysms1
2Active Not RecruitingTreatmentLarynx / LIP / Oral Cavity / Pharynx1
2Active Not RecruitingTreatmentMarginal Zone Lymphoma of Ocular Adnexal1
2Active Not RecruitingTreatmentPain NOS1
2Active Not RecruitingTreatmentPrimary Systemic Amyloidosis1
2CompletedNot AvailableEye Dryness1
2CompletedBasic ScienceAortic Aneurysm, Abdominal1
2CompletedPreventionCardiopulmonary Bypass / Coronary Artery Bypass Graft Surgery Patients / Reperfusion Injury1
2CompletedPreventionCo-Infection / Mansonella Perstans Infection / Mycobacterium marinum infection / Tuberculosis Infection1
2CompletedPreventionRas-wildtype Colorectal Cancer1
2CompletedPreventionRash Due to Epidermal Growth Factor Receptor Inhibitors1
2CompletedSupportive CareAdvanced Malignant Neoplasm / Dermatologic Complication / Dermatologic Complications / Neoplasms, Malignant1
2CompletedTreatmentAcne Rosacea1
2CompletedTreatmentAcne Vulgaris1
2CompletedTreatmentChronic Rhinosinusitis / Polyps, Nasal1
2CompletedTreatmentCystic Fibrosis (CF)1
2CompletedTreatmentDiabetic Foot Ulcers (DFU)1
2CompletedTreatmentBacterial blepharitis / Eye Dryness / Meibomianitis1
2CompletedTreatmentLeft Ventricular Remodeling / Myocardial Infarction1
2CompletedTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
2CompletedTreatmentMansonella Perstans Infection / Mp Microfilaremia1
2CompletedTreatmentNon-Hodgkin's Lymphoma (NHL)1
2CompletedTreatmentPelvic Inflammatory Disease (PID)1
2CompletedTreatmentPeriodontal Diseases / Periodontitis1
2CompletedTreatmentPeriodontitis, Chronic1
2CompletedTreatmentPosterior Blepharitis1
2CompletedTreatmentRetinopathy, Diabetic2
2CompletedTreatmentProphylaxis of cardiomyopathy / Transthyretin Amyloidosis1
2CompletedTreatmentTuberculosis Infection1
2CompletedTreatmentUrethritis1
2Not Yet RecruitingPreventionHeart Failure / ST Segment Elevation Myocardial Infarction (STEMI)1
2Not Yet RecruitingTreatmentMethicillin-Resistant Staphylococcus Aureus (MRSA) / Skin-structure infections1
2RecruitingTreatmentAneurysm, Coronary / Mucocutaneous Lymph Node Syndrome1
2RecruitingTreatmentAtopic Dermatitis (AD) / Dermatitis, Eczematous / Skin Diseases / Skin Diseases, Genetic / Skin Inflammation1
2RecruitingTreatmentCarcinoma, Breast / Endometrial Clear Cell Adenocarcinoma / Endometrial Serous Adenocarcinoma / Uterine Corpus Cancer / Uterine Corpus Carcinosarcoma1
2RecruitingTreatmentChlamydophila Pneumoniae Infections / Coronary Heart Disease (CHD)1
2RecruitingTreatmentColorectal Cancers / Head and Neck Carcinoma1
2RecruitingTreatmentCrohn's Disease (CD)1
2RecruitingTreatmentCutaneous T-Cell Lymphoma (CTCL) / Mycosis Fungoides (MF) / Sezary Syndrome1
2RecruitingTreatmentHereditary Haemorrhagic Telangiectasia (HHT)1
2RecruitingTreatmentMalignant Pleural Effusions1
2RecruitingTreatmentResectable Pancreatic Cancers1
2RecruitingTreatmentSeizures1
2RecruitingTreatmentSkin Toxicities1
2RecruitingTreatmentUlcerative Colitis (UC)1
2TerminatedTreatmentAdult Diffuse Large B-Cell Lymphoma / Chronic Lymphocytic Leukaemia (CLL) / Follicular Lymphoma (FL) / Malignant Lymphoma - Lymphoplasmacytic / Marginal Zone B-Cell Lymphoma / Recurrent Mantle Cell Lymphoma / Small Lymphocytic Lymphoma (SLL) / T-Cell Lymphomas / Waldenström's Macroglobulinemia (WM)1
2TerminatedTreatmentMinor Intra-uterine Abnormalities1
2TerminatedTreatmentNon-ischaemic Cardiomyopathy / Systolic Heart Failure (NYHA II-III)1
2TerminatedTreatmentPolyp of Nasal Sinus1
2Unknown StatusPreventionMucositis1
2Unknown StatusTreatmentAcne1
2Unknown StatusTreatmentAutoimmune Diseases / Endocrine System Diseases / Eye Diseases / Eye Diseases, Hereditary / Graves Diseases / Graves Ophthalmopathy / Hyperthyroidism / Immune System Diseases / Thyroid Diseases1
2Unknown StatusTreatmentPlague1
2, 3Active Not RecruitingTreatmentAcute Myocardial Infarction (AMI) / Cardiovascular Disease (CVD) / Vascular Diseases1
2, 3Active Not RecruitingTreatmentDry Macular Degeneration1
2, 3CompletedNot AvailableJarisch Herxheimer Reaction / Relapsing Fever, Tick-Borne1
2, 3CompletedTreatmentDiabetes Mellitus With Periodontal Disease1
2, 3RecruitingTreatmentCardiac AL Amyloidosis1
2, 3Unknown StatusTreatmentAcne / Inflammatory Reaction1
2, 3Unknown StatusTreatmentEye Burns1
3Active Not RecruitingTreatmentFilariasis / Lymphatic Filariasis / Lymphedema of the extremities3
3CompletedNot AvailableMycoplasma Infections / Persian Gulf Syndrome1
3CompletedDiagnosticLyme Neuroborreliosis1
3CompletedSupportive CareMetastatic Cancers1
3CompletedTreatmentAcne1
3CompletedTreatmentAcne Rosacea1
3CompletedTreatmentAlzheimer's Disease (AD)1
3CompletedTreatmentAndrogen Excess / Menstrual Irregularities / Polycystic Ovarian Syndrome (PCOS)1
3CompletedTreatmentChlamydial Infections1
3CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
3CompletedTreatmentLyme Disease2
3CompletedTreatmentOsteoarthritis (OA)1
3CompletedTreatmentPeriodontitis1
3CompletedTreatmentPeriodontitis, Chronic1
3CompletedTreatmentReactive Arthritis / Reiter's Disease1
3CompletedTreatmentScrub Typhus1
3CompletedTreatmentSevere Acne Vulgaris1
3CompletedTreatmentSyphilis1
3CompletedTreatmentUrethritis1
3CompletedTreatmentUrogential Chlamydia Trachomatis Infection1
3CompletedTreatmentUterine Hemorrhage1
3Enrolling by InvitationTreatmentNeuroborreliosis, Borrelia Burgdorferi1
3RecruitingTreatmentAcne Vulgaris1
3RecruitingTreatmentAnterior Wall Myocardial Infarction / Heart Failure / Remodeling, Ventricular / ST Elevation Myocardial Infarction1
3RecruitingTreatmentESI-related Bleeding1
3RecruitingTreatmentIndigestion1
3RecruitingTreatmentMalignancies / Overall Survival / Quality of Life1
3RecruitingTreatmentMalignant Lymphomas1
3RecruitingTreatmentTTR Cardiac Amyloidosis1
3TerminatedTreatmentAsthma Bronchial2
3Unknown StatusNot AvailableChronic Obstructive Pulmonary Disease (COPD)1
3Unknown StatusTreatmentAlzheimer's Disease (AD)1
3Unknown StatusTreatmentMetastatic Colorectal Cancers / Skin Toxicities1
4CompletedBasic ScienceBacterial Infections1
4CompletedPreventionPregnancy Termination / Vomiting1
4CompletedPreventionRabies1
4CompletedSupportive CareAcne Rosacea1
4CompletedTreatmentAcne2
4CompletedTreatmentAcne Rosacea3
4CompletedTreatmentAcne Vulgaris3
4CompletedTreatmentBMI >30 kg/m2 / Type 2 Diabetes Mellitus1
4CompletedTreatmentBorrelia Infection / Lyme Disease1
4CompletedTreatmentBorreliosis / Early Lyme Disease / Erythema Chronicum Migrans / Lyme Disease1
4CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4CompletedTreatmentCoxiella Infection / Fatigue Syndrome, Chronic / Q Fever1
4CompletedTreatmentCystic Fibrosis (CF)1
4CompletedTreatmentErythema Chronicum Migrans / Post-Lyme Disease Symptoms1
4CompletedTreatmentFevers1
4CompletedTreatmentFilarial; Infestation1
4CompletedTreatmentLyme Neuroborreliosis1
4CompletedTreatmentLymphangioleiomyomatosis / Tuberous Sclerosis1
4CompletedTreatmentPapulopustular Rosacea (PPR)2
4CompletedTreatmentPeriodontal Diseases / Type 2 Diabetes Mellitus1
4CompletedTreatmentSinusitis1
4CompletedTreatmentUrinary Bladder, Overactive1
4CompletedTreatmentBacterial blepharitis1
4Not Yet RecruitingPreventionChlamydia Trachomatis Infection / Human Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS) / Neisseria Gonorrheae Infection / Syphilis Infection1
4Not Yet RecruitingPreventionSexually Transmitted Infections (STIs) / Syphilis1
4Not Yet RecruitingTreatmentAnal infection / Chlamydia Trachomatis Infection / Vaginal Infections1
4RecruitingTreatmentAdhesive Capsulitis / Adhesive Capsulitis of Shoulder / Adhesive Capsulitis of Unspecified Shoulder1
4RecruitingTreatmentAnal chlamydia infection1
4RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)2
4RecruitingTreatmentDry Eye Syndromes / Meibomian Gland Dysfunction (MGD)1
4TerminatedTreatmentAdvanced Cancers / Malignant Pleural Effusions1
4TerminatedTreatmentBladder Pain Syndrome / Chronic Pelvic Pain Syndrome (CPPS)1
4TerminatedTreatmentPeriodontitis1
4TerminatedTreatmentSeptic Abortion1
4Unknown StatusTreatmentCervicitis / Chlamydia Trachomatis / Genital Mycoplasma Infection / Urethritis1
4Unknown StatusTreatmentChronic Obstructive Pulmonary Disease (COPD) / Inflammatory Reaction / Pulmonary Emphysema1
4Unknown StatusTreatmentEndometrial Bleeding / Periodontal Diseases1
4WithdrawnPreventionCardiovascular Disease (CVD)1
4WithdrawnTreatmentChronic Obstructive Pulmonary Disease (COPD)1
Not AvailableActive Not RecruitingTreatmentAcne Rosacea1
Not AvailableActive Not RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD) / Emphysema / Human Immunodeficiency Virus (HIV)1
Not AvailableActive Not RecruitingTreatmentMethicillin-Resistant Staphylococcus Aureus (MRSA)1
Not AvailableCompletedNot AvailableErythema Chronicum Migrans1
Not AvailableCompletedNot AvailableHealthy Volunteers2
Not AvailableCompletedNot AvailableLyme Neuroborreliosis1
Not AvailableCompletedNot AvailableMycoplasma Pneumoniae1
Not AvailableCompletedNot AvailablePeriodontal Diseases / Psoriatic Arthritis / Rheumatoid Arthritis1
Not AvailableCompletedBasic ScienceCognitive Dysfunctions / Paresis / Paresthesia / Radicular Pain / Tiredness1
Not AvailableCompletedPreventionFirst Trimester Abortion1
Not AvailableCompletedPreventionMethicillin Resistant Staphylococcus Aureus Skin Infections1
Not AvailableCompletedPreventionOsteoarthritis (OA)1
Not AvailableCompletedPreventionSyphilis1
Not AvailableCompletedTreatmentAcne Vulgaris / Diet Modification1
Not AvailableCompletedTreatmentAortic Aneurysms1
Not AvailableCompletedTreatmentCystic Fibrosis (CF)1
Not AvailableCompletedTreatmentDiabetes Mellitus With Periodontal Disease1
Not AvailableCompletedTreatmentGastritis1
Not AvailableCompletedTreatmentOral Contraceptives (OC)1
Not AvailableCompletedTreatmentScrub Typhus1
Not AvailableCompletedTreatmentUlcerative Colitis (UC)1
Not AvailableEnrolling by InvitationPreventionPropionibacterium1
Not AvailableNot Yet RecruitingNot AvailableSTIs Prevention1
Not AvailableRecruitingNot AvailableBullous Pemphigoid (BP)1
Not AvailableRecruitingPreventionMotility Disorders / Staphylococcus Aureus1
Not AvailableRecruitingTreatmentAmyloidosis; Systemic1
Not AvailableRecruitingTreatmentAtypical pneumonia1
Not AvailableRecruitingTreatmentMultiple Erythema Migrans1
Not AvailableRecruitingTreatmentPneumonia, Mycoplasma1
Not AvailableRecruitingTreatmentProsthetic Joint Infection1
Not AvailableRecruitingTreatmentTick Borne Encephalitis (TBE)1
Not AvailableRecruitingTreatmentTick-borne Encephalitis (TBE)1
Not AvailableTerminatedTreatmentUlcerative Colitis (UC)1
Not AvailableUnknown StatusTreatmentBreakthrough Bleeding1
Not AvailableUnknown StatusTreatmentLateral Epicondylalgia (Tennis Elbow)1
Not AvailableUnknown StatusTreatmentSuspected Early Lyme Neuroborreliosis1
Not AvailableWithdrawnPreventionSeroma1
Not AvailableWithdrawnSupportive CareLung Cancer Non-Small Cell Cancer (NSCLC)1
Not AvailableWithdrawnTreatmentHeadache Disorders, Primary / Migraine / Migraine Disorders / Migraine With Aura / Migraine Without Aura1
Not AvailableWithdrawnTreatmentRotator Cuff Injury1

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/1
KitOral50 mg/500mg
KitTopical
Capsule, delayed release pelletsOral100 mg/1
Capsule, delayed release pelletsOral75 mg/1
Tablet, delayed releaseOral150 mg/1
Capsule, extended releaseOral100 mg
Tablet, delayed releaseOral120 mg/1
Tablet, delayed releaseOral60 mg/1
TabletOral100 mg
CapsuleOral40 mg/1
CapsuleOral75 mg/1
For suspensionOral25 mg/5mL
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 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, delayed releaseOral80 mg/1
Tablet, film coatedOral100 1/1
Tablet, film coatedOral100 mg/1
Tablet, film coatedOral150 mg/1
Tablet, film coatedOral20 mg/1
TabletOral150 mg/1
TabletOral50 mg/1
TabletOral75 mg/1
CapsuleOral50 mg/50mg
CapsuleOral100 mg/100mg
KitTopical50 mg/1
KitOral100 mg/1
Capsule, delayed release pelletsOral40 mg/1
CapsuleOral20 mg
TabletOral20 mg/1
CapsuleOral100 mg
SyrupOral50 mg/5mL
PowderIntravenous100 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)
US6958161No2005-10-252022-12-15Us
US8715724No2014-05-062028-02-03Us
US7211267No2007-05-012022-04-05Us
US7232572No2007-06-192022-04-05Us
US7749532No2010-07-062027-12-19Us
US8206740No2012-06-262025-12-24Us
US8394405No2013-03-122024-04-07Us
US8394406No2013-03-122024-04-07Us
US8470364No2013-06-252024-04-07Us
US8603506No2013-12-102022-04-05Us
US5789395No1998-08-042016-08-30Us
US5919775No1999-07-062016-08-30Us
US8709478No2014-04-292024-04-07Us
US9241946No2016-01-262022-04-05Us
US9511031No2016-12-062034-10-23Us
US9446057No2016-09-202034-12-23Us
US9295652No2016-03-292034-10-23Us
US10058564No2018-08-282022-04-05Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

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)2.93ChemAxon
pKa (Strongest Basic)7.46ChemAxon
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

Taxonomy

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
Tetracycline / Naphthacene / Tetracene / Anthracene carboxylic acid or derivatives / Tetralin / Aryl ketone / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Cyclohexenone / Aralkylamine
show 24 more
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
tetracyclines (CHEBI:50845) / Linear tetracyclines (C06973) / Linear tetracyclines (LMPK07000001)

Targets

1. 16S rRNA
Kind
Nucleotide
Organism
Enteric bacteria and other eubacteria
Pharmacological action
Yes
Actions
Binder
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]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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. [PubMed:10716067]
  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. [PubMed:9399990]
  3. CYP3A4 document, CTEP [File]
  4. MEDICATIONS METABOLIZED BY CYTOCHROME P450 3A4 [File]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  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. [PubMed:11855680]
  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. [PubMed:11850258]
  2. A ROLE OF P-GLYCOPROTEIN IN MODULATION OF ANTIBIOTIC PHARMACOKINETICS [File]

Drug created on June 13, 2005 07:24 / Updated on August 21, 2019 23:30