General
Preferred name
DOXYCYCLINE
Synonyms
DOXYCYCLINE HYDROCHLORIDE ()
DOXYCYCLINE HYDRATE ()
Vibrox ()
Vibramycin-D ()
Vibramycin Acne Pack ()
Doxatet ()
Ramysis ()
Cyclodox ()
Nordox ()
Demix 50 ()
Doxy ()
Doxylar ()
Demix 100 ()
Vibramycin 50 ()
Doxycycline hydrochloride hemiethanolate hemihydrate ()
Doxycycline Hyclate ()
DOXYCYCLINE ANHYDROUS ()
Doxycycline (hydrochloride hemiethanolate hemihydrate) ()
WC2031 ()
Doxycycline (hydrochloride) ()
Doxycycline (monohydrate) ()
Doxycycline Hyclate (WC2031) ()
Doxycycline monohydrate ()
Vibramycin, Doxytetracycline, Doxiciclina, Doxycyclinum ()
Doxycycline hcl ()
NSC-756751 ()
Spanor ()
Atridox ()
Alodox ()
Doxy 100 ()
Monodoks ()
Doxyprex ()
Doxicrisol ()
Vibramycin Hyclate ()
Doxy-Lemmon ()
Acticlate cap ()
Doryx ()
Azudoxat ()
Periostat ()
Doxycyclini hyclas ()
Mespafin ()
Tetradox ()
Lymepak ()
Duradoxal ()
Doxychel Hyclate ()
Vibravenos ()
Tetraclean ()
Unacil ()
Clinofug ()
Granudoxy ()
NSC-741421 ()
Diocimex ()
Ronaxan ()
Zadorin ()
Retens ()
Doxy 200 ()
Doryx mpc ()
Doxy-Caps ()
Vibramycin ()
Vibraveineuse ()
Doxycycline hydrochloride hydrate ()
Vibra-Tabs ()
Acticlate ()
Anhydrous doxycycline ()
Doxycycline (anhydrous) ()
Doxychel ()
Monodox ()
Oracea ()
Supracyclin ()
Doxirobe ()
Doxylin ()
GS-3065 ()
Xyrosa ()
Doxiciclina ()
Doxycycline ()
DOXYCYCLINE CALCIUM ()
AB-08 ()
AB08 ()
DMSC ()
DOXYCYCLINE FOSFATEX ()
Doxycycline-d3 (hyclate) ()
Doxycycline (hydrate) ()
P&D ID
PD010144
CAS
17086-28-1
24390-14-5
10592-13-9
564-25-0
Tags
available
drug
drug candidate
Approved by
FDA
First approval
1967
1974
Drug Status
withdrawn
approved
vet_approved
investigational
Max Phase
2.0
4.0
3.0
Drug indication
Antibacterial,Antibacterial
Antibacterial
Antiprotozoal
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
ROE Mainly the urine and feces as active and unchanged drug [FDA 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 [F3055].
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 [A174025]. 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 [FDA label]. Doxycycline shows favorable intra-cellular penetration, with bacteriostatic activity on a wide range of bacteria [A174028]. Doxycycline has antiparasitic effects [A372], [A373], [A174025]. In addition to the above effects, this drug has demonstrated anti-inflammatory actions, which may help to manage inflammatory conditions such as rosacea [A174031].
HALF-LIFE 16.33 hr (± 4.53 sd) [FDA label].
MOA 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 [A174046], [A19429], [A174070]. The 30S subunit is the smaller subunit of the ribosome of prokaryotes, including bacteria[F3073]. Tetracyclines such as doxycycline are thought to inhibit translation by binding to the 16S rRNA portion of the ribosome [A174040], 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 [F3052].
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 [FDA label]. The following are some of the major infections that may be treated with doxycycline [FDA 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 [FDA label].
METABOLISM Doxycycline is metabolized in the liver and gastrointestinal tract and concentrated in bile [FDA label], [F3055]. Major metabolic pathways of doxycycline have not been identified, however, enzyme inducers have been found to decrease the half-life of doxycycline [F3055].
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 [FDA label]. Absorption is not significantly affected by the concomitant ingestion of food or milk [F3052]. Peak serum levels of approximately 2.6 mcg/ml are reached at 2 hours following a 200 mg tablet oral dose [F3052].
MOA 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 [A174046], [A19429], [A174070]. The 30S subunit is the smaller subunit of the ribosome of prokaryotes, including bacteria[F3073]. ; ; Tetracyclines such as doxycycline are thought to inhibit translation by binding to the 16S rRNA portion of the ribosome [A174040], 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 [F3052].
METABOLISM Doxycycline is metabolized in the liver and gastrointestinal tract and concentrated in bile [FDA label], [F3055].; Major metabolic pathways of doxycycline have not been identified, however, enzyme inducers have been found to decrease the half-life of doxycycline [F3055].; ;
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 [FDA label].; ; The following are some of the major infections that may be treated with doxycycline [FDA 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 [FDA label].
DESCRIPTION Cyclooxygenase inhibitor; NSAID (Tocris Bioactive Compound Library)
DESCRIPTION 6-deoxytetracycline antibiotic; interferes with protein synthesis (LOPAC library)
Cell lines
5
Organisms
6
Compound Sets
22
AdooQ Bioactive Compound Library
A17545
Cayman Chemical Bioactives
14422
35830
28528
ChEMBL Approved Drugs
CHEMBL3989740
CHEMBL1433
CHEMBL2364574
CHEMBL1200699
ChEMBL Drugs
CHEMBL1256723
CHEMBL3989740
CHEMBL1433
CHEMBL2364574
CHEMBL1200699
CHEMBL2106418
Drug Repurposing Hub
DrugBank
DB00254
DrugBank Approved Drugs
DB00254
DrugCentral
961
DrugCentral Approved Drugs
961
Enamine BioReference Compounds
LOPAC library
MedChem Express Bioactive Compound Library
HY-N0565A
HY-N0565
HY-W008923
HY-N0565B
NCATS Inxight Approved Drugs
334895S862
NPC Screening Collection
Other bioactive compounds
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
doxycycline-hyclate
doxycycline
doxycycline-monohydrate
The Pathogen Box
The Spectrum Collection
Tocris Bioactive Compound Library
4090
Withdrawn 2.0
w182
External IDs
140
Properties
(calculated by RDKit )
Molecular Weight
444.15
Hydrogen Bond Acceptors
9
Hydrogen Bond Donors
6
Rotatable Bonds
2
Ring Count
4
Aromatic Ring Count
1
cLogP
-0.35
TPSA
181.62
Fraction CSP3
0.41
Chiral centers
6.0
Largest ring
6.0
QED
0.33
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Selectivity
Protein synthesis
Disease
REFERENCE COMPOUNDS
Primary Target
Matrix Metalloproteases
MOA
Inhibitor
bacterial 30S ribosomal subunit inhibitor, metalloproteinase inhibitor
Indication
periodontitis
Target
MMP8
antibiotic
Bacterial
MMP
Parasite
Antineoplastic and Immunosuppressive Antibiotics,MMP
Antibiotics,Antineoplastic and Immunosuppressive Antibiotics,Bacterial,MMP
Antibiotics
ATC
A01AB22
J01AA02
Toxicity type
hematological
Pathway
Anti-infection
Metabolic Enzyme/Protease
Source data