CHEBI:50845 - doxycycline

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ChEBI Name doxycycline
ChEBI ID CHEBI:50845
Definition Tetracycline in which the 5β-hydrogen is replaced by a hydroxy group, while the 6α-hydroxy group is replaced by hydrogen. A semi-synthetic tetracycline antibiotic, it is used to inhibit bacterial protein synthesis and treat non-gonococcal urethritis and cervicitis, exacerbations of bronchitis in patients with chronic obstructive pulmonary disease (COPD), and adult periodontitis.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:42135, CHEBI:4713
Supplier Information ChemicalBook:CB8663342, eMolecules:4775684, ZINC000016052277
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Doxycycline is a broad-spectrum antibiotic of the tetracycline class used in the treatment of infections caused by bacteria and certain parasites. It is used to treat bacterial pneumonia, acne, chlamydia infections, Lyme disease, cholera, typhus, and syphilis. It is also used to prevent malaria. Doxycycline may be taken by mouth or by injection into a vein. Common side effects include diarrhea, nausea, vomiting, abdominal pain, and an increased risk of sunburn. Use during pregnancy is not recommended. Like other agents of the tetracycline class, it either slows or kills bacteria by inhibiting protein production. It kills malaria by targeting a plastid organelle, the apicoplast. Doxycycline was patented in 1957 and came into commercial use in 1967. It is on the World Health Organization's List of Essential Medicines. Doxycycline is available as a generic medicine. In 2022, it was the 68th most commonly prescribed medication in the United States, with more than 9 million prescriptions.
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Formula C22H24N2O8
Net Charge 0
Average Mass 444.43464
Monoisotopic Mass 444.15327
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
InChIKey JBIWCJUYHHGXTC-AKNGSSGZSA-N
SMILES [H][C@@]12[C@@H](C)c3cccc(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
Roles Classification
Biological Role(s): antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
antibacterial drug
A drug used to treat or prevent bacterial infections.
immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via tetracyclines )
Application(s): antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
antibacterial drug
A drug used to treat or prevent bacterial infections.
geroprotector
Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
anti-inflammatory agent
Any compound that has anti-inflammatory effects.
immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing doxycycline (CHEBI:50845) has role anti-inflammatory agent (CHEBI:67079)
doxycycline (CHEBI:50845) has role antibacterial drug (CHEBI:36047)
doxycycline (CHEBI:50845) has role antimalarial (CHEBI:38068)
doxycycline (CHEBI:50845) has role geroprotector (CHEBI:176497)
doxycycline (CHEBI:50845) has role immunomodulator (CHEBI:50846)
doxycycline (CHEBI:50845) is a tetracyclines (CHEBI:26895)
Incoming doxycycline HCl (CHEBI:652992) has part doxycycline (CHEBI:50845)
doxycycline monohydrate (CHEBI:60648) has part doxycycline (CHEBI:50845)
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
INNs Sources
doxiciclina ChemIDplus
doxycycline KEGG DRUG
doxycyclinum ChemIDplus
Synonyms Sources
(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 PDBeChem
5-hydroxy-α-6-deoxytetracycline ChemIDplus
6α-deoxy-5-oxytetracycline ChemIDplus
Doxycyclin ChEBI
Doxycycline KEGG COMPOUND
doxycycline (anhydrous) ChemIDplus
Brand Names Sources
Jenacyclin DrugBank
Supracyclin DrugBank
Vibramycin DrugBank
Manual Xrefs Databases
10469369 ChemSpider
1840 VSDB
961 DrugCentral
C00017127 KNApSAcK
C06973 KEGG COMPOUND
CPD-19256 MetaCyc
D07876 KEGG DRUG
DB00254 DrugBank
Doxycycline Wikipedia
DXT PDBeChem
HMDB0014399 HMDB
LMPK07000001 LIPID MAPS
US3019260 Patent
US3200149 Patent
View more database links
Registry Numbers Types Sources
3041790 Reaxys Registry Number Reaxys
564-25-0 CAS Registry Number KEGG COMPOUND
564-25-0 CAS Registry Number ChemIDplus
Citations
Varga JM, Kalchschmid G, Klein GF, Fritsch P (1991)
Mechanism of allergic cross-reactions--I. Multispecific binding of ligands to a mouse monoclonal anti-DNP IgE antibody.
Molecular immunology 28, 641-654 [PubMed:1650428]
[show Abstract]
Rubins JB, Charboneau D, Alter MD, Bitterman PB, Kratzke RA (2001)
Inhibition of mesothelioma cell growth in vitro by doxycycline.
The Journal of laboratory and clinical medicine 138, 101-106 [PubMed:11477376]
[show Abstract]
Bendeck MP, Conte M, Zhang M, Nili N, Strauss BH, Farwell SM (2002)
Doxycycline modulates smooth muscle cell growth, migration, and matrix remodeling after arterial injury.
The American journal of pathology 160, 1089-1095 [PubMed:11891205]
[show Abstract]
Mealey KL, Barhoumi R, Burghardt RC, Safe S, Kochevar DT (2002)
Doxycycline induces expression of P glycoprotein in MCF-7 breast carcinoma cells.
Antimicrobial agents and chemotherapy 46, 755-761 [PubMed:11850258]
[show Abstract]
Franco C, Ho B, Mulholland D, Hou G, Islam M, Donaldson K, Bendeck MP (2006)
Doxycycline alters vascular smooth muscle cell adhesion, migration, and reorganization of fibrillar collagen matrices.
The American journal of pathology 168, 1697-1709 [PubMed:16651635]
[show Abstract]
Ortqvist A, Holmberg H, Norman C, Cars O (2009)
[Doxycycline is no antitussive agent. Antibiotics in acute bronchitis both unnecessary and risky].
Lakartidningen 106, 1666-1667 [PubMed:19630297]
Houtkooper RH, Mouchiroud L, Ryu D, Moullan N, Katsyuba E, Knott G, Williams RW, Auwerx J (2013)
Mitonuclear protein imbalance as a conserved longevity mechanism.
Nature 497, 451-457 [PubMed:23698443]
[show Abstract]
Ye X, Linton JM, Schork NJ, Buck LB, Petrascheck M (2014)
A pharmacological network for lifespan extension in Caenorhabditis elegans.
Aging cell 13, 206-215 [PubMed:24134630]
[show Abstract]
Miow QH, Vallejo AF, Wang Y, Hong JM, Bai C, Teo FS, Wang AD, Loh HR, Tan TZ, Ding Y, She HW, Gan SH, Paton NI, Lum J, Tay A, Chee CB, Tambyah PA, Polak ME, Wang YT, Singhal A, Elkington PT, Friedland JS, Ong CW (2021)
Doxycycline host-directed therapy in human pulmonary tuberculosis.
The Journal of clinical investigation 131, 141895 [PubMed:34128838]
[show Abstract]
Varma S, Nathanson J, Dowlatshahi M, Del Portillo A, Ramirez I, Garcia-Carrasquillo R (2021)
Doxycycline-induced cholestatic liver injury.
Clinical journal of gastroenterology 14, 1503-1510 [PubMed:34228348]
[show Abstract]
Sartini I, Łebkowska-Wieruszewska B, Lisowski A, Poapolathep A, Sitovs A, Giorgi M (2021)
Doxycycline pharmacokinetics in geese.
Journal of veterinary pharmacology and therapeutics 44, 975-981 [PubMed:34318509]
[show Abstract]
Simmons JD, Hawn TR (2021)
Remodeling the matrix: doxycycline modulates tuberculosis immunopathology.
The Journal of clinical investigation 131, 151668 [PubMed:34338231]
[show Abstract]
Tribuiani N, de Souza J, de Queiroz Junior MA, Baldo DA, de Campos Orsi V, Oshima-Franco Y (2022)
In Situ Effects of Doxycycline on Neuromuscular Junction in Mice.
Current molecular medicine 22, 349-353 [PubMed:34355683]
[show Abstract]
Hong Y, Staniorski C, Pollack D, Evans S (2023)
Doxycycline-Induced Gastric Perforation.
The American surgeon 89, 4926-4928 [PubMed:34551605]
[show Abstract]
Alsaadi M, Tezcan G, Tezcan G, Garanina EE, Hamza S, McIntyre A, Rizvanov AA, Khaiboullina SF (2021)
Doxycycline Attenuates Cancer Cell Growth by Suppressing NLRP3-Mediated Inflammation.
Pharmaceuticals (Basel, Switzerland) 14, 852 [PubMed:34577552]
[show Abstract]
Last Modified
29 September 2021