File:Doxycycline_structure.svg · Wikimedia Commons · See Wikimedia Commons
doxycycline
Sign in to saveAlso known as GS-3065, 6-alpha-deoxy-5-oxytetracycline, (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, 6α-deoxy-5-oxytetracycline, doxycycline anhydrous, 5-hydroxy-α-6-deoxytetracycline, 6alpha-deoxy-5-oxytetracycline, 5-hydroxy-alpha-6-deoxytetracycline
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, and is sometimes used to prevent malaria. Doxycycline may be taken by mouth or intravenously.
OverviewAI-generated
Doxycycline is a chemical compound with the formula C₂₂H₂₄N₂O₈. Its mass is listed as 444.1533, while its weight is recorded as 444.4. The substance has a charge of 0 and an xlogp value of -0.7.
Structural data for doxycycline includes specific SMILES notations and an InChIKey. The compound possesses 6 hydrogen bond donors and 9 hydrogen bond acceptors, with a topological polar surface area of 182.
Research on doxycycline is extensive, with 23,884 entries found in PubMed. Additionally, the subject is referenced by 572 other encyclopedia articles.
Synthesized by Vinony from 17 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Key facts
- Drug.UNII
- 334895S862
- Drug.image
- Doxycycline structure.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200
- Drug.image2
- Doxycycline ball-and-stick model from xtal 2012.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Vibramycin, others
- Drug.MedlinePlus
- a682063
- Drug.DailyMedID
- Doxycycline
- Drug.pregnancy_AU
- D
- Drug.routes_of_administration
- By mouth, intravenous
- Drug.ATC_prefix
- J01
- Drug.ATC_suffix
- AA02
- Drug.legal_AU
- S4
- Drug.legal_UK
- POM
- Drug.legal_US
- Rx-only
- Drug.bioavailability
- ~100%
- Drug.protein_bound
- 80–90%
via Wikipedia infobox
Chemical data
- Formula
- C22H24N2O8
- Molecular weight
- 444.4 g/mol
- IUPAC name
- (4S,4aR,5S,5aR,6R,12aR)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
- SMILES
- C[C@@H]1[C@H]2[C@@H]([C@H]3[C@@H](C(=O)C(=C([C@]3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O
- InChIKey
- SGKRLCUYIXIAHR-AKNGSSGZSA-N
- XLogP
- -0.7
- Polar surface area
- 182 Ų
- H-bond donors
- 6
- H-bond acceptors
- 9
- Formal charge
- 0
via PubChem
Research
23,884 papers- Minocycline and Doxycycline: More Than Antibiotics.ReviewCurrent molecular pharmacology · 2021Singh S, Khanna D, Kalra SDOI: 10.2174/1874467214666210210122628
- Doxycycline.ReviewTherapeutic drug monitoring · 1982Cunha BA, Sibley CM, Ristuccia AMDOI: 10.1097/00007691-198206000-00001
- [Doxycycline].ReviewAnnales de dermatologie et de venereologie · 2002Bonnetblanc JM
- Doxycycline revisited.ReviewArchives of internal medicine · 1997Joshi N, Miller DQ
- [Doxycycline].Medecine tropicale : revue du Corps de sante colonial · 2009Aupee O, Almeras D, Le Garlantezec P et al.
- [Doxycycline--the forgotten antibiotic].ReviewMedizinische Klinik (Munich, Germany : 1983) · 2000Ziegler T, Winkler C, Wege K et al.DOI: 10.1007/pl00002075
- Doxycycline re-revisited.Archives of internal medicine · 1999Cunha BADOI: 10.1001/archinte.159.9.1006
- Doxycycline as an antimalarial: Impact on travellers' diarrhoea and doxycycline resistance among various stool bacteria - Prospective study and literature review.ReviewTravel medicine and infectious disease · 2022Kantele A, Mero S, Lääveri TDOI: 10.1016/j.tmaid.2022.102403
via PubMed
Wikidata facts
- Mass
- 444.1533
- Manufacturer
- Pfizer
- Has use
- medication
Show 8 more facts
- medical condition treated
- typhus
- chemical formula
- C₂₂H₂₄N₂O₈
- World Health Organisation international non-proprietary name
- doxycycline
- isomeric SMILES
- C[C@H]1C2=CC=CC(=C2C(=O)C3=C([C@]4([C@@H]([C@H]([C@H]13)O)[C@@H](C(=C(C4=O)C(=O)N)O)N(C)C)O)O)O
- canonical SMILES
- CC1C2=CC=CC(=C2C(=O)C3=C(C4(C(C(C13)O)C(C(=C(C4=O)C(=O)N)O)N(C)C)O)O)O
- Commons category
- Doxycycline
- significant drug interaction
- carbamazepin
- found in taxon
- Streptomyces hygroscopicus
Sources (8)
via Wikidata · CC0
~33 min read
Encyclopedic overview
37 sectionsContents
- Medical uses
- Antibacterial
- General indications
- Indications for Gram-negative bacteria
- Indications for Gram-positive bacteria
- Penicillin contraindication
- Use as adjunctive therapy
- As prophylaxis against sexually transmitted infections
- Use in combination
- Antimalarial
- Deworming
- Spectrum of susceptibility
- Sclerotherapy
- Off-label use
- Routes of administration
- Contraindications
- Pregnancy and lactation
- Adverse effects
- Interactions
- Pharmacology
- Pharmacodynamics
- Mechanism of action
- Absorption and excretion
- Chemistry
- Chemical properties
- History
- Society and culture
- Brand names
- Generic availability
- Research
- Research reagent
- Medical conditions
- Dosing
- Anti-inflammatory agent
- Wound healing
- References
- External links
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, and is sometimes used to prevent malaria. Doxycycline may be taken by mouth or intravenously.
Common side effects include diarrhea, nausea, vomiting, abdominal pain, and an increased risk of sunburn. Use during pregnancy is not recommended. Doxycycline can be used in children of all ages, including for Lyme disease and rickettsial infections. Like other agents of the tetracycline class, it slows or kills bacteria by inhibiting protein production. It kills Plasmodium—microorganisms associated with malaria—by targeting a plastid organelle, the apicoplast.
Excerpted from Wikipedia’s “doxycycline” article, available under the CC BY-SA 4.0 licence.