Minocycline

Minocycline
Clinical data
Trade namesMinocin, others
AHFS/Drugs.comMonograph
MedlinePlusa682101
License data
Pregnancy
category
Routes of
administration		By mouth, intravenous, topical
Drug classAntibiotic; Tetracycline antibiotic
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability90–100%[4]
Protein binding70–75%[5]
MetabolismLiver[5]
Elimination half-life15.5 h (11–26 h)[2][4][5]
ExcretionMostly fecal, 10–15% renal[5]
Identifiers
IUPAC name
  • (2E,4S,4aR,5aS,12aR)-2-(Amino-hydroxy-methylidene)-4,7-bis(dimethylamino)-10,11,12a-trihydroxy-4a,5,5a,6- tetrahydro-4H-tetracene-1,3,12-trione[6]
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.226.626
Chemical and physical data
FormulaC23H27N3O7
Molar mass457.483 g·mol−1
3D model (JSmol)
Specific rotation = −166°[5]
Solubility in waterLow
SMILES
  • CN(C)c1ccc(c2c1C[C@H]3C[C@H]4[C@@H](C(=C(C(=O)[C@]4(C(=C3C2=O)O)O)C(=O)N)O)N(C)C)O
InChI
  • InChI=1S/C23H27N3O7/c1-25(2)12-5-6-13(27)15-10(12)7-9-8-11-17(26(3)4)19(29)16(22(24)32)21(31)23(11,33)20(30)14(9)18(15)28/h5-6,9,11,17,27,29-30,33H,7-8H2,1-4H3,(H2,24,32)/t9-,11-,17-,23-/m0/s1
  • Key:DYKFCLLONBREIL-KVUCHLLUSA-N

Minocycline, sold under the brand name Minocin among others, is a tetracycline antibiotic medication used to treat a number of bacterial infections such as some occurring in certain forms of pneumonia.[2][4][7] It is generally (but not always) less preferred than the tetracycline doxycycline.[4][7] Minocycline is also used for the treatment of acne and rheumatoid arthritis.[7][3] It is taken by mouth or applied to the skin.[4][3]

Common side effects include nausea, diarrhea, dizziness, allergic reactions, and kidney problems.[4] Serious side effects may include anaphylaxis, a lupus-like syndrome, and easy sunburning.[4] Use in the later part of pregnancy may harm the baby and safety during breastfeeding is unclear.[8] It works by decreasing a bacterium's ability to make protein thus stopping its growth.[4]

Minocycline was patented in 1961 and came into commercial use in 1971.[9] It is available as a generic medication.[7][10] In 2022, it was the 269th most commonly prescribed medication in the United States, with more than 900,000 prescriptions.[11][12]

  1. ^ "Minocycline Use During Pregnancy". Drugs.com. 4 December 2018. Retrieved 16 May 2020.
  2. ^ a b c "Minocin- minocycline hydrochloride injection". DailyMed. 28 July 2021. Retrieved 19 February 2023.
  3. ^ a b c "Amzeeq- minocycline aerosol, foam". DailyMed. 25 January 2023. Retrieved 18 February 2023.
  4. ^ a b c d e f g h "Minocycline Hydrochloride Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 23 March 2019.
  5. ^ a b c d e Dinnendahl V, Fricke U, eds. (2010). "Minocyclin". Arzneistoff-Profile (in German). Vol. 7 (24 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. ISBN 978-3-7741-9846-3.
  6. ^ "Minocycline". go.drugbank.com.
  7. ^ a b c d British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 556. ISBN 9780857113382.
  8. ^ "Minocycline Use During Pregnancy". Drugs.com. Retrieved 3 March 2019.
  9. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 489. ISBN 9783527607495.
  10. ^ "First Generic Drug Approvals". U.S. Food and Drug Administration. 17 October 2022. Archived from the original on 12 June 2019. Retrieved 28 November 2022.
  11. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  12. ^ "Minocycline Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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