Meclocycline

Meclocycline (INN) is a tetracycline antibiotic.[1] It is used topically (i.e. for skin infections) as it is totally insoluble in water and may cause liver and kidney damage if given systemically.

Meclocycline
Skeletal formula of meclocycline
Ball-and-stick model of the meclocycline molecule
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • (2E,4S,4aR,5S,5aR,12aS)-2-[Amino(hydroxy)methylene]-7-chloro-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methylene-4a,5a,6,12a-tetrahydrotetracene-1,3,12(2H,4H,5H)-trione
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.016.309
Chemical and physical data
FormulaC22H21ClN2O8
Molar mass476.87 g·mol−1
3D model (JSmol)
  • CN(C)[C@H]1[C@@H]2[C@H]([C@@H]3C(=C)C4=C(C=CC(=C4C(=O)C3=C([C@@]2(C(=O)C(=C1O)C(=O)N)O)O)O)Cl)O
  • InChI=1S/C22H21ClN2O8/c1-6-9-7(23)4-5-8(26)11(9)16(27)12-10(6)17(28)14-15(25(2)3)18(29)13(21(24)32)20(31)22(14,33)19(12)30/h4-5,10,14-15,17,26,28-30,33H,1H2,2-3H3,(H2,24,32)/t10-,14-,15+,17+,22+/m1/s1 ☒N
  • Key:GGQJXCQBBONZFX-IWVLMIASSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Its production for medical use has been discontinued.[2] It was previously sold in the United States by Pfizer under the brand name Meclan.[3]

References
  1. "Meclocycline sulfosalicylate". pubchem.ncbi.nlm.nih.gov. Retrieved 3 January 2019.
  2. "Orange Book: Approved Drug Products with Therapeutic Equivalence Evaluations". www.accessdata.fda.gov. Retrieved 3 January 2019.
  3. "MECLAN Drugs@FDA: FDA-Approved Drugs". www.accessdata.fda.gov. United States Food and Drug Administration. 11 August 2022. Retrieved 2022-08-11.
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