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

Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
ATC code	D10AF04 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name (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	2013-58-3
PubChem CID	54676539
ChemSpider	16735890
UNII	23Q8M2HE6S
KEGG	D02476
ChEMBL	ChEMBL1237124
CompTox Dashboard (EPA)	DTXSID4048567
ECHA InfoCard	100.016.309
Chemical and physical data
Formula	C22H21ClN2O8
Molar mass	476.87 g·mol^−1
3D model (JSmol)	Interactive image
SMILES 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 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 Key:GGQJXCQBBONZFX-IWVLMIASSA-N
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Its production for medical use has been discontinued.[2]

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.