Meclocycline

Chemical compound

D10AF04 (WHO)

Legal statusLegal 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^Y

PubChem CID

54676539

ChemSpider

16735890^N

UNII

23Q8M2HE6S

KEGG

D02476^Y

ChEMBL

ChEMBL1237124^N

CompTox Dashboard (EPA)

DTXSID4048567

ECHA InfoCard100.016.309

Chemical and physical dataFormulaC₂₂H₂₁ClN₂O₈Molar mass476.87 g·mol⁻¹3D 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^N
Key:GGQJXCQBBONZFX-IWVLMIASSA-N^N

^NY (what is this?) (verify)

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.^{[citation needed]}

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

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

Antibacterials that inhibit protein synthesis (J01A, J01B, J01F, J01G, QJ01XQ)

30S

Aminoglycosides
(initiation inhibitors)

-mycin (Streptomyces)	Streptomycin^# Dihydrostreptomycin Neomycin^# Framycetin Paromomycin^# Ribostamycin Kanamycin Amikacin^# Arbekacin Bekanamycin Dibekacin Tobramycin (+loteprednol) Spectinomycin^# Hygromycin B Totomycin Apramycin Nourseothricin
-micin (Micromonospora)	Gentamicin^# Netilmicin Sisomicin Micronomicin Plazomicin^# Isepamicin Verdamicin Astromicin
other	Butirosin

Tetracycline antibiotics
(tRNA binding)

Tetracyclines	Doxycycline^# Chlortetracycline Clomocycline Demeclocycline Eravacycline Lymecycline Meclocycline^‡ Metacycline Minocycline Omadacycline Oxytetracycline Penimepicycline Rolitetracycline Sarecycline Tetracycline^#
Glycylcyclines	Tigecycline

50S

Oxazolidinone
(initiation inhibitors)

Peptidyl transferase

Amphenicols	Chloramphenicol^# Azidamfenicol Thiamphenicol Florfenicol
Pleuromutilins	Azamulin Lefamulin Retapamulin Tiamulin Valnemulin

MLS (transpeptidation/translocation)

Macrolides	Azithromycin^# Boromycin Carbomycin Carrimycin Clarithromycin^# Dirithromycin Erythromycin^# Flurithromycin Gamithromycin Josamycin Kitasamycin Midecamycin Miocamycin Oleandomycin Rokitamycin Roxithromycin Solithromycin Spiramycin Telithromycin Tildipirosin Tilmicosin Troleandomycin Tulathromycin Tylosin Tylvalosin
Ketolides	Telithromycin^‡ Cethromycin Solithromycin^†
Lincosamides	Clindamycin^# Lincomycin Pirlimycin
Streptogramins	Pristinamycin (IA, IIA, IIB) NXL103 (Flopristin, Linopristin) Quinupristin/dalfopristin (Dalfopristin, Quinupristin) Streptogramin A Streptogramin B Virginiamycin (S1)