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Meclocycline

Meclocycline structure

CAS No:
2013-58-3
Formula:
C22H21ClN2O8
Chemical Name:
Meclocycline
Synonyms:
2-Naphthacenecarboxamide,7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-,(4S,4aR,5S,5aR,12aS)-;2-Naphthacenecarboxamide,7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-;2-Naphthacenecarboxamide,7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-,[4S-(4α,4aα,5α,5aα,12aα)]-;(4S,4aR,5S,5aR,12aS)-7-Chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-2-naphthacenecarboxamide;GS 2989;Meclocycline;7-Chloro-6-methylene-5-oxytetracycline;NSC 78502;97357-83-0;101673-57-8;3738-54-3;803670-40-8
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Meclocycline is a member of tetracyclines.|Meclocycline is under investigation in clinical trial NCT00385515 (Efficacy of SNX-1012 in the Treatment of Oral Mucositis).

Meclocycline Basic Attributes

Molecular Weight：

476.867

Exact Mass：

476.86

EC Number：

217-938-3

UNII：

23Q8M2HE6S

DSSTox ID：

DTXSID4048567

ATC Code：

D - Dermatologicals

Characteristics

PSA：

181.62000

XLogP3：

0.91580

Density：

1.72g/cm3

Boiling Point：

716.4ºC at 760mmHg

Flash Point：

387.1ºC

Water Solubility：

Soluble

Toxicity：

LD50 in mice (mg/kg): >5000 orally, 425 i.p. (Bernardi)

Toxicity

Toxicity Summary：

Oral LD50 of 6443mg/kg in rats [MSDS].

Protein Binding：

Estimated plasma protein binding of ~75-91% based on that of demeclocycline due to structural similarity.

Drug Information

Drug Indication：

Currently under investigation for the topical treatment of ulcerative oral mucositis

Pharmacology：

Tetracyclines such as meclocycline are broad spectrum bacteriostatic agents. Meclocyclin likely inhibits the growth of bacterial species present in the damaged oral mucosa, allowing the immune system to more easily eliminate infections.

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

Absorption：

Estimated oral bioavailability of ~66% and tmax of 4h based on that of demeclocycline due to structural similarity.|Estimated urinary excretion of ~40% and fecal excretion of ~43% based on that of demeclocycline due to structural similarity.|Estimated Vd of 121L based on that of demeclocycline due to structural similarity.

Metabolism/Metabolites：

Most tetracyclines are not metabolized. It is unlikely that meclocycline would be metabolized.

Biological Half-Life：

Half life estimated to be ~5.6h based on that of chlortetracycline due to structural similarity.

Mechanism of Action：

As a tetracycline, meclocycline likely works by reversably associating with the 30s subint of the bacterial ribosome. A likely binding site for tetracyclines has been identified on protein S7 of this subunit. This association blocks the association of aminoacyl-tRNA with the ribosome, inhibiting protein synthesis. Ultimately this inhibits bacterial growth due to a lack of proteins necessary for reproduction.

MeSH Entry Terms：

7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-2-naphthacene carboxamide

Meclocycline Use and Manufacturing

Meclocycline is a semi-synthetic tetracycline prepared by dehydration of the 6-hydroxy group of chlortetracycline to yield an exocyclic 6-methylene. Meclocycline is a close structural analogue of methacycline. Like all tetracyclines, meclocycline shows broad spectrum antibacterial and antiprotozoan activity and acts by binding to the 30S and 50S ribosomal sub-units, blocking protein synthesis. Meclocycline has been extensively cited in the literature with over 400 references.

Computed Properties

Molecular Weight:476.9
XLogP3:0.9
Hydrogen Bond Donor Count:6
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:2
Exact Mass:476.0986433
Monoisotopic Mass:476.0986433
Topological Polar Surface Area:182
Heavy Atom Count:33
Complexity:1040
Defined Atom Stereocenter Count:5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes