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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H22N2O8
Molecular Weight 442.4187
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHACYCLINE

SMILES

CN(C)[C@H]1[C@@H]2[C@@H](O)[C@@H]3C(=C)C4=CC=CC(O)=C4C(=O)C3=C(O)[C@]2(O)C(=O)C(C(N)=O)=C1O

InChI

InChIKey=MHIGBKBJSQVXNH-IWVLMIASSA-N
InChI=1S/C22H22N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-6,10,14-15,17,25,27-29,32H,1H2,2-3H3,(H2,23,31)/t10-,14-,15+,17+,22+/m1/s1

HIDE SMILES / InChI

Description

Methacycline is a tetracycline antibiotic. Similar to other tetracyclines, it has a wide spectrum of antimicrobial action. It is active against most Gram-positive bacteria (pneumococci, streptococci, staphylococci) and Gram-negative bacteria (E. coli, salmonella, shigella, etc.), and towards agents causing onithosis, psittacosis, trachoma, and some Protozoa. Like other tetracyclines, the general usefulness of methacycline has been reduced with the onset of bacterial resistance. Methacycline inhibits the binding of aminoacyl-tRNA to the mRNA-ribosome complex. Methacycline inhibits cell growth by inhibiting translation. It binds to the 16S part of the 30S ribosomal subunit and prevents the amino-acyl tRNA from binding to the A site of the ribosome. Methacycline is mostly used for the treatment of acute bacterial exacerbations of chronic bronchitis.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
RONDOMYCIN

Cmax

ValueDoseCo-administeredAnalytePopulation
4 μg/mL
200 mg 1 times / day multiple, intravenous
METHACYCLINE serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
47.5 μg × h/mL
200 mg 1 times / day multiple, intravenous
METHACYCLINE serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
16 h
200 mg 1 times / day multiple, intravenous
METHACYCLINE serum
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
600 mg daily in 2 divided doses.
Route of Administration: Oral
In Vitro Use Guide
Methacycline inhibited Pseudomonas pseudomallei strains with MIC means ranged from 1.3 to 2.7 ug/ml.