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
SMILES
[H][C@@]12[C@@H](O)[C@]3([H])C(=C)C4=CC=CC(O)=C4C(=O)C3=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@H]2N(C)C
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
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.
Approval Year
Cmax
Value | Dose | Co-administered | Analyte | Population |
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4 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4199710/ |
200 mg 1 times / day multiple, intravenous dose: 200 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
METHACYCLINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
47.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4199710/ |
200 mg 1 times / day multiple, intravenous dose: 200 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
METHACYCLINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
16 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4199710/ |
200 mg 1 times / day multiple, intravenous dose: 200 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
METHACYCLINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
600 mg 1 times / day steady, oral Dose: 600 mg, 1 times / day Route: oral Route: steady Dose: 600 mg, 1 times / day Sources: |
unhealthy, adult n = 62 Health Status: unhealthy Condition: bronchitis Age Group: adult Sex: unknown Population Size: 62 Sources: |
Disc. AE: Gastrointestinal disorders... AEs leading to discontinuation/dose reduction: Gastrointestinal disorders (3 patients) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Gastrointestinal disorders | 3 patients Disc. AE |
600 mg 1 times / day steady, oral Dose: 600 mg, 1 times / day Route: oral Route: steady Dose: 600 mg, 1 times / day Sources: |
unhealthy, adult n = 62 Health Status: unhealthy Condition: bronchitis Age Group: adult Sex: unknown Population Size: 62 Sources: |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/5111303
Methacycline inhibited Pseudomonas pseudomallei strains with MIC means ranged from 1.3 to 2.7 ug/ml.
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WHO-VATC |
QJ01AA05
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NCI_THESAURUS |
C1595
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WHO-ATC |
J01AA05
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D008690
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IR235I7C5P
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METACYCLINE
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1727
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CHEMBL249837
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914-00-1
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DTXSID2023272
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1330
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m7285
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213-017-5
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DB00931
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100000088208
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SUB08801MIG
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C61839
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6805
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6812
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3118
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)