Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C22H22N2O8.C7H6O6S |
| Molecular Weight | 660.603 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)C1=C(O)C=CC(=C1)S(O)(=O)=O.CN(C)[C@H]2[C@@H]3[C@@H](O)[C@@H]4C(=C)C5=CC=CC(O)=C5C(=O)C4=C(O)[C@]3(O)C(=O)C(C(N)=O)=C2O
InChI
InChIKey=DTKXPIQFZWVUTQ-CCHMMTNSSA-N
InChI=1S/C22H22N2O8.C7H6O6S/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;8-6-2-1-4(14(11,12)13)3-5(6)7(9)10/h4-6,10,14-15,17,25,27-29,32H,1H2,2-3H3,(H2,23,31);1-3,8H,(H,9,10)(H,11,12,13)/t10-,14-,15+,17+,22+;/m1./s1
| Molecular Formula | C7H6O6S |
| Molecular Weight | 218.184 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C22H22N2O8 |
| Molecular Weight | 442.4187 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|---|---|---|---|---|
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 Health Status: unhealthy Age Group: adult Sex: unknown 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 Health Status: unhealthy Age Group: adult Sex: unknown 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.
| Substance Class |
Chemical
Created
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admin
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Edited
Mon Mar 31 17:45:56 GMT 2025
by
admin
on
Mon Mar 31 17:45:56 GMT 2025
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| Record UNII |
A66FFJ6QXS
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| Record Status |
Validated (UNII)
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A66FFJ6QXS
Created by
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24358-92-7
Created by
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE |