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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H22N2O8.C7H6O6S
Molecular Weight 660.6048
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHACYCLINE 5-SULFOSALICYLATE

SMILES

C=C1c2cccc(c2C(=O)C3=C([C@]4([C@]([H])([C@@]([H])(C(=C(C4=O)C(=N)O)O)N(C)C)[C@]([H])([C@]13[H])O)O)O)O.c1cc(c(cc1S(=O)(=O)O)C(=O)O)O

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

HIDE SMILES / InChI

Molecular Formula C7H6O6S
Molecular Weight 218.1853
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C22H22N2O8
Molecular Weight 442.4195
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
RONDOMYCIN

Approved Use

Rondomycin Indication: For the treatment of acute bacterial exacerbations of chronic bronchitis
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
4 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
47.5 μg × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
16 h
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

Doses

DosePopulationAdverse 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

AEs

AESignificanceDosePopulation
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:
PubMed

PubMed

TitleDatePubMed
Methacycline and demeclocycline in relation to sunlight.
1971 Apr 12
Protective activity of tetracycline analogs against the cytopathic effect of the human immunodeficiency viruses in CEM cells.
1990 Jan-Feb
Patents

Sample Use Guides

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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 13:57:51 UTC 2021
Edited
by admin
on Sat Jun 26 13:57:51 UTC 2021
Record UNII
A66FFJ6QXS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHACYCLINE 5-SULFOSALICYLATE
Common Name English
BENZOIC ACID, 2-HYDROXY-5-SULFO-, COMPD. WITH (4S-(4.ALPHA.,4A.ALPHA.,5.ALPHA.,5A.ALPHA.,12A.ALPHA.))-4-(DIMETHYLAMINO)-1,4,4A,5,5A,6,11,12A-OCTAHYDRO-3,5,10,12,12A-PENTAHYDROXY-6-METHYLENE-1,11-DIOXO-2-NAPHTHACENECARBOXAMIDE (1:1)
Systematic Name English
2-NAPHTHACENECARBOXAMIDE, 4-(DIMETHYLAMINO)-1,4,4A,5,5A,6,11,12A-OCTAHYDRO-3,5,10,12,12A-PENTAHYDROXY-6-METHYLENE-1,11-DIOXO-, (4S-(4.ALPHA.,4A.ALPHA.,5.ALPHA.,5A.ALPHA.,12A.ALPHA.))-, MONO(2-HYDROXY-5-SULFOBENZOATE) (SALT)
Systematic Name English
Code System Code Type Description
FDA UNII
A66FFJ6QXS
Created by admin on Sat Jun 26 13:57:51 UTC 2021 , Edited by admin on Sat Jun 26 13:57:51 UTC 2021
PRIMARY
CAS
24358-92-7
Created by admin on Sat Jun 26 13:57:51 UTC 2021 , Edited by admin on Sat Jun 26 13:57:51 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE