U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H22N2O8
Molecular Weight 442.4195
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHACYCLINE

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

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
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
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.
Name Type Language
METHACYCLINE
HSDB   MART.   MI   USAN   VANDF  
USAN  
Official Name English
METHACYCLINE [VANDF]
Common Name English
6-DEOXY-6-DEMETHYL-6-METHYLENE-5-OXYTETRACYCLINE
Common Name English
METHACYCLINE [USAN]
Common Name English
DOXYCYCLINE HYCLATE SPECIFIED IMPURITY B [EP]
Common Name English
METACYCLINE [INN]
Common Name English
DOXYCYCLINE MONOHYDRATE SPECIFIED IMPURITY B [EP]
Common Name English
DOXYCYCLINE IMPURITY B
Common Name English
DOXYCYCLINE MONOHYDRATE IMPURITY B [EP]
Common Name English
METACYCLINE [WHO-DD]
Common Name English
METHACYCLINE [MI]
Common Name English
METHACYCLINE [MART.]
Common Name English
4-(DIMETHYLAMINO)-1,4,4A,5,5A,6,11,12A-OCTAHYDRO-3,5,10,12,12A-PENTAHYDROXY-6-METHYLENE-1,11-DIOXO-2-NAPHTHACENECARBOXAMIDE
Common Name English
DOXYCYCLINE HYCLATE IMPURITY B [EP]
Common 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.))-
Common Name English
METACYCLINE
INN   WHO-DD  
INN  
Official Name English
METHACYCLINE [HSDB]
Common Name English
GS-2876
Code English
Classification Tree Code System Code
WHO-VATC QJ01AA05
Created by admin on Sat Jun 26 08:13:44 UTC 2021 , Edited by admin on Sat Jun 26 08:13:44 UTC 2021
NCI_THESAURUS C1595
Created by admin on Sat Jun 26 08:13:44 UTC 2021 , Edited by admin on Sat Jun 26 08:13:44 UTC 2021
WHO-ATC J01AA05
Created by admin on Sat Jun 26 08:13:44 UTC 2021 , Edited by admin on Sat Jun 26 08:13:44 UTC 2021
Code System Code Type Description
MESH
D008690
Created by admin on Sat Jun 26 08:13:44 UTC 2021 , Edited by admin on Sat Jun 26 08:13:44 UTC 2021
PRIMARY
FDA UNII
IR235I7C5P
Created by admin on Sat Jun 26 08:13:44 UTC 2021 , Edited by admin on Sat Jun 26 08:13:44 UTC 2021
PRIMARY
WIKIPEDIA
METACYCLINE
Created by admin on Sat Jun 26 08:13:44 UTC 2021 , Edited by admin on Sat Jun 26 08:13:44 UTC 2021
PRIMARY
DRUG CENTRAL
1727
Created by admin on Sat Jun 26 08:13:44 UTC 2021 , Edited by admin on Sat Jun 26 08:13:44 UTC 2021
PRIMARY
ChEMBL
CHEMBL249837
Created by admin on Sat Jun 26 08:13:44 UTC 2021 , Edited by admin on Sat Jun 26 08:13:44 UTC 2021
PRIMARY
CAS
914-00-1
Created by admin on Sat Jun 26 08:13:44 UTC 2021 , Edited by admin on Sat Jun 26 08:13:44 UTC 2021
PRIMARY
EPA CompTox
914-00-1
Created by admin on Sat Jun 26 08:13:44 UTC 2021 , Edited by admin on Sat Jun 26 08:13:44 UTC 2021
PRIMARY
INN
1330
Created by admin on Sat Jun 26 08:13:44 UTC 2021 , Edited by admin on Sat Jun 26 08:13:44 UTC 2021
PRIMARY
MERCK INDEX
M7285
Created by admin on Sat Jun 26 08:13:44 UTC 2021 , Edited by admin on Sat Jun 26 08:13:44 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
213-017-5
Created by admin on Sat Jun 26 08:13:44 UTC 2021 , Edited by admin on Sat Jun 26 08:13:44 UTC 2021
PRIMARY
DRUG BANK
DB00931
Created by admin on Sat Jun 26 08:13:44 UTC 2021 , Edited by admin on Sat Jun 26 08:13:44 UTC 2021
PRIMARY
EVMPD
SUB08801MIG
Created by admin on Sat Jun 26 08:13:44 UTC 2021 , Edited by admin on Sat Jun 26 08:13:44 UTC 2021
PRIMARY
NCI_THESAURUS
C61839
Created by admin on Sat Jun 26 08:13:44 UTC 2021 , Edited by admin on Sat Jun 26 08:13:44 UTC 2021
PRIMARY
RXCUI
6812
Created by admin on Sat Jun 26 08:13:44 UTC 2021 , Edited by admin on Sat Jun 26 08:13:44 UTC 2021
PRIMARY RxNorm
HSDB
3118
Created by admin on Sat Jun 26 08:13:44 UTC 2021 , Edited by admin on Sat Jun 26 08:13:44 UTC 2021
PRIMARY