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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H22N2O8.ClH
Molecular Weight 478.8804
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHACYCLINE HYDROCHLORIDE

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.Cl

InChI

InChIKey=VZQARNDJLLWXGL-CCHMMTNSSA-N
InChI=1S/C22H22N2O8.ClH/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);1H/t10-,14-,15+,17+,22+;/m1./s1

HIDE SMILES / InChI

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

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 Fri Jun 25 22:05:16 UTC 2021
Edited
by admin
on Fri Jun 25 22:05:16 UTC 2021
Record UNII
9GJ0N7ZAP0
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHACYCLINE HYDROCHLORIDE
JAN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
METACYCLINE HYDROCHLORIDE [WHO-DD]
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 MONOHYDROCHLORIDE
Common Name English
METHACYCLINE HYDROCHLORIDE [VANDF]
Common Name English
METHACYCLINE HYDROCHLORIDE [MI]
Common Name English
METHACYCLINE HYDROCHLORIDE [JAN]
Common Name English
METACYCLINE HYDROCHLORIDE
WHO-DD  
Common Name English
RONDOMYCIN
Brand Name English
METHACYCLINE HCL
Common Name English
METHACYCLINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
NSC-757835
Code English
METHACYCLINE HYDROCHLORIDE [USP-RS]
Common Name English
METHACYCLINE HYDROCHLORIDE [USP]
Common Name English
METHACYCLINE HYDROCHLORIDE [MART.]
Common Name English
NSC-356465
Code English
Classification Tree Code System Code
NCI_THESAURUS C1595
Created by admin on Fri Jun 25 22:05:16 UTC 2021 , Edited by admin on Fri Jun 25 22:05:16 UTC 2021
Code System Code Type Description
RXCUI
235554
Created by admin on Fri Jun 25 22:05:16 UTC 2021 , Edited by admin on Fri Jun 25 22:05:16 UTC 2021
PRIMARY RxNorm
DRUG BANK
DBSALT001479
Created by admin on Fri Jun 25 22:05:16 UTC 2021 , Edited by admin on Fri Jun 25 22:05:16 UTC 2021
PRIMARY
EPA CompTox
3963-95-9
Created by admin on Fri Jun 25 22:05:16 UTC 2021 , Edited by admin on Fri Jun 25 22:05:16 UTC 2021
PRIMARY
CAS
3963-95-9
Created by admin on Fri Jun 25 22:05:16 UTC 2021 , Edited by admin on Fri Jun 25 22:05:16 UTC 2021
PRIMARY
USP_CATALOG
1397006
Created by admin on Fri Jun 25 22:05:16 UTC 2021 , Edited by admin on Fri Jun 25 22:05:16 UTC 2021
PRIMARY USP-RS
ECHA (EC/EINECS)
223-568-3
Created by admin on Fri Jun 25 22:05:16 UTC 2021 , Edited by admin on Fri Jun 25 22:05:16 UTC 2021
PRIMARY
EVMPD
SUB03183MIG
Created by admin on Fri Jun 25 22:05:16 UTC 2021 , Edited by admin on Fri Jun 25 22:05:16 UTC 2021
PRIMARY
NCI_THESAURUS
C47608
Created by admin on Fri Jun 25 22:05:16 UTC 2021 , Edited by admin on Fri Jun 25 22:05:16 UTC 2021
PRIMARY
ChEMBL
CHEMBL249837
Created by admin on Fri Jun 25 22:05:16 UTC 2021 , Edited by admin on Fri Jun 25 22:05:16 UTC 2021
PRIMARY
FDA UNII
9GJ0N7ZAP0
Created by admin on Fri Jun 25 22:05:16 UTC 2021 , Edited by admin on Fri Jun 25 22:05:16 UTC 2021
PRIMARY
MERCK INDEX
M7285
Created by admin on Fri Jun 25 22:05:16 UTC 2021 , Edited by admin on Fri Jun 25 22:05:16 UTC 2021
PRIMARY Merck Index
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY