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

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H22N2O8.ClH
Molecular Weight 478.88
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHACYCLINE HYDROCHLORIDE

SMILES

Cl.[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=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
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.
Name Type Language
METHACYCLINE HYDROCHLORIDE
JAN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF  
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
Metacycline hydrochloride [WHO-DD]
Common 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 [MART.]
Common Name English
NSC-356465
Code English
METHACYCLINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1595
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Code System Code Type Description
RXCUI
235554
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PRIMARY RxNorm
CHEBI
6805
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PRIMARY
DRUG BANK
DBSALT001479
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PRIMARY
EPA CompTox
DTXSID5045382
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PRIMARY
CAS
3963-95-9
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PRIMARY
NSC
757835
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PRIMARY
SMS_ID
100000091464
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PRIMARY
ECHA (EC/EINECS)
223-568-3
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PRIMARY
EVMPD
SUB03183MIG
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PRIMARY
NCI_THESAURUS
C47608
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PRIMARY
ChEMBL
CHEMBL249837
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PRIMARY
FDA UNII
9GJ0N7ZAP0
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PRIMARY
RS_ITEM_NUM
1397006
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PRIMARY
NSC
356465
Created by admin on Fri Dec 15 15:03:15 GMT 2023 , Edited by admin on Fri Dec 15 15:03:15 GMT 2023
PRIMARY
MERCK INDEX
m7285
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PRIMARY Merck Index