METHACYCLINE HYDROCHLORIDE

US Previously Marketed

First approved in 1966

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 Search

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

Molecular Formula	C22H22N2O8
Molecular Weight	442.4187
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.drugbank.ca/drugs/DB00931 | http://www.tabletwise.com/us/rondomycin-capsule | http://www.tabletwise.com/us/rondomycin-capsule

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial 70S ribosome 179 Target ID: CHEMBL2363135 Sources: https://www.drugbank.ca/drugs/DB00931 \| https://www.ncbi.nlm.nih.gov/pubmed/15156014 \| https://www.ncbi.nlm.nih.gov/pubmed/17035842 \| https://www.ncbi.nlm.nih.gov/pubmed/18220943	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic bronchitis 51 Sources: http://www.tabletwise.com/us/rondomycin-capsule http://www.minclinic.ru/drugs/drugs_eng/R/Rondomycin.html http://www.druglib.com/activeingredient/methacycline/	Curative		Approved 8429	RONDOMYCIN Approved Use Rondomycin Indication: For the treatment of acute bacterial exacerbations of chronic bronchitis

C_max

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

T_1/2

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: https://pubmed.ncbi.nlm.nih.gov/4968585/	unhealthy, adult n = 62 Health Status: unhealthy Condition: bronchitis Age Group: adult Sex: unknown Population Size: 62 Sources: https://pubmed.ncbi.nlm.nih.gov/4968585/	Disc. AE: Gastrointestinal disorders... AEs leading to discontinuation/dose reduction: Gastrointestinal disorders (3 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/4968585/

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: https://pubmed.ncbi.nlm.nih.gov/4968585/	unhealthy, adult n = 62 Health Status: unhealthy Condition: bronchitis Age Group: adult Sex: unknown Population Size: 62 Sources: https://pubmed.ncbi.nlm.nih.gov/4968585/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:6805	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6805
ChemicalBook	CB0105251	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0105251
ZINC	ZINC000085650610	http://zinc15.docking.org/substances/ZINC000085650610
eMolecules	2725962	https://www.emolecules.com/cgi-bin/more?vid=2725962

PubMed

Title	Date	PubMed
Methacycline and demeclocycline in relation to sunlight.	1971 Apr 12	5107921
Protective activity of tetracycline analogs against the cytopathic effect of the human immunodeficiency viruses in CEM cells.	1990 Jan-Feb	2326552

Patents

Sample Use Guides

In Vivo Use Guide

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 Dec 15 15:03:15 GMT 2023` Edited by `admin` on `Fri Dec 15 15:03:15 GMT 2023`
Record UNII	9GJ0N7ZAP0
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METHACYCLINE HYDROCHLORIDE

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

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