methacycline

Trade name: rondomycin

Small moleculeapproved

Approved

Jan 1, 1966

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. — NCATS

Clinical trial activity

0 trials · 0 clinical orgs · 2 marketing orgs

Phase 1

Phase 2

Phase 3

Phase 4

Timeline

1960s

Jan 1, 1966
Earliest FDA Approval
Jun 1, 1966
Carter-Wallace — First NDA Organization
Jun 1, 1966
Carter-Wallace — NDA Organization

Indications

Approved for

Bronchitis, Chronic

Mechanism of action

Bacterial 70S ribosomeINHIBITOR
Bacterial 70S ribosome inhibitor
16s RRNA

Approval history

approvedJan 1, 1966

Chemistry & pharmacology

Loading structure…

SMILES

C=C1c2cccc(O)c2C(=O)C2=C(O)[C@]3(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@@H]3[C@@H](O)[C@H]12

Mol. weight: 442.42 g/mol
Lipinski Ro5: 1 violation(s)
Rule of 3: No
Chirality: Single Stereoisomer
Inorganic: No
Polymer: No
Delivery: Oral
Availability: Discontinued

Oral

Yes

Parenteral

Topical

Sources

Also known as

6-demethyl-6-deoxy-5-hydroxy-6-methylenetetracycline
6-demethyl-6-deoxy-5-hydroxy-6-methylenetetracycline
6-deoxy-6-demethyl-6-methylene-5-oxytetracycline
6-deoxy-6-demethyl-6-methylene-5-oxytetracycline
6-methylene-5-hydroxytetracycline
6-methylene-5-hydroxytetracycline
6-methylene-5-oxytetracycline
6-methylene-5-oxytetracycline
6-methyleneoxytetracycline
6-methyleneoxytetracycline
gs-2876
gs-2876
metacycline
metacycline
metacycline
metacycline
metacycline
methacyclin
methacyclin
methacycline
methacycline
methacycline
methacycline
methacycline
methacycline
methacycline
methacycline hcl
methacycline hcl
methacycline hcl
methacycline hydrochloride
methacycline hydrochloride
methacycline hydrochloride
methacycline hydrochloride
methacyclinum
methacyclinum
methylenecycline
methylenecycline
motc
motc
rondomycin
rondomycin
rondomycin
rondomycin
rondomycin
rondomycin
rondomycin
tri-methacycline
tri-methacycline

Organizations

Marketing (2)

Organization	Org type	Relationship	Date
Carter-Wallace	For profit	NDA	Jun 1, 1966
Medpointe	For profit	MKTG	—