oxytetracycline

Trade name: terramycin

Small moleculeapproved

Approved

Jan 29, 1964

Oxytetracycline, a tetracycline analog isolated from the actinomycete streptomyces rimosus, was the second of the broad-spectrum tetracycline group of antibiotics to be discovered The drug is used for the prophylaxis and local treatment of superficial ocular infections due to oxytetracycline- and polymyxin-sensitive organisms for animal use only. These infections include the following: Ocular infections due to streptococci, rickettsiae E. coli, and A. aerogenes (such as conjunctivitis, keratitis, pinkeye, corneal ulcer, and blepharitis in dogs); ocular infections due to secondary bacterial complications associated with distemper in dogs; and ocular infections due to bacterial inflammatory conditions which may occur secondary to other diseases in dogs. Allergic reactions may occasionally occur. Treatment should be discontinued if reactions are severe. If new infections due to nonsensitive bacteria or fungi appear during therapy, appropriate measures should be taken. Oxytetracycline inhibits cell growth by inhibiting translation. It binds to the 30S ribosomal subunit and prevents the amino-acyl tRNA from binding to the A site of the ribosome. The binding is reversible in nature. Oxytetracycline is lipophilic and can easily pass through the cell membrane or passively diffuses through porin channels in the bacterial membrane. — NCATS

Clinical trial activity

3 trials · 5 clinical orgs · 7 marketing orgs

Phase 1

Phase 2

Phase 3

Phase 4

Earliest trial started May 1, 2010 (NCT01032499)

Timeline

1960s

Jan 29, 1964
Earliest FDA Approval
Jan 29, 1964
Proter — Marketing Organization
Sep 8, 1964
Pfizer — First NDA Organization
Sep 8, 1964
Pfizer — NDA Organization
Sep 15, 1964
Pfizer — Marketing Organization
Jul 8, 1965
Casper Pharma LLC — Marketing Organization
Jul 8, 1965
Casper Pharma LLC — NDA Secondary Org
Aug 9, 1967
Impax Laboratories — Marketing Organization
Aug 11, 1967
John J. Ferrante — Marketing Organization
Sep 29, 1967
Hikma — Marketing Organization

2010s

Jan 1, 2010
Earliest Phase 3 Sponsor(trial)

2020s

Jan 1, 2021
Earliest Phase 1 Sponsor(trial)

Indications

Approved for

Eye Infections

Studied for

Mechanism of action

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

Combination products

terra-cortril
with urea
terramycin
with lidocaine
terramycin w/ polymyxin b sulfate
with polymyxin b sulfate

Approval history

approvedJan 29, 1964

Chemistry & pharmacology

Loading structure…

SMILES

CN(C)[C@@H]1C([O-])=C(C(N)=O)C(=O)[C@@]2(O)C(O)=C3C(=O)c4c(O)cccc4[C@@](C)(O)[C@H]3[C@H](O)[C@@H]12.CN(C)[C@@H]1C([O-])=C(C(N)=O)C(=O)[C@@]2(O)C(O)=C3C(=O)c4c(O)cccc4[C@@](C)(O)[C@H]3[C@H](O)[C@@H]12.[Ca+2]

Mol. weight: 958.94 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

5-hydroxytetracycline
5-hydroxytetracycline
berkmycen
berkmycen
chemocycline
e703
e703
embryostat
embryostat
galenomycin
hi-tet
hydroxytetracyclinum
hydroxytetracyclinum
imperacin
imperacin
mepatar
mepatar
microtet
oxitetraciclina
oxitetraciclina
oxitetracycline
oxitetracycline
oxtc
oxtc
oxy-kesso-tetra
oxy-kesso-tetra
oxymycin
oxymycin
oxyterracin
oxyterracin
oxyterracine
oxyterracine
oxytetracyclin
oxytetracyclin
oxytetracycline
oxytetracycline
oxytetracycline
oxytetracycline
oxytetracycline
oxytetracycline
oxytetracycline
oxytetracycline
oxytetracycline
oxytetracycline
oxytetracycline
oxytetracycline
oxytétracycline
oxytétracycline
oxytetracycline amphoteric
oxytetracycline amphoteric
oxytetracycline anhydrous
oxytetracycline (anhydrous)
oxytetracycline (anhydrous)
oxytetracycline calcium
oxytetracycline calcium
oxytetracycline calcium
oxytetracycline calcium
oxytetracycline dihydrate
oxytetracycline hcl
oxytetracycline hcl
oxytetracycline hcl
oxytetracycline hydrochloride
oxytetracycline hydrochloride
oxytetracycline hydrochloride
oxytetracycline hydrochloride
oxytetracyclinum
oxytetracyclinum
oxytetramix-250
terrafungine
terrafungine
terramycin
terramycin
terramycin
terramycin
terramycin
tetraplex
unimycin
unimycin

Clinical trials

NCT ID	Phase	Start date	Sponsor(s)
NCT05177640	Phase 1	Jun 17, 2021	Molecular Targeting Technologies, Inc., University of Antwerp
NCT03892330	Phase 4	Jun 1, 2019	Shengjing Hospital
NCT01032499	Phase 3	May 1, 2010	Faculdade de Medicina do ABC, Laboratorios Goulart S.A.

Showing 3 of 3 trials

Page 1 / 1

Organizations

Research & Development (5)

Organization	Org type	Trials	As lead sponsor	Phases	Earliest year
Faculdade de Medicina do ABC	Academic/Hospital	1	0	1	2010
Laboratorios Goulart S.A.	For profit	1	1	1	2010
Molecular Targeting Technologies, Inc.	For profit	1	0	1	2021
Shengjing Hospital	Academic/Hospital	1	1	1	2019
University of Antwerp	Academic/Hospital	1	1	1	2021

5 organizations

Page 1 / 1

Marketing (10)

Organization	Org type	Relationship	Date
Casper Pharma LLC	For profit	MKTG	Jul 8, 1965
Casper Pharma LLC	For profit	NDA2	Jul 8, 1965
Hikma	For profit	MKTG	Sep 29, 1967
Hikma	For profit	SYN	Sep 29, 1967
Impax Laboratories	For profit	MKTG	Aug 9, 1967
John J. Ferrante	For profit	MKTG	Aug 11, 1967
Pfizer	For profit	NDA	Sep 8, 1964
Pfizer	For profit	MKTG	Sep 15, 1964
Proter	For profit	MKTG	Jan 29, 1964
Puracap Pharmaceutical	For profit	MKTG	—