sulfisoxazole

Trade name: gantrisin

Small moleculeapproved

Approved

Jul 29, 1948

Sulfisoxazole is a sulfonamide antibacterial antibiotic. The sulfonamides are synthetic bacteriostatic antibiotics with a wide spectrum against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfisoxazole acetyl in combination with erythromycin ethylsuccinate is used for treatment of ACUTE OTITIS MEDIA in children that is caused by susceptible strains of Haemophilus influenzae. Sulfisoxazole acetyl is a prodrug of sulfisoxazole. Acetyl group is added to make the drug poorly water soluble, and is hydrolyzed in vivo to the active drug. Sulfisoxazole and its acetylated metabolites are excreted primarily by the kidneys through glomerular filtration. Sulfisoxazole is a competitive inhibitor of the enzyme dihydropteroate synthetase. It inhibits bacterial synthesis of dihydrofolic acid by preventing the condensation of the pteridine with para-aminobenzoic acid (PABA), a substrate of the enzyme dihydropteroate synthetase. The inhibited reaction is necessary in these organisms for the synthesis of folic acid — NCATS

Clinical trial activity

1 trials · 1 clinical orgs · 23 marketing orgs

Phase 1

Phase 2

Phase 3

Phase 4

Earliest trial started Jun 20, 2019 (NCT03978559)

Timeline

1940s

Jul 29, 1948
Earliest FDA Approval

1950s

Dec 4, 1953
Roche — First NDA Organization
Dec 4, 1953
Roche — NDA Organization

1970s

Jun 7, 1971
Alta Pharma — Marketing Organization
Jun 15, 1972
Solvay — Marketing Organization
Feb 9, 1973
MK Labs — Marketing Organization
Feb 13, 1973
West-Ward Pharmaceutical — Marketing Organization
Mar 6, 1974
Ani Pharmaceuticals — Marketing Organization
Jan 22, 1975
Johnson and Johnson — Marketing Organization
Feb 13, 1975
Barr Laboratories — Marketing Organization
Jan 5, 1977
Parke-Davis — Marketing Organization
Jan 5, 1977
Warner Lambert — Marketing Organization
Jun 13, 1977
Aurobindo Pharma — Marketing Organization
Jun 13, 1977
Rising Pharmaceuticals — Marketing Organization
Mar 6, 1978
Lannett Company, Inc. — Marketing Organization
Nov 29, 1979
Abbott — Marketing Organization
Nov 29, 1979
Abbott — NDA Secondary Org

1980s

Mar 29, 1983
Vitarine — Marketing Organization

Indications

Approved for

Otitis Media (approved 1988)

Studied for

Pneumonia, Pneumocystis · Phase 4

Mechanism of action

Bacterial dihydropteroate synthaseINHIBITOR
folP inhibitor
Broad spectrum
- Dihydropteroate synthase (folP) ↗

Combination products

azo gantrisin
with phenazopyridine
pediazole
with erythromycin
Also known as eryzole

Approval history

approvedJul 29, 1948

Chemistry & pharmacology

Loading structure…

SMILES

Cc1noc(NS(=O)(=O)c2ccc(N)cc2)c1C

Mol. weight: 267.31 g/mol
Lipinski Ro5: Pass
Rule of 3: No
Chirality: Achiral Molecule
Inorganic: No
Polymer: No
Delivery: Oral, Parenteral, Topical
Availability: Discontinued

Oral

Yes

Parenteral

Yes

Topical

Yes

Sources

Also known as

3,4-dimethyl-5-sulfanilamidoisoxazole
3,4-dimethyl-5-sulfanilamidoisoxazole
3,4-dimethyl-5-sulfonamidoisoxazole
3,4-dimethyl-5-sulfonamidoisoxazole
3,4-dimethyl-5-sulphanilamidoisoxazole
3,4-dimethyl-5-sulphanilamidoisoxazole
3,4-dimethyl-5-sulphonamidoisoxazole
3,4-dimethyl-5-sulphonamidoisoxazole
3,4-dimethylisoxazole-5-sulfanilamide
3,4-dimethylisoxazole-5-sulfanilamide
3,4-dimethylisoxazole-5-sulphanilamide
3,4-dimethylisoxazole-5-sulphanilamide
4-amino-n-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamide
4-amino-n-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamide
4-amino-n-(3,4-dimethyl-5-isoxazolyl)benzenesulphonamide
4-amino-n-(3,4-dimethyl-5-isoxazolyl)benzenesulphonamide
5-(4-aminophenylsulfonamido)-3,4-dimethylisoxazole
5-(4-aminophenylsulfonamido)-3,4-dimethylisoxazole
5-(p-aminobenzenesulfonamido)-3,4-dimethylisoxazole
5-(p-aminobenzenesulfonamido)-3,4-dimethylisoxazole
5-(p-aminobenzenesulphonamido)-3,4-dimethylisoxazole
5-(p-aminobenzenesulphonamido)-3,4-dimethylisoxazole
5-sulfanilamido-3,4-dimethylisoxazole
5-sulfanilamido-3,4-dimethylisoxazole
5-sulphanilamido-3,4-dimethyl-isoxazole
5-sulphanilamido-3,4-dimethyl-isoxazole
acetylsulfisoxazole
acetylsulfisoxazole
acetylsulfisoxazole
alphazole
entusil
entusil
erythromycin, 2-amino-5-((aminoacetyl)methylamino)-2,3,5-trideoxy-1-o-(2,6-diamino-2,3,4,6,7-pentadeoxy-beta-l-lyxo-heptopyranosyl)-, (1alpha,2beta,2aalpha,3aalpha)-
eryzole
eryzole
gantrisin
gantrisin
gantrisin
gantrisin
gantrisin pediatric
gantrisin pediatric
lipo gantrisin
lipo gantrisin
mk 0641
mk-0641
n(1)-(3,4-dimethyl-5-isoxazolyl)sulfanilamide
n(1)-(3,4-dimethyl-5-isoxazolyl)sulfanilamide
n(1)-(3,4-dimethyl-5-isoxazolyl)sulphanilamide
n(1)-(3,4-dimethyl-5-isoxazolyl)sulphanilamide
n'-(3,4)dimethylisoxazol-5-yl-sulphanilamide
n'-(3,4)dimethylisoxazol-5-yl-sulphanilamide
neazolin
neazolin
nu-445
nu-445
pediazole
pediazole
pediazole
sosol
sosol
soxazole
soxazole
soxomide
sulfadimethylisoxazole
sulfadimethylisoxazole
sulfadimethylisoxazole
sulfafurazol
sulfafurazol
sulfafurazol
sulfafurazole
sulfafurazole
sulfafurazole
sulfafurazole
sulfafurazole
sulfafurazole diolamine
sulfafurazole diolamine
sulfafurazole diolamine
sulfafurazole diolamine
sulfafurazole diolamine
sulfafurazole diolamine
sulfafurazolum
sulfafurazolum
sulfaisoxazole
sulfaisoxazole
sulfaisoxazole
sulfalar
sulfalar
sulfasoxazole
sulfasoxazole
sulfazin
sulfisonazole
sulfisonazole
sulfisoxasole
sulfisoxasole
sulfisoxazol
sulfisoxazol
sulfisoxazol
sulfisoxazole
sulfisoxazole
sulfisoxazole
sulfisoxazole
sulfisoxazole
sulfisoxazole
sulfisoxazole
sulfisoxazole
sulfisoxazole acetyl
sulfisoxazole acetyl
sulfisoxazole acetyl
sulfisoxazole acetyl
sulfisoxazole acetyl
sulfisoxazole acetyl
sulfisoxazole dialamine
sulfisoxazole diolamine
sulfisoxazole diolamine
sulfisoxazole diolamine
sulfisoxazole diolamine
sulfofurazole
sulfofurazole
sulphadimethylisoxazole
sulphadimethylisoxazole
sulphafurazol
sulphafurazol
sulphafurazole
sulphafurazole
sulphafurazole
sulphafurazole
sulphaisoxazole
sulphaisoxazole
sulphisoxazol
sulphisoxazol
sulphofurazole
sulphofurazole
sulsoxin
sulsoxin

Clinical trials

NCT ID	Phase	Start date	Sponsor(s)
NCT03978559	Phase 4	Jun 20, 2019	Chinese Academy of Medical Sciences

Showing 1 of 1 trials

Page 1 / 1

Organizations

Research & Development (1)

Organization	Org type	Trials	As lead sponsor	Phases	Earliest year
Chinese Academy of Medical Sciences	Academic/Hospital	1	1	1	2019

1 organizations

Page 1 / 1

Marketing (26)

Organization	Org type	Relationship	Date
Abbott	For profit	MKTG	Nov 29, 1979
Abbott	For profit	NDA2	Nov 29, 1979
Alta Pharma	For profit	MKTG	Jun 7, 1971
Ani Pharmaceuticals	For profit	MKTG	Mar 6, 1974
Ani Pharmaceuticals	For profit	SYN	Mar 6, 1974
Aurobindo Pharma	For profit	MKTG	Jun 13, 1977
Barr Laboratories	For profit	MKTG	Feb 13, 1975
Bausch Health Companies	For profit	MKTG	—
Eli Lilly	For profit	NDA2	—
Heather Pharma	For profit	MKTG	—
Impax Laboratories	For profit	MKTG	—
Johnson and Johnson	For profit	MKTG	Jan 22, 1975
Lannett Company, Inc.	For profit	MKTG	Mar 6, 1978
Lannett Company, Inc.	For profit	SYN	Nov 5, 1980
Lederle	For profit	MKTG	—
MK Labs	For profit	MKTG	Feb 9, 1973
Parke-Davis	For profit	MKTG	Jan 5, 1977
Puracap Pharmaceutical	For profit	MKTG	—
Rising Pharmaceuticals	For profit	MKTG	Jun 13, 1977
Roche	For profit	NDA	Dec 4, 1953
Roxane Laboratories	For profit	MKTG	—
Solvay	For profit	MKTG	Jun 15, 1972
Vitarine	For profit	MKTG	Mar 29, 1983
Warner Lambert	For profit	MKTG	Jan 5, 1977
Watson Pharmaceuticals	For profit	MKTG	—
West-Ward Pharmaceutical	For profit	MKTG	Feb 13, 1973