sulfamethazine

Small moleculeapproved

Approved

Aug 16, 1949

Sulfamethazine is a sulfonamide used to treat a variety of bacterial diseases in animals. It inhibits bacterial synthesis of dihydrofolic acid by competing with para-aminobenzoic acid (PABA) for binding to dihydropteroate synthetase (dihydrofolate synthetase). — NCATS

Clinical trial activity

0 trials · 0 clinical orgs · 10 marketing orgs

Phase 1

Phase 2

Phase 3

Phase 4

Timeline

1940s

Aug 16, 1949
American Cyanamid — Earliest FDA Approval
Aug 16, 1949
Lederle — NDA Secondary Org
Aug 16, 1949
American Cyanamid — NDA Secondary Org
Aug 16, 1949
American Cyanamid — NDA Organization

1970s

Jan 23, 1974
Impax Laboratories — Marketing Organization
Jun 2, 1976
Alpharma — Marketing Organization
Aug 24, 1978
Lannett Company, Inc. — Marketing Organization

Indications

Approved for

Communicable Diseases

Mechanism of action

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

Combination products

trisulfapyrimidines
with sulfamerazine, sulfadiazine

Approval history

approvedAug 16, 1949

Chemistry & pharmacology

Loading structure…

SMILES

CC1=CC(C)=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=N1

Mol. weight: 278.33 g/mol
Lipinski Ro5: Pass
Rule of 3: No
Chirality: Achiral Molecule
Inorganic: No
Polymer: No
Delivery: Oral
Availability: Discontinued

Oral

Yes

Parenteral

Topical

Sources

Also known as

2-(4-aminobenzenesulfonamido)-4,6-dimethylpyrimidine
2-(4-aminobenzenesulfonamido)-4,6-dimethylpyrimidine
2-(4-aminobenzenesulfonamido)-4-methylpyrimidine
2-(4-aminobenzenesulfonamido)-4-methylpyrimidine
2-(p-aminobenzenesulfonamido)-4,6-dimethylpyrimidine
2-(p-aminobenzenesulfonamido)-4,6-dimethylpyrimidine
2-sulfanilamido-4,6-dimethylpyrimidine
2-sulfanilamido-4,6-dimethylpyrimidine
4,6-dimethyl-2-sulfanilamidopyrimidine
4,6-dimethyl-2-sulfanilamidopyrimidine
4-amino-n-(4,6-dimethyl-pyrimidin-2-yl)-benzenesulfonamide
4-amino-n-(4,6-dimethyl-pyrimidin-2-yl)-benzenesulfonamide
4-amino-n-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide
4-amino-n-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide
6-(4'-aminobenzol-sulfonamido)-2,4-dimethylpyrimidin
6-(4'-aminobenzol-sulfonamido)-2,4-dimethylpyrimidin
n(1)-(4,6-dimethyl-2-pyrimidinyl)sulfanilamide
n(1)-(4,6-dimethyl-2-pyrimidinyl)sulfanilamide
n(1)-(4,6-dimethyl-2-pyrimidyl)sulfanilamide
n(1)-(4,6-dimethyl-2-pyrimidyl)sulfanilamide
n(1)-(4-methyl-2-pyrimidinyl)sulfanilamide
n(1)-(4-methyl-2-pyrimidinyl)sulfanilamide
n-(4,6-dimethyl-2-pyrimidyl)sulfanilamide
n-(4,6-dimethyl-2-pyrimidyl)sulfanilamide
(p-aminobenzolsulfonyl)-2-amino-4,6-dimethylpyrimidin
(p-aminobenzolsulfonyl)-2-amino-4,6-dimethylpyrimidin
smz
smz
smz-med 454
sulfadimerazine
sulfadimethyldiazine
sulfadimethyldiazine
sulfadimethyldiazine
sulfadimethylpyrimidine
sulfadimethylpyrimidine
sulfadimidina
sulfadimidina
sulfadimidine
sulfadimidine
sulfadimidine
sulfadimidine
sulfadimidine
sulfadimidine
sulfadimidine
sulfadimidinum
sulfadimidinum
sulfametazina
sulfametazina
sulfametazyny
sulfametazyny
sulfamethazine
sulfamethazine
sulfamethazine
sulfamethazine
sulfamethazine
sulfamethazine
sulfamethazine sodium
sulfamethazine sodium salt
sulfamethazine (trisulfapyrimidines)
sulfamethazine (trisulfapyrimidines)
sulfamezathine
sulfamezathine
sulfamezathine ('s-mez')
sulphadimethylpyrimidine
sulphadimethylpyrimidine
sulphamethazine
sulphamethazine

Organizations

Marketing (12)

Organization	Org type	Relationship	Date
Alpharma	For profit	MKTG	Jun 2, 1976
American Cyanamid	For profit	NDA2	Aug 16, 1949
American Cyanamid	For profit	NDA	Aug 16, 1949
American Home Products	For profit	MKTG	—
Bristol-Myers Squibb	For profit	NDA2	—
Eli Lilly	For profit	NDA2	—
Forest Laboratories	For profit	MKTG	—
Impax Laboratories	For profit	MKTG	Jan 23, 1974
Lannett Company, Inc.	For profit	MKTG	Aug 24, 1978
Lannett Company, Inc.	For profit	SYN	Jun 12, 1975
Lederle	For profit	NDA2	Aug 16, 1949
Puracap Pharmaceutical	For profit	MKTG	—