sulfadiazine

Trade name: sulfadiazine

Small moleculeapproved

Approved

Aug 11, 1941

Sulfadiazine is a sulfonamide 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. Sulfonamides inhibit multiplication of bacteria by acting as competitive inhibitors of p-aminobenzoic acid in the folic acid metabolism cycle. Bacterial sensitivity is the same for the various sulfonamides, and resistance to one sulfonamide indicates resistance to all. Most sulfonamides are readily absorbed orally. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. The sulfonamides are widely distributed throughout all tissues. High levels are achieved in pleural, peritoneal, synovial, and ocular fluids. Although these drugs are no longer used to treat meningitis, CSF levels are high in meningeal infections. Their antibacterial action is inhibited by pus. Sulfadiazine is a competitive inhibitor of the bacterial enzyme dihydropteroate synthetase. This enzyme is needed for the proper processing of para-aminobenzoic acid (PABA) which is essential for folic acid synthesis. The inhibited reaction is necessary in these organisms for the synthesis of folic acid. Used for the treatment of rheumatic fever and meningococcal meningitis. — NCATS

Clinical trial activity

5 trials · 6 clinical orgs · 15 marketing orgs

Phase 1

Phase 2

Phase 3

Phase 4

Earliest trial started Nov 2, 1999 (NCT00000794)

Timeline

1940s

Aug 11, 1941
Lederle — Earliest FDA Approval
Aug 11, 1941
Lederle — NDA Organization
Aug 11, 1941
American Cyanamid — NDA Secondary Org
Aug 26, 1941
Eli Lilly — NDA Secondary Org

1970s

Jan 23, 1974
Impax Laboratories — Marketing Organization
Jun 2, 1976
Alpharma — Marketing Organization
Jul 5, 1978
Lannett Company, Inc. — Marketing Organization
Jul 5, 1978
Chartwell Pharmaceuticals — Marketing Organization

1990s

Jul 29, 1994
Epic Pharma Llc — Marketing Organization
Jul 29, 1994
Sandoz — Marketing Organization
Jan 1, 1999
Earliest Phase 2 Sponsor(trial)

2000s

Jan 1, 2005
Earliest Phase 3 Sponsor(trial)

Indications

Approved for

Studied for

Mechanism of action

Bacterial dihydropteroate synthaseANTAGONIST
folP antagonist
- Dihydropteroate synthase (folP) ↗

Combination products

sulfonamides duplex
with sulfamerazine
trisulfapyrimidines
with sulfamethazine, sulfamerazine

Approval history

approvedAug 11, 1941

Chemistry & pharmacology

Loading structure…

SMILES

NC1=CC=C(C=C1)S(=O)(=O)NC2=NC=CC=N2

Mol. weight: 250.277 g/mol
Lipinski Ro5: Pass
Rule of 3: No
Chirality: Achiral Molecule
Inorganic: No
Polymer: No
Availability: Prescription Only

Oral

Parenteral

Topical

Sources

Also known as

2-(p-aminobenzenesulphonamido)pyridine
2-(p-aminobenzenesulphonamido)pyridine
2-sulfanilamidopyridin
2-sulfanilamidopyridin
2-sulfanilamidopyridine
2-sulfanilamidopyridine
2-sulfanilamidopyrimidine
2-sulfanilamidopyrimidine
2-sulfanilylaminopyridine
2-sulfanilylaminopyridine
2-sulfanilylaminopyrimidine
2-sulfanilylaminopyrimidine
2-sulfapyridine
2-sulfapyridine
4-(2-pyridinylsulfonyl)aniline
4-(2-pyridinylsulfonyl)aniline
4-[(2-pyridylamino)sulfonyl]aniline
4-[(2-pyridylamino)sulfonyl]aniline
4-amino-n,2-pyridinylbenzenesulfonamide
4-amino-n,2-pyridinylbenzenesulfonamide
4-amino-n-2-pyrimidinylbenzenesulfonamide
4-amino-n-2-pyrimidinylbenzenesulfonamide
4-amino-n-pyridin-2-yl-benzenesulfonamide
4-amino-n-pyridin-2-yl-benzenesulfonamide
adiazine
adiazine
cerium-flamazine
cerous nitrate - sulfadiazine silver
cerous nitrate, sulfadiazine silver drug combination
coccoclase
coccoclase
coco-diazine
coco-diazine
diazyl
diazyl
flammacerium
flammacerium
flammacerium
microsulfon
microsulfon
n(1)-2-pyrimidinylsulfanilamide
n(1)-2-pyrimidinylsulfanilamide
n1-2-pyrimidinylsulfanilamide
n1-2-pyrimidinylsulfanilamide
n(1)-2-pyrimidylsulfanilamide
n(1)-2-pyrimidylsulfanilamide
n1-2-pyrimidylsulfanilamide
n1-2-pyrimidylsulfanilamide
sildaflo
sildaflo
ssd
ssd
ssd af
ssd af
sulfacombin
sulfacombin
sulfadiazina
sulfadiazina
sulfadiazine
sulfadiazine
sulfadiazine
sulfadiazine
sulfadiazine
sulfadiazine
sulfadiazine
sulfadiazine
sulfadiazine
sulfadiazine silver
sulfadiazine silver
sulfadiazine silver
sulfadiazine silver
sulfadiazine silver
sulfadiazine silver
sulfadiazine, silver
sulfadiazine, silver
sulfadiazine, silver
sulfadiazine silver salt
sulfadiazine silver salt
sulfadiazine (trisulfapyrimidines)
sulfadiazine (trisulfapyrimidines)
sulfadiazinum
sulfadiazinum
sulfapyrimidine
sulfapyrimidine
sulfapyrimidine
sulfapyrimidine
sulfolex
sulfolex
sulphadiazine
sulphadiazine
sulphadiazine
sulphadiazine
thermazene
thermazene

Clinical trials

NCT ID	Phase	Start date	Sponsor(s)
NCT01189448	Phase 3	Nov 1, 2010	University of Paris
NCT00372294	Phase 3	Jul 1, 2005	Shahid Beheshti University of Medical Sciences
NCT00367081	Phase 4	May 1, 2003	Chiangmai University, Rajavithi Hospital, Bangkok
NCT00004317	Phase 4	Jul 1, 2000	National Institute of Allergy and Infectious Diseases (NIAID), University of Chicago
NCT00000794	Phase 2	Nov 2, 1999	National Institute of Allergy and Infectious Diseases (NIAID)

Showing 5 of 5 trials

Page 1 / 1

Organizations

Research & Development (6)

Organization	Org type	Trials	As lead sponsor	Phases	Earliest year
National Institute of Allergy and Infectious Diseases (NIAID)	Government	2	2	2	1999
Chiangmai University	Academic/Hospital	1	0	1	2003
Rajavithi Hospital, Bangkok	Academic/Hospital	1	1	1	2003
Shahid Beheshti University of Medical Sciences	Academic/Hospital	1	1	1	2005
University of Chicago	Academic/Hospital	1	0	1	2000
University of Paris	Academic/Hospital	1	1	1	2010

6 organizations

Page 1 / 1

Marketing (17)

Organization	Org type	Relationship	Date
AbbVie	For profit	NDA2	—
Alpharma	For profit	MKTG	Jun 2, 1976
American Cyanamid	For profit	NDA2	Aug 11, 1941
American Home Products	For profit	MKTG	—
Bristol-Myers Squibb	For profit	NDA2	—
Chartwell Pharmaceuticals	For profit	MKTG	Jul 5, 1978
Eli Lilly	For profit	NDA2	Aug 26, 1941
Epic Pharma Llc	For profit	MKTG	Jul 29, 1994
Epic Pharma Llc	For profit	SYN	Jul 29, 1994
Everylife Foundation for Rare Diseases	Academic/Hospital	MKTG	—
Forest Laboratories	For profit	MKTG	—
Impax Laboratories	For profit	MKTG	Jan 23, 1974
Lannett Company, Inc.	For profit	MKTG	Jul 5, 1978
Lannett Company, Inc.	For profit	SYN	Jun 12, 1975
Lederle	For profit	NDA	Aug 11, 1941
Puracap Pharmaceutical	For profit	MKTG	—
Sandoz	For profit	MKTG	Jul 29, 1994