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Details

Stereochemistry ACHIRAL
Molecular Formula 2C10H9N4O2S.Zn
Molecular Weight 563.947
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULFADIAZINE ZINC

SMILES

[Zn++].NC1=CC=C(C=C1)S(=O)(=O)[N-]C2=NC=CC=N2.NC3=CC=C(C=C3)S(=O)(=O)[N-]C4=NC=CC=N4

InChI

InChIKey=RXXROIWDLGTUIN-UHFFFAOYSA-N
InChI=1S/2C10H9N4O2S.Zn/c2*11-8-2-4-9(5-3-8)17(15,16)14-10-12-6-1-7-13-10;/h2*1-7H,11H2;/q2*-1;+2

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/dosage/sulfadiazine.html

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Sulfadiazine

Approved Use

Sulfadiazine tablets USP are indicated in the following conditions: Chancroid Trachoma Inclusion conjunctivitis Nocardiosis Urinary tract infections (primarily pyelonephritis, pyelitis and cystitis) in the absence of obstructive uropathy or foreign bodies, when these infections are caused by susceptible strains of the following organisms: Escherichia coli, Klebsiella species, Enterobacter species, Staphylococcus aureus, Proteus mirabilis and P. vulgaris. Sulfadiazine should be used for urinary tract infections only after use of more soluble sulfonamides has been unsuccessful. Toxoplasmosis encephalitis in patients with and without acquired immunodeficiency syndrome, as adjunctive therapy with pyrimethamine. Malaria due to chloroquine-resistant strains of Plasmodium falciparum, when used as adjunctive therapy. Prophylaxis of meningococcal meningitis when sulfonamide-sensitive group A strains are known to prevail in family groups or larger closed populations (the prophylactic usefulness of sulfonamides when group B or C infections are prevalent is not proved and may be harmful in closed population groups). Meningococcal meningitis, when the organism has been demonstrated to be susceptible. Acute otitis media due to Haemophilusinfluenzae, when used concomitantly with adequate doses of penicillin. Prophylaxis against recurrences of rheumatic fever, as an alternative to penicillin. H. influenzae meningitis, as adjunctive therapy with parental streptomycin.

Launch Date

1994
Curative
Sulfadiazine

Approved Use

Sulfadiazine tablets USP are indicated in the following conditions: Chancroid Trachoma Inclusion conjunctivitis Nocardiosis Urinary tract infections (primarily pyelonephritis, pyelitis and cystitis) in the absence of obstructive uropathy or foreign bodies, when these infections are caused by susceptible strains of the following organisms: Escherichia coli, Klebsiella species, Enterobacter species, Staphylococcus aureus, Proteus mirabilis and P. vulgaris. Sulfadiazine should be used for urinary tract infections only after use of more soluble sulfonamides has been unsuccessful. Toxoplasmosis encephalitis in patients with and without acquired immunodeficiency syndrome, as adjunctive therapy with pyrimethamine. Malaria due to chloroquine-resistant strains of Plasmodium falciparum, when used as adjunctive therapy. Prophylaxis of meningococcal meningitis when sulfonamide-sensitive group A strains are known to prevail in family groups or larger closed populations (the prophylactic usefulness of sulfonamides when group B or C infections are prevalent is not proved and may be harmful in closed population groups). Meningococcal meningitis, when the organism has been demonstrated to be susceptible. Acute otitis media due to Haemophilusinfluenzae, when used concomitantly with adequate doses of penicillin. Prophylaxis against recurrences of rheumatic fever, as an alternative to penicillin. H. influenzae meningitis, as adjunctive therapy with parental streptomycin.

Launch Date

1994
Curative
Sulfadiazine

Approved Use

Sulfadiazine tablets USP are indicated in the following conditions: Chancroid Trachoma Inclusion conjunctivitis Nocardiosis Urinary tract infections (primarily pyelonephritis, pyelitis and cystitis) in the absence of obstructive uropathy or foreign bodies, when these infections are caused by susceptible strains of the following organisms: Escherichia coli, Klebsiella species, Enterobacter species, Staphylococcus aureus, Proteus mirabilis and P. vulgaris. Sulfadiazine should be used for urinary tract infections only after use of more soluble sulfonamides has been unsuccessful. Toxoplasmosis encephalitis in patients with and without acquired immunodeficiency syndrome, as adjunctive therapy with pyrimethamine. Malaria due to chloroquine-resistant strains of Plasmodium falciparum, when used as adjunctive therapy. Prophylaxis of meningococcal meningitis when sulfonamide-sensitive group A strains are known to prevail in family groups or larger closed populations (the prophylactic usefulness of sulfonamides when group B or C infections are prevalent is not proved and may be harmful in closed population groups). Meningococcal meningitis, when the organism has been demonstrated to be susceptible. Acute otitis media due to Haemophilusinfluenzae, when used concomitantly with adequate doses of penicillin. Prophylaxis against recurrences of rheumatic fever, as an alternative to penicillin. H. influenzae meningitis, as adjunctive therapy with parental streptomycin.

Launch Date

1994
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
84.9 μg/mL
2 g 2 times / day steady-state, oral
dose: 2 g
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
SULFADIAZINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1.247 μg × h/mL
2 g 2 times / day steady-state, oral
dose: 2 g
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
SULFADIAZINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
11.9 h
2 g 2 times / day steady-state, oral
dose: 2 g
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
SULFADIAZINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
4 g 1 times / day steady, oral
Recommended
Dose: 4 g, 1 times / day
Route: oral
Route: steady
Dose: 4 g, 1 times / day
Co-administed with::
pyrimethamine(50 mg oral; 1/day)
folinic acid(15 mg oral; 1/day)
Sources: Page: p.36, 38
unhealthy, 16 - 80
n = 22
Health Status: unhealthy
Condition: Ocular toxoplasmosis
Age Group: 16 - 80
Sex: M+F
Population Size: 22
Sources: Page: p.36, 38
Disc. AE: Stenocardia, Distress gastrointestinal...
Other AEs: Thrombopenia, Creatinine serum increased...
AEs leading to
discontinuation/dose reduction:
Stenocardia (grade 3, 5%)
Distress gastrointestinal (grade 3, 5%)
Skin rash (grade 3, 5%)
Other AEs:
Thrombopenia (9%)
Creatinine serum increased (5%)
Elevated liver enzyme levels (5%)
Malaise (23%)
Diarrhea (5%)
Sources: Page: p.36, 38
1 g 4 times / day steady, oral
Recommended
Dose: 1 g, 4 times / day
Route: oral
Route: steady
Dose: 1 g, 4 times / day
Co-administed with::
pyrimethamine(50-75 mg oral; 1/day)
Sources: Page: p.4
unhealthy, 29.81
n = 16
Health Status: unhealthy
Condition: Cerebral toxoplasmosis
Age Group: 29.81
Sex: M+F
Population Size: 16
Sources: Page: p.4
Disc. AE: Stevens Johnson syndrome, Thrombocytopenia...
Other AEs: Skin rash, Neutropenia...
AEs leading to
discontinuation/dose reduction:
Stevens Johnson syndrome (grade 3, 1.16%)
Thrombocytopenia (grade 4, 25%)
Major bleed (grade 4, 25%)
Other AEs:
Skin rash (1.16%)
Neutropenia (18.75%)
Febrile neutropenia (1.16%)
Sources: Page: p.4
6 g 1 times / day steady, oral (max)
Recommended
Dose: 6 g, 1 times / day
Route: oral
Route: steady
Dose: 6 g, 1 times / day
Co-administed with::
pyrimethamine(50-75 mg oral; 1/day)
Sources: Page: p.476
unhealthy, 33.8
n = 29
Health Status: unhealthy
Condition: Central nervous system toxoplasmosis
Age Group: 33.8
Sex: M+F
Population Size: 29
Sources: Page: p.476
Disc. AE: Skin rash, Neutropenia...
AEs leading to
discontinuation/dose reduction:
Skin rash (grade 3, 17.24%)
Neutropenia (grade 3, 3.45%)
Acute renal failure (grade 3, 6.9%)
Sources: Page: p.476
AEs

AEs

AESignificanceDosePopulation
Malaise 23%
4 g 1 times / day steady, oral
Recommended
Dose: 4 g, 1 times / day
Route: oral
Route: steady
Dose: 4 g, 1 times / day
Co-administed with::
pyrimethamine(50 mg oral; 1/day)
folinic acid(15 mg oral; 1/day)
Sources: Page: p.36, 38
unhealthy, 16 - 80
n = 22
Health Status: unhealthy
Condition: Ocular toxoplasmosis
Age Group: 16 - 80
Sex: M+F
Population Size: 22
Sources: Page: p.36, 38
Creatinine serum increased 5%
4 g 1 times / day steady, oral
Recommended
Dose: 4 g, 1 times / day
Route: oral
Route: steady
Dose: 4 g, 1 times / day
Co-administed with::
pyrimethamine(50 mg oral; 1/day)
folinic acid(15 mg oral; 1/day)
Sources: Page: p.36, 38
unhealthy, 16 - 80
n = 22
Health Status: unhealthy
Condition: Ocular toxoplasmosis
Age Group: 16 - 80
Sex: M+F
Population Size: 22
Sources: Page: p.36, 38
Diarrhea 5%
4 g 1 times / day steady, oral
Recommended
Dose: 4 g, 1 times / day
Route: oral
Route: steady
Dose: 4 g, 1 times / day
Co-administed with::
pyrimethamine(50 mg oral; 1/day)
folinic acid(15 mg oral; 1/day)
Sources: Page: p.36, 38
unhealthy, 16 - 80
n = 22
Health Status: unhealthy
Condition: Ocular toxoplasmosis
Age Group: 16 - 80
Sex: M+F
Population Size: 22
Sources: Page: p.36, 38
Elevated liver enzyme levels 5%
4 g 1 times / day steady, oral
Recommended
Dose: 4 g, 1 times / day
Route: oral
Route: steady
Dose: 4 g, 1 times / day
Co-administed with::
pyrimethamine(50 mg oral; 1/day)
folinic acid(15 mg oral; 1/day)
Sources: Page: p.36, 38
unhealthy, 16 - 80
n = 22
Health Status: unhealthy
Condition: Ocular toxoplasmosis
Age Group: 16 - 80
Sex: M+F
Population Size: 22
Sources: Page: p.36, 38
Thrombopenia 9%
4 g 1 times / day steady, oral
Recommended
Dose: 4 g, 1 times / day
Route: oral
Route: steady
Dose: 4 g, 1 times / day
Co-administed with::
pyrimethamine(50 mg oral; 1/day)
folinic acid(15 mg oral; 1/day)
Sources: Page: p.36, 38
unhealthy, 16 - 80
n = 22
Health Status: unhealthy
Condition: Ocular toxoplasmosis
Age Group: 16 - 80
Sex: M+F
Population Size: 22
Sources: Page: p.36, 38
Distress gastrointestinal grade 3, 5%
Disc. AE
4 g 1 times / day steady, oral
Recommended
Dose: 4 g, 1 times / day
Route: oral
Route: steady
Dose: 4 g, 1 times / day
Co-administed with::
pyrimethamine(50 mg oral; 1/day)
folinic acid(15 mg oral; 1/day)
Sources: Page: p.36, 38
unhealthy, 16 - 80
n = 22
Health Status: unhealthy
Condition: Ocular toxoplasmosis
Age Group: 16 - 80
Sex: M+F
Population Size: 22
Sources: Page: p.36, 38
Skin rash grade 3, 5%
Disc. AE
4 g 1 times / day steady, oral
Recommended
Dose: 4 g, 1 times / day
Route: oral
Route: steady
Dose: 4 g, 1 times / day
Co-administed with::
pyrimethamine(50 mg oral; 1/day)
folinic acid(15 mg oral; 1/day)
Sources: Page: p.36, 38
unhealthy, 16 - 80
n = 22
Health Status: unhealthy
Condition: Ocular toxoplasmosis
Age Group: 16 - 80
Sex: M+F
Population Size: 22
Sources: Page: p.36, 38
Stenocardia grade 3, 5%
Disc. AE
4 g 1 times / day steady, oral
Recommended
Dose: 4 g, 1 times / day
Route: oral
Route: steady
Dose: 4 g, 1 times / day
Co-administed with::
pyrimethamine(50 mg oral; 1/day)
folinic acid(15 mg oral; 1/day)
Sources: Page: p.36, 38
unhealthy, 16 - 80
n = 22
Health Status: unhealthy
Condition: Ocular toxoplasmosis
Age Group: 16 - 80
Sex: M+F
Population Size: 22
Sources: Page: p.36, 38
Febrile neutropenia 1.16%
1 g 4 times / day steady, oral
Recommended
Dose: 1 g, 4 times / day
Route: oral
Route: steady
Dose: 1 g, 4 times / day
Co-administed with::
pyrimethamine(50-75 mg oral; 1/day)
Sources: Page: p.4
unhealthy, 29.81
n = 16
Health Status: unhealthy
Condition: Cerebral toxoplasmosis
Age Group: 29.81
Sex: M+F
Population Size: 16
Sources: Page: p.4
Skin rash 1.16%
1 g 4 times / day steady, oral
Recommended
Dose: 1 g, 4 times / day
Route: oral
Route: steady
Dose: 1 g, 4 times / day
Co-administed with::
pyrimethamine(50-75 mg oral; 1/day)
Sources: Page: p.4
unhealthy, 29.81
n = 16
Health Status: unhealthy
Condition: Cerebral toxoplasmosis
Age Group: 29.81
Sex: M+F
Population Size: 16
Sources: Page: p.4
Neutropenia 18.75%
1 g 4 times / day steady, oral
Recommended
Dose: 1 g, 4 times / day
Route: oral
Route: steady
Dose: 1 g, 4 times / day
Co-administed with::
pyrimethamine(50-75 mg oral; 1/day)
Sources: Page: p.4
unhealthy, 29.81
n = 16
Health Status: unhealthy
Condition: Cerebral toxoplasmosis
Age Group: 29.81
Sex: M+F
Population Size: 16
Sources: Page: p.4
Stevens Johnson syndrome grade 3, 1.16%
Disc. AE
1 g 4 times / day steady, oral
Recommended
Dose: 1 g, 4 times / day
Route: oral
Route: steady
Dose: 1 g, 4 times / day
Co-administed with::
pyrimethamine(50-75 mg oral; 1/day)
Sources: Page: p.4
unhealthy, 29.81
n = 16
Health Status: unhealthy
Condition: Cerebral toxoplasmosis
Age Group: 29.81
Sex: M+F
Population Size: 16
Sources: Page: p.4
Major bleed grade 4, 25%
Disc. AE
1 g 4 times / day steady, oral
Recommended
Dose: 1 g, 4 times / day
Route: oral
Route: steady
Dose: 1 g, 4 times / day
Co-administed with::
pyrimethamine(50-75 mg oral; 1/day)
Sources: Page: p.4
unhealthy, 29.81
n = 16
Health Status: unhealthy
Condition: Cerebral toxoplasmosis
Age Group: 29.81
Sex: M+F
Population Size: 16
Sources: Page: p.4
Thrombocytopenia grade 4, 25%
Disc. AE
1 g 4 times / day steady, oral
Recommended
Dose: 1 g, 4 times / day
Route: oral
Route: steady
Dose: 1 g, 4 times / day
Co-administed with::
pyrimethamine(50-75 mg oral; 1/day)
Sources: Page: p.4
unhealthy, 29.81
n = 16
Health Status: unhealthy
Condition: Cerebral toxoplasmosis
Age Group: 29.81
Sex: M+F
Population Size: 16
Sources: Page: p.4
Skin rash grade 3, 17.24%
Disc. AE
6 g 1 times / day steady, oral (max)
Recommended
Dose: 6 g, 1 times / day
Route: oral
Route: steady
Dose: 6 g, 1 times / day
Co-administed with::
pyrimethamine(50-75 mg oral; 1/day)
Sources: Page: p.476
unhealthy, 33.8
n = 29
Health Status: unhealthy
Condition: Central nervous system toxoplasmosis
Age Group: 33.8
Sex: M+F
Population Size: 29
Sources: Page: p.476
Neutropenia grade 3, 3.45%
Disc. AE
6 g 1 times / day steady, oral (max)
Recommended
Dose: 6 g, 1 times / day
Route: oral
Route: steady
Dose: 6 g, 1 times / day
Co-administed with::
pyrimethamine(50-75 mg oral; 1/day)
Sources: Page: p.476
unhealthy, 33.8
n = 29
Health Status: unhealthy
Condition: Central nervous system toxoplasmosis
Age Group: 33.8
Sex: M+F
Population Size: 29
Sources: Page: p.476
Acute renal failure grade 3, 6.9%
Disc. AE
6 g 1 times / day steady, oral (max)
Recommended
Dose: 6 g, 1 times / day
Route: oral
Route: steady
Dose: 6 g, 1 times / day
Co-administed with::
pyrimethamine(50-75 mg oral; 1/day)
Sources: Page: p.476
unhealthy, 33.8
n = 29
Health Status: unhealthy
Condition: Central nervous system toxoplasmosis
Age Group: 33.8
Sex: M+F
Population Size: 29
Sources: Page: p.476
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 6.65 uM]
Drug as victim
PubMed

PubMed

TitleDatePubMed
Sulfadiazine-induced crystalluria and renal failure in a patient with AIDS.
1999 May-Jun
Patterns of sulfadiazine acute nephrotoxicity.
2000 Jul
Anti-toxoplasma activities of antiretroviral drugs and interactions with pyrimethamine and sulfadiazine in vitro.
2000 Sep
Matrix solid-phase dispersion extraction and high-performance liquid chromatographic determination of residual sulfonamides in chicken.
2001 Dec 7
In vitro quantitative analysis of (3)H-uracil incorporation by Sarcocytis neurona to determine efficacy of anti-protozoal agents.
2001 Feb 26
Systematic review of antimicrobial agents used for chronic wounds.
2001 Jan
Toxoplasmosis, a severe complication in allogeneic hematopoietic stem cell transplantation: successful treatment strategies during a 5-year single-center experience.
2001 Jan
Treatment of dogs infected with Hepatozoon americanum: 53 cases (1989-1998).
2001 Jan 1
Characterization of nine Pasteurella multocida isolates from avian cholera outbreaks in Indonesia.
2001 Jan-Mar
Antimicrobial susceptibility of starter culture bacteria used in Norwegian dairy products.
2001 Jul 20
Wound healing activity of the aqueous extract of Thespesia populnea fruit.
2001 Jun
Exposure to liquid sulfur mustard.
2001 Jun
Burns and injuries resulting from the use of gel candles.
2001 May-Jun
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
A novel kind of antitumour drugs using sulfonamide as parent compound.
2001 Nov-Dec
Suspected protozoal myeloencephalitis in a two-month-old colt.
2001 Sep 1
Phase II study assessing the effectiveness of Biafine cream as a prophylactic agent for radiation-induced acute skin toxicity to the breast in women undergoing radiotherapy with concomitant CMF chemotherapy.
2001 Sep 1
New simple liquid chromatographic method for the determination of trimethoprim, sulfadiazine and N4-acetylsulfadiazine in plasma of broilers.
2002 Apr 5
Outbreak of serogroup W135 meningococcal disease after the Hajj pilgrimage, Europe, 2000.
2002 Aug
[Increased serum and urinary levels of silver during treatment with topical silver sulfadiazine].
2002 Feb
Effects of silver sulphadiazine on the production of exoproteins by Staphylococcus aureus.
2002 Jan
Atypical anterior optic neuropathy caused by toxoplasmosis.
2002 Jan
Anal canal amputation and necrosis of the anal sphinchter due to electric current injury.
2002 Jun
Control of wound infections using a bilayer chitosan wound dressing with sustainable antibiotic delivery.
2002 Mar 5
[Topical agents used in the treatment of burns].
2002 Mar-Apr
[Glanders--a potential disease for biological warfare in humans and animals].
2002 May
Silver. 2: Toxicity in mammals and how its products aid wound repair.
2002 May
Unsuspected Toxoplasma gondii empyema in a bone marrow transplant recipient.
2002 May 1
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Can also be used topically http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.Set_Current_Drug&ApplNo=018810&DrugName=THERMAZENE&ActiveIngred=SILVER%20SULFADIAZINE&SponsorApplicant=THEPHARMANETWORK%20LLC&ProductMktStatus=1&goto=Search.DrugDetails
Usual Adult Dose for Toxoplasmosis Toxoplasmic encephalitis: Initial dose: Pyrimethamine 200 mg orally once Maintenance dose: <60 kg: Sulfadiazine 1 g orally every 6 hours plus pyrimethamine 50 mg orally once a day. >=60 kg: Sulfadiazine 1500 mg orally every 6 hours plus pyrimethamine 75 mg orally once a day. In addition, leucovorin 10 to 20 mg/day orally (may increase up to 50 mg/day).
Route of Administration: Oral
Sulfadiazine inhibited Pseudomonas aeruginosa with MIC 256 ug/mL
Name Type Language
SULFADIAZINE ZINC
Common Name English
Zinc Sulfadiazine [WHO-DD]
Common Name English
ZINC SULFADIAZINE
WHO-DD  
Common Name English
BENZENESULFONAMIDE, 4-AMINO-N-2-PYRIMIDINYL-, ZINC SALT (2:1)
Common Name English
Code System Code Type Description
PUBCHEM
152849
Created by admin on Sat Dec 16 06:41:11 GMT 2023 , Edited by admin on Sat Dec 16 06:41:11 GMT 2023
PRIMARY
FDA UNII
5FE7HP0JMG
Created by admin on Sat Dec 16 06:41:11 GMT 2023 , Edited by admin on Sat Dec 16 06:41:11 GMT 2023
PRIMARY
CAS
69858-60-2
Created by admin on Sat Dec 16 06:41:11 GMT 2023 , Edited by admin on Sat Dec 16 06:41:11 GMT 2023
PRIMARY