Sulfadiazine

Details

• Internal ID: 8d862756-6e02-4b2d-8d7e-e3da61be8fd6
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzenesulfonamides > Aminobenzenesulfonamides
• IUPAC Name: 4-amino-N-pyrimidin-2-ylbenzenesulfonamide
• SMILES (Canonical): C1=CN=C(N=C1)NS(=O)(=O)C2=CC=C(C=C2)N
• SMILES (Isomeric): C1=CN=C(N=C1)NS(=O)(=O)C2=CC=C(C=C2)N
• InChI: InChI=1S/C10H10N4O2S/c11-8-2-4-9(5-3-8)17(15,16)14-10-12-6-1-7-13-10/h1-7H,11H2,(H,12,13,14)
• InChI Key: SEEPANYCNGTZFQ-UHFFFAOYSA-N
• Popularity: 8,704 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₀N₄O₂S
• Molecular Weight: 250.28 g/mol
• Exact Mass: 250.05244675 g/mol
• Topological Polar Surface Area (TPSA): 106.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): 0.86
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 68-35-9
• Sulphadiazine
• Sulfapyrimidine
• Sulfadiazin
• Sulfazine
• Adiazine
• Sulfadiazene
• Adiazin
• Debenal
• Pyrimal
• Liquadiazine
• Sulfapyrimidin
• Coco-Diazine
• 2-Sulfanilamidopyrimidine
• Cremodiazine
• Cremotres
• Deltazina
• Diazolone
• Eskadiazine
• Microsulfon
• Palatrize
• Piridisir
• Quadramoid
• Sanodiazine
• Spofadrizine
• Sterazine
• Sulfatryl
• Sulfonsol
• Theradiazine
• Trifonamide
• Neazine
• Pirimal
• Quadetts
• Truozine
• Trisem
• Honey diazine
• Sulfanilamidopyrimidine
• Lipo-Diazine
• Lipo-Levazine
• Tri-Sulfameth
• Metha-Meridiazine
• Sulfadiazina
• Sulfadiazinum
• Diazovit
• Neotrizine
• Sulfolex
• Terfonyl
• Diazin
• Sulfose
• Sulphadiazine E
• Triple Sulfas
• Di-Azo-Mul
• Thi-Di-Mer
• 2-Sulfanilylaminopyrimidine
• Sulfapirimidin
• 4-amino-N-(pyrimidin-2-yl)benzenesulfonamide
• Pecta-diazine, suspension
• Solfadiazina
• Codiazine
• Silvadene
• Benzenesulfonamide, 4-amino-N-2-pyrimidinyl-
• 4-amino-N-pyrimidin-2-ylbenzenesulfonamide
• 2-Sulfanilamidopyrimidin
• Pyrimidine, 2-sulfanilamido-
• RP 2616
• N(1)-2-pyrimidylsulfanilamide
• N(1)-2-pyrimidinylsulfanilamide
• 2-Sulfapyrimidine
• 4-AMINO-N-2-PYRIMIDINYLBENZENESULFONAMIDE
• N(sup 1)-2-Pyrimidinylsulfanilamide
• Sulfadiazinum [INN-Latin]
• Sulfanilamide, N1-2-pyrimidinyl-
• S.N. 112
• Sulfadiazina [INN-Spanish]
• A 306
• CHEBI:9328
• Sulfanilamide, N(sup 1)-2-pyrimidinyl-
• 4-amino-N-(pyrimidin-2-yl)benzene-1-sulfonamide
• Sulfanilamide, N1-2(1H)-pyrimidinylidene-
• 4-amino-N-pyrimidin-2-yl-benzenesulfonamide
• A-306
• EINECS 200-685-8
• NSC 35600
• Sildaflo
• BRN 0235192
• DTXSID7044130
• 4-Amino-N-2-pyrimidinyl-benzenesulfonamide
• AI3-01047
• N(sup1)-2-Pyrimidylsulfanilamide
• UNII-0N7609K889
• silver sulfadiazine
• N(sup1)-2-Pyrimidinylsulfanilamide
• NSC35600
• CHEMBL439
• S. N. 112
• 0N7609K889
• DTXCID5024130
• Sulfadiazine [USP:INN:BAN:JAN]
• 5-25-10-00067 (Beilstein Handbook Reference)
• SULFOSE COMPONENT SULFADIAZINE
• NSC-35600
• TERFONYL COMPONENT SULFADIAZINE
• LANTRISUL COMPONENT SULFADIAZINE
• SULFALOID COMPONENT SULFADIAZINE
• SDZ
• CAS-68-35-9
• NEOTRIZINE COMPONENT SULFADIAZINE
• SULFADIAZINE COMPONENT OF SULFOSE
• NCGC00016305-01
• SULFADIAZINE COMPONENT OF TERFONYL
• TRISULFAPYRIMIDINES (SULFADIAZINE)
• CocoDiazine
• SULFADIAZINE COMPONENT OF LANTRISUL
• SULFADIAZINE COMPONENT OF SULFALOID
• Solfadiazina [DCIT]
• SULFADIAZINE COMPONENT OF NEOTRIZINE
• Sulfadiazine 100 microg/mL in Acetonitrile
• TRIPLE SULFOID COMPONENT SULFADIAZINE
• NSC117870
• Sulfapyrimidin [German]
• SULFADIAZINE COMPONENT OF TRIPLE SULFOID
• Sulfadiazinum (INN-Latin)
• Sulfadiazina (INN-Spanish)
• SULFADIAZINE (MART.)
• SULFADIAZINE [MART.]
• SULFADIAZINE (USP-RS)
• SULFADIAZINE [USP-RS]
• SULFADIAZINE (EP MONOGRAPH)
• SULFADIAZINE (USP IMPURITY)
• Sulfadiazine (USP:INN:BAN:JAN)
• SULFADIAZINE [EP MONOGRAPH]
• SULFADIAZINE [USP IMPURITY]
• SULFADIAZINE (USP MONOGRAPH)
• SULFADIAZINE [USP MONOGRAPH]
• 2-Sulfanilamidopyrimidin [German]
• A-306 (VAN)
• SMR000059113
• Sulfadiazine (TN)
• N-(2-Pyrimidinyl)sulfanilamide
• SULFADIMIDINE IMPURITY B (EP IMPURITY)
• SULFADIMIDINE IMPURITY B [EP IMPURITY]
• rBPI21 & Sulfa
• RP-2616
• 4-Amino-N-(2-pyrimidinyl)benzenesulfonamide
• SR-01000002973
• SSD
• MFCD00006065
• 2-Sulfanilamido-pyrimidine
• diazine
• ulfadiazine
• CRL-8131 & Sulfadiazine
• N1-2-Pyrimidinylsulfanilamide
• Sulfadiazine (JAN/USP/INN)
• Sulfadiazine Base
• Sulfadiazine,(S)
• Trisulfapyrimidine, oral suspension
• Prestwick_428
• Spectrum_000986
• Sulfadiazina Reig Jofre
• Sulfacombin (Salt/Mix)
• Prestwick0_000023
• Prestwick1_000023
• Prestwick2_000023
• Prestwick3_000023
• Spectrum2_001319
• Spectrum3_001362
• Spectrum4_000342
• Spectrum5_000992
• SULFADIAZINE [MI]
• [(4-aminophenyl)sulfonyl]pyrimidin-2-ylamine
• SULFADIAZINE [INN]
• SULFADIAZINE [JAN]
• Epitope ID:140083
• N1-2-Pyrimidylsulfanilamide
• Sulfadiazine, >=99.0%
• SULFADIAZINE [VANDF]
• Oprea1_081078
• SCHEMBL24176
• BSPBio_000085
• BSPBio_002884
• KBioGR_000743
• KBioSS_001466
• MLS000069423
• MLS006011457
• 720 - Sulfonamides in fish
• DivK1c_000543
• SPECTRUM1500546
• SULFADIAZINE [WHO-DD]
• SPBio_001417
• SPBio_002006
• BPBio1_000095
• WLN: T6N CNJ BMSWR DZ
• GTPL12635
• HMS501L05
• KBio1_000543
• KBio2_001466
• KBio2_004034
• KBio2_006602
• KBio3_002104
• SULFADIAZINE [GREEN BOOK]
• NINDS_000543
• GLXC-25873
• HMS1568E07
• HMS1921A13
• HMS2090P09
• HMS2092I15
• HMS2095E07
• HMS2235D19
• HMS3371L19
• HMS3655I10
• HMS3712E07
• Pharmakon1600-01500546
• SULFADIAZINE [ORANGE BOOK]
• AMY33423
• BCP12140
• HY-B0273
• Tox21_110360
• BDBM50166571
• CCG-39257
• NSC757324
• Recombinant bactericidal/permeability-increasing protein & Sulfadiazine
• s1770
• 2-(p-Aminobenzenesulfonamido)pyrimidin
• AKOS000119073
• DB00359
• KS-1144
• NSC-757324
• 2-(4-Aminobenzenesulfonamido)pyrimidine
• 4-amino-N-2-pyrimidylbenzenesulfonamide
• IDI1_000543
• NCGC00016305-02
• NCGC00016305-03
• NCGC00016305-04
• NCGC00016305-05
• NCGC00016305-06
• NCGC00016305-09
• NCGC00016305-10
• NCGC00016305-11
• NCGC00023291-03
• NCGC00023291-04
• SULFADIAZINE (TRISULFAPYRIMIDINES)
• 2-(4-Aminobenzenesulfonylamino)pyrimidine
• AC-26817
• 4-amino-N-2-pyrimidinyl benzenesulfonamide
• SBI-0051520.P003
• 4-[[(Pyrimidin-2-yl)amino]sulfonyl]aniline
• AB00052095
• FT-0674739
• FT-0674740
• FT-0674741
• S0579
• Sulfadiazine 1000 microg/mL in Acetonitrile
• Sulfadiazine for identification of impurity F
• SW196657-3
• 4-amino-N-(2-pyrimidinyl) benzenesulfonamide
• EN300-19076
• 4-Amino-N-(2-pyrimidinyl)benzenesulfonamide #
• C07658
• D00587
• D92267
• Trisulfapyrimidine, oral suspension (Salt/Mix)
• AB00052095-13
• AB00052095-14
• AB00052095_15
• AB00052095_16
• Benzenesulfonamide, 4-amino-N-(2-pyrimidinyl)-
• Sulfadiazine, VETRANAL(TM), analytical standard
• A836115
• Q-201759
• Q2555060
• SR-01000002973-2
• SR-01000002973-3
• BRD-K32273377-001-05-4
• BRD-K32273377-001-09-6
• 4-AMINO-N-(2-PYRIMIDINYL)-1-BENZENESULFONAMIDE
• F1657-1720
• Sulfadiazine, certified reference material, TraceCERT(R)
• TRISULFAPYRIMIDINES (SULFADIAZINE) [ORANGE BOOK]
• Z104472626
• Sulfadiazine, European Pharmacopoeia (EP) Reference Standard
• Sulfadiazine, United States Pharmacopeia (USP) Reference Standard
• 4-Amino-N-(2-pyrimidinyl)benzenesulfonamide, N1-(Pyrimidin-2-yl)sulfanilamide
• Sulfadiazine, Pharmaceutical Secondary Standard; Certified Reference Material
• 141582-64-1
• Sulfadiazine for identification of impurity F, European Pharmacopoeia (EP) Reference Standard

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9705	97.05%
Caco-2	+	0.8916	89.16%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	+	0.9714	97.14%
Subcellular localzation	Mitochondria	0.5997	59.97%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9847	98.47%
OATP1B3 inhibitior	+	0.9492	94.92%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9291	92.91%
P-glycoprotein inhibitior	-	0.9663	96.63%
P-glycoprotein substrate	-	0.9500	95.00%
CYP3A4 substrate	-	0.8024	80.24%
CYP2C9 substrate	+	1.0000	100.00%
CYP2D6 substrate	-	0.8083	80.83%
CYP3A4 inhibition	-	0.9020	90.20%
CYP2C9 inhibition	-	0.9220	92.20%
CYP2C19 inhibition	-	0.9693	96.93%
CYP2D6 inhibition	-	0.9548	95.48%
CYP1A2 inhibition	-	0.9574	95.74%
CYP2C8 inhibition	-	0.9752	97.52%
CYP inhibitory promiscuity	-	0.8569	85.69%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8023	80.23%
Carcinogenicity (trinary)	Non-required	0.5084	50.84%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9388	93.88%
Skin irritation	-	0.6158	61.58%
Skin corrosion	-	0.9559	95.59%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8042	80.42%
Micronuclear	+	0.9300	93.00%
Hepatotoxicity	+	0.9500	95.00%
skin sensitisation	-	0.8938	89.38%
Respiratory toxicity	+	0.9222	92.22%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.5604	56.04%
Acute Oral Toxicity (c)	III	0.6777	67.77%
Estrogen receptor binding	-	0.7581	75.81%
Androgen receptor binding	-	0.7339	73.39%
Thyroid receptor binding	-	0.6584	65.84%
Glucocorticoid receptor binding	-	0.8661	86.61%
Aromatase binding	+	0.5645	56.45%
PPAR gamma	-	0.8236	82.36%
Honey bee toxicity	-	0.9547	95.47%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.8500	85.00%
Fish aquatic toxicity	+	0.7461	74.61%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	177.8 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3401	O75469	Pregnane X receptor	94.92%	94.73%
CHEMBL3038469	P24941	CDK2/Cyclin A	94.23%	91.38%
CHEMBL1952	P04818	Thymidylate synthase	92.49%	93.53%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.04%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.28%	96.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	90.22%	95.83%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	89.22%	96.90%
CHEMBL226	P30542	Adenosine A1 receptor	88.16%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.20%	96.09%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	85.78%	95.48%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	85.04%	88.00%
CHEMBL255	P29275	Adenosine A2b receptor	84.46%	98.59%
CHEMBL308	P06493	Cyclin-dependent kinase 1	84.42%	91.73%
CHEMBL5932	P53671	LIM domain kinase 2	83.29%	96.49%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	82.68%	96.67%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.26%	94.45%
CHEMBL3902	P09211	Glutathione S-transferase Pi	81.93%	93.81%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	81.19%	93.10%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 5215
• LOTUS: LTS0252910
• wikiData: Q2555060