Sulfamethoxazole

Details

• Internal ID: 3e119f40-5254-4692-8719-623e6e8a8296
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzenesulfonamides > Aminobenzenesulfonamides
• IUPAC Name: 4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide
• SMILES (Canonical): CC1=CC(=NO1)NS(=O)(=O)C2=CC=C(C=C2)N
• SMILES (Isomeric): CC1=CC(=NO1)NS(=O)(=O)C2=CC=C(C=C2)N
• InChI: InChI=1S/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13)
• InChI Key: JLKIGFTWXXRPMT-UHFFFAOYSA-N
• Popularity: 20,438 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₁N₃O₃S
• Molecular Weight: 253.28 g/mol
• Exact Mass: 253.05211239 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.37
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 723-46-6
• Gantanol
• Sulphamethoxazole
• Sulfisomezole
• Sulfamethoxazol
• Metoxal
• Sulfamethylisoxazole
• 4-Amino-N-(5-methyl-3-isoxazolyl)benzenesulfonamide
• Simsinomin
• Radonil
• Sinomin
• Sulphamethoxazol
• Sulpha-methoxizole
• Sulfamethalazole
• Azo-gantanol
• Sulphamethylisoxazole
• 4-amino-N-(5-methylisoxazol-3-yl)benzenesulfonamide
• Bactrim
• Urobak
• Ro 4-2130
• Sulfamethoxizole
• Gantanol-DS
• 3-Sulfanilamido-5-methylisoxazole
• Gamazole
• Sulfamethoxazolum
• Sulfametoxazol
• Solfametossazolo
• 4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide
• Sulphisomezole
• 5-Methyl-3-sulfanilamidoisoxazole
• MS 53
• 3-Sulphanilamido-5-methylisoxazole
• 5-Methyl-3-sulphanil-amidoisoxazole
• Benzenesulfonamide, 4-amino-N-(5-methyl-3-isoxazolyl)-
• 3-(p-Aminophenylsulfonamido)-5-methylisoxazole
• 5-Methyl-3-sulfanylamidoisoxazole
• N'-(5-Methyl-3-isoxazolyl)sulfanilamide
• N1-(5-Methyl-3-isoxazolyl)sulfanilamide
• N'-(5-Methylisoxazol-3-yl)sulphanilamide
• 3-(para-Aminophenylsulphonamido)-5-methylisoxazole
• A047
• SMX
• CCRIS 567
• Sulfametoxazol [INN-Spanish]
• Sulfamethoxazolum [INN-Latin]
• Sulfanilamide, N1-(5-methyl-3-isoxazolyl)-
• CHEBI:9332
• HSDB 3186
• N(sup 1)-(5-Methyl-3-isoxazolyl)sulphanilamide
• STX-608
• EINECS 211-963-3
• Sulfanilamide, N'-(5-methyl-3-isoxazolyl)-
• UNII-JE42381TNV
• NSC 147832
• NSC-147832
• Ro-4-2130
• N(sup 1)-(5-Methyl-3-isoxazolyl)sulfanilamide
• 4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzene-1-sulfonamide
• BRN 0226453
• JE42381TNV
• N'-(5-Methyl-3-isoxazole)sulfanilamide
• DTXSID8026064
• Ro 6-2580/11
• 4-Amino-N-(5-methyl-isoxazol-3-yl)-benzenesulfonamide
• 4-AMINO-N-(5-METHYL-3-ISOXAZOYL)BENZENESULFONAMIDE
• MFCD00010546
• NSC147832
• Sulfanilamide, N(1)-(5-methyl-3-isoxazolyl)-
• CHEMBL443
• MLS000069732
• DTXCID006064
• N(sup1)-(5-Methyl-3-isoxazolyl)sulfanilamide
• 5-Methyl-3-sulfonylamidoisoxazole
• 3-(p-Aminobenzenesulfonamido)-5-methylisoxazole
• Ro-42130
• 4-Amino-N-(5-methyl-3-isoxazolyl)-benzenesulfonamide
• COTRIM COMPONENT SULFAMETHOXAZOLE
• SEPTRA COMPONENT SULFAMETHOXAZOLE
• BACTRIM COMPONENT SULFAMETHOXAZOLE
• NCGC00016533-05
• NCGC00186654-01
• UROPLUS COMPONENT SULFAMETHOXAZOLE
• CAS-723-46-6
• SMR000058223
• SULFATRIM COMPONENT SULFAMETHOXAZOLE
• SULMEPRIM COMPONENT SULFAMETHOXAZOLE
• Co-trimethoxazole component sulfamethoxazole
• SULFAMETHOXAZOLE COMPONENT OF COTRIM
• SULFAMETHOXAZOLE COMPONENT OF SEPTRA
• BACTRIM DS COMPONENT SULFAMETHOXAZOLE
• Sulfamethoxazole [USAN:USP:INN:BAN:JAN]
• SULFAMETHOXAZOLE COMPONENT OF BACTRIM
• SULFAMETHOXAZOLE COMPONENT OF UROPLUS
• AZO GANTANOL COMPONENT SULFAMETHOXAZOLE
• COTRIM D.S. COMPONENT SULFAMETHOXAZOLE
• SULFAMETHOXAZOLE COMPONENT OF SULFATRIM
• SULFAMETHOXAZOLE COMPONENT OF SULMEPRIM
• SULFAMETHOPRIM COMPONENT SULFAMETHOXAZOLE
• Sulfamethoxazole 100 microg/mL in Acetonitrile
• SULFAMETHOXAZOLE COMPONENT OF BACTRIM DS
• Solfametossazolo [DCIT]
• SULFAMETHOXAZOLE COMPONENT OF AZO GANTANOL
• SULFAMETHOXAZOLE COMPONENT OF COTRIM D.S.
• 3-METHYL-1-(4-SULFOAMIDOPHENYL)-5-PYRA&
• BACTRIM PEDIATRIC COMPONENT SULFAMETHOXAZOLE
• SULFAMETHOXAZOLE COMPONENT OF SULFAMETHOPRIM
• Sulfametoxazol (INN-Spanish)
• Sulfamethoxazolum (INN-Latin)
• SULFAMETHOXAZOLE (IARC)
• SULFAMETHOXAZOLE [IARC]
• SULFAMETHOXAZOLE COMPONENT OF BACTRIM PEDIATRIC
• SULFAMETHOXAZOLE (MART.)
• SULFAMETHOXAZOLE [MART.]
• SULFAMETHOXAZOLE (USP-RS)
• SULFAMETHOXAZOLE [USP-RS]
• SULFAMETHOXAZOLE (EP MONOGRAPH)
• SULFAMETHOXAZOLE [EP MONOGRAPH]
• SULFAMETHOXAZOLE (USP MONOGRAPH)
• SULFAMETHOXAZOLE [USP MONOGRAPH]
• 144930-01-8
• Sulfamethoxazole (USAN:USP:INN:BAN:JAN)
• SR-01000000217
• sulfametoxazolo
• ulfamethoxazole
• Sulfamethoxazole; 4-Amino-N-(5-methylisoxazol-3-yl)benzenesulfonamide
• 08D
• Prestwick_453
• Septran (Salt/Mix)
• Septrin (Salt/Mix)
• Sulfamethoxazole,(S)
• Eusaprim (Salt/Mix)
• Spectrum_000994
• Sulfamethoxazole(USAN)
• starbld0000281
• Opera_ID_882
• Maybridge1_007190
• Prestwick0_000177
• Prestwick1_000177
• Prestwick2_000177
• Prestwick3_000177
• Spectrum2_000788
• Spectrum3_000584
• Spectrum4_000345
• Spectrum5_000982
• Epitope ID:114999
• Co-trimoxazole (Salt/Mix)
• SCHEMBL3656
• Oprea1_114486
• Oprea1_285680
• BSPBio_000073
• BSPBio_002028
• KBioGR_000749
• KBioSS_001474
• SULFAMETHOXAZOLE [MI]
• MLS001055354
• MLS001074165
• MLS006011871
• BIDD:GT0731
• DivK1c_000649
• SPECTRUM1500550
• SULFAMETHOXAZOLE [INN]
• SULFAMETHOXAZOLE [JAN]
• SPBio_000896
• SPBio_001994
• SULFAMETHOXAZOLE [HSDB]
• SULFAMETHOXAZOLE [USAN]
• [(4-aminophenyl)sulfonyl](5-methylisoxazol-3-yl)amine
• BPBio1_000081
• SULFAMETHOXAZOLE [VANDF]
• component of Bactrim (Salt/Mix)
• GTPL10933
• HMS502A11
• HMS561O18
• JLKIGFTWXXRPMT-UHFFFAOYSA-
• KBio1_000649
• KBio2_001474
• KBio2_004042
• KBio2_006610
• KBio3_001528
• J01EC01
• STX 608
• SULFAMETHOXAZOLE [WHO-DD]
• SULFAMETHOXAZOLE [WHO-IP]
• WLN: T5NOJ C1 EMSWR DZ
• NINDS_000649
• HMS1568D15
• HMS1921A21
• HMS2092K03
• HMS2095D15
• HMS2233L13
• HMS3259E06
• HMS3372M22
• HMS3655O22
• HMS3712D15
• Pharmakon1600-01500550
• BCP02881
• HY-B0322
• Sulfamethoxazole (JP17/USP/INN)
• Sulfamethoxazole, analytical standard
• Tox21_110480
• Tox21_200353
• BDBM50029770
• CCG-40166
• NSC757328
• s1915
• SULFAMETHOXAZOLE [ORANGE BOOK]
• AKOS000200952
• component of Azo Gantanol (Salt/Mix)
• Tox21_110480_1
• BS-3542
• DB01015
• NC00537
• NSC-757328
• RP-2145
• IDI1_000649
• SULFAMETHOXAZOLUM [WHO-IP LATIN]
• NCGC00016533-01
• NCGC00016533-02
• NCGC00016533-03
• NCGC00016533-04
• NCGC00016533-06
• NCGC00016533-07
• NCGC00016533-08
• NCGC00016533-09
• NCGC00016533-10
• NCGC00016533-11
• NCGC00016533-12
• NCGC00016533-14
• NCGC00021995-03
• NCGC00021995-04
• NCGC00021995-05
• NCGC00257907-01
• AC-11118
• SY018888
• BCP0726000283
• N'-(5-Methyl-3-isoxazolyl)-Sulfanilamide
• N1-(5-methyl-3-isoxazolyl)-Sulfanilamide
• N1-(5-Methyl-3-isoxazolyl)sulphanilamide
• SBI-0051524.P003
• AB00052099
• BB 0242379
• FT-0602616
• N^1-(5-Methyl-3-isoxazolyl)-Sulfanilamide
• SW196670-3
• EN300-18400
• C07315
• D00447
• F12027
• AB00052099-14
• AB00052099-16
• AB00052099_17
• AB00052099_18
• Sulfamethoxazole 1000 microg/mL in Acetonitrile
• N'-(5-METHYL-3-ISOXAZOYLYL)SULFANILAMIDE
• Ndimethyl1-(5-methyl-3-isoxazolyl)-Sulfanilamide
• Q415843
• N(1)-(5-METHYL-3-ISOXAZOLYL)SULFANILAMIDE
• Q-201762
• SR-01000000217-2
• SR-01000000217-3
• Sulfamethoxazole, VETRANAL(TM), analytical standard
• 4-Amino-N-(5-methylisoxazol-3-yl)benzenesulphonamide
• BRD-K28494619-001-05-0
• BRD-K28494619-001-15-9
• BRD-K28494619-001-26-6
• Z57198677
• 4-Amino-N-(5-methyl-isoxazol-3-yl)-benzene sulfonamide
• 4-AMINO-N-(5-METHYL-3-ISOAZOLYL)BENZENESULFONAMIDE
• Sulfamethoxazole, British Pharmacopoeia (BP) Reference Standard
• Sulfamethoxazole, certified reference material, TraceCERT(R)
• 4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide; SMX; SMZ
• Sulfamethoxazole, European Pharmacopoeia (EP) Reference Standard
• Sulfamethoxazole, United States Pharmacopeia (USP) Reference Standard
• Sulfamethoxazole, Pharmaceutical Secondary Standard; Certified Reference Material
• 129378-89-8
• InChI=1/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9887	98.87%
Caco-2	-	0.6327	63.27%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	+	0.9714	97.14%
Subcellular localzation	Mitochondria	0.4068	40.68%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9695	96.95%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9045	90.45%
P-glycoprotein inhibitior	-	0.9606	96.06%
P-glycoprotein substrate	-	0.9363	93.63%
CYP3A4 substrate	-	0.6988	69.88%
CYP2C9 substrate	-	0.5000	50.00%
CYP2D6 substrate	-	0.8793	87.93%
CYP3A4 inhibition	-	0.9744	97.44%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9882	98.82%
CYP inhibitory promiscuity	-	0.7151	71.51%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6986	69.86%
Carcinogenicity (trinary)	Non-required	0.5543	55.43%
Eye corrosion	-	0.9863	98.63%
Eye irritation	-	0.9026	90.26%
Skin irritation	-	0.6416	64.16%
Skin corrosion	-	0.9383	93.83%
Ames mutagenesis	-	0.9637	96.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.7261	72.61%
Micronuclear	+	0.9500	95.00%
Hepatotoxicity	+	0.9000	90.00%
skin sensitisation	-	0.8806	88.06%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.4671	46.71%
Acute Oral Toxicity (c)	IV	0.6184	61.84%
Estrogen receptor binding	-	0.8421	84.21%
Androgen receptor binding	-	0.7831	78.31%
Thyroid receptor binding	-	0.5326	53.26%
Glucocorticoid receptor binding	-	0.8000	80.00%
Aromatase binding	-	0.6453	64.53%
PPAR gamma	-	0.7010	70.10%
Honey bee toxicity	-	0.9462	94.62%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.8500	85.00%
Fish aquatic toxicity	+	0.7404	74.04%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3401	O75469	Pregnane X receptor	98.39%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.49%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.43%	96.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	90.13%	96.90%
CHEMBL1952	P04818	Thymidylate synthase	88.37%	93.53%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	87.20%	93.65%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	87.02%	95.48%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.71%	94.00%
CHEMBL5932	P53671	LIM domain kinase 2	86.70%	96.49%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.49%	94.80%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.27%	86.33%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	82.54%	81.11%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.53%	100.00%
CHEMBL2581	P07339	Cathepsin D	81.86%	98.95%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.04%	90.71%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	80.19%	88.00%

Plants that contains it

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Cross-Links

• PubChem: 5329
• LOTUS: LTS0183106
• wikiData: Q415843