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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:43 UTC

HMDB ID

HMDB0014715

Secondary Accession Numbers

HMDB14715

Metabolite Identification

Common Name

Sulfamethizole

Description

Sulfamethizole, also known as rufol or thiosulfil, belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring. Sulfamethizole is a drug which is used for the treatment of urinary tract infection. Based on a literature review a significant number of articles have been published on Sulfamethizole.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

576
  Mrv0541 02231214472D          

 17 18  0  0  0  0            999 V2000
    2.4751    0.6631    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.9433    1.5651    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    0.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    1.4882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2758    2.7212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -2.6369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0828    2.8927    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -0.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -0.5744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -0.5744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -1.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -1.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.9007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4953    2.1782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3158    2.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  4  2  0  0  0  0
  1  5  1  0  0  0  0
  1  9  1  0  0  0  0
  2 15  1  0  0  0  0
  2 16  1  0  0  0  0
  5 15  1  0  0  0  0
  6  8  1  0  0  0  0
  6 15  2  0  0  0  0
  7 12  1  0  0  0  0
  8 16  2  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  2  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014715

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=NN=C(NS(=O)(=O)C2=CC=C(N)C=C2)S1

> <INCHI_IDENTIFIER>
InChI=1S/C9H10N4O2S2/c1-6-11-12-9(16-6)13-17(14,15)8-4-2-7(10)3-5-8/h2-5H,10H2,1H3,(H,12,13)

> <INCHI_KEY>
VACCAVUAMIDAGB-UHFFFAOYSA-N

> <FORMULA>
C9H10N4O2S2

> <MOLECULAR_WEIGHT>
270.331

> <EXACT_MASS>
270.024516964

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
26.264209134273333

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzene-1-sulfonamide

> <ALOGPS_LOGP>
0.53

> <JCHEM_LOGP>
0.21434596466666644

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.707642187543112

> <JCHEM_PKA_STRONGEST_BASIC>
1.951757408153643

> <JCHEM_POLAR_SURFACE_AREA>
97.97

> <JCHEM_REFRACTIVITY>
66.8358

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sulfamethizole

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 576                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       4.620   1.238   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0       7.361   2.922   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0       3.080   1.238   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.160   1.238   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       4.620   2.778   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       6.115   5.080   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       4.620  -4.922   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       7.621   5.400   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       4.620  -0.302   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.286  -1.072   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.954  -1.072   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.620  -3.382   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.286  -2.612   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.954  -2.612   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.954   3.548   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.391   4.066   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.923   3.905   0.000  0.00  0.00           C+0
CONECT    1    3    4    5    9                                             
CONECT    2   15   16                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    1   15                                                       
CONECT    6    8   15                                                       
CONECT    7   12                                                            
CONECT    8    6   16                                                       
CONECT    9    1   10   11                                                  
CONECT   10    9   13                                                       
CONECT   11    9   14                                                       
CONECT   12    7   13   14                                                  
CONECT   13   10   12                                                       
CONECT   14   11   12                                                       
CONECT   15    2    5    6                                                  
CONECT   16    2    8   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0014715
HETATM    1  C1  UNL     1       4.863   1.435  -1.027  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.728   0.570  -0.565  1.00  0.00           C  
HETATM    3  N1  UNL     1       2.802   0.819   0.354  1.00  0.00           N  
HETATM    4  N2  UNL     1       1.917  -0.040   0.610  1.00  0.00           N  
HETATM    5  C3  UNL     1       1.906  -1.200  -0.039  1.00  0.00           C  
HETATM    6  N3  UNL     1       0.995  -2.302   0.100  1.00  0.00           N  
HETATM    7  S1  UNL     1      -0.307  -2.307   1.190  1.00  0.00           S  
HETATM    8  O1  UNL     1      -1.061  -3.595   1.089  1.00  0.00           O  
HETATM    9  O2  UNL     1       0.130  -2.064   2.606  1.00  0.00           O  
HETATM   10  C4  UNL     1      -1.401  -0.991   0.762  1.00  0.00           C  
HETATM   11  C5  UNL     1      -1.236   0.248   1.343  1.00  0.00           C  
HETATM   12  C6  UNL     1      -2.089   1.295   1.014  1.00  0.00           C  
HETATM   13  C7  UNL     1      -3.112   1.119   0.107  1.00  0.00           C  
HETATM   14  N4  UNL     1      -3.951   2.213  -0.193  1.00  0.00           N  
HETATM   15  C8  UNL     1      -3.256  -0.126  -0.458  1.00  0.00           C  
HETATM   16  C9  UNL     1      -2.420  -1.178  -0.146  1.00  0.00           C  
HETATM   17  S2  UNL     1       3.258  -1.011  -1.068  1.00  0.00           S  
HETATM   18  H1  UNL     1       4.534   2.271  -1.648  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.499   0.778  -1.674  1.00  0.00           H  
HETATM   20  H3  UNL     1       5.487   1.752  -0.183  1.00  0.00           H  
HETATM   21  H4  UNL     1       1.162  -3.125  -0.508  1.00  0.00           H  
HETATM   22  H5  UNL     1      -0.434   0.386   2.055  1.00  0.00           H  
HETATM   23  H6  UNL     1      -1.908   2.240   1.502  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.997   2.570  -1.160  1.00  0.00           H  
HETATM   25  H8  UNL     1      -4.513   2.651   0.552  1.00  0.00           H  
HETATM   26  H9  UNL     1      -4.064  -0.254  -1.170  1.00  0.00           H  
HETATM   27  H10 UNL     1      -2.532  -2.154  -0.588  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3   17
CONECT    3    4
CONECT    4    5    5
CONECT    5    6   17
CONECT    6    7   21
CONECT    7    8    8    9    9
CONECT    7   10
CONECT   10   11   11   16
CONECT   11   12   22
CONECT   12   13   13   23
CONECT   13   14   15
CONECT   14   24   25
CONECT   15   16   16   26
CONECT   16   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Rufol	ChEBI
Sulfamethizol	ChEBI
Sulfamethizolum	ChEBI
Sulfamethylthiadiazole	ChEBI
Sulfametizol	ChEBI
Sulphamethazole	ChEBI
Sulphamethiozole	ChEBI
Thiosulfil	Kegg
Sulphamethizol	Generator
Sulphamethizolum	Generator
Sulphamethylthiadiazole	Generator
Sulphametizol	Generator
Sulfamethazole	Generator
Sulfamethiozole	Generator
Thiosulphil	Generator
Sulphamethizole	Generator
Urgo brand OF sulfamethizole	HMDB
FNA brand OF sulfamethizole	HMDB
FNA, sulfamethizol	HMDB
Sulfamethizol fna	HMDB
Wyeth brand OF sulfamethizole	HMDB

Chemical Formula

C₉H₁₀N₄O₂S₂

Average Molecular Weight

270.331

Monoisotopic Molecular Weight

270.024516964

IUPAC Name

4-amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzene-1-sulfonamide

Traditional Name

sulfamethizole

CAS Registry Number

144-82-1

SMILES

CC1=NN=C(NS(=O)(=O)C2=CC=C(N)C=C2)S1

InChI Identifier

InChI=1S/C9H10N4O2S2/c1-6-11-12-9(16-6)13-17(14,15)8-4-2-7(10)3-5-8/h2-5H,10H2,1H3,(H,12,13)

InChI Key

VACCAVUAMIDAGB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonamides

Direct Parent

Aminobenzenesulfonamides

Alternative Parents

Substituents

Aminobenzenesulfonamide
Benzenesulfonyl group
Aniline or substituted anilines
Organosulfonic acid amide
Azole
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Thiadiazole
Aminosulfonyl compound
Heteroaromatic compound
Organoheterocyclic compound
Azacycle
Organonitrogen compound
Amine
Organic oxygen compound
Organic nitrogen compound
Organosulfur compound
Organopnictogen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

sulfonamide (CHEBI:9331 )
thiadiazoles (CHEBI:9331 )
sulfonamide antibiotic (CHEBI:9331 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0014715)
Membrane (HMDB: HMDB0014715)

Source

Exogenous

Exogenous (HMDB: HMDB0014715)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	208 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.61 g/L	Not Available
LogP	0.9	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.61 g/L	ALOGPS
logP	0.53	ALOGPS
logP	0.21	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	6.71	ChemAxon
pKa (Strongest Basic)	1.95	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	97.97 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	66.84 m³·mol⁻¹	ChemAxon
Polarizability	26.26 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	160.453	31661259
DarkChem	[M-H]-	161.399	31661259
DeepCCS	[M+H]+	157.083	30932474
DeepCCS	[M-H]-	154.725	30932474
DeepCCS	[M-2H]-	188.152	30932474
DeepCCS	[M+Na]+	163.279	30932474
AllCCS	[M+H]+	159.0	32859911
AllCCS	[M+H-H2O]+	155.4	32859911
AllCCS	[M+NH4]+	162.4	32859911
AllCCS	[M+Na]+	163.4	32859911
AllCCS	[M-H]-	155.3	32859911
AllCCS	[M+Na-2H]-	155.4	32859911
AllCCS	[M+HCOO]-	155.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.42 minutes	32390414
Predicted by Siyang on May 30, 2022	10.0272 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.14 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	709.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	260.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	72.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	163.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	43.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	240.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	301.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	371.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	630.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	76.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	850.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	193.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	255.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	460.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	366.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	354.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sulfamethizole	CC1=NN=C(NS(=O)(=O)C2=CC=C(N)C=C2)S1	4183.1	Standard polar	33892256
Sulfamethizole	CC1=NN=C(NS(=O)(=O)C2=CC=C(N)C=C2)S1	2600.9	Standard non polar	33892256
Sulfamethizole	CC1=NN=C(NS(=O)(=O)C2=CC=C(N)C=C2)S1	2998.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sulfamethizole,1TMS,isomer #1	CC1=NN=C(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)S1	2992.8	Semi standard non polar	33892256
Sulfamethizole,1TMS,isomer #1	CC1=NN=C(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)S1	2612.8	Standard non polar	33892256
Sulfamethizole,1TMS,isomer #1	CC1=NN=C(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)S1	4152.9	Standard polar	33892256
Sulfamethizole,1TMS,isomer #2	CC1=NN=C(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)S1	2675.9	Semi standard non polar	33892256
Sulfamethizole,1TMS,isomer #2	CC1=NN=C(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)S1	2510.1	Standard non polar	33892256
Sulfamethizole,1TMS,isomer #2	CC1=NN=C(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)S1	4033.0	Standard polar	33892256
Sulfamethizole,2TMS,isomer #1	CC1=NN=C(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)S1	2700.4	Semi standard non polar	33892256
Sulfamethizole,2TMS,isomer #1	CC1=NN=C(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)S1	2652.4	Standard non polar	33892256
Sulfamethizole,2TMS,isomer #1	CC1=NN=C(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)S1	3491.9	Standard polar	33892256
Sulfamethizole,2TMS,isomer #2	CC1=NN=C(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)S1	2818.4	Semi standard non polar	33892256
Sulfamethizole,2TMS,isomer #2	CC1=NN=C(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)S1	2734.0	Standard non polar	33892256
Sulfamethizole,2TMS,isomer #2	CC1=NN=C(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)S1	3891.5	Standard polar	33892256
Sulfamethizole,3TMS,isomer #1	CC1=NN=C(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)S1	2625.0	Semi standard non polar	33892256
Sulfamethizole,3TMS,isomer #1	CC1=NN=C(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)S1	2765.2	Standard non polar	33892256
Sulfamethizole,3TMS,isomer #1	CC1=NN=C(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)S1	3288.3	Standard polar	33892256
Sulfamethizole,1TBDMS,isomer #1	CC1=NN=C(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)S1	3250.8	Semi standard non polar	33892256
Sulfamethizole,1TBDMS,isomer #1	CC1=NN=C(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)S1	2839.7	Standard non polar	33892256
Sulfamethizole,1TBDMS,isomer #1	CC1=NN=C(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)S1	4146.6	Standard polar	33892256
Sulfamethizole,1TBDMS,isomer #2	CC1=NN=C(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)S1	2929.9	Semi standard non polar	33892256
Sulfamethizole,1TBDMS,isomer #2	CC1=NN=C(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)S1	2741.4	Standard non polar	33892256
Sulfamethizole,1TBDMS,isomer #2	CC1=NN=C(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)S1	3995.2	Standard polar	33892256
Sulfamethizole,2TBDMS,isomer #1	CC1=NN=C(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)S1	3205.6	Semi standard non polar	33892256
Sulfamethizole,2TBDMS,isomer #1	CC1=NN=C(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)S1	3110.2	Standard non polar	33892256
Sulfamethizole,2TBDMS,isomer #1	CC1=NN=C(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)S1	3529.9	Standard polar	33892256
Sulfamethizole,2TBDMS,isomer #2	CC1=NN=C(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)S1	3366.1	Semi standard non polar	33892256
Sulfamethizole,2TBDMS,isomer #2	CC1=NN=C(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)S1	3178.1	Standard non polar	33892256
Sulfamethizole,2TBDMS,isomer #2	CC1=NN=C(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)S1	3880.3	Standard polar	33892256
Sulfamethizole,3TBDMS,isomer #1	CC1=NN=C(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)S1	3348.5	Semi standard non polar	33892256
Sulfamethizole,3TBDMS,isomer #1	CC1=NN=C(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)S1	3441.6	Standard non polar	33892256
Sulfamethizole,3TBDMS,isomer #1	CC1=NN=C(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)S1	3416.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Sulfamethizole GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9520000000-612be3b68261ab7e44e0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sulfamethizole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sulfamethizole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfamethizole LC-ESI-qTof , Positive-QTOF	splash10-0a4i-6921000000-126773aad654d2eed32d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfamethizole LC-ESI-QTOF , positive-QTOF	splash10-0a4i-1900000000-d28aaee868ff14cf276c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfamethizole , positive-QTOF	splash10-0a4i-2930000000-baa3fcc8543e75aae150	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfamethizole , positive-QTOF	splash10-0a4i-6921000000-126773aad654d2eed32d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfamethizole -1V, Positive-QTOF	splash10-0a4i-1900000000-be6bc1fbe226f471ada1	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamethizole 10V, Positive-QTOF	splash10-0fk9-0190000000-65b647815b272c211343	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamethizole 20V, Positive-QTOF	splash10-0pi0-1980000000-7fadab7f248de98fdf2f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamethizole 40V, Positive-QTOF	splash10-0v0r-9020000000-38dd107f4616bd2bbcf5	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamethizole 10V, Negative-QTOF	splash10-014i-0090000000-e6595fd414c007267574	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamethizole 20V, Negative-QTOF	splash10-02t9-1490000000-e623f31f5c64f3fc4b1e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamethizole 40V, Negative-QTOF	splash10-0a4i-5920000000-b4846ad87d713bf15d8a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamethizole 10V, Positive-QTOF	splash10-0ab9-0940000000-5f9fea338a3259e1358b	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamethizole 20V, Positive-QTOF	splash10-0a4i-4900000000-294de38d9541211580c5	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamethizole 40V, Positive-QTOF	splash10-014i-9000000000-c0447fdeace53d9b33ef	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamethizole 10V, Negative-QTOF	splash10-014i-0090000000-37863beaac79d46e4d4d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamethizole 20V, Negative-QTOF	splash10-066r-1690000000-571175f48422a730717e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamethizole 40V, Negative-QTOF	splash10-0a4i-2900000000-98411d72ae7ea399e430	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00576	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00576	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00576

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5137

KEGG Compound ID

C08050

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sulfamethizole

METLIN ID

Not Available

PubChem Compound

5328

PDB ID

Not Available

ChEBI ID

9331

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Watanabe H, Hastings JW: Inhibition of bioluminescence in Photobacterium phosphoreum by sulfamethizole and its stimulation by thymine. Biochim Biophys Acta. 1990 Jun 26;1017(3):229-34. [PubMed:2372557 ]
Kerrn MB, Frimodt-Moller N, Espersen F: Effects of sulfamethizole and amdinocillin against Escherichia coli strains (with various susceptibilities) in an ascending urinary tract infection mouse model. Antimicrob Agents Chemother. 2003 Mar;47(3):1002-9. [PubMed:12604534 ]
Ratanajamit C, Skriver MV, Norgaard M, Jepsen P, Schonheyder HC, Sorensen HT: Adverse pregnancy outcome in users of sulfamethizole during pregnancy: a population-based observational study. J Antimicrob Chemother. 2003 Nov;52(5):837-41. Epub 2003 Sep 30. [PubMed:14519675 ]

Enzymes

Enzyme Details

1. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Showing metabocard for Sulfamethizole (HMDB0014715)

MOL for HMDB0014715 (Sulfamethizole)

3D MOL for HMDB0014715 (Sulfamethizole)

3D SDF for HMDB0014715 (Sulfamethizole)

3D-SDF for HMDB0014715 (Sulfamethizole)

PDB for HMDB0014715 (Sulfamethizole)

3D PDB for HMDB0014715 (Sulfamethizole)

SMILES for HMDB0014715 (Sulfamethizole)

INCHI for HMDB0014715 (Sulfamethizole)

Structure for HMDB0014715 (Sulfamethizole)

3D Structure for HMDB0014715 (Sulfamethizole)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References