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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (33) Show 33 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:50 UTC

HMDB ID

HMDB0015045

Secondary Accession Numbers

HMDB15045

Metabolite Identification

Common Name

Zonisamide

Description

Zonisamide is a sulfonamide anticonvulsant approved for use as an adjunctive therapy in adults with partial-onset seizures. Zonisamide may be a carbonic anhydrase inhibitor although this is not one of the primary mechanisms of action. Zonisamide may act by blocking repetitive firing of voltage-gated sodium channels leading to a reduction of T-type calcium channel currents, or by binding allosterically to GABA receptors. This latter action may inhibit the uptake of the inhibitory neurotransmitter GABA while enhancing the uptake of the excitatory neurotransmitter glutamate.

Structure

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

909
  Mrv0541 02231215052D          

 14 15  0  0  0  0            999 V2000
    4.9232    0.8180    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8596   -1.4641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7530    1.6253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0934    0.0107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3411   -0.8003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7304    0.9881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159    0.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8596   -0.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.2128    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  6  1  0  0  0  0
  1  7  1  0  0  0  0
  2  5  1  0  0  0  0
  2 10  1  0  0  0  0
  5  8  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 10 12  2  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015045

> <DATABASE_NAME>
hmdb

> <SMILES>
NS(=O)(=O)CC1=NOC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C8H8N2O3S/c9-14(11,12)5-7-6-3-1-2-4-8(6)13-10-7/h1-4H,5H2,(H2,9,11,12)

> <INCHI_KEY>
UBQNRHZMVUUOMG-UHFFFAOYSA-N

> <FORMULA>
C8H8N2O3S

> <MOLECULAR_WEIGHT>
212.226

> <EXACT_MASS>
212.025562822

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
19.479884394972984

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,2-benzoxazol-3-ylmethanesulfonamide

> <ALOGPS_LOGP>
0.67

> <JCHEM_LOGP>
0.1106864246666666

> <ALOGPS_LOGS>
-2.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.835940037486687

> <JCHEM_PKA_STRONGEST_BASIC>
-1.761405576584465

> <JCHEM_POLAR_SURFACE_AREA>
86.19

> <JCHEM_REFRACTIVITY>
50.2984

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.09e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
zonisamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 909                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       9.190   1.527   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       7.205  -2.733   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       8.872   3.034   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.508   0.020   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       8.103  -1.494   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      10.697   1.844   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.683   1.209   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.205  -0.255   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.747  -0.724   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.747  -2.264   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414   0.046   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414  -3.034   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.080  -0.724   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080  -2.264   0.000  0.00  0.00           C+0
CONECT    1    3    4    6    7                                             
CONECT    2    5   10                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    2    8                                                       
CONECT    6    1                                                            
CONECT    7    1    8                                                       
CONECT    8    5    7    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    2    9   12                                                  
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   14                                                       
CONECT   14   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2-Benzisoxazole-3-methanesulfonamide	ChEBI
3-(Sulfamoylmethyl)-1,2-benzisoxazole	ChEBI
Benzo[D]isoxazol-3-yl-methanesulfonamide	ChEBI
Zonisamida	ChEBI
Zonisamidum	ChEBI
Excegran	Kegg
1,2-Benzisoxazole-3-methanesulphonamide	Generator
3-(Sulphamoylmethyl)-1,2-benzisoxazole	Generator
Benzo[D]isoxazol-3-yl-methanesulphonamide	Generator
3-Sulfamoylmethyl-1,2-benzisoxazole	HMDB
Elan brand OF zonisamide	HMDB
Zonisamide monosodium	HMDB
Zonegran	HMDB
3 Sulfamoylmethyl 1,2 benzisoxazole	HMDB

Chemical Formula

C₈H₈N₂O₃S

Average Molecular Weight

212.226

Monoisotopic Molecular Weight

212.025562822

IUPAC Name

1,2-benzoxazol-3-ylmethanesulfonamide

Traditional Name

zonisamide

CAS Registry Number

68291-97-4

SMILES

NS(=O)(=O)CC1=NOC2=CC=CC=C12

InChI Identifier

InChI=1S/C8H8N2O3S/c9-14(11,12)5-7-6-3-1-2-4-8(6)13-10-7/h1-4H,5H2,(H2,9,11,12)

InChI Key

UBQNRHZMVUUOMG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzisoxazoles. These are aromatic compounds containing a benzene ring fused to an isoxazole ring. Isoxazole is five-membered ring with three carbon atoms, and an oxygen atom next to a nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzisoxazoles

Sub Class

Not Available

Direct Parent

Benzisoxazoles

Alternative Parents

Substituents

Benzisoxazole
Organic sulfonic acid amide
Organosulfonic acid amide
Benzenoid
Azole
Isoxazole
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Aminosulfonyl compound
Heteroaromatic compound
Azacycle
Oxacycle
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Organosulfur compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

sulfonamide (CHEBI:10127 )
1,2-benzoxazoles (CHEBI:10127 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

anticonvulsant (HMDB: HMDB0015045)
protective agent (HMDB: HMDB0015045)

Pharmaceutical industry

central nervous system drug (HMDB: HMDB0015045)

Indirect biological role

antioxidant (HMDB: HMDB0015045)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	161 - 163 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2.09 g/L	Not Available
LogP	0.5	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.09 g/L	ALOGPS
logP	0.67	ALOGPS
logP	0.11	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	9.84	ChemAxon
pKa (Strongest Basic)	-1.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	86.19 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	50.3 m³·mol⁻¹	ChemAxon
Polarizability	19.48 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]+	145.314	31661259
DarkChem	[M-H]-	142.399	31661259
DeepCCS	[M-2H]-	169.989	30932474
DeepCCS	[M+Na]+	144.562	30932474
AllCCS	[M+H]+	144.8	32859911
AllCCS	[M+H-H2O]+	140.7	32859911
AllCCS	[M+NH4]+	148.7	32859911
AllCCS	[M+Na]+	149.8	32859911
AllCCS	[M-H]-	140.8	32859911
AllCCS	[M+Na-2H]-	141.1	32859911
AllCCS	[M+HCOO]-	141.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Zonisamide	NS(=O)(=O)CC1=NOC2=CC=CC=C12	3193.0	Standard polar	33892256
Zonisamide	NS(=O)(=O)CC1=NOC2=CC=CC=C12	1833.8	Standard non polar	33892256
Zonisamide	NS(=O)(=O)CC1=NOC2=CC=CC=C12	1999.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Zonisamide,1TMS,isomer #1	C[Si](C)(C)NS(=O)(=O)CC1=NOC2=CC=CC=C12	2092.0	Semi standard non polar	33892256
Zonisamide,1TMS,isomer #1	C[Si](C)(C)NS(=O)(=O)CC1=NOC2=CC=CC=C12	2038.5	Standard non polar	33892256
Zonisamide,1TMS,isomer #1	C[Si](C)(C)NS(=O)(=O)CC1=NOC2=CC=CC=C12	3079.8	Standard polar	33892256
Zonisamide,2TMS,isomer #1	C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)CC1=NOC2=CC=CC=C12	2159.0	Semi standard non polar	33892256
Zonisamide,2TMS,isomer #1	C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)CC1=NOC2=CC=CC=C12	2236.6	Standard non polar	33892256
Zonisamide,2TMS,isomer #1	C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)CC1=NOC2=CC=CC=C12	2961.0	Standard polar	33892256
Zonisamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NS(=O)(=O)CC1=NOC2=CC=CC=C12	2322.3	Semi standard non polar	33892256
Zonisamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NS(=O)(=O)CC1=NOC2=CC=CC=C12	2301.3	Standard non polar	33892256
Zonisamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NS(=O)(=O)CC1=NOC2=CC=CC=C12	3066.6	Standard polar	33892256
Zonisamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)CC1=NOC2=CC=CC=C12	2681.1	Semi standard non polar	33892256
Zonisamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)CC1=NOC2=CC=CC=C12	2752.4	Standard non polar	33892256
Zonisamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)CC1=NOC2=CC=CC=C12	2971.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Zonisamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-1900000000-073e3341083b72e5e4ce	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zonisamide 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 - Zonisamide LC-ESI-qTof , Positive-QTOF	splash10-0gx0-0940000000-22533c93dd06de52f6a8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zonisamide LC-ESI-QFT , negative-QTOF	splash10-014i-0900000000-c05ae650c884adcaba5a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zonisamide LC-ESI-QFT , negative-QTOF	splash10-014i-0900000000-477908537d156d43e3a9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zonisamide LC-ESI-QFT , negative-QTOF	splash10-014i-0900000000-f537644668fbc9b2e02b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zonisamide LC-ESI-QFT , negative-QTOF	splash10-014i-1900000000-6359b9c8e68ec5477b26	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zonisamide LC-ESI-QFT , negative-QTOF	splash10-014i-3900000000-db3cf8881465259c48ca	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zonisamide LC-ESI-QFT , negative-QTOF	splash10-014i-6900000000-cd4c8b86f36ce38b3a49	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zonisamide LC-ESI-QFT , positive-QTOF	splash10-0udi-0930000000-a0dd3941aea211aeb201	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zonisamide LC-ESI-QFT , positive-QTOF	splash10-0udi-0900000000-88938a9c69a2d4daf36a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zonisamide LC-ESI-QFT , positive-QTOF	splash10-0udi-2900000000-3440f1648bff05d21a31	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zonisamide LC-ESI-QFT , positive-QTOF	splash10-0udi-5900000000-a727755cf1e18764e9d0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zonisamide LC-ESI-QFT , positive-QTOF	splash10-0udj-9600000000-aa8a18a9ab17508f689d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zonisamide LC-ESI-QFT , positive-QTOF	splash10-0udj-9200000000-41d7e769a93444ba3751	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zonisamide , positive-QTOF	splash10-0gx0-0940000000-22533c93dd06de52f6a8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zonisamide 90V, Negative-QTOF	splash10-014i-6900000000-939416688f52f3115006	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zonisamide 75V, Negative-QTOF	splash10-014i-3900000000-cbdf90b73153e2a0fbe8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zonisamide 45V, Positive-QTOF	splash10-0udi-2900000000-3440f1648bff05d21a31	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zonisamide 45V, Negative-QTOF	splash10-014i-0900000000-5a5537d57ee730d36955	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zonisamide 60V, Negative-QTOF	splash10-014i-1900000000-e876f2ad2510dae90ae9	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zonisamide 10V, Positive-QTOF	splash10-03di-0190000000-beb3210644ad8c7d48b5	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zonisamide 20V, Positive-QTOF	splash10-03di-1790000000-685d923694e188b3784f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zonisamide 40V, Positive-QTOF	splash10-0udi-6900000000-84377f08dd399ceffa08	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zonisamide 10V, Negative-QTOF	splash10-03di-0190000000-072fa6d7f1016dc5122f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zonisamide 20V, Negative-QTOF	splash10-01q9-3970000000-14adb301eed37c18b5f7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zonisamide 40V, Negative-QTOF	splash10-004i-9000000000-e80af2cb8bf5e38fe770	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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 DB00909	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00909	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00909

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5532

KEGG Compound ID

C07504

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Zonisamide

METLIN ID

Not Available

PubChem Compound

5734

PDB ID

ZON

ChEBI ID

10127

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)

Not Available

General References

Kothare SV, Kaleyias J: Zonisamide: review of pharmacology, clinical efficacy, tolerability, and safety. Expert Opin Drug Metab Toxicol. 2008 Apr;4(4):493-506. doi: 10.1517/17425255.4.4.493 . [PubMed:18433351 ]
Schulze-Bonhage A: Zonisamide in the treatment of epilepsy. Expert Opin Pharmacother. 2010 Jan;11(1):115-26. doi: 10.1517/14656560903468728. [PubMed:20001433 ]
Sobieszek G, Borowicz KK, Kimber-Trojnar Z, Malek R, Piskorska B, Czuczwar SJ: Zonisamide: a new antiepileptic drug. Pol J Pharmacol. 2003 Sep-Oct;55(5):683-9. [PubMed:14704463 ]
Leppik IE: Zonisamide: chemistry, mechanism of action, and pharmacokinetics. Seizure. 2004 Dec;13 Suppl 1:S5-9; discussion S10. [PubMed:15511691 ]
Farooq MU, Moore PW, Bhatt A, Aburashed R, Kassab MY: Therapeutic role of zonisamide in neuropsychiatric disorders. Mini Rev Med Chem. 2008 Sep;8(10):968-75. [PubMed:18782051 ]
Murata M, Horiuchi E, Kanazawa I: Zonisamide has beneficial effects on Parkinson's disease patients. Neurosci Res. 2001 Dec;41(4):397-9. [PubMed:11755227 ]
Peters DH, Sorkin EM: Zonisamide. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in epilepsy. Drugs. 1993 May;45(5):760-87. [PubMed:7686468 ]
Gadde KM, Franciscy DM, Wagner HR 2nd, Krishnan KR: Zonisamide for weight loss in obese adults: a randomized controlled trial. JAMA. 2003 Apr 9;289(14):1820-5. [PubMed:12684361 ]
Ueda Y, Doi T, Tokumaru J, Willmore LJ: Effect of zonisamide on molecular regulation of glutamate and GABA transporter proteins during epileptogenesis in rats with hippocampal seizures. Brain Res Mol Brain Res. 2003 Aug 19;116(1-2):1-6. [PubMed:12941455 ]
Hasegawa H: Utilization of zonisamide in patients with chronic pain or epilepsy refractory to other treatments: a retrospective, open label, uncontrolled study in a VA hospital. Curr Med Res Opin. 2004 May;20(5):577-80. [PubMed:15140322 ]

Only showing the first 10 proteins. There are 33 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Aldehyde oxidase

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: AOX1
Uniprot ID:: Q06278
Molecular weight:: 147916.735

References

Sugihara K, Kitamura S, Tatsumi K: Involvement of mammalian liver cytosols and aldehyde oxidase in reductive metabolism of zonisamide. Drug Metab Dispos. 1996 Feb;24(2):199-202. [PubMed:8742231 ]
Kitamura S, Ohashi KNK, Sugihara K, Hosokawa R, Akagawa Y, Ohta S: Extremely high drug-reductase activity based on aldehyde oxidase in monkey liver. Biol Pharm Bull. 2001 Jul;24(7):856-9. [PubMed:11456132 ]

Enzyme Details

2. Amine oxidase [flavin-containing] B

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:: MAOB
Uniprot ID:: P27338
Molecular weight:: 58762.475

References

Sonsalla PK, Wong LY, Winnik B, Buckley B: The antiepileptic drug zonisamide inhibits MAO-B and attenuates MPTP toxicity in mice: clinical relevance. Exp Neurol. 2010 Feb;221(2):329-34. doi: 10.1016/j.expneurol.2009.11.018. Epub 2009 Dec 4. [PubMed:19948168 ]
Murata M: Novel therapeutic effects of the anti-convulsant, zonisamide, on Parkinson's disease. Curr Pharm Des. 2004;10(6):687-93. [PubMed:14965331 ]
Murata M, Horiuchi E, Kanazawa I: Zonisamide has beneficial effects on Parkinson's disease patients. Neurosci Res. 2001 Dec;41(4):397-9. [PubMed:11755227 ]
Okada M, Kaneko S, Hirano T, Mizuno K, Kondo T, Otani K, Fukushima Y: Effects of zonisamide on dopaminergic system. Epilepsy Res. 1995 Nov;22(3):193-205. [PubMed:8991786 ]
Murata M: Zonisamide: a new drug for Parkinson's disease. Drugs Today (Barc). 2010 Apr;46(4):251-8. doi: 10.1358/dot.2010.46.4.1490077. [PubMed:20502722 ]
Okada M: [Effects of carbamazepine and zonisamide on dopaminergic system in rat striatum and hippocampus]. Nihon Shinkei Seishin Yakurigaku Zasshi. 1994 Oct;14(5):337-54. [PubMed:7856330 ]
Farooq MU, Moore PW, Bhatt A, Aburashed R, Kassab MY: Therapeutic role of zonisamide in neuropsychiatric disorders. Mini Rev Med Chem. 2008 Sep;8(10):968-75. [PubMed:18782051 ]

Enzyme Details

3. Amine oxidase [flavin-containing] A

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:: MAOA
Uniprot ID:: P21397
Molecular weight:: 59681.27

References

Okada M, Kaneko S, Hirano T, Mizuno K, Kondo T, Otani K, Fukushima Y: Effects of zonisamide on dopaminergic system. Epilepsy Res. 1995 Nov;22(3):193-205. [PubMed:8991786 ]
Murata M: Zonisamide: a new drug for Parkinson's disease. Drugs Today (Barc). 2010 Apr;46(4):251-8. doi: 10.1358/dot.2010.46.4.1490077. [PubMed:20502722 ]

Enzyme Details

4. Cytochrome P450 3A4

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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Nakasa H, Komiya M, Ohmori S, Rikihisa T, Kiuchi M, Kitada M: Characterization of human liver microsomal cytochrome P450 involved in the reductive metabolism of zonisamide. Mol Pharmacol. 1993 Jul;44(1):216-21. [PubMed:8341274 ]
Schulze-Bonhage A: Zonisamide in the treatment of epilepsy. Expert Opin Pharmacother. 2010 Jan;11(1):115-26. doi: 10.1517/14656560903468728. [PubMed:20001433 ]
Zaccara G, Specchio LM: Long-term safety and effectiveness of zonisamide in the treatment of epilepsy: a review of the literature. Neuropsychiatr Dis Treat. 2009;5:249-59. Epub 2009 May 20. [PubMed:19557119 ]
Nakasa H, Nakamura H, Ono S, Tsutsui M, Kiuchi M, Ohmori S, Kitada M: Prediction of drug-drug interactions of zonisamide metabolism in humans from in vitro data. Eur J Clin Pharmacol. 1998 Apr;54(2):177-83. [PubMed:9626925 ]
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 ]

Enzyme Details

5. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

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 ]

Enzyme Details

6. Carbonic anhydrase 1

General function:: Involved in carbonate dehydratase activity
Specific function:: Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name:: CA1
Uniprot ID:: P00915
Molecular weight:: 28870.0

References

De Simone G, Di Fiore A, Menchise V, Pedone C, Antel J, Casini A, Scozzafava A, Wurl M, Supuran CT: Carbonic anhydrase inhibitors. Zonisamide is an effective inhibitor of the cytosolic isozyme II and mitochondrial isozyme V: solution and X-ray crystallographic studies. Bioorg Med Chem Lett. 2005 May 2;15(9):2315-20. [PubMed:15837316 ]
Supuran CT, Di Fiore A, De Simone G: Carbonic anhydrase inhibitors as emerging drugs for the treatment of obesity. Expert Opin Emerg Drugs. 2008 Jun;13(2):383-92. doi: 10.1517/14728214.13.2.383 . [PubMed:18537527 ]
Shank RP, Smith-Swintosky VL, Maryanoff BE: Carbonic anhydrase inhibition. Insight into the characteristics of zonisamide, topiramate, and the sulfamide cognate of topiramate. J Enzyme Inhib Med Chem. 2008 Apr;23(2):271-6. doi: 10.1080/14756360701507001 . [PubMed:18343915 ]
Masuda Y, Karasawa T: Inhibitory effect of zonisamide on human carbonic anhydrase in vitro. Arzneimittelforschung. 1993 Apr;43(4):416-8. [PubMed:8494570 ]
Farooq MU, Moore PW, Bhatt A, Aburashed R, Kassab MY: Therapeutic role of zonisamide in neuropsychiatric disorders. Mini Rev Med Chem. 2008 Sep;8(10):968-75. [PubMed:18782051 ]
Temperini C, Cecchi A, Boyle NA, Scozzafava A, Cabeza JE, Wentworth P Jr, Blackburn GM, Supuran CT: Carbonic anhydrase inhibitors. Interaction of 2-N,N-dimethylamino-1,3,4-thiadiazole-5-methanesulfonamide with 12 mammalian isoforms: kinetic and X-ray crystallographic studies. Bioorg Med Chem Lett. 2008 Feb 1;18(3):999-1005. Epub 2007 Dec 15. [PubMed:18162396 ]
Biton V: Clinical pharmacology and mechanism of action of zonisamide. Clin Neuropharmacol. 2007 Jul-Aug;30(4):230-40. [PubMed:17762320 ]
Authors unspecified: Zonisamide: new drug. No advantage in refractory partial epilepsy. Prescrire Int. 2007 Jun;16(89):95-7. [PubMed:17582922 ]

Enzyme Details

7. Carbonic anhydrase 2

General function:: Involved in carbonate dehydratase activity
Specific function:: Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion into the anterior chamber of the eye.
Gene Name:: CA2
Uniprot ID:: P00918
Molecular weight:: 29245.895

References

De Simone G, Scozzafava A, Supuran CT: Which carbonic anhydrases are targeted by the antiepileptic sulfonamides and sulfamates? Chem Biol Drug Des. 2009 Sep;74(3):317-21. doi: 10.1111/j.1747-0285.2009.00857.x. [PubMed:19703035 ]
Supuran CT, Di Fiore A, De Simone G: Carbonic anhydrase inhibitors as emerging drugs for the treatment of obesity. Expert Opin Emerg Drugs. 2008 Jun;13(2):383-92. doi: 10.1517/14728214.13.2.383 . [PubMed:18537527 ]
Shank RP, Smith-Swintosky VL, Maryanoff BE: Carbonic anhydrase inhibition. Insight into the characteristics of zonisamide, topiramate, and the sulfamide cognate of topiramate. J Enzyme Inhib Med Chem. 2008 Apr;23(2):271-6. doi: 10.1080/14756360701507001 . [PubMed:18343915 ]
De Simone G, Di Fiore A, Menchise V, Pedone C, Antel J, Casini A, Scozzafava A, Wurl M, Supuran CT: Carbonic anhydrase inhibitors. Zonisamide is an effective inhibitor of the cytosolic isozyme II and mitochondrial isozyme V: solution and X-ray crystallographic studies. Bioorg Med Chem Lett. 2005 May 2;15(9):2315-20. [PubMed:15837316 ]
Masuda Y, Karasawa T: Inhibitory effect of zonisamide on human carbonic anhydrase in vitro. Arzneimittelforschung. 1993 Apr;43(4):416-8. [PubMed:8494570 ]
Farooq MU, Moore PW, Bhatt A, Aburashed R, Kassab MY: Therapeutic role of zonisamide in neuropsychiatric disorders. Mini Rev Med Chem. 2008 Sep;8(10):968-75. [PubMed:18782051 ]
Temperini C, Cecchi A, Boyle NA, Scozzafava A, Cabeza JE, Wentworth P Jr, Blackburn GM, Supuran CT: Carbonic anhydrase inhibitors. Interaction of 2-N,N-dimethylamino-1,3,4-thiadiazole-5-methanesulfonamide with 12 mammalian isoforms: kinetic and X-ray crystallographic studies. Bioorg Med Chem Lett. 2008 Feb 1;18(3):999-1005. Epub 2007 Dec 15. [PubMed:18162396 ]
Biton V: Clinical pharmacology and mechanism of action of zonisamide. Clin Neuropharmacol. 2007 Jul-Aug;30(4):230-40. [PubMed:17762320 ]
Authors unspecified: Zonisamide: new drug. No advantage in refractory partial epilepsy. Prescrire Int. 2007 Jun;16(89):95-7. [PubMed:17582922 ]

Enzyme Details

8. Carbonic anhydrase 5A, mitochondrial

General function:: Involved in carbonate dehydratase activity
Specific function:: Reversible hydration of carbon dioxide. Low activity.
Gene Name:: CA5A
Uniprot ID:: P35218
Molecular weight:: 34750.21

References

De Simone G, Scozzafava A, Supuran CT: Which carbonic anhydrases are targeted by the antiepileptic sulfonamides and sulfamates? Chem Biol Drug Des. 2009 Sep;74(3):317-21. doi: 10.1111/j.1747-0285.2009.00857.x. [PubMed:19703035 ]
Supuran CT, Di Fiore A, De Simone G: Carbonic anhydrase inhibitors as emerging drugs for the treatment of obesity. Expert Opin Emerg Drugs. 2008 Jun;13(2):383-92. doi: 10.1517/14728214.13.2.383 . [PubMed:18537527 ]
De Simone G, Di Fiore A, Menchise V, Pedone C, Antel J, Casini A, Scozzafava A, Wurl M, Supuran CT: Carbonic anhydrase inhibitors. Zonisamide is an effective inhibitor of the cytosolic isozyme II and mitochondrial isozyme V: solution and X-ray crystallographic studies. Bioorg Med Chem Lett. 2005 May 2;15(9):2315-20. [PubMed:15837316 ]
Farooq MU, Moore PW, Bhatt A, Aburashed R, Kassab MY: Therapeutic role of zonisamide in neuropsychiatric disorders. Mini Rev Med Chem. 2008 Sep;8(10):968-75. [PubMed:18782051 ]
Biton V: Clinical pharmacology and mechanism of action of zonisamide. Clin Neuropharmacol. 2007 Jul-Aug;30(4):230-40. [PubMed:17762320 ]
Authors unspecified: Zonisamide: new drug. No advantage in refractory partial epilepsy. Prescrire Int. 2007 Jun;16(89):95-7. [PubMed:17582922 ]

Enzyme Details

9. Carbonic anhydrase-related protein 10

General function:: Inorganic ion transport and metabolism
Specific function:: Does not have a catalytic activity
Gene Name:: CA10
Uniprot ID:: Q9NS85
Molecular weight:: 37562.7

References

De Simone G, Scozzafava A, Supuran CT: Which carbonic anhydrases are targeted by the antiepileptic sulfonamides and sulfamates? Chem Biol Drug Des. 2009 Sep;74(3):317-21. doi: 10.1111/j.1747-0285.2009.00857.x. [PubMed:19703035 ]
Supuran CT, Di Fiore A, De Simone G: Carbonic anhydrase inhibitors as emerging drugs for the treatment of obesity. Expert Opin Emerg Drugs. 2008 Jun;13(2):383-92. doi: 10.1517/14728214.13.2.383 . [PubMed:18537527 ]
Farooq MU, Moore PW, Bhatt A, Aburashed R, Kassab MY: Therapeutic role of zonisamide in neuropsychiatric disorders. Mini Rev Med Chem. 2008 Sep;8(10):968-75. [PubMed:18782051 ]
Biton V: Clinical pharmacology and mechanism of action of zonisamide. Clin Neuropharmacol. 2007 Jul-Aug;30(4):230-40. [PubMed:17762320 ]
Authors unspecified: Zonisamide: new drug. No advantage in refractory partial epilepsy. Prescrire Int. 2007 Jun;16(89):95-7. [PubMed:17582922 ]

Enzyme Details

10. Carbonic anhydrase 3

General function:: Involved in carbonate dehydratase activity
Specific function:: Reversible hydration of carbon dioxide.
Gene Name:: CA3
Uniprot ID:: P07451
Molecular weight:: 29557.215

References

De Simone G, Scozzafava A, Supuran CT: Which carbonic anhydrases are targeted by the antiepileptic sulfonamides and sulfamates? Chem Biol Drug Des. 2009 Sep;74(3):317-21. doi: 10.1111/j.1747-0285.2009.00857.x. [PubMed:19703035 ]
Supuran CT, Di Fiore A, De Simone G: Carbonic anhydrase inhibitors as emerging drugs for the treatment of obesity. Expert Opin Emerg Drugs. 2008 Jun;13(2):383-92. doi: 10.1517/14728214.13.2.383 . [PubMed:18537527 ]
Farooq MU, Moore PW, Bhatt A, Aburashed R, Kassab MY: Therapeutic role of zonisamide in neuropsychiatric disorders. Mini Rev Med Chem. 2008 Sep;8(10):968-75. [PubMed:18782051 ]
Temperini C, Cecchi A, Boyle NA, Scozzafava A, Cabeza JE, Wentworth P Jr, Blackburn GM, Supuran CT: Carbonic anhydrase inhibitors. Interaction of 2-N,N-dimethylamino-1,3,4-thiadiazole-5-methanesulfonamide with 12 mammalian isoforms: kinetic and X-ray crystallographic studies. Bioorg Med Chem Lett. 2008 Feb 1;18(3):999-1005. Epub 2007 Dec 15. [PubMed:18162396 ]
Biton V: Clinical pharmacology and mechanism of action of zonisamide. Clin Neuropharmacol. 2007 Jul-Aug;30(4):230-40. [PubMed:17762320 ]
Authors unspecified: Zonisamide: new drug. No advantage in refractory partial epilepsy. Prescrire Int. 2007 Jun;16(89):95-7. [PubMed:17582922 ]

Only showing the first 10 proteins. There are 33 proteins in total.

Show all enzymes and transporters

Showing metabocard for Zonisamide (HMDB0015045)

MOL for HMDB0015045 (Zonisamide)

3D MOL for HMDB0015045 (Zonisamide)

3D SDF for HMDB0015045 (Zonisamide)

3D-SDF for HMDB0015045 (Zonisamide)

PDB for HMDB0015045 (Zonisamide)

3D PDB for HMDB0015045 (Zonisamide)

SMILES for HMDB0015045 (Zonisamide)

INCHI for HMDB0015045 (Zonisamide)

Structure for HMDB0015045 (Zonisamide)

3D Structure for HMDB0015045 (Zonisamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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