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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:45 UTC

HMDB ID

HMDB0014841

Secondary Accession Numbers

HMDB14841

Metabolite Identification

Common Name

Methazolamide

Description

Methazolamide is only found in individuals that have used or taken this drug. It is a potent carbonic anhydrase inhibitor that is used as a diuretic and in the treatment of glaucoma. [PubChem]Inhibition of carbonic anhydrase in the ciliary processes of the eye decreases aqueous humor secretion, presumably by slowing the formation of bicarbonate ions with subsequent reduction in sodium and fluid transport.

Structure

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

703
  Mrv0541 02231214562D          

 14 14  0  0  0  0            999 V2000
    2.6437    0.8136    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.9537    0.1462    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9763    0.3287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3111    1.2986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4348    0.4656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5412   -1.1234    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8737   -0.6385    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1588    1.4811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9932   -0.8934    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1287    0.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2086   -0.6385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5412   -1.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6064   -0.3413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3910   -0.5963    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  8  1  0  0  0  0
  1 10  1  0  0  0  0
  2 10  1  0  0  0  0
  2 11  1  0  0  0  0
  5 13  2  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7 10  2  0  0  0  0
  9 11  2  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014841

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1N=C(S\C1=N/C(C)=O)S(N)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H8N4O3S2/c1-3(10)7-4-9(2)8-5(13-4)14(6,11)12/h1-2H3,(H2,6,11,12)/b7-4-

> <INCHI_KEY>
FLOSMHQXBMRNHR-DAXSKMNVSA-N

> <FORMULA>
C5H8N4O3S2

> <MOLECULAR_WEIGHT>
236.272

> <EXACT_MASS>
236.003781522

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
21.17002056557853

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(2Z)-3-methyl-5-sulfamoyl-2,3-dihydro-1,3,4-thiadiazol-2-ylidene]acetamide

> <ALOGPS_LOGP>
-0.20

> <JCHEM_LOGP>
-0.593433132

> <ALOGPS_LOGS>
-2.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.433883629944784

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.058321873803521

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6404575283873846

> <JCHEM_POLAR_SURFACE_AREA>
105.19

> <JCHEM_REFRACTIVITY>
51.29709999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.74e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methazolamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 703                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       4.935   1.519   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0       7.380   0.273   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0       3.689   0.614   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.181   2.424   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      10.145   0.869   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       6.610  -2.097   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       5.364  -1.192   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       4.030   2.765   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       9.321  -1.668   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       5.840   0.273   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.856  -1.192   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.610  -3.637   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.465  -0.637   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.930  -1.113   0.000  0.00  0.00           C+0
CONECT    1    3    4    8   10                                             
CONECT    2   10   11                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5   13                                                            
CONECT    6    7   11   12                                                  
CONECT    7    6   10                                                       
CONECT    8    1                                                            
CONECT    9   11   13                                                       
CONECT   10    1    2    7                                                  
CONECT   11    2    6    9                                                  
CONECT   12    6                                                            
CONECT   13    5    9   14                                                  
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
N-[(2Z)-3-Methyl-5-sulphamoyl-2,3-dihydro-1,3,4-thiadiazol-2-ylidene]acetamide	Generator

Chemical Formula

C₅H₈N₄O₃S₂

Average Molecular Weight

236.272

Monoisotopic Molecular Weight

236.003781522

IUPAC Name

N-[(2Z)-3-methyl-5-sulfamoyl-2,3-dihydro-1,3,4-thiadiazol-2-ylidene]acetamide

Traditional Name

methazolamide

CAS Registry Number

554-57-4

SMILES

CN1N=C(S\C1=N/C(C)=O)S(N)(=O)=O

InChI Identifier

InChI=1S/C5H8N4O3S2/c1-3(10)7-4-9(2)8-5(13-4)14(6,11)12/h1-2H3,(H2,6,11,12)/b7-4-

InChI Key

FLOSMHQXBMRNHR-DAXSKMNVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thiadiazole sulfonamides. These are heterocyclic compounds containing a thiazole ring substituted by at least one sulfonamide group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Thiadiazoles

Direct Parent

Thiadiazole sulfonamides

Alternative Parents

Substituents

1,3,4-thiadiazole-2-sulfonamide
Organosulfonic acid amide
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Heteroaromatic compound
Aminosulfonyl compound
N-acylimine
Carboxylic acid derivative
Azacycle
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

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

Cytoplasm (HMDB: HMDB0014841)
Membrane (HMDB: HMDB0014841)

Source

Exogenous

Exogenous (HMDB: HMDB0014841)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	213.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.74 g/L	Not Available
LogP	-1.6	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.74 g/L	ALOGPS
logP	-0.2	ALOGPS
logP	-0.59	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	10.06	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	105.19 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	51.3 m³·mol⁻¹	ChemAxon
Polarizability	21.17 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
DeepCCS	[M+H]+	142.695	30932474
DeepCCS	[M-H]-	140.285	30932474
DeepCCS	[M-2H]-	175.857	30932474
DeepCCS	[M+Na]+	151.395	30932474
AllCCS	[M+H]+	148.0	32859911
AllCCS	[M+H-H2O]+	144.5	32859911
AllCCS	[M+NH4]+	151.2	32859911
AllCCS	[M+Na]+	152.1	32859911
AllCCS	[M-H]-	142.4	32859911
AllCCS	[M+Na-2H]-	143.3	32859911
AllCCS	[M+HCOO]-	144.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methazolamide	CN1N=C(S\C1=N/C(C)=O)S(N)(=O)=O	3313.4	Standard polar	33892256
Methazolamide	CN1N=C(S\C1=N/C(C)=O)S(N)(=O)=O	2191.0	Standard non polar	33892256
Methazolamide	CN1N=C(S\C1=N/C(C)=O)S(N)(=O)=O	2213.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methazolamide,1TMS,isomer #1	CC(=O)/N=C1\SC(S(=O)(=O)N[Si](C)(C)C)=NN1C	2252.0	Semi standard non polar	33892256
Methazolamide,1TMS,isomer #1	CC(=O)/N=C1\SC(S(=O)(=O)N[Si](C)(C)C)=NN1C	2137.0	Standard non polar	33892256
Methazolamide,1TMS,isomer #1	CC(=O)/N=C1\SC(S(=O)(=O)N[Si](C)(C)C)=NN1C	3586.7	Standard polar	33892256
Methazolamide,2TMS,isomer #1	CC(=O)/N=C1\SC(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=NN1C	2176.8	Semi standard non polar	33892256
Methazolamide,2TMS,isomer #1	CC(=O)/N=C1\SC(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=NN1C	2284.3	Standard non polar	33892256
Methazolamide,2TMS,isomer #1	CC(=O)/N=C1\SC(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=NN1C	3347.1	Standard polar	33892256
Methazolamide,1TBDMS,isomer #1	CC(=O)/N=C1\SC(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=NN1C	2475.9	Semi standard non polar	33892256
Methazolamide,1TBDMS,isomer #1	CC(=O)/N=C1\SC(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=NN1C	2386.1	Standard non polar	33892256
Methazolamide,1TBDMS,isomer #1	CC(=O)/N=C1\SC(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=NN1C	3623.3	Standard polar	33892256
Methazolamide,2TBDMS,isomer #1	CC(=O)/N=C1\SC(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NN1C	2683.7	Semi standard non polar	33892256
Methazolamide,2TBDMS,isomer #1	CC(=O)/N=C1\SC(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NN1C	2782.0	Standard non polar	33892256
Methazolamide,2TBDMS,isomer #1	CC(=O)/N=C1\SC(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NN1C	3344.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Methazolamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-8910000000-d79f8dbccda85c20411e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methazolamide 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 - Methazolamide LC-ESI-qTof , Positive-QTOF	splash10-0002-0910000000-ca8f92da783db6e21a35	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methazolamide , positive-QTOF	splash10-0002-0910000000-ca8f92da783db6e21a35	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methazolamide 10V, Positive-QTOF	splash10-000j-0980000000-0dc1629a939c52957bd5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methazolamide 20V, Positive-QTOF	splash10-002b-2900000000-cc5c9ddc1453362c9307	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methazolamide 40V, Positive-QTOF	splash10-0pbl-9500000000-2645af521c3f0fd0d9a8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methazolamide 10V, Negative-QTOF	splash10-0zi9-6900000000-b7435fee36ef96d7b3c8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methazolamide 20V, Negative-QTOF	splash10-0pb9-9300000000-82e3550c4c02656efc72	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methazolamide 40V, Negative-QTOF	splash10-0a4i-9000000000-0c465fc9b9cc19219155	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methazolamide 10V, Positive-QTOF	splash10-0002-0920000000-18645677608e88c6ded9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methazolamide 20V, Positive-QTOF	splash10-0002-0900000000-171c34971379dd9babb0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methazolamide 40V, Positive-QTOF	splash10-0a4i-9400000000-01c8dfbfd8cd2abd0b16	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methazolamide 10V, Negative-QTOF	splash10-004i-9420000000-0f6f9dde303196d60952	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methazolamide 20V, Negative-QTOF	splash10-004i-9200000000-bba805ad098bb8343ca2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methazolamide 40V, Negative-QTOF	splash10-056r-9100000000-4f3f0da75468c61edf72	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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 DB00703	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00703	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3958

KEGG Compound ID

C07764

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methazolamide

METLIN ID

Not Available

PubChem Compound

5353756

PDB ID

MZM

ChEBI ID

150028

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

Iyer GR, Bellantone RA, Taft DR: In vitro characterization of the erythrocyte distribution of methazolamide: a model of erythrocyte transport and binding kinetics. J Pharmacokinet Biopharm. 1999 Feb;27(1):45-66. [PubMed:10533697 ]
Shirato S, Kagaya F, Suzuki Y, Joukou S: Stevens-Johnson syndrome induced by methazolamide treatment. Arch Ophthalmol. 1997 Apr;115(4):550-3. [PubMed:9109770 ]
Skorobohach BJ, Ward DA, Hendrix DV: Effects of oral administration of methazolamide on intraocular pressure and aqueous humor flow rate in clinically normal dogs. Am J Vet Res. 2003 Feb;64(2):183-7. [PubMed:12602587 ]

Enzymes

Enzyme Details

1. 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

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

2. 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 ]

Enzyme Details

3. 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

4. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

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

5. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

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

Ilies MA, Masereel B, Rolin S, Scozzafava A, Campeanu G, Cimpeanu V, Supuran CT: Carbonic anhydrase inhibitors: aromatic and heterocyclic sulfonamides incorporating adamantyl moieties with strong anticonvulsant activity. Bioorg Med Chem. 2004 May 15;12(10):2717-26. [PubMed:15110853 ]
Winum JY, Casini A, Mincione F, Starnotti M, Montero JL, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: N-(p-sulfamoylphenyl)-alpha-D-glycopyranosylamines as topically acting antiglaucoma agents in hypertensive rabbits. Bioorg Med Chem Lett. 2004 Jan 5;14(1):225-9. [PubMed:14684332 ]
Iyer GR, Bellantone RA, Taft DR: In vitro characterization of the erythrocyte distribution of methazolamide: a model of erythrocyte transport and binding kinetics. J Pharmacokinet Biopharm. 1999 Feb;27(1):45-66. [PubMed:10533697 ]
Scozzafava A, Briganti F, Ilies MA, Supuran CT: Carbonic anhydrase inhibitors: synthesis of membrane-impermeant low molecular weight sulfonamides possessing in vivo selectivity for the membrane-bound versus cytosolic isozymes. J Med Chem. 2000 Jan 27;43(2):292-300. [PubMed:10649985 ]
Lindskog S: Structure and mechanism of carbonic anhydrase. Pharmacol Ther. 1997;74(1):1-20. [PubMed:9336012 ]

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

Mincione F, Scozzafava A, Supuran CT: The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents. Curr Pharm Des. 2008;14(7):649-54. [PubMed:18336310 ]

Enzyme Details

8. Carbonic anhydrase 4

General function:: Involved in carbonate dehydratase activity
Specific function:: Reversible hydration of carbon dioxide. May stimulate the sodium/bicarbonate transporter activity of SLC4A4 that acts in pH homeostasis. It is essential for acid overload removal from the retina and retina epithelium, and acid release in the choriocapillaris in the choroid.
Gene Name:: CA4
Uniprot ID:: P22748
Molecular weight:: 35032.075

References

Mincione F, Scozzafava A, Supuran CT: The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents. Curr Pharm Des. 2008;14(7):649-54. [PubMed:18336310 ]

Enzyme Details

9. Carbonic anhydrase 7

General function:: Involved in carbonate dehydratase activity
Specific function:: Reversible hydration of carbon dioxide.
Gene Name:: CA7
Uniprot ID:: P43166
Molecular weight:: 23451.435

References

Mincione F, Scozzafava A, Supuran CT: The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents. Curr Pharm Des. 2008;14(7):649-54. [PubMed:18336310 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Uwai Y, Saito H, Hashimoto Y, Inui KI: Interaction and transport of thiazide diuretics, loop diuretics, and acetazolamide via rat renal organic anion transporter rOAT1. J Pharmacol Exp Ther. 2000 Oct;295(1):261-5. [PubMed:10991988 ]

Showing metabocard for Methazolamide (HMDB0014841)

MOL for HMDB0014841 (Methazolamide)

3D MOL for HMDB0014841 (Methazolamide)

3D SDF for HMDB0014841 (Methazolamide)

3D-SDF for HMDB0014841 (Methazolamide)

PDB for HMDB0014841 (Methazolamide)

3D PDB for HMDB0014841 (Methazolamide)

SMILES for HMDB0014841 (Methazolamide)

INCHI for HMDB0014841 (Methazolamide)

Structure for HMDB0014841 (Methazolamide)

3D Structure for HMDB0014841 (Methazolamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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Transporters

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