Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (8)transporters (1) Show 9 proteins XML

enzymes (8)transporters (1) Show 9 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:48 UTC

HMDB ID

HMDB0014957

Secondary Accession Numbers

HMDB14957

Metabolite Identification

Common Name

Acetazolamide

Description

One of the carbonic anhydrase inhibitors that is sometimes effective against absence seizures. It is sometimes useful also as an adjunct in the treatment of tonic-clonic, myoclonic, and atonic seizures, particularly in women whose seizures occur or are exacerbated at specific times in the menstrual cycle. However, its usefulness is transient often because of rapid development of tolerance. Its antiepileptic effect may be due to its inhibitory effect on brain carbonic anhydrase, which leads to an increased transneuronal chloride gradient, increased chloride current, and increased inhibition. (From Smith and Reynard, Textbook of Pharmacology, 1991, p337)

Structure

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

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 819                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      11.110  -0.536   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0       8.400  -0.965   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0      10.634  -2.001   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.586   0.928   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       4.865   2.001   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       5.689  -0.536   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       9.170   1.404   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      12.575  -1.012   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       7.630   1.404   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       9.645  -0.060   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.154  -0.060   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.545   0.494   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.080   0.018   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   12                                                            
CONECT    6   11   12                                                       
CONECT    7    9   10                                                       
CONECT    8    1                                                            
CONECT    9    7   11                                                       
CONECT   10    1    2    7                                                  
CONECT   11    2    6    9                                                  
CONECT   12    5    6   13                                                  
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Acetylamino-1,3,4-thiadiazole-5-sulfonamide	ChEBI
5-ACETAMIDO-1,3,4-thiadiazole-2-sulfonamide	ChEBI
5-Acetylamino-1,3,4-thiadiazole-2-sulfonamide	ChEBI
Acetazolamida	ChEBI
Acetazolamidum	ChEBI
Defiltran	ChEBI
Diacarb	ChEBI
Diamox	ChEBI
Diluran	ChEBI
Glaupax	ChEBI
N-[5-(Aminosulfonyl)-1,3,4-thiadiazol-2-yl]acetamide	ChEBI
N-[5-(Aminosulfonyl)-1,3,5-thiadiazol-2-yl]acetamide	ChEBI
2-Acetylamino-1,3,4-thiadiazole-5-sulphonamide	Generator
5-ACETAMIDO-1,3,4-thiadiazole-2-sulphonamide	Generator
5-Acetylamino-1,3,4-thiadiazole-2-sulphonamide	Generator
N-[5-(Aminosulphonyl)-1,3,4-thiadiazol-2-yl]acetamide	Generator
N-[5-(Aminosulphonyl)-1,3,5-thiadiazol-2-yl]acetamide	Generator
Acetamidothiadiazolesulfonamide	HMDB
Acetazolamid	HMDB
Acetazolamine	HMDB
Acetazoleamide	HMDB
Acetozalamide	HMDB
Carbonic anhydrase inhibitor 6063	HMDB
Acetazolamide llorens brand	HMDB
Acetazolamide medphano brand	HMDB
Acetazolamide novopharm brand	HMDB
Acetazolamide wassermann brand	HMDB
Ak-zol	HMDB
Apo acetazolamide	HMDB
Apo-acetazolamide	HMDB
Cyanamid brand OF acetazolamide preparation	HMDB
Edemox	HMDB
Huma zolamide	HMDB
HumaZolamide	HMDB
Lederle brand OF acetazolamide preparation	HMDB
Llorens brand OF acetazolamide	HMDB
Monosodium salt acetazolamide	HMDB
Wassermann brand OF acetazolamide	HMDB
Acetazolamide chiesi brand	HMDB
Acetazolamide dioptic brand	HMDB
Acetazolamide grin brand	HMDB
Acetazolamide sodium, (sterile)	HMDB
Acetazolamide, monosodium salt	HMDB
Grin brand OF acetazolamide	HMDB
Medphano brand OF acetazolamide	HMDB
Orion brand OF acetazolamide	HMDB
Théraplix brand OF acetazolamide preparation	HMDB
Whelehan brand OF acetazolamide preparation	HMDB
Wyeth brand OF acetazolamide preparation	HMDB
Acetadiazol	HMDB
Acetazolam	HMDB
Acetazolamide icn brand	HMDB
Acetazolamide jumer brand	HMDB
Ak zol	HMDB
Ciba vision brand OF acetazolamide	HMDB
Diuramide	HMDB
Défiltran	HMDB
Glauconox	HMDB
Jumer brand OF acetazolamide	HMDB
Storz brand OF acetazolamide preparation	HMDB
Acetazolamide apotex brand	HMDB
Acetazolamide orion brand	HMDB
AkZol	HMDB
ApoAcetazolamide	HMDB
Apotex brand OF acetazolamide	HMDB
Chiesi brand OF acetazolamide	HMDB
Dioptic brand OF acetazolamide	HMDB
Huma-zolamide	HMDB
ICN brand OF acetazolamide	HMDB
Novopharm brand OF acetazolamide	HMDB

Chemical Formula

C₄H₆N₄O₃S₂

Average Molecular Weight

222.245

Monoisotopic Molecular Weight

221.988131458

IUPAC Name

N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide

Traditional Name

acetazolamide

CAS Registry Number

59-66-5

SMILES

CC(=O)NC1=NN=C(S1)S(N)(=O)=O

InChI Identifier

InChI=1S/C4H6N4O3S2/c1-2(9)6-3-7-8-4(12-3)13(5,10)11/h1H3,(H2,5,10,11)(H,6,7,9)

InChI Key

BZKPWHYZMXOIDC-UHFFFAOYSA-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

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:27690 )
sulfonamide (CHEBI:27690 )
thiadiazoles (CHEBI:27690 )
a small molecule (CPD0-1626 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014957)
Membrane (HMDB: HMDB0014957)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	260.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2.79 g/L	Not Available
LogP	-0.26	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	140.748	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000931

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.79 g/L	ALOGPS
logP	-0.39	ALOGPS
logP	-1	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	6.93	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	115.04 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.36 m³·mol⁻¹	ChemAxon
Polarizability	19.16 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
DarkChem	[M+H]+	148.629	31661259
DarkChem	[M-H]-	144.028	31661259
DeepCCS	[M+H]+	137.214	30932474
DeepCCS	[M-H]-	133.994	30932474
DeepCCS	[M-2H]-	170.938	30932474
DeepCCS	[M+Na]+	146.477	30932474
AllCCS	[M+H]+	145.2	32859911
AllCCS	[M+H-H2O]+	141.5	32859911
AllCCS	[M+NH4]+	148.7	32859911
AllCCS	[M+Na]+	149.7	32859911
AllCCS	[M-H]-	139.1	32859911
AllCCS	[M+Na-2H]-	140.1	32859911
AllCCS	[M+HCOO]-	141.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Acetazolamide	CC(=O)NC1=NN=C(S1)S(N)(=O)=O	3352.2	Standard polar	33892256
Acetazolamide	CC(=O)NC1=NN=C(S1)S(N)(=O)=O	2292.2	Standard non polar	33892256
Acetazolamide	CC(=O)NC1=NN=C(S1)S(N)(=O)=O	2491.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Acetazolamide,1TMS,isomer #1	CC(=O)NC1=NN=C(S(=O)(=O)N[Si](C)(C)C)S1	2424.4	Semi standard non polar	33892256
Acetazolamide,1TMS,isomer #1	CC(=O)NC1=NN=C(S(=O)(=O)N[Si](C)(C)C)S1	2124.2	Standard non polar	33892256
Acetazolamide,1TMS,isomer #1	CC(=O)NC1=NN=C(S(=O)(=O)N[Si](C)(C)C)S1	3716.5	Standard polar	33892256
Acetazolamide,1TMS,isomer #2	CC(=O)N(C1=NN=C(S(N)(=O)=O)S1)[Si](C)(C)C	2230.7	Semi standard non polar	33892256
Acetazolamide,1TMS,isomer #2	CC(=O)N(C1=NN=C(S(N)(=O)=O)S1)[Si](C)(C)C	2109.3	Standard non polar	33892256
Acetazolamide,1TMS,isomer #2	CC(=O)N(C1=NN=C(S(N)(=O)=O)S1)[Si](C)(C)C	4121.0	Standard polar	33892256
Acetazolamide,2TMS,isomer #1	CC(=O)N(C1=NN=C(S(=O)(=O)N[Si](C)(C)C)S1)[Si](C)(C)C	2208.6	Semi standard non polar	33892256
Acetazolamide,2TMS,isomer #1	CC(=O)N(C1=NN=C(S(=O)(=O)N[Si](C)(C)C)S1)[Si](C)(C)C	2206.7	Standard non polar	33892256
Acetazolamide,2TMS,isomer #1	CC(=O)N(C1=NN=C(S(=O)(=O)N[Si](C)(C)C)S1)[Si](C)(C)C	3180.9	Standard polar	33892256
Acetazolamide,2TMS,isomer #2	CC(=O)NC1=NN=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)S1	2378.3	Semi standard non polar	33892256
Acetazolamide,2TMS,isomer #2	CC(=O)NC1=NN=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)S1	2275.4	Standard non polar	33892256
Acetazolamide,2TMS,isomer #2	CC(=O)NC1=NN=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)S1	3483.1	Standard polar	33892256
Acetazolamide,3TMS,isomer #1	CC(=O)N(C1=NN=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)S1)[Si](C)(C)C	2212.0	Semi standard non polar	33892256
Acetazolamide,3TMS,isomer #1	CC(=O)N(C1=NN=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)S1)[Si](C)(C)C	2391.4	Standard non polar	33892256
Acetazolamide,3TMS,isomer #1	CC(=O)N(C1=NN=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)S1)[Si](C)(C)C	2955.8	Standard polar	33892256
Acetazolamide,1TBDMS,isomer #1	CC(=O)NC1=NN=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)S1	2674.7	Semi standard non polar	33892256
Acetazolamide,1TBDMS,isomer #1	CC(=O)NC1=NN=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)S1	2375.2	Standard non polar	33892256
Acetazolamide,1TBDMS,isomer #1	CC(=O)NC1=NN=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)S1	3763.1	Standard polar	33892256
Acetazolamide,1TBDMS,isomer #2	CC(=O)N(C1=NN=C(S(N)(=O)=O)S1)[Si](C)(C)C(C)(C)C	2463.2	Semi standard non polar	33892256
Acetazolamide,1TBDMS,isomer #2	CC(=O)N(C1=NN=C(S(N)(=O)=O)S1)[Si](C)(C)C(C)(C)C	2357.4	Standard non polar	33892256
Acetazolamide,1TBDMS,isomer #2	CC(=O)N(C1=NN=C(S(N)(=O)=O)S1)[Si](C)(C)C(C)(C)C	4120.1	Standard polar	33892256
Acetazolamide,2TBDMS,isomer #1	CC(=O)N(C1=NN=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)S1)[Si](C)(C)C(C)(C)C	2652.2	Semi standard non polar	33892256
Acetazolamide,2TBDMS,isomer #1	CC(=O)N(C1=NN=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)S1)[Si](C)(C)C(C)(C)C	2726.8	Standard non polar	33892256
Acetazolamide,2TBDMS,isomer #1	CC(=O)N(C1=NN=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)S1)[Si](C)(C)C(C)(C)C	3220.4	Standard polar	33892256
Acetazolamide,2TBDMS,isomer #2	CC(=O)NC1=NN=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S1	2910.6	Semi standard non polar	33892256
Acetazolamide,2TBDMS,isomer #2	CC(=O)NC1=NN=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S1	2749.2	Standard non polar	33892256
Acetazolamide,2TBDMS,isomer #2	CC(=O)NC1=NN=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S1	3511.2	Standard polar	33892256
Acetazolamide,3TBDMS,isomer #1	CC(=O)N(C1=NN=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S1)[Si](C)(C)C(C)(C)C	2871.5	Semi standard non polar	33892256
Acetazolamide,3TBDMS,isomer #1	CC(=O)N(C1=NN=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S1)[Si](C)(C)C(C)(C)C	3129.3	Standard non polar	33892256
Acetazolamide,3TBDMS,isomer #1	CC(=O)N(C1=NN=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S1)[Si](C)(C)C(C)(C)C	3100.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Acetazolamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-00fu-3900000000-d066d2601c8f3d625916	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acetazolamide 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 - Acetazolamide LC-ESI-QFT , negative-QTOF	splash10-00e9-9070000000-e2f68ded4939412340f7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acetazolamide LC-ESI-QFT , negative-QTOF	splash10-001i-9020000000-59775cde1cab229764b9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acetazolamide LC-ESI-QFT , negative-QTOF	splash10-001i-9000000000-1ee1fd41bb44b523dd8e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acetazolamide LC-ESI-QFT , negative-QTOF	splash10-001i-9000000000-de6c64393f3dc86c15b1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acetazolamide LC-ESI-QFT , negative-QTOF	splash10-001i-9000000000-7158c10cba32f3b3896b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acetazolamide LC-ESI-QFT , negative-QTOF	splash10-06si-9000000000-32cc006b3850024fd5b7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acetazolamide LC-ESI-QFT , positive-QTOF	splash10-00e9-0890000000-f407810fc44461e62ecb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acetazolamide LC-ESI-QFT , positive-QTOF	splash10-001i-0920000000-6dd62d0ae588814e0cf2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acetazolamide LC-ESI-QFT , positive-QTOF	splash10-001i-0900000000-6b6d74d2f34efd5f876a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acetazolamide LC-ESI-QFT , positive-QTOF	splash10-001i-1900000000-05fedd43edecd53593c2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acetazolamide LC-ESI-QFT , positive-QTOF	splash10-001i-5900000000-76456c439130c5477d45	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acetazolamide LC-ESI-QFT , positive-QTOF	splash10-00e9-9300000000-5ca7214eb79224d3dc21	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acetazolamide 90V, Positive-QTOF	splash10-00di-9100000000-5c1fd2ab9115264ac80e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acetazolamide 75V, Positive-QTOF	splash10-00e9-9600000000-0f3f02e34ccd222b9945	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acetazolamide 30V, Negative-QTOF	splash10-001i-9020000000-4a4eee8592c5e2c479a6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acetazolamide 15V, Negative-QTOF	splash10-05gi-9050000000-60e5a530176c676d7bb7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acetazolamide 30V, Negative-QTOF	splash10-053r-9010000000-6b286dca2a293b7acdad	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acetazolamide 45V, Negative-QTOF	splash10-001i-9000000000-1eacda33d690a3ee19dd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acetazolamide 60V, Positive-QTOF	splash10-001i-3900000000-af42c297c411f1e9dfa6	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetazolamide 10V, Positive-QTOF	splash10-00di-0090000000-b9d984e83e00c2e23943	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetazolamide 20V, Positive-QTOF	splash10-01x0-1950000000-c5bb42824cbdfdaae48d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetazolamide 40V, Positive-QTOF	splash10-0ufr-2890000000-5f098f8e1576ee3ffaa7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetazolamide 10V, Negative-QTOF	splash10-05fu-7890000000-3e47220ae52b55be57f4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetazolamide 20V, Negative-QTOF	splash10-003r-9400000000-78f160649efa3b627e2c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetazolamide 40V, Negative-QTOF	splash10-001i-9300000000-6ecab458fac9db3ee404	2016-08-03	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 DB00819	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00819	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00819

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

1909

KEGG Compound ID

C06805

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Acetazolamide

METLIN ID

Not Available

PubChem Compound

1986

PDB ID

AZM

ChEBI ID

27690

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

Not Available

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. 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

Puscas I, Coltau M, Pasca R: Nonsteroidal anti-inflammatory drugs activate carbonic anhydrase by a direct mechanism of action. J Pharmacol Exp Ther. 1996 Jun;277(3):1464-6. [PubMed:8667211 ]
Meierkord H, Grunig F, Gutschmidt U, Gutierrez R, Pfeiffer M, Draguhn A, Bruckner C, Heinemann U: Sodium bromide: effects on different patterns of epileptiform activity, extracellular pH changes and GABAergic inhibition. Naunyn Schmiedebergs Arch Pharmacol. 2000 Jan;361(1):25-32. [PubMed:10651143 ]
Puscas I, Ifrim M, Maghiar T, Coltau M, Domuta G, Baican M, Hecht A: Indomethacin activates carbonic anhydrase and antagonizes the effect of the specific carbonic anhydrase inhibitor acetazolamide, by a direct mechanism of action. Int J Clin Pharmacol Ther. 2001 Jun;39(6):265-70. [PubMed:11430635 ]
Puscas I, Coltau M, Baican M, Domuta G, Hecht A: Vasodilatory effect of diuretics is dependent on inhibition of vascular smooth muscle carbonic anhydrase by a direct mechanism of action. Drugs Exp Clin Res. 1999;25(6):271-9. [PubMed:10713865 ]
Perez Velazquez JL: Bicarbonate-dependent depolarizing potentials in pyramidal cells and interneurons during epileptiform activity. Eur J Neurosci. 2003 Sep;18(5):1337-42. [PubMed:12956733 ]
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

3. 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

Avvaru BS, Wagner JM, Maresca A, Scozzafava A, Robbins AH, Supuran CT, McKenna R: Carbonic anhydrase inhibitors. The X-ray crystal structure of human isoform II in adduct with an adamantyl analogue of acetazolamide resides in a less utilized binding pocket than most hydrophobic inhibitors. Bioorg Med Chem Lett. 2010 Aug 1;20(15):4376-81. doi: 10.1016/j.bmcl.2010.06.082. Epub 2010 Jun 17. [PubMed:20605094 ]
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

4. 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

Avvaru BS, Wagner JM, Maresca A, Scozzafava A, Robbins AH, Supuran CT, McKenna R: Carbonic anhydrase inhibitors. The X-ray crystal structure of human isoform II in adduct with an adamantyl analogue of acetazolamide resides in a less utilized binding pocket than most hydrophobic inhibitors. Bioorg Med Chem Lett. 2010 Aug 1;20(15):4376-81. doi: 10.1016/j.bmcl.2010.06.082. Epub 2010 Jun 17. [PubMed:20605094 ]

Enzyme Details

5. 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

Avvaru BS, Wagner JM, Maresca A, Scozzafava A, Robbins AH, Supuran CT, McKenna R: Carbonic anhydrase inhibitors. The X-ray crystal structure of human isoform II in adduct with an adamantyl analogue of acetazolamide resides in a less utilized binding pocket than most hydrophobic inhibitors. Bioorg Med Chem Lett. 2010 Aug 1;20(15):4376-81. doi: 10.1016/j.bmcl.2010.06.082. Epub 2010 Jun 17. [PubMed:20605094 ]
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

6. Carbonic anhydrase 14

General function:: Inorganic ion transport and metabolism
Specific function:: Reversible hydration of carbon dioxide.
Gene Name:: CA14
Uniprot ID:: Q9ULX7
Molecular weight:: 37667.37

References

Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

7. 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 ]

Enzyme Details

8. Aquaporin-1

General function:: Involved in transporter activity
Specific function:: Forms a water-specific channel that provides the plasma membranes of red cells and kidney proximal tubules with high permeability to water, thereby permitting water to move in the direction of an osmotic gradient
Gene Name:: AQP1
Uniprot ID:: P29972
Molecular weight:: 28525.7

References

Xiang Y, Ma B, Li T, Yu HM, Li XJ: Acetazolamide suppresses tumor metastasis and related protein expression in mice bearing Lewis lung carcinoma. Acta Pharmacol Sin. 2002 Aug;23(8):745-51. [PubMed:12147198 ]
Mu SM, Ji XH, Ma B, Yu HM, Li XJ: [Differential protein analysis in rat renal proximal tubule epithelial cells in response to acetazolamide and its relation with the inhibition of AQP1]. Yao Xue Xue Bao. 2003 Mar;38(3):169-72. [PubMed:12830709 ]
Ma B, Xiang Y, Mu SM, Li T, Yu HM, Li XJ: Effects of acetazolamide and anordiol on osmotic water permeability in AQP1-cRNA injected Xenopus oocyte. Acta Pharmacol Sin. 2004 Jan;25(1):90-7. [PubMed:14704128 ]
Oshio K, Song Y, Verkman AS, Manley GT: Aquaporin-1 deletion reduces osmotic water permeability and cerebrospinal fluid production. Acta Neurochir Suppl. 2003;86:525-8. [PubMed:14753499 ]
Xiang Y, Ma B, Li T, Gao JW, Yu HM, Li XJ: Acetazolamide inhibits aquaporin-1 protein expression and angiogenesis. Acta Pharmacol Sin. 2004 Jun;25(6):812-6. [PubMed:15169637 ]

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 Acetazolamide (HMDB0014957)

MOL for HMDB0014957 (Acetazolamide)

3D MOL for HMDB0014957 (Acetazolamide)

3D SDF for HMDB0014957 (Acetazolamide)

3D-SDF for HMDB0014957 (Acetazolamide)

PDB for HMDB0014957 (Acetazolamide)

3D PDB for HMDB0014957 (Acetazolamide)

SMILES for HMDB0014957 (Acetazolamide)

INCHI for HMDB0014957 (Acetazolamide)

Structure for HMDB0014957 (Acetazolamide)

3D Structure for HMDB0014957 (Acetazolamide)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

References

References

References

References

References

References

Transporters

References