ContaminantDB: Acetazolamide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 03:36:40 UTC

Update Date

2016-11-09 01:15:25 UTC

Accession Number

CHEM016545

Identification

Common Name

Acetazolamide

Class

Small Molecule

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)

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

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 Mass

222.245 g/mol

Monoisotopic Mass

221.988 g/mol

CAS Registry Number

59-66-5

IUPAC Name

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

Traditional Name

acetazolamide

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted 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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00fu-3900000000-d066d2601c8f3d625916	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00e9-9070000000-e2f68ded4939412340f7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-001i-9020000000-59775cde1cab229764b9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-001i-9000000000-1ee1fd41bb44b523dd8e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-001i-9000000000-de6c64393f3dc86c15b1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-001i-9000000000-7158c10cba32f3b3896b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-06si-9000000000-32cc006b3850024fd5b7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00e9-0890000000-f407810fc44461e62ecb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-0920000000-6dd62d0ae588814e0cf2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-0900000000-6b6d74d2f34efd5f876a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-1900000000-05fedd43edecd53593c2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-5900000000-76456c439130c5477d45	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00e9-9300000000-5ca7214eb79224d3dc21	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-00di-9100000000-5c1fd2ab9115264ac80e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-00e9-9600000000-0f3f02e34ccd222b9945	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-001i-9020000000-4a4eee8592c5e2c479a6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-05gi-9050000000-60e5a530176c676d7bb7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-053r-9010000000-6b286dca2a293b7acdad	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-001i-9000000000-1eacda33d690a3ee19dd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-001i-3900000000-af42c297c411f1e9dfa6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0090000000-b9d984e83e00c2e23943	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01x0-1950000000-c5bb42824cbdfdaae48d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ufr-2890000000-5f098f8e1576ee3ffaa7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05fu-7890000000-3e47220ae52b55be57f4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-9400000000-78f160649efa3b627e2c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9300000000-6ecab458fac9db3ee404	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00819

HMDB ID

HMDB0014957

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Acetazolamide (CHEM016545)

Structure for CHEM016545: Acetazolamide