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Merck

1005004

USP

Acetazolamide

United States Pharmacopeia (USP) Reference Standard

Synonym(s):

5-Acetamido-1,3,4-thiadiazole-2-sulfonamide, N-(5-Sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide, N-(5-[Aminosulfonyl]-1,3,4-thiadiazol-2-yl)acetamide

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About This Item

Empirical Formula (Hill Notation):
C4H6N4O3S2
CAS Number:
59-66-5
Molecular Weight:
222.25
NACRES:
NA.24
PubChem Substance ID:
329748132
UNSPSC Code:
41116107
MDL number:
MFCD00003105

Key Documents

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Product Name

Acetazolamide, United States Pharmacopeia (USP) Reference Standard

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)

SMILES string

CC(=O)Nc1nnc(s1)S(N)(=O)=O

InChI key

BZKPWHYZMXOIDC-UHFFFAOYSA-N

grade

pharmaceutical primary standard

API family

acetazolamide

manufacturer/tradename

USP

application(s)

pharmaceutical (small molecule)

format

neat

Gene Information

human ... CA1(759), CA12(771), CA2(760), CA4(762)

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Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Application

Acetazolamide USP reference standard, intended for use in specified quality tests and assays as specified in the USP compendia. Also, for use with USP monographs such as:
  • Acetazolamide Compounded Oral Suspension
  • Acetazolamide Extended-Release Capsules
  • Acetazolamide for Injection
  • Acetazolamide Tablets
Carbonic anhydrase inhibitor; increases cerebral blood flow.

Biochem/physiol Actions

Inhibits water permeability of membranes by interacting with aquaporins

General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Other Notes

Sales restrictions may apply.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Substances Subject to be Indicated Names

ishl_indicated

Substances Subject to be Notified Names

ishl_notified

1005004-2G:

jan

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Certificates of Analysis (COA)

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W G Reiss et al.
The Annals of pharmacotherapy, 30(5), 514-519 (1996-05-01)
To summarize the pharmacology, pharmacokinetics, efficacy, and safety of acetazolamide and to evaluate its therapeutic role in patients with epilepsy. A computerized search of the MEDLINE (OVID) database (1966-1994) was used to identify publications regarding acetazolamide. The MEDLINE search was
Sergio Caravita et al.
Chest, 147(1), 120-131 (2014-09-05)
Nocturnal periodic breathing occurs more frequently in men than in women with various clinical and pathophysiologic conditions. The mechanisms accounting for this sex-related difference are not completely understood. Acetazolamide effectively counteracts nocturnal periodic breathing, but it has been investigated almost
Sinan Bilginer et al.
Journal of enzyme inhibition and medicinal chemistry, 29(4), 495-499 (2013-07-03)
A series of phenols incorporating tertiary amine and trans-pyridylethenyl-carbonyl moieties were assayed as inhibitors of the β-carbonic anhydrase (CA, EC 4.2.1.1) from Saccharomyces cerevisiae, ScCA. One of these compounds was a low nanomolar ScCA inhibitor, whereas the remaining ones inhibited
Neil D Ritchie et al.
Journal of travel medicine, 19(5), 298-307 (2012-09-05)
Acetazolamide has been reported to be effective in the prevention of acute mountain sickness (AMS). Our aim was to conduct a systematic review of randomized, placebo-controlled trials of acetazolamide in the prevention of AMS. Studies were identified by searching the
A S Vagal et al.
AJNR. American journal of neuroradiology, 30(5), 876-884 (2009-02-28)
The acetazolamide (ACZ) challenge test is a useful clinical tool and a reliable predictor of critically reduced perfusion. In patients with chronic steno-occlusive disease, the ability to maintain normal cerebral blood flow by reducing vascular resistance secondary to autoregulatory vasodilation
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