Acetazolamide
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MedKoo CAT#: 329408

CAS#: 59-66-5

Description: Acetazolamide, also known as Diamox and PIM-005, is a carbonic anhydrase inhibitor that is sometimes effective against absence seizures. Acetazolamide 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. Acetazolamide's 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.


Chemical Structure

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Acetazolamide
CAS# 59-66-5

Theoretical Analysis

MedKoo Cat#: 329408
Name: Acetazolamide
CAS#: 59-66-5
Chemical Formula: C4H6N4O3S2
Exact Mass: 221.9881
Molecular Weight: 222.237
Elemental Analysis: C, 21.62; H, 2.72; N, 25.21; O, 21.60; S, 28.85

Price and Availability

Size Price Availability Quantity
10.0g USD 150.0 2 Weeks
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Synonym: Acetazolamide; Diamox; Diluran; Glaupax; Defiltran; PIM005; PIM 005; PIM-005

IUPAC/Chemical Name: N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide

InChi Key: BZKPWHYZMXOIDC-UHFFFAOYSA-N

InChi Code: 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 Code: O=S(C1=NN=C(NC(C)=O)S1)(N)=O

Appearance: Light yellow to with crystalline solid.

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 222.237 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Wang K, Smith ZM, Buxton RB, Swenson ER, Dubowitz DJ. Acetazolamide during acute hypoxia improves tissue oxygenation in the human brain. J Appl Physiol (1985). 2015 Dec 15;119(12):1494-500. doi: 10.1152/japplphysiol.00117.2015. PubMed PMID: 26472861; PubMed Central PMCID: PMC4683345.

2: Kattah JC, Pula JH, Mejico LJ, McDermott MP, Kupersmith MJ, Wall M. CSF pressure, papilledema grade, and response to acetazolamide in the Idiopathic Intracranial Hypertension Treatment Trial. J Neurol. 2015 Oct;262(10):2271-4. doi: 10.1007/s00415-015-7838-9. PubMed PMID: 26159101.

3: Faisy C, Meziani F, Planquette B, Clavel M, Gacouin A, Bornstain C, Schneider F, Duguet A, Gibot S, Lerolle N, Ricard JD, Sanchez O, Djibre M, Ricome JL, Rabbat A, Heming N, Urien S, Esvan M, Katsahian S; DIABOLO Investigators.. Effect of Acetazolamide vs Placebo on Duration of Invasive Mechanical Ventilation Among Patients With Chronic Obstructive Pulmonary Disease: A Randomized Clinical Trial. JAMA. 2016 Feb 2;315(5):480-8. doi: 10.1001/jama.2016.0019. PubMed PMID: 26836730.

4: Harrison MF, Anderson PJ, Johnson JB, Richert M, Miller AD, Johnson BD. Acute Mountain Sickness Symptom Severity at the South Pole: The Influence of Self-Selected Prophylaxis with Acetazolamide. PLoS One. 2016 Feb 5;11(2):e0148206. doi: 10.1371/journal.pone.0148206. PubMed PMID: 26848757; PubMed Central PMCID: PMC4744068.

5: Leibrock CB, Alesutan I, Voelkl J, Michael D, Castor T, Kohlhofer U, Quintanilla-Martinez L, Kübler L, Mannheim JG, Pichler BJ, Rosenblatt KP, Kuro-o M, Lang F. Acetazolamide sensitive tissue calcification and aging of klotho-hypomorphic mice. J Mol Med (Berl). 2016 Jan;94(1):95-106. doi: 10.1007/s00109-015-1331-x. PubMed PMID: 26307633.

6: Faull OK, Robertson J, Thomas O, Bradwell AR, Antoniades CA, Pattinson KT; Birmingham Medical Research Expeditionary Society.. The effect of acetazolamide on saccadic latency at 3459 meters. Wilderness Environ Med. 2015 Mar;26(1):72-7. doi: 10.1016/j.wem.2014.08.017. PubMed PMID: 25712298.

7: Zingerman B, Herman-Edelstein M, Erman A, Bar Sheshet Itach S, Ori Y, Rozen-Zvi B, Gafter U, Chagnac A. Effect of Acetazolamide on Obesity-Induced Glomerular Hyperfiltration: A Randomized Controlled Trial. PLoS One. 2015 Sep 14;10(9):e0137163. doi: 10.1371/journal.pone.0137163. PubMed PMID: 26367377; PubMed Central PMCID: PMC4569381.

8: Kolecka M, Ondreka N, Moritz A, Kramer M, Schmidt MJ. Effect of acetazolamide and subsequent ventriculo-peritoneal shunting on clinical signs and ventricular volumes in dogs with internal hydrocephalus. Acta Vet Scand. 2015 Sep 4;57:49. doi: 10.1186/s13028-015-0137-8. PubMed PMID: 26337283; PubMed Central PMCID: PMC4558722.

9: Zhang L, Reyes R, Lee W, Chen CL, Chan L, Sujirakul T, Chang S, Tsang SH. Rapid resolution of retinoschisis with acetazolamide. Doc Ophthalmol. 2015 Aug;131(1):63-70. doi: 10.1007/s10633-015-9496-8. PubMed PMID: 25796216; PubMed Central PMCID: PMC4504776.

10: Hirano Y, Takuwa H, Yoshida E, Nishikido F, Nakajima Y, Wakizaka H, Yamaya T. Washout rate in rat brain irradiated by a (11)C beam after acetazolamide loading using a small single-ring OpenPET prototype. Phys Med Biol. 2016 Mar 7;61(5):1875-87. doi: 10.1088/0031-9155/61/5/1875. PubMed PMID: 26863938.

11: Arngrim N, Schytz HW, Asghar MS, Amin FM, Hougaard A, Larsen VA, de Koning PJ, Larsson HB, Olesen J, Ashina M. Association of acetazolamide infusion with headache and cranial artery dilation in healthy volunteers. Pain. 2014 Aug;155(8):1649-58. doi: 10.1016/j.pain.2014.05.019. PubMed PMID: 24861583.

12: Ulrich S, Keusch S, Hildenbrand FF, Lo Cascio C, Huber LC, Tanner FC, Speich R, Bloch KE. Effect of nocturnal oxygen and acetazolamide on exercise performance in patients with pre-capillary pulmonary hypertension and sleep-disturbed breathing: randomized, double-blind, cross-over trial. Eur Heart J. 2015 Mar 7;36(10):615-23. doi: 10.1093/eurheartj/eht540. PubMed PMID: 24366914.

13: Finer G, Price HE, Shore RM, White KE, Langman CB. Hyperphosphatemic familial tumoral calcinosis: response to acetazolamide and postulated mechanisms. Am J Med Genet A. 2014 Jun;164A(6):1545-9. doi: 10.1002/ajmg.a.36476. PubMed PMID: 24668887.

14: Bar A, Cies J, Stapleton K, Tauber D, Chopra A, Shore PM. Acetazolamide therapy for metabolic alkalosis in critically ill pediatric patients. Pediatr Crit Care Med. 2015 Feb;16(2):e34-40. doi: 10.1097/PCC.0000000000000313. PubMed PMID: 25647140.

15: Caravita S, Faini A, Lombardi C, Valentini M, Gregorini F, Rossi J, Meriggi P, Di Rienzo M, Bilo G, Agostoni P, Parati G. Sex and acetazolamide effects on chemoreflex and periodic breathing during sleep at altitude. Chest. 2015 Jan;147(1):120-31. doi: 10.1378/chest.14-0317. PubMed PMID: 25188815.