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ацетазоламид , أسيتازولاميد [, 乙酰唑胺 , ACETAZOLAMIDE

GENERIC

Aug 022016

ChemSpider 2D Image | acetazolamide | C4H6N4O3S2

ACETAZOLAMIDE

ацетазоламид , أسيتازولاميد [, 乙酰唑胺 ,

CAS 59-66-5

Acetamide, N-(5-(aminosulfonyl)-1,3,4-thiadiazol-2-yl)-

MW 222.245,MF C₄H₆N₄O₃S₂

Title: Acetazolamide

CAS Registry Number: 59-66-5

CAS Name: N-[5-(Aminosulfonyl)-1,3,4-thiadiazol-2-yl]acetamide

Additional Names: 5-acetamido-1,3,4-thiadiazole-2-sulfonamide; 2-acetylamino-1,3,4-thiadiazole-5-sulfonamide

Manufacturers’ Codes: 6063

Trademarks: Acetamox (Tobishi-Santen); Atenezol (Tsuruhara); Défiltran (Gallier); Diamox (Barr); Didoc (Sawai); Diuriwas (IFI); Donmox (Horita); Edemox (Wassermann); Fonurit (Chinoin); Glaupax (Erco)

Molecular Formula: C4H6N4O3S2

Molecular Weight: 222.25

Percent Composition: C 21.62%, H 2.72%, N 25.21%, O 21.60%, S 28.85%

Literature References: Carbonic anhydrase inhibitor. Prepn: R. O. Roblin, J. W. Clapp, J. Am. Chem. Soc. 72, 4890 (1950); J. W. Clapp, R. O. Roblin, US 2554816 (1951 to Am. Cyanamid). HPLC determn in pharmaceuticals: Z. S. Gomaa, Biomed. Chromatogr. 7, 134 (1993). Effect on retinal circulation: S. M. B. Rassam et al., Eye 7, 697 (1993). Clinical trial in postoperative elevation of intraocular pressure: I. D. Ladas et al., Br. J. Ophthalmol. 77, 136 (1993). Comprehensive description: J. Parasrampuria, Anal. Profiles Drug Subs. Excip. 22, 1-32 (1993). Review of efficacy in acute mountain sickness: L. D. Ried et al.,J. Wilderness Med. 5, 34-48 (1994).

Properties: Crystals from water, mp 258-259° (effervescence). Weak acid. pKa 7.2. Sparingly sol in cold water. Slightly sol in alcohol, acetone. Practically insol in carbon tetrachloride, chloroform, ether. Soly (mg/ml): polyethylene glycol-400 87.81; propylene glycol 7.44; ethanol 3.93; glycerin 3.65; water 0.72.

Melting point: mp 258-259° (effervescence)

pKa: pKa 7.2

Derivative Type: Sodium salt

CAS Registry Number: 1424-27-7

Trademarks: Vetamox (Am. Cyanamid)

Therap-Cat: Antiglaucoma; diuretic; in treatment of acute mountain sickness.

Therap-Cat-Vet: Diuretic.

Keywords: Antiglaucoma; Carbonic Anhydrase Inhibitor; Diuretic; Sulfonamide Derivatives.

Starting reaction occurs in-between hydrazine hydrate and ammonium thiocyanate that produces 1, 2-bis (thiocarbamoyl) hydrazine which on further treatment with phosgene undergoesrearrangements, particularly molecular rearrangement through loss of ammonia to form 5-amino-2-mercapto-1, 3, 4-thiadiazole. Upon acylation of 5-amino-2-mercapto-1, 3, 4-thiadiazole gives a corresponding amide which on oxidation with aqueous chlorine affords the 2-sulphonyl chloride. The final step essentially consists of amidation by treatment with ammonia.

1H NMR

Paper

¹⁴N NQR, ¹H NMR and DFT/QTAIM study of hydrogen bonding and polymorphism in selected solid 1,3,4-thiadiazole derivatives

Janez Seliger,*^a^b Veselko Žagar^a and Jolanta N. Latosińska^c

Corresponding authors

^a»Jozef Stefan« Institute, Jamova 39, 1000 Ljubljana, Slovenia
E-mail: janez.seliger@fmf.uni-lj.si
Fax: +386 1 2517281
Tel: +386 1 4766576

^bFaculty of Mathematics and Physics, University of Ljubljana, Jadranska 19, 1000 Ljubljana, Slovenia

^cFaculty of Physics, Adam Mickiewicz University, Umultowska 85, 61-614 Poznań, Poland

Phys. Chem. Chem. Phys., 2010,12, 13007-13019

DOI: 10.1039/C0CP00195C, http://pubs.rsc.org/en/content/articlelanding/2010/cp/c0cp00195c#!divAbstract

Graphical abstract: 14N NQR, 1H NMR and DFT/QTAIM study of hydrogen bonding and polymorphism in selected solid 1,3,4-thiadiazole derivatives

The 1,3,4-thiadiazole derivatives (2-amino-1,3,4-thiadiazole, acetazolamide, sulfamethizole) have been studied experimentally in the solid state by ¹H–¹⁴N NQDR spectroscopy and theoretically by Density Functional Theory (DFT). The specific pattern of the intra and intermolecular interactions in 1,3,4-thiadiazole derivatives is described within the QTAIM (Quantum Theory of Atoms in Molecules)/DFT formalism. The results obtained in this work suggest that considerable differences in the NQR parameters permit differentiation even between specific pure association polymorphic forms and indicate that the stronger hydrogen bonds are accompanied by the larger η and smaller ν₋ and e²Qq/h values. The degree of π-electron delocalization within the 1,3,4-thiadiazole ring and hydrogen bonds is a result of the interplay between the substituents and can be easily observed as a change in NQR parameters at N atoms. In the absence of X-ray data NQR parameters can clarify the details of crystallographic structure revealing information on intermolecular interactions.

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