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.
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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
*
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
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
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.
////////////ацетазоламид , أسيتازولاميد [, 乙酰唑胺 , ACETAZOLAMIDE
CC(=O)NC1=NN=C(S1)S(N)(=O)=O
WELSHPOOL, WALES, UNITED KINGDOM
Welshpool is a town in the county of Powys in Wales, in the historic
county of Montgomeryshire. Welshpool is located 4 miles (6 km) from
the Wales–England border. The town is low-lying on the River Severn.
It was initially known as Pool but its name was changed to Welshpool in
1835 to distinguish it from the town of Poole in England. It has a
population of 6,269 (United Kingdom Census 2001). Some things to see
in Welshpool are the many Georgian architecture and the Powis Castle.
The local economy is primarily based upon agriculture and local industry.
The Smithfield Livestock Market is the largest one-day sheep market in
Europe, whilst the town's industrial estates are home to numerous
different types of small industry. Due to the town's small size and
population, the attraction of high street stores is limited, meaning
many of the residents are forced to shop in neighboring towns.
February is normally the coldest month with average temperatures between
34 and 46 degrees Fahrenheit. July is normally the warmest month with
average temperatures between 52 and 71 degrees F. I don't have a
record of rainfall or snowfall.
I hope you enjoy seeing this area, Welshpool, Wales.
~Marsha~
ALONG THE MONTGOMERY CANAL
NARROWBOAT ON CANAL
THE ROAD IN WELSHPOOL
DOWNTOWN WELSHPOOL
TOWN HALL
WELSHPOOL & LLANFAIR RAILROAD
MOAT FARM BED & BREAKFAST
THE ROYAL OAK HOTEL
POWIS ARMS HOTEL
HOLIDAY COTTAGES
THE OLD STATION
ST. URC CHURCH
WELSHPOOL AIRPORT
SCENERY
LAKE VYMWY
WELSHPOOL MOTORWAYS
AIR AMBULANCE EUROCOPTER
LLANERCHYDOL HALL
****************************************************************
POWIS CASTLE
INSIDE THE CASTLE
CASTLE GROUNDS
COTTAGE ON THE GROUNDS
****************************************************************
HOMES IN THE AREA
OLD PHOTOS
////////
Welshpool is a town in the county of Powys in Wales, in the historic
county of Montgomeryshire. Welshpool is located 4 miles (6 km) from
the Wales–England border. The town is low-lying on the River Severn.
It was initially known as Pool but its name was changed to Welshpool in
1835 to distinguish it from the town of Poole in England. It has a
population of 6,269 (United Kingdom Census 2001). Some things to see
in Welshpool are the many Georgian architecture and the Powis Castle.
The local economy is primarily based upon agriculture and local industry.
The Smithfield Livestock Market is the largest one-day sheep market in
Europe, whilst the town's industrial estates are home to numerous
different types of small industry. Due to the town's small size and
population, the attraction of high street stores is limited, meaning
many of the residents are forced to shop in neighboring towns.
February is normally the coldest month with average temperatures between
34 and 46 degrees Fahrenheit. July is normally the warmest month with
average temperatures between 52 and 71 degrees F. I don't have a
record of rainfall or snowfall.
I hope you enjoy seeing this area, Welshpool, Wales.
~Marsha~
ALONG THE MONTGOMERY CANAL
NARROWBOAT ON CANAL
THE ROAD IN WELSHPOOL
DOWNTOWN WELSHPOOL
TOWN HALL
WELSHPOOL & LLANFAIR RAILROAD
MOAT FARM BED & BREAKFAST
THE ROYAL OAK HOTEL
POWIS ARMS HOTEL
HOLIDAY COTTAGES
THE OLD STATION
ST. URC CHURCH
WELSHPOOL AIRPORT
SCENERY
LAKE VYMWY
WELSHPOOL MOTORWAYS
AIR AMBULANCE EUROCOPTER
LLANERCHYDOL HALL
****************************************************************
POWIS CASTLE
INSIDE THE CASTLE
CASTLE GROUNDS
COTTAGE ON THE GROUNDS
****************************************************************
HOMES IN THE AREA
OLD PHOTOS
