Xipamide Struktur

Xipamid

Bezeichnung:Xipamid

CAS-Nr14293-44-8

Englisch Name:Xipamide

CBNumberCB7875012

SummenformelC15H15ClN2O4S

Molgewicht354.81

MOL-Datei14293-44-8.mol

Synonyma

Xipamid

Xipamid physikalisch-chemischer Eigenschaften

Schmelzpunkt	255-256 °C
Dichte	1.2743 (rough estimate)
Brechungsindex	1.6100 (estimate)
storage temp.	Inert atmosphere,Store in freezer, under -20°C
Löslichkeit	DMSO: soluble20mg/mL, clear
pka	pKa 4.75±0.04(0.4% MeOH in H2O) (Uncertain)
Aggregatzustand	powder
Farbe	white to beige
Wasserlöslichkeit	58mg/L(25 ºC)
CAS Datenbank	14293-44-8(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26
WGK Germany	3
HS Code	2935909099

Gefahreninformationscode (GHS)

Xipamide Chemische Eigenschaften,Einsatz,Produktion Methoden

Chemische Eigenschaften
Off-White Solid
Originator
Aquaphor,Beiersdorf,W. Germany ,1971
Verwenden
Xipamide is a diuretic and antihypertensive agent.
Definition
ChEBI: Xipamide is a member of benzamides.
Manufacturing Process
The 4-chloro-5-sulfamyl salicylic acid used as starting point was prepared in the following way:
(a) 4-Chloro-5-Chlorosulfonyl Salicylic Acid: 100 grams 4-chloro salicylic acid was added portionwise with stirring at about -5°C to 275 ml chlorosulfonic acid. The temperature was not allowed to rise above +3°C. At the end of the addition, the solution formed was stirred for 1 hour in an ice bath, then for 1 hour at 20°C and finally for 2 1/2 hours at 80°C oil bath temperature. Then the dark brown solution, after ensuing slow cooling with vigorous stirring, was poured onto ice; the precipitate was vacuum filtered, washed with water and dried. After recrystallization from toluene the compound formed had a melting point of 181° to 183°C.
(b) 4-Chloro-5-Sulfamyl Salicylic Acid: 40 grams 4-chloro-5-chlorosulfonyl salicylic acid obtained from (a) was added portionwise with stirring to 250 ml liquid ammonia. This was allowed to stand for 2 hours, then the precipitate was vacuum filtered and dissolved in 500 ml water. The solution was filtered and the filtrate was treated with 2 N hydrochloric acid until no more precipitation occurred. The 4-chloro-5-sulfamyl salicylic acid obtained as the precipitate was filtered off and finally recrystallized from water, MP 258° to 260°C.
5.0 grams 4-chloro-5-sulfamyl salicylic acid was suspended in 100 ml water- free chlorobenzene and then 2.44 grams of 2,6-dimethylaniline and 0.9 ml phosphorus trichloride were added to the suspension in turn. The reaction mixture was heated under reflux for 5 hours. After cooling, the chlorobenzene was separated from the precipitate by decantation. The latter was finally collected on a filter and washed, first with chlorobenzene and, after drying, with 2 N hydrochloric acid and water. The compound obtained by recrystallization from methanol had a melting point of 256°C.
Therapeutic Function
Diuretic, Antihypertensive
Biologische Aktivität
Xipamide is a sulfonamide diuretic th at blocks sodium reabsorption in the distal tubules of the kidney, resulting in increased urine output. Xiopamide also blocks the cystic fibrosis transmembrane conductance regulator (CFTR) chloride channel.
Clinical Use
Thiazide diuretic:
Hypertension
Oedema
Arzneimittelwechselwirkung
Potentially hazardous interactions with other drugs
Analgesics: increased risk of nephrotoxicity with NSAIDs; antagonism of diuretic effect.
Anti-arrhythmics: hypokalaemia leads to increased cardiac toxicity; effects of lidocaine and mexiletine antagonised.
Antibacterials: avoid administration with lymecycline.
Antidepressants: increased risk of hypokalaemia with reboxetine; enhanced hypotensive effect with MAOIs; increased risk of postural hypotension with tricyclics.
Antiepileptics: increased risk of hyponatraemia with carbamazepine.
Antifungals: increased risk of hypokalaemia with amphotericin.
Antihypertensives: enhanced hypotensive effect; increased risk of first dose hypotension with postsynaptic alpha-blockers like prazosin; hypokalaemia increases risk of ventricular arrhythmias with sotalol.
Antipsychotics: hypokalaemia increases risk of ventricular arrhythmias with amisulpride; enhanced hypotensive effect with phenothiazines; hypokalaemia increases risk of ventricular arrhythmias with pimozide - avoid concomitant use.
Atomoxetine: hypokalaemia increases risk of ventricular arrhythmias.
Cardiac glycosides: increased toxicity if hypokalaemia occurs.
Ciclosporin: increased risk of nephrotoxicity and possibly hypomagnesaemia.
Cytotoxics: increased risk of ventricular arrhythmias due to hypokalaemia with arsenic trioxide; increased risk of nephrotoxicity and ototoxicity with platinum compounds.
Lithium excretion reduced (increased toxicity).
Stoffwechsel
Xipamide is excreted in the urine, partly unchanged and partly in the form of the glucuronide metabolite.
In patients with renal impairment excretion in the bile becomes more prominent.

Xipamide Upstream-Materialien And Downstream Produkte

Xipamid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

14293-44-8, Xipamide Verwandte Suche:

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