- Xipamide
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- $1.00 / 1KG
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2020-02-01
- CAS:14293-44-8
- Min. Order: 1KG
- Purity: Min98% HPLC
- Supply Ability: g/kg/ton
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| | Xipamide Basic information |
| | Xipamide Chemical Properties |
| Melting point | 255-256 °C | | density | 1.2743 (rough estimate) | | refractive index | 1.6100 (estimate) | | storage temp. | Inert atmosphere,Store in freezer, under -20°C | | solubility | DMSO: soluble20mg/mL, clear | | pka | pKa 4.75±0.04(0.4% MeOH
in H2O) (Uncertain) | | form | powder | | color | white to beige | | Water Solubility | 58mg/L(25 ºC) | | CAS DataBase Reference | 14293-44-8(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26 | | WGK Germany | 3 | | HS Code | 2935909099 |
| | Xipamide Usage And Synthesis |
| Chemical Properties | Off-White Solid | | Originator | Aquaphor,Beiersdorf,W. Germany ,1971 | | Uses | 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 | | Clinical Use | Thiazide diuretic:
Hypertension
Oedema | | Drug interactions | 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). | | Metabolism | 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 Preparation Products And Raw materials |
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