| Identification | More | [Name]
Xipamide | [CAS]
14293-44-8 | [Synonyms]
Xipamide
XIPAMIDE (IN HOUSE)
4-Chloro-5-sulfamoyl-2',6'-salicyloxylidide
5-(Aminosulfonyl)-4-chloro-N-(2,6-dimethylphenyl)-2-hydroxybenzamide
Benzamide,5-(aminosulfonyl)-4-chloro-N-(2,6-dimethylphenyl)-2-hydroxy-
4-Chloro-2-hydroxy-N-(2,6-dimethylphenyl)-5-sulfamoylbenzamide
Aquaphor(diuretic)
Be-1293
Bei-1293
MJF-10938 | [EINECS(EC#)]
238-216-4 | [Molecular Formula]
C15H15ClN2O4S | [MDL Number]
MFCD00865927 | [Molecular Weight]
354.809 | [MOL File]
14293-44-8.mol |
| Chemical Properties | Back Directory | [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 | [form ]
powder | [pka]
pKa 4.75±0.04(0.4% MeOH
in H2O) (Uncertain) | [color ]
white to beige | [Water Solubility ]
58mg/L(25 ºC) | [InChI]
1S/C15H15ClN2O4S/c1-8-4-3-5-9(2)14(8)18-15(20)10-6-13(23(17,21)22)11(16)7-12(10)19/h3-7,19H,1-2H3,(H,18,20)(H2,17,21,22) | [InChIKey]
MTZBBNMLMNBNJL-UHFFFAOYSA-N | [SMILES]
[S](=O)(=O)(N)c1c(cc(c(c1)C(=O)Nc2c(cccc2C)C)O)Cl | [CAS DataBase Reference]
14293-44-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
36/37/38 | [Safety Statements ]
26 | [WGK Germany ]
3 | [HS Code ]
2935909099 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [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 | [Biological Activity]
Xipamide is a sulfonamide diuretic th at blocks sodium reabsorption in the distal tubules of the kidneyresulting in increased urine output. Xiopamide also blocks the cystic fibrosis transmembrane conductance regulator (CFTR) chloride channel. | [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. |
|
| Company Name: |
J & K SCIENTIFIC LTD.
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18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
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Dishman Group
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021-67121166-834 |
| Website: |
www.dishman.net.cn |
| Company Name: |
Finetech Industry Limited
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+86-27-8746-5837 +86-18627785180 |
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https://www.finetechnology-ind.com/ |
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