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Losartan potassium

Description References
Product Name
Losartan potassium
CAS No.
124750-99-8
Chemical Name
Losartan potassium
Synonyms
MK-95;MK 954;COZAAR;DUP 753;mk-0954;Aradois;l-158086;dupont753;thanolpotassium;DuP-753 potassium
CBNumber
CB1442564
Molecular Formula
C22H23ClKN6O
Formula Weight
462.01
MOL File
124750-99-8.mol
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Losartan potassium Property

Melting point:
263-265°C
storage temp. 
Inert atmosphere,Room Temperature
solubility 
Freely soluble in water and in methanol, slightly soluble in acetonitrile.
form 
powder or crystals
Merck 
14,5583
BRN 
5845770
InChIKey
OXCMYAYHXIHQOA-UHFFFAOYSA-N
CAS DataBase Reference
124750-99-8(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36/37/39
WGK Germany 
3
RTECS 
NI6755100
HS Code 
2933290000
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
61188
Product name
Losartan potassium
Purity
analytical standard
Packaging
100mg
Price
$172
Updated
2021/03/22
Sigma-Aldrich
Product number
Y0001062
Product name
Losartan potassium
Purity
European Pharmacopoeia (EP) Reference Standard
Price
$190
Updated
2021/03/22
Sigma-Aldrich
Product number
1370462
Product name
Losartan potassium
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
150mg
Price
$366
Updated
2021/03/22
TCI Chemical
Product number
L0232
Product name
Losartan Potassium
Purity
>98.0%(HPLC)(T)
Packaging
5g
Price
$144
Updated
2021/03/22
TCI Chemical
Product number
L0232
Product name
Losartan Potassium
Purity
>98.0%(HPLC)(T)
Packaging
25g
Price
$489
Updated
2021/03/22
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Losartan potassium Chemical Properties,Usage,Production

Description

As a angiotensin II receptor antagonist, Losartan Potassium is the potassium salt of losartan with antihypertensive activity, which is mainly used in the therapy of high blood pressure (hypertension) and diabetic nephropathy. It functions by relaxing blood vessels so that blood can flow more easily. It is also effective to help protect the kidneys from damage caused by diabetes and lower the risks of stroke in patients suffering from hypertension and myocardial enlargement. Besides, recent study has suggested that losartan is beneficial to reverse age related dysfunction in maintaining normal blood pressure and cellular energy usage on mitochondria and it can probably be used to treat left ventricular hypertrophy. It may also be used as an alternative agent for the treatment of systolic dysfunction, myocardial infarction, coronary artery disease, and heart failure.

References

https://en.wikipedia.org/wiki/Losartan
https://www.drugbank.ca/drugs/DB00678
https://pubchem.ncbi.nlm.nih.gov/compound/11751549#section=Top
http://www.medicinenet.com/losartan-oral/article.htm

Description

Losartan potassium is the first potent and selective non-peptide angiotensin II (AT II) AT1 receptor antagonist introduced to the market as a once-daily oral antihypertensive. It is efficacious and long lasting in controlling blood pressure in spontaneous hypertensive rats, in patients with essential hypertension in addition to those patients with renal impairment. Since losartan functions by competitive antagonism at the level of receptor, which represents the most direct way of selectively inhibiting the renin-angiotensin system (RAS) independent of the source of AT II, its use has been reported to be free of the coughing side effect exhibited by the ACE inhibitors. In contrast to calcium channel blockers, losartan does not appear to cause ankle edema, headache and tachycardia. It is also reported to be in clinical trials for the treatment of heart failure. Other reports indicate that losartan may have potential efficacy as an anxiolytic, an antiglaucoma agent, in addition to in providing protection against stroke and in preventing the myointimal proliferative response of the vascular wall after coronary angioplasty and surgery.

Chemical Properties

White to Off-White Crystalline Powder

Originator

DuPont Merck (U.S.A.)

Uses

A nonpeptide angiotensin II AT1-receptor antagonist. Antihypertensive.

Uses

antihypertensive, AT1 angiotensin II antagonist

Uses

Coronary vasodilator used in the diagnosis of coronary heart disease (adenosine A2A agonist).

Manufacturing Process

2-Butyl-4-chloro-1-(2'-(tetrazol-5-yl)biphenyl-4-ylmethyl)-1H-imidazole-5- methanolpotassium was synthesized in 5 stages.
1. Methyl 4'-methylbiphenyl-2-carboxylate (44.2 mmol), 0.5 N KOH in methanol (133 mmol), and water (50 mL) were mixed and refluxed under nitrogen. After 5 hours, the solvent was removed in vacuo and water (200 mL) and ethyl acetate (200 mL) added. The aqueous layer was acidified with concentrated hydrochloric acid to a pH of 3 and the layers were separated. The aqueous phase was extracted with ethyl acetate, the organic layers collected, dried (MgSO4) and the solvent removed in vacuo to yield 8.71 g of a 4'-methylbiphenyl-2-carboxylic acid, melting point 140.0-145.0°C.
2. 4'-Methylbiphenyl-2-carboxylic acid (41 mmol) and thionyl chloride (411 mmol) were mixed and refluxed for 2 hours. The excess thionyl chloride was removed in vacuo and the residue was taken up in toluene. The toluene was removed by rotary evaporation. The crude acid chloride was then added slowly to cold (0°C) concentrated NH4OH (50 mL) so that the temperature was kept below 15°C. After 15 minutes of stirring, water (100 mL) was added and solids precipitated. These were collected, washed with water and dried under high vacuum over P2O5 to yield 7.45 g of a white solid, melting point 126.0-128.5°C. The above product amide (35 mmol) and thionyl chloride (353 mmol) were mixed and refluxed for 3 hours. The thionyl chloride was removed using the same procedure as described above. The residue was washed with a little hexane to yield 6.64 g of 4'-methyl-2-cyanobiphenyl, melting point 44.0- 47.0°C.
3. 4'-Methyl-2-cyanobiphenyl (5.59 g) was brominated using benzoyl peroxide as an initiator. The product was recrystallized from ether to yield 4.7 g of 4'- bromomethyl-2-cyanobiphenyl, melting point 114.5-120.0°C.
4. 4'-Bromomethyl-2-cyanobiphenyl (4.6 g) was alkylated onto 2-n-butyl-4- chloro-5-(hydroxymethyl)-imidazole. For separation of the product was used a flash chromatography in 1:1 hexane/ethyl acetate over silica gel. The regioisomeric products yielded 2.53 g of the faster eluting isomer. Recrystallization from acetonitrile yielded 1.57 g of analytically pure 2-n-butyl4-chloro-1-[2'-cyanobiphenyl-4-yl)methyl]-5-(hydroxymethyl)-imidazole, melting point 153.5 -155.5°C.
5. 2-n-Butyl-4-chloro-1-[(2'-cyanobiphenyl-4-yl)-methyl]-5-(hydroxymethyl)- imidazole (10 mmole), sodium azide (10 mmol), and ammonium chloride (30 mmol) were mixed in DMF (150 mL) under N2 at 100°C for 2 days, after which the temperature was raised to 120°C for 6 days. The reaction was cooled and 3 more equivalents each of ammonium chloride and sodium azide were added. The reaction was again heated for 5 days at 120°C. The reaction was cooled, the inorganic salts filtered, and the filtrate solvent removed in vacuo. Water (200 mL) and ethyl acetate (200 mL) were added to the residue and the layers were separated. The aqueous layer was extracted with ethyl acetate, the organic layers were collected, dried (MgSO4) and the solvent removed in vacuo, to yield a dark yellow oil. The product was purified by flash chromatography in 100% ethyl acetate to 100% ethanol over silica gel to yield 5.60 g of a light yellow 2-n-butyl-4-chloro-5-hydroxymethyl-1-[(2'-(1Htetrazol-5-yl)biphenyl-4-yl)methyl]imidazole. Recrystallization from acetonitrile yielded 4.36 g of light yellow crystals which still melted broadly. The crystals were taken up in 100 mL of hot acetonitrile. The solid that did not dissolve was filtered off to yield 1.04 g of product as a light yellow solid, melting point of 2-n-butyl-4-chloro-5-hydroxymethyl-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4- yl)methyl]imidazole 183.5-184.5°C.
2-n-Butyl-4-chloro-5-hydroxymethyl-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4- yl)methyl]imidazole may be converted to potassium salt.

brand name

Cozaar (Merck).

Therapeutic Function

Antihypertensive

Biological Activity

Selective non-peptide angiotensin AT 1 receptor antagonist. Inhibits the contractile effects of angiotensin II on rabbit aorta and jugular vein (pA 2 = 8.27). Orally active antihypertensive agent.

Losartan potassium Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Losartan potassium manufacturers

WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Product
Losartan potassium 124750-99-8
Price
US $0.00/KG
Min. Order
100g
Purity
98%+
Supply Ability
100kg
Release date
2020-11-20
Hebei Lingding Biological Technology Co., Ltd
Product
Losartan potassium 124750-99-8
Price
US $1000.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
9000kg/per week
Release date
2021-09-03
Sinoway Industrial co., ltd.
Product
Losartan Potassium 124750-99-8
Price
US $0.00/KG
Min. Order
2KG
Purity
USP
Supply Ability
20tons
Release date
2021-07-12

124750-99-8, Losartan potassiumRelated Search:


  • 2-BUTYL-4-CHLORO-1-[[2'-(1H-TETRAZOL-5YL)[1,1'-BIPHENYL]-4-YL]METHYL]-1H-IMIDAZOLE-5-METHANOL
  • 2-butyl-4-chloro-1-[[2'-(1h-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1h-imidazole-5-methanol monopotassium salt
  • 2-BUTYL-4-CHLORO-1-[[2'-(1H-TETRAZOLE-5-YL)[1,1'-BIPHENYL]-4-YL]METHYL]-1H-IMIDAZOLE-5-METHANOL, POTASSIUM SALT
  • LOSARTAN MONOPOTASSIUM SALT
  • LOSARTAN POTASSIUM
  • LOSARTAN POTASSIUM SALT
  • MK 954
  • 1h-imidazole-5-methanol,2-butyl-4-chloro-1-((2’-(1h-tetrazol-5-yl)(1,1’-biphe
  • 2-butyl-4-chloro-1-(2’-(tetrazol-5-yl)biphenyl-4-ylmethyl)-1h-imidazole-5-me
  • Losartan Potassium (250 mg)
  • 2-Butyl-4-chloro-1-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]Methyl]-1H-iMidaz
  • Losartan potassiuM API
  • 2-Butyl-4-chloro-1-[[2'-(1H-tetrazol-5-yl)-1,1'-biphenyl-4-yl]methyl]imidazole-5-methanol Potassium Salt
  • Losartan PotassiuM/Losartan K
  • COZAAR
  • DUP 753
  • Losartan PotassiuM (DuP 753)
  • 2-butyl-4-chloro-1-[[2'-(2H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol, potassium salt (1:1)
  • Losartan Potassium (150 mg)
  • potassium (1-((2'-(2H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-butyl-4-chloro-1H-imidazol-5-yl)methanolate
  • potassium (2-butyl-4-chloro-1-{[2'-(2H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazol-5-yl)methanolate
  • potassium [2-butyl-5-chloro-3-[[4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl]met
  • potassium [2-butyl-5-chloro-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]-4-imidazolyl]methanolate
  • potassium [2-butyl-5-chloro-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanolate
  • potassium [2-butyl-5-chloro-3-[4-[2-(2H-tetrazol-5-yl)phenyl]benzyl]imidazol-4-yl]methanolate
  • Losartan potassium Joyce
  • [2-butyl-5-chloro-3-[[4-[2-(1,2,3-triaza-4-azanidacyclopenta-2,5-dien-5-yl)phenyl]phenyl]methyl]-4-imidazolyl]methanol
  • DuP-753 potassium
  • dupont753
  • l-158086
  • mk-0954
  • thanolpotassium
  • 2-butyl-4-chloro-1-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]- 1H-imidazole-5-methanol,monopotassium salt
  • MK-95
  • LOSARTANPOTASSIUM(SUBJECTTOPATENTFREE)
  • 2-Butyl-4-chloro-1-[[2'-(1H-tetrazol-5-yl)[1,1'-
  • Aradois
  • 2-Butyl-4-chloro-1-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanolpotassiumsalt
  • Potassium (2-butyl-4-chloro-1-{[2'-(2H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazol-5-yl)me
  • Potassium chloride sha Tanzania
  • Losartan potassium 124750-99-8
  • Losartan Pottasium
  • Losartan potassium Solution, 100ppm
  • Potassium 2-Butyl-4-chloro-[1-[[2'-(5-tetrazolyl)biphenyl-4-yl]methyl]-5-imidazolyl]methanolate
  • Losartan potassium CRS
  • LosartanPotassium&gt
  • Losartan Potassium RS
  • (1-((2'-(2H-Tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-butyl-4-chloro-1H-imidazol-5-yl)methanol, potassium salt
  • Losartan potassium USP/EP/BP
  • 124750-99-8
  • C22H22CIKN6O
  • C22H23ClKN6O
  • C22H22ClKN6O
  • C22H22CIKN6OK
  • C22H23ClN6OK
  • API
  • Cardiovascular APIs
  • Aromatics