ChemicalBook >> CAS DataBase List >>Losartan

Losartan

CAS No.
114798-26-4
Chemical Name:
Losartan
Synonyms
LOS;dup89;LOSARTAN;Compound 89;Losartan(base);Losartan (DUP 89);nyl)-4-yl)methyl)-;Losartan (DuP-753);Losartan USP/EP/BP;LosartanC22H23C1N60
CBNumber:
CB8120081
Molecular Formula:
C22H23ClN6O
Molecular Weight:
422.91
MDL Number:
MFCD00865831
MOL File:
114798-26-4.mol
MSDS File:
SDS
Last updated:2024-11-09 19:38:33

Losartan Properties

Melting point 183-184 C
Boiling point 682.0±65.0 °C(Predicted)
Density 1.35±0.1 g/cm3(Predicted)
vapor pressure 0.002Pa at 20℃
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
solubility DMSO (Slightly), Methanol (Slightly)
form Solid
pka 5-6(at 25℃)
color White to Off-White
Water Solubility 4.8mg/L at 20℃
LogP 1.1 at 20℃
CAS DataBase Reference 114798-26-4(CAS DataBase Reference)
FDA UNII JMS50MPO89
ATC code C09CA01
EPA Substance Registry System 1H-Imidazole-5-methanol, 2-butyl-4-chloro-1-[[2'-(2H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]- (114798-26-4)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS08
Signal word  Danger
Hazard statements  H317-H360FD-H362
Precautionary statements  P202-P260-P263-P280-P302+P352-P308+P313
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36

Losartan price More Price(22)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
TRC L470470 Losartan 114798-26-4 500mg $385 2021-12-16 Buy
Biorbyt Ltd orb134724 Losartan >99% 114798-26-4 1g $606.9 2021-12-16 Buy
Medical Isotopes, Inc. D34052 Losartan-d6HCl 114798-26-4 5mg $1500 2021-12-16 Buy
ChemScene CS-2116 Losartan 99.55% 114798-26-4 500mg $50 2021-12-16 Buy
Biosynth Carbosynth BL164640 Losartan 114798-26-4 100mg $50 2021-12-16 Buy
Product number Packaging Price Buy
L470470 500mg $385 Buy
orb134724 1g $606.9 Buy
D34052 5mg $1500 Buy
CS-2116 500mg $50 Buy
BL164640 100mg $50 Buy

Losartan Chemical Properties,Uses,Production

Originator

Alsartan, Aristo Pharmaceutical Ltd., India

Uses

Losartan is a nonpeptide angiotensin II AT1-receptor antagonist. Antihypertensive.

Uses

antihypertensive;antagonist of angiotensin type 1

Definition

ChEBI: A biphenylyltetrazole where a 1,1'-biphenyl group is attached at the 5-position and has an additional trisubstituted imidazol-1-ylmethyl group at the 4'-position

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

General Description

Losartan, 2-butyl-4-chloro-1-[p-(o-1H-tetrazol-5-yl-phenyl)benzyl]imidazole-5-methanol monopotassiumsalt (Cozarr), was the first nonpeptide imidazole to beintroduced as an orally active angiotensin II antagonist withhigh specificity for AT1. When administered to patients, itundergoes extensive first-pass metabolism, with the 5-methanol being oxidized to a carboxylic acid. This metabolismis mediated by CYP 2C9 and 3A4 isozymes. The 5-methanol metabolite is approximately 15 times more potentthan the parent hydroxyl compound. Because the parent hydroxylcompound has affinity for the AT1 receptor, strictlyspeaking, it is not a prodrug.

Flammability and Explosibility

Non flammable

Global( 280)Suppliers
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View Lastest Price from Losartan manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Losartan pictures 2024-11-09 Losartan
114798-26-4
US $50.00 / g 99.79% 10g TargetMol Chemicals Inc.
Losartan pictures 2024-11-08 Losartan
114798-26-4
US $50.00 / g 99.79% 10g TargetMol Chemicals Inc.
Losartan pictures 2024-11-08 Losartan
114798-26-4
US $0.00-0.00 / Kg/Bag 1Kg/Bag 99% up, High Density 20 tons Sinoway Industrial co., ltd.
  • Losartan pictures
  • Losartan
    114798-26-4
  • US $50.00 / g
  • 99.79%
  • TargetMol Chemicals Inc.
  • Losartan pictures
  • Losartan
    114798-26-4
  • US $50.00 / g
  • 99.79%
  • TargetMol Chemicals Inc.
  • Losartan pictures
  • Losartan
    114798-26-4
  • US $0.00-0.00 / Kg/Bag
  • 99% up, High Density
  • Sinoway Industrial co., ltd.

Losartan Spectrum

2-Butyl-4-chloro-5-(hydroxymethyl)-1-[(2'-(1H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole Compound 89 2-n-butyl-4-chloro-5-hydroxyMethyl-1-[(2'-(1H-tetrazole-5-yl)biph 2-Butyl-4-chloro-1-[[2'-(2H-tetrazol-5-yl)-biphenyl-4-yl]methyl]-1H-imidazol-5-methanol (2-butyl-4-chloro-1-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazol-5-yl)methanol dup89 nyl)-4-yl)methyl)- 2-butyl-4-chloro-1-[p-(o-1h-tetrazol-5-ylphenyl)benzyl]imidazole-5- methanol LOSARTAN LosartanC22H23C1N60 1h-imidazole-5-methanol, 2-butyl-4-chloro-1-((2'-(1h-tetrazol-5-yl)(1,1'- biphenyl)-4-yl)methyl)- (1-((2-(1H-TETRAZOL-5-YL)BIPHENYL-4-YL)METHYL)-2-BUTYL-4-CHLORO-1H-IMIDAZOL-5-YL)METHANOL (LOSARTAN) 2-Butyl-4-chloro-1-[[2’-(1H-tetrazol-5-y1)[1,1'-biphenyl]’4’y1]methyl]-1H-imidazole-5-methanol 2-Butyl-3-[[2'-(2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl]methyl]-5-chloro-3H-imidazole-4-methanol (2-BUTYL-4-CHLORO-1-{[2'-(1H-TETRAZOL-5-YL)-4-BIPHENYLYL]METHYL}-1H-IMIDAZOL-5-YL)METHANOL Losartan (DuP-753) [2-butyl-5-chloro-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]-4-imidazolyl]methanol 1H-Imidazole-5-methanol, 2-butyl-4-chloro-1-[[2'-(2H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]- Losartan Potassium Form-I Losartan USP/EP/BP 2-Butyl-4-chloro-1[[(2'-(1 H-tetrazole-5-yl) (1,1'-biphenyl)-4yl]methyl]-1H imidazole-5-methanol (Losartan) Losartan (DUP 89) LosartanQ: What is Losartan Q: What is the CAS Number of Losartan Q: What is the storage condition of Losartan Q: What are the applications of Losartan LOS Benzaldehyde,3,4-dichloro-6-hydroxy- (3-oxo-1lambda3,2-benziodoxol-5-yl)acetate Losartan(base) 2 butyl 4-chloro-1[(2-(1H-tetrazole-5[1,1 biphenyl]-4-yl]methyl]-H imidazole-5methanol (1-((2'-(1H-Tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-butyl-4-chloro-1H-imidazol-5-yl)methanol Losartan in methanol 114798-26-4 C22H23ClN6O Isotopically Labeled Pharmaceutical Reference Standard