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Losartan

Losartan structure

CAS No:
114798-26-4
Formula:
C22H23ClN6O
Chemical Name:
Losartan
Synonyms:
1H-Imidazole-5-methanol,2-butyl-4-chloro-1-[[2′-(2H-tetrazol-5-yl)[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]-;2-Butyl-4-chloro-1-[[2′-(2H-tetrazol-5-yl)[1,1′-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol;DUP 89;Losartan;Lortaan;2-Butyl-4-chloro-1-[[2′-(1H-tetrazol-5-yl)-1,1′-biphenyl-4-yl]methyl]-1H-imidazole-5-methanol;Angizaar;Allisartan;1-[1-[[2′-(2H-Tetrazol-5-yl)biphenyl-4-yl]methyl]-2-butyl-4-chloro-1H-imidazol-5-yl]methanol;Lozap;Xartan;[2-Butyl-5-chloro-3-[2′-(2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-imidazol-4-yl]-methanol;[2-Butyl-5-chloro-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol;[2-Butyl-4-chloro-1-([4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl]methyl)-1H-imidazol-5-yl]methanol
Categories:
Active Pharmaceutical Ingredients > Circulatory System Drugs

Description

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'-positionLosartan, 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-me

Losartan Basic Attributes

Molecular Weight：

422.91

Exact Mass：

422.91

EC Number：

1312995-182-4

HScode：

2933990090

Characteristics

PSA：

92.5

XLogP3：

4.3

Appearance：

Solid

Density：

1.35±0.1 g/cm3(Predicted)

Melting Point：

184 °C

Boiling Point：

682.0±65.0 °C(Predicted)

Flash Point：

366.3±34.3 °C

Refractive Index：

1.681

Water Solubility：

4.70e-03 g/L

Storage Conditions：

Conditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place. Store under inert gas. Moisture sensitive.

Vapor Pressure：

5.44X10-18 mm Hg at 25 deg C (est)

PKA：

5.5None

Safety Information

Packing level：

III

Hazard category：

4.3

Transport codes：

3278

wgk germany：

hazard class code：

36/37/38

safety instructions：

26-36

Marks：

Stability/Shelf Life：

Stable under recommended storage conditions.

Precautionary statement(s)：

P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

Hazard Statements：

H315

Losartan Use and Manufacturing

Methods of Manufacturing

A solution of losartan (0.42 g) in a mixture of tetrahydrofuran (3 ml) and chlorobenzene (6 ml) is stirred thoroughly with an aqueous solution of hydriodic acid (0.1 molar, 10.5 ml) with gentle warming. The aqueous phase is separated and transferred to a rotary evaporator flask. High vacuum is applied and the flask is maintained at an external temperature of about 40C and rotated rapidly to remove the majority of the solvent as quickly as possible. The flask and amorphous product is then placed in a desiccator containing a dish of phosphoric oxide drying agent, and dried under high vacuum to a residual solvent level of below 0.2%. Yield 0.55 g. X-ray powder diffraction shows a single very broad diffraction peak typical of non-crystalline material. (50 mg, 118 mumol), chloroacetic acid (13.4 mg, 142 mumol) and dimethylaminopyridine (2.8 mg, 27 mumol) were dissolved in THF (4 ml) and cooled to 0 C. Diisopropylcarbodiimide (23 mul, 142 mumol) was added and stirring continued at 0 C. for 90 mins, after which the mixture was allowed to warm to room temperature. The reaction was monitored by thin layer chromatography (5% of (10% NH4OH in MeOH) in DCM). After overnight stirring, the reaction was deemed complete and the mixture was diluted with DCM (10 ml) and washed with 0.1 M HCl (15 ml) and brine (15 ml). The organic portion was dried over Na2SO4 and solvents removed in vacuo. Further drying under vacuum gave chloroacetyl

Uses

antihypertensive;antagonist of angiotensin type 1

Computed Properties

Molecular Weight:422.9
XLogP3:4.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:8
Exact Mass:422.1621871
Monoisotopic Mass:422.1621871
Topological Polar Surface Area:92.5
Heavy Atom Count:30
Complexity:520
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

1-Methylimidazole

Methanol

Drug Function and Efficacy

Blocks the vasoconstrictor and aldosterone-secreting effects of angiotensin II by selectively blocking the binding of angiotensin II to the AT1 receptor, leading to vasodilation and reduced blood pressure.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

LOSARTAN POTASSIUM AND HYDROCHLOROTHIAZIDE- losartan potassium and hydrochlorothiazide_tablet
Manufacturer	Proficient Rx LP

Registered Holders

ATUL BIOSCIENCE LTD

United States
Active
DR. REDDY'S LABORATORIES LIMITED

European Union
Active
HETERO LABS LIMITED

European Union
Active

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