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Cas Database

Name	Losartan carboxylic acid	EINECS	N/A
CAS No.	124750-92-1	Density	1.41 g/cm³
PSA	109.58000	LogP	4.47270
Solubility	N/A	Melting Point	130-132 °C
Formula	C₂₂H₂₁ClN₆O₂	Boiling Point	707.8 °C at 760 mmHg
Molecular Weight	436.901	Flash Point	381.8 °C
Transport Information	N/A	Appearance	Light-Yellow Solid
Safety	24/25	Risk Codes	N/A
Molecular Structure		Hazard Symbols	N/A
Synonyms	1H-Imidazole-5-carboxylicacid, 2-butyl-4-chloro-1-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-(9CI);E 3174;EXP 3174;	Article Data	23

Losartan carboxylic acid Synthetic route

: 947330-97-4
2-butyl-4-chloro-1-[2'-(1H-tetrazol-5-yl) 1,1'-biphenyl-methyl]imidazole-5-carboxylic acid ethyl ester

: 124750-92-1
2-butyl-4-chloro-1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylic acid

Conditions

Conditions	Yield
With sodium hydroxide In ethanol at 90℃; for 20h;	90%

: 124750-99-8
cozaar

: 124750-92-1
2-butyl-4-chloro-1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylic acid

Conditions

Conditions	Yield
Stage #1: cozaar With potassium permanganate In water at -5 - 50℃; for 16h; Stage #2: With hydrogenchloride In water pH=2 - 3;	89.1%
Stage #1: cozaar With potassium hydroxide In water at 2℃; for 2h; Stage #2: With sodium periodate; ruthenium trichloride In water; isopropyl alcohol at 4 - 20℃; for 22h; Stage #3: With phosphoric acid In water; isopropyl alcohol for 0.5h;
Stage #1: cozaar With ruthenium trichloride; potassium hydroxide; sodium periodate In water at 0℃; Stage #2: With phosphoric acid In water; isopropyl alcohol at 30℃; for 0.5h;

: 114798-26-4
lorsartan

: 124750-92-1
2-butyl-4-chloro-1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylic acid

Conditions

Conditions	Yield
With pyridine; potassium permanganate; tetrabutyl-ammonium chloride In water; acetone at 40 - 50℃; for 1h; Product distribution / selectivity;	78%
With sodium periodate; ruthenium(III) trichloride hydrate; potassium hydroxide In water at 0℃;
Stage #1: lorsartan With sodium periodate; ruthenium (III) chloride monohydrate; potassium hydroxide In water at 0℃; Stage #2: In water; isopropyl alcohol at 25℃; for 2.5h; Stage #3: With phosphoric acid In water; isopropyl alcohol at 30℃; for 0.5h;
With cytochrome P450 2C9 Enzymatic reaction;
With cytochrome b5; NADPH In aq. phosphate buffer at 37℃; for 0.75h; Kinetics; Reagent/catalyst; Enzymatic reaction;

: 124750-99-8
losartan potassium

: 124750-92-1
2-butyl-4-chloro-1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylic acid

Conditions

Conditions	Yield
Stage #1: losartan potassium With pyridine; potassium permanganate; tetrabutyl-ammonium chloride In water; acetone at 40 - 50℃; for 1h; Stage #2: With hydrogenchloride In water; acetone Product distribution / selectivity;	72%
Stage #1: losartan potassium With potassium hydroxide In water at 2℃; for 2h; Stage #2: With sodium periodate; ruthenium trichloride In water at 4 - 6.5℃; for 19h;

: 124750-99-8
cozaar

A: 114798-36-6
2-n-Butyl-4-chloro-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-imidazole-5-carboxaldehyde

B: 124750-92-1
2-butyl-4-chloro-1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylic acid

Conditions

Conditions	Yield
With manganese(IV) oxide In water at 80 - 180℃; for 0.833333h; microwave irradiation;	A 0.253 mmol B 64%
With manganese(IV) oxide In water at 80 - 180℃; for 0.25h; microwave irradiation;	A 60% B n/a

: 114798-36-6
2-n-Butyl-4-chloro-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-imidazole-5-carboxaldehyde

: 124750-92-1
2-butyl-4-chloro-1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylic acid

Conditions

Conditions	Yield
With potassium permanganate; potassium hydroxide In water; N,N-dimethyl-formamide at 20 - 30℃; for 2h; Large scale;

: 2-n-butyl-5-chloro-3H-imidazole-4-carboxylic acid ethyl ester

: 124750-92-1
2-butyl-4-chloro-1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrabutylammomium bromide; sodium hydroxide / toluene / 20 h / 60 °C 2: sodium azide; trimethylamine hydrochloride / toluene; 1-methyl-pyrrolidin-2-one / 43 h / 60 °C 3: sodium hydroxide / ethanol / 20 h / 90 °C View Scheme

: 114772-54-2
4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile

: 124750-92-1
2-butyl-4-chloro-1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrabutylammomium bromide; sodium hydroxide / toluene / 20 h / 60 °C 2: sodium azide; trimethylamine hydrochloride / toluene; 1-methyl-pyrrolidin-2-one / 43 h / 60 °C 3: sodium hydroxide / ethanol / 20 h / 90 °C View Scheme

Losartan carboxylic acid Specification

The CAS register number of Losartan carboxylic acid is 124750-92-1. It also can be called as 2-Butyl-4-chloro-1-[2'-(1H-tetrazol-5-yl)biphenyl-4-ylmethyl]imidazole-5-carboxylic acid and the IUPAC name about this chemical is 2-butyl-5-chloro-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-carboxylic acid. The molecular formula about this chemical is C₂₂H₂₁ClN₆O₂and molecular weight is 436.89. It belongs to the following product categories, such as Intermediates & Fine Chemicals; Metabolites & Impurities; Pharmaceuticals and so on. This chemical can be used as a metabolite of Losartan.

Physical properties about Losartan carboxylic acid are: (1)ACD/LogP: 3.61; (2)ACD/LogD (pH 5.5): -0.1; (3)ACD/LogD (pH 7.4): -0.53; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 8; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 8; (11)Polar Surface Area: 87.72Å²; (12)Index of Refraction: 1.695; (13)Molar Refractivity: 119.08 cm³; (14)Molar Volume: 309.7 cm³; (15)Polarizability: 47.21x10^-24cm³; (16)Surface Tension: 56.7 dyne/cm; (17)Enthalpy of Vaporization: 108.7 kJ/mol; (18)Boiling Point: 707.8 °C at 760 mmHg; (19)Vapour Pressure: 5.04E-21 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)c1c(Cl)nc(n1Cc4ccc(c2ccccc2c3nnnn3)cc4)CCCC
(2)InChI: InChI=1/C22H21ClN6O2/c1-2-3-8-18-24-20(23)19(22(30)31)29(18)13-14-9-11-15(12-10-14)16-6-4-5-7-17(16)21-25-27-28-26-21/h4-7,9-12H,2-3,8,13H2,1H3,(H,30,31)(H,25,26,27,28)
(3)InChIKey: ZEUXAIYYDDCIRX-UHFFFAOYAJ
(4)Std. InChI: InChI=1S/C22H21ClN6O2/c1-2-3-8-18-24-20(23)19(22(30)31)29(18)13-14-9-11-15(12-10-14)16-6-4-5-7-17(16)21-25-27-28-26-21/h4-7,9-12H,2-3,8,13H2,1H3,(H,30,31)(H,25,26,27,28)
(5)Std. InChIKey: ZEUXAIYYDDCIRX-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	441mg/kg (441mg/kg)	SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE BEHAVIORAL: TREMOR LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Kiso to Rinsho. Clinical Report. Vol. 28, Pg. 3959, 1994.

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