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Basic Information

Molecular Structure:
CAS No.:	103577-45-3
Name:	Lansoprazole
Article Data:	62
Cas Database

Formula:	C₁₆H₁₄F₃N₃O₂S
Molecular Weight:	369.367
Synonyms:	Amarin;Promp;Monolitum;Lanz;Prevacid (TN);Ulpax;Lansoprazolum [INN-Latin];Takepron;Blason;2-(((3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl)methyl)sulfinyl)benzimidazole;Ilsatec;A 65006;Bamalite;Prevacid SoluTab;Lansopep;2-(((3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl)methyl)sulfinyl)-1H-benzimidazole;Limpidex;Pro Ulco;Zoton;Lanproton;Lansoprazol [INN-Spanish];Lansoprazole [USAN:BAN:INN];Ogastro;1H-Benzimidazole, 2-(((3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl)methyl)sulfinyl)-;AG 1749;Dakar;1H-Benzimidazole,2-[[[3-methyl-4-(2,2,2- trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-;Agopton;2-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl]-1H-benzoimidazole;Prosogan;
EINECS:	2017-001-1
Density:	1.5 g/cm³
Melting Point:	178-182 °C
Boiling Point:	555.8 °C at 760 mmHg
Flash Point:	289.9 °C
Appearance:	white crystalline powder
Hazard Symbols:	Xi
Risk Codes:	36/37/38
Safety:	26-36
PSA:	87.08000
LogP:	4.38090

Synthetic route

: 103577-40-8
lansoprazole sulfide

: 103577-45-3
lansoprasole

Conditions

Conditions	Yield
With 2C5H8N2*VO2F; dihydrogen peroxide In ethanol at 10 - 15℃; for 2h; Temperature; Industrial scale;	100%
With dihydrogen peroxide; methyltrioxorhenium(VII) In 2,2,2-trifluoroethanol; water at 0℃; for 1h; Product distribution / selectivity;	98%
With magnesium monoperoxyphthalate hexahydrate In ethanol; water at -20 - -10℃; for 4h;	95%

: 3-methyl-4-(2,2,2-trifluoroethoxy)-2-chloromethylpyridine hydrochloride

: 134469-07-1
Benzimidazol-2-thiol

: 103577-45-3
lansoprasole

Conditions

Conditions	Yield
Stage #1: 3-methyl-4-(2,2,2-trifluoroethoxy)-2-chloromethylpyridine hydrochloride; Benzimidazol-2-thiol With carboxy chlorine; sodium carbonate In methanol at 64℃; for 3h; Stage #2: With titanium(IV) isopropylate In water; toluene at 28 - 55℃; for 1.83333h; Temperature; Solvent; Reagent/catalyst; Further stages;	98%

: lansoprazole hydrate acetonitrile solvate

: 103577-45-3
lansoprasole

Conditions

Conditions	Yield
With ammonia In water; acetonitrile at 0 - 40℃; for 3.5h; Product distribution / selectivity;	95.2%
With ammonia In water; acetone at 30 - 35℃; Product distribution / selectivity;	79%
In water at 15 - 30℃; Product distribution / selectivity;

: lansoprazole sulphide hydrate

: 180330-54-5
water ethanol

: 103577-45-3
lansoprasole

Conditions

Conditions	Yield
With dihydrogen peroxide; sodium thiosulfate In vanadium(V) oxide; dichloromethane; tert-butyl alcohol	93.2%
With dihydrogen peroxide; sodium thiosulfate In vanadium(V) oxide; dichloromethane; tert-butyl alcohol	93.2%
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In ethanol; chloroform

: 207790-96-3
iansoprazole ethanol hydrate

: 103577-45-3
lansoprasole

Conditions

Conditions	Yield
In water at 40℃; Product distribution / selectivity;	93%
With triethylamine In water; acetonitrile at 35℃; Product distribution / selectivity;	92%
In water; acetonitrile at 35℃; Product distribution / selectivity;	92%

: 2-({[3-methyl-4-(2,2,2-trifluoroethoxy)-1,4-dihydropyridin-2-yl]methyl}sulfinyl)-1H-benzimidazole

: 103577-45-3
lansoprasole

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In toluene at 0 - 10℃; for 9h; Solvent; Reagent/catalyst; Temperature;	93%

: 2-[(RS)-[(4-chloro-3-methylpyridin-2-yl)methyl]sulfinyl]-1H-benzimidazole

: 75-89-8
2,2,2-trifluoroethanol

: 420-87-1
sodium 2,2,2-trifluoroethanolate

: 103577-45-3
lansoprasole

Conditions

Conditions	Yield
In dimethyl sulfoxide at 90 - 100℃; Solvent; Large scale;	92.1%

...Expand

: lansoprazole sulphide hydrate

Vanadium(IV) acetylacetonate: Vanadium(IV) acetylacetonate

: 180330-54-5
water ethanol

: 103577-45-3
lansoprasole

Conditions

Conditions	Yield
With dihydrogen peroxide; sodium thiosulfate In ethanol	91%
With dihydrogen peroxide; sodium thiosulfate In ethanol	91%

...Expand

: 75-89-8
2,2,2-trifluoroethanol

: 2-(((4-nitro-3-methyl-2-pyridyl)methyl)sulfinyl)benzimidazole

: 420-87-1
sodium 2,2,2-trifluoroethanolate

: 103577-45-3
lansoprasole

Conditions

Conditions	Yield
In dimethyl sulfoxide at 90 - 100℃; Solvent; Large scale;	90.8%

...Expand

: sodium vanadate

: lansoprazole sulphide hydrate

: 180330-54-5
water ethanol

: 103577-45-3
lansoprasole

Conditions

Conditions	Yield
With dihydrogen peroxide; sodium thiosulfate In ethanol	90.5%
With dihydrogen peroxide; sodium thiosulfate In ethanol	90.5%

...Expand

Raw Materials

Downstream Products

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Specification

The Lansoprazole with CAS registry number of 103577-45-3 is also known as 1H-Benzimidazole, 2-(((3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl)methyl)sulfinyl)-. The IUPAC name is 2-[[3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl]-1H-benzimidazole. It belongs to product categories of Active Pharmaceutical Ingredients; Intermediates & Fine Chemicals; Pharmaceuticals; Sulfur & Selenium Compounds; Ion Pump Inhibitors; Monovalent Ion Channels; Voltage-gated Ion Channels; ATPase; Pharmaceutical Intermediates. In addition, the formula is C₁₆H₁₄F₃N₃O₂S and the molecular weight is 369.36. This chemical is a white crystalline powder and should be sealed in cool place without light. What's more, it can be used for the treatment of duodenal ulcer embolism and it is a proton-pump inhibitor (PPI) which prevents the stomach from producing gastric acid.

Physical properties about Lansoprazole are: (1)ACD/LogP: 2.76; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.75; (4)ACD/LogD (pH 7.4): 2.76; (5)ACD/BCF (pH 5.5): 72.3; (6)ACD/BCF (pH 7.4): 72.89; (7)ACD/KOC (pH 5.5): 740.79; (8)ACD/KOC (pH 7.4): 746.86; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Index of Refraction: 1.635; (13)Molar Refractivity: 88.03 cm³; (14)Molar Volume: 245.8 cm³; (15)Surface Tension: 68.9 dyne/cm; (16)Density: 1.5 g/cm³; (17)Flash Point: 289.9 °C; (18)Enthalpy of Vaporization: 83.72 kJ/mol; (19)Boiling Point: 555.8 °C at 760 mmHg; (20)Vapour Pressure: 2.16E-12 mmHg at 25 °C.

Preparation of Lansoprazole: it is prepared by reaction of 2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethylsulfanyl]-1H-benzoimidazole. The reaction needs reagent m-chloroperbenzoic acid and solvent CHCl₃ with other condition of ice-cooling. The yield is about 45%.

Lansoprazole is prepared by reaction of 2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethylsulfanyl]-1H-benzoimidazole.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. During using it, wear suitable protective clothing. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: CC1=C(C=CN=C1CS(=O)C2=NC3=CC=CC=C3N2)OCC(F)(F)F
2. InChI: InChI=1S/C16H14F3N3O2S/c1-10-13(20-7-6-14(10)24-9-16(17,
18)19)8-25(23)15-21-11-4-2-3-5-12(11)22-15/h2-7H,8-9H2,1H3,(H,21,22)
3. InChIKey: MJIHNNLFOKEZEW-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LD	oral	> 2gm/kg (2000mg/kg)		Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 35, Pg. 387, 1993.
mouse	LD50	intraperitoneal	> 5gm/kg (5000mg/kg)	BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: MUSCLE WEAKNESS KIDNEY, URETER, AND BLADDER: OTHER CHANGES	Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 18(Suppl,
mouse	LD50	oral	> 5gm/kg (5000mg/kg)	KIDNEY, URETER, AND BLADDER: OTHER CHANGES	Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 18(Suppl,
mouse	LD50	subcutaneous	> 5gm/kg (5000mg/kg)		Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 18(Suppl,
mouse	LDLo	intravenous	75mg/kg (75mg/kg)	SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 24, Pg. 905, 1996.
rat	LD50	intraperitoneal	5gm/kg (5000mg/kg)	BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: MUSCLE WEAKNESS LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 18(Suppl,
rat	LD50	oral	> 5gm/kg (5000mg/kg)		Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 18(Suppl,
rat	LD50	subcutaneous	> 5gm/kg (5000mg/kg)		Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 18(Suppl,
rat	LDLo	intravenous	58mg/kg (58mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 24, Pg. 905, 1996.