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103577-45-3

Basic Information
CAS No.: 103577-45-3
Name: Lansoprazole
Article Data: 62
Molecular Structure:
Molecular Structure of 103577-45-3 (Lansoprazole)
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: IrritantXi
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With dihydrogen peroxide; sodium thiosulfate In vanadium(V) oxide; dichloromethane; tert-butyl alcohol93.2%
With dihydrogen peroxide; sodium thiosulfate In vanadium(V) oxide; dichloromethane; tert-butyl alcohol93.2%
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In ethanol; chloroform
207790-96-3

iansoprazole ethanol hydrate

103577-45-3

lansoprasole

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

lansoprazole sulphide hydrate

Vanadium(IV) acetylacetonate

Vanadium(IV) acetylacetonate

180330-54-5

water ethanol

103577-45-3

lansoprasole

Conditions
ConditionsYield
With dihydrogen peroxide; sodium thiosulfate In ethanol91%
With dihydrogen peroxide; sodium thiosulfate In ethanol91%
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
ConditionsYield
In dimethyl sulfoxide at 90 - 100℃; Solvent; Large scale;90.8%

sodium vanadate

lansoprazole sulphide hydrate

180330-54-5

water ethanol

103577-45-3

lansoprasole

Conditions
ConditionsYield
With dihydrogen peroxide; sodium thiosulfate In ethanol90.5%
With dihydrogen peroxide; sodium thiosulfate In ethanol90.5%
Downstream Products
138530-95-7
138530-94-6
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    Synonyms: LANSOPRAZOLE, RELATED COMPOUND A2-[[[3-METHYL-4-(2,2,2-TRIFLOUROETHOXY)-2-PYRIDYL]METHYL]SULFONYL]BENZIMIDAZOLE USP STANDARD;LANSOPRAZOLE, MM(CRM STANDARD);LANSOPRAZOLE USP(CRM STANDARD);2-[3-METHYL-4-(2,2,2-TRIFLUORO-ETHOXY)-PYRIDIN-2-YL

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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.