ChemicalBook >> CAS DataBase List >>R-(+)-Lansoprazole

R-(+)-Lansoprazole

CAS No.
138530-94-6
Chemical Name:
R-(+)-Lansoprazole
Synonyms
Dexlansoprazole;TAK 390;T 168390;D-lansoprazole;Dexlansaprazole;Dexlanzoprazole;T 168390,TAK 390;(+)-Lansoprazole;R-(+)-Lansoprazole;Lansoprazole R-Isomer
CBNumber:
CB71269821
Molecular Formula:
C16H14F3N3O2S
Molecular Weight:
369.36
MDL Number:
MFCD13196699
MOL File:
138530-94-6.mol
Last updated:2024-03-22 14:56:24

R-(+)-Lansoprazole Properties

Melting point 66-68?C
Boiling point 555.8±60.0 °C(Predicted)
Density 1.50±0.1 g/cm3(Predicted)
storage temp. Sealed in dry,2-8°C
solubility Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
form Solid
pka 9.56±0.10(Predicted)
color Off-White to Dark Brown
Stability Hygroscopic
FDA UNII UYE4T5I70X
ATC code A02BC06

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS08,GHS07
Signal word  Warning
Hazard statements  H317-H373
Precautionary statements  P260-P314-P501-P261-P272-P280-P302+P352-P333+P313-P321-P363-P501
NFPA 704
0
2 0

R-(+)-Lansoprazole price More Price(22)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich SML2624 Dexlansoprazole ≥98% (HPLC) 138530-94-6 50mg $97.7 2024-03-01 Buy
Cayman Chemical 18235 (R)-Lansoprazole ≥98% 138530-94-6 10mg $32 2024-03-01 Buy
Cayman Chemical 18235 (R)-Lansoprazole ≥98% 138530-94-6 50mg $109 2024-03-01 Buy
Cayman Chemical 18235 (R)-Lansoprazole ≥98% 138530-94-6 100mg $199 2024-03-01 Buy
TRC L175010 (R)-Lansoprazole 138530-94-6 50mg $70 2021-12-16 Buy
Product number Packaging Price Buy
SML2624 50mg $97.7 Buy
18235 10mg $32 Buy
18235 50mg $109 Buy
18235 100mg $199 Buy
L175010 50mg $70 Buy

R-(+)-Lansoprazole Chemical Properties,Uses,Production

Description

The mechanism of PPIs involves the irreversible binding to the hydrogen/potassium adenosine triphosphatase enzyme system, commonly referred to as the gastric proton pump, of the gastric parietal cell. As the last stage in gastric acid secretion, blockade of the gastric proton pump is an effective treatment for a variety of diseases requiring acid suppression, such as heartburn, peptic ulcers, and GERD. Dexlansoprazole is the latest PPI to hit the market, joining the ranks of omeprazole, rabeprazole, pantoprazole, esomeprazole, and lansoprazole, and is the Renantiomer of the racemic lansoprazole. Compared to its predecessors, dexlansoprazole exhibits improved pharmacokinetics with slower clearance and longer terminal half-life. In addition, dexlansoprazole utilizes a novel DDR technology; drug release is optimized through the use of granules with different pH-dependent dissolution profiles, thereby providing an initial release in the proximal small intestine within 1-2 h of administration followed by a subsequent release at distal regions of the small intestine several hours later. With its longer duration of action culminating in more effective acid suppression, dexlansoprazole may have an advantage over conventional PPIs that possess single release formulations (immediate or delayed). Similar to all PPIs, dexlansoprazole is a prodrug that consists of pyridine and benzimidazole rings with a latent sulfenamide moiety. In order to form the disulfide bond with cysteine residues of the proton pump, dexlansoprazole must be activated through two protonations followed by a spontaneous rearrangement to unmask the sulfenamide.

Description

Lansoprazole is a proton pump inhibitor that irreversibly inactivates the H+/K+-stimulated ATPase pumps in parietal cells, inhibiting gastric acid secretion and increasing intragastric pH. It is a 1:1 racemic mixture of (R)-lansoprazole and (S)-lansoprazole, both of which are pharmacologically active. (R)-Lansoprazole is an enantiomerically pure form of lansoprazole. It can inhibit acid formation in isolated canine parietal cells with an IC50 value of 59 nM and inhibit the H+/K+-ATPase with an IC50 value of 4.2 μM.

Chemical Properties

Brown Solid

Originator

Takeda (Japan)

Uses

Acts as a gastric proton pump inhibitor and an antiulcerative

Uses

antiulcer, proton pump inhibitor

Uses

The R-enantiomer of Lansoprazole; a gastric proton pump inhibitor. An antiulcerative

Definition

ChEBI: Dexlansoprazole is a sulfoxide and a member of benzimidazoles.

brand name

Kapidex

Clinical Use

Takeda Pharmaceuticals received approval of dexlansoprazole, a dual release formulation of the (R)-isomer of lansoprazol proton pump inhibitor (PPI) already in the market, from the FDA in January 2009. Dexlansoprazole is a delayed release capsule for the oncedaily, oral treatment of heartburn associated with symptomatic non-erosive gastroesophageal reflux disease (GERD), the healing of erosive esophagitis (EE) and the maintenance of healed EE. The dual release formulation is designed to provide two separate releases of medication, one at 1–2 h and then another at 4–5 h after treatment, for extended efficacy in the treatment of GERD.

Side effects

The most commonly recorded adverse reactions that occurred at a higher incidence than placebo were diarrhea, abdominal pain, nausea, vomiting, flatulence, and upper respiratory tract infection. As dexlansoprazole inhibits gastric acid secretion, its use is expected to interfere with the absorption of drugs with pH-dependent oral bioavailability. Since the HIV protease inhibitor atazanavir is dependent on gastric acid for absorption, dexlansoprazole should not be co-administered with atazanavir to avoid a loss of therapeutic efficacy. While co-administration of dexlansoprazole did not affect the pharmacokinetics of warfarin or INR (international normalized ratio: the ratio of a patient s prothrombin time to a normal sample), there have been reports of increased INR and prothrombin time in patients receiving concomitant treatment with PPIs and warfarin. Since increases in INR and prothrombin time may lead to abnormal bleeding and possibly death, concomitant use of dexlansoprazole and warfarin may necessitate monitoring for increases in INR and prothrombin time.

Synthesis

Similar to the synthesis of the chiral sulfoxide of armodafinil vide supra, the preparation of the chiral sulfoxide of lansoprazole utilized the catalytic oxidation method developed by Kagan and co-workers (the Scheme). Two routes have been reported that describe the preparation of dexlansoprazole on large scale. The first route developed by Takeda reacts commercially available thioether 29, also used to make lansoprazole, under the Kagan asymmetric oxidation conditions and the alternative route utilizes the cheaper commercial intermediate nitrosulfide 30 in the analogous asymmetric oxidation by Kagan). Thus, the catalyst complex consisting of (+)-DET, Ti(OiPr)4 and water was formed in the presence of thioether 29 in toluene at 30¨C40??C. The reaction mixture was then cooled to 5 ??C and DIPEA and cumene hydroperoxide (CMHP) were added to give, after aqueous work-up and in situ crystallization from the organic layer, dexlansoprazole (VI) in 98% ee. No yield was given in the patent. An alternate, but similar, sequence was also described wherein the nitrosulfide intermediate 30 was subjected to similar oxidative conditions that gave intermediate nitro compound 31 in 80% yield and 98% ee. Compound 31 was treated with KOH and trifluoroethanol to provide dexlansoprazole (VI).

Synthesis_138530-94-6

R-(+)-Lansoprazole Preparation Products And Raw materials

Global( 302)Suppliers
Supplier Tel Email Country ProdList Advantage
Henan Bao Enluo International TradeCo.,LTD
+86-17331933971 +86-17331933971 deasea125996@gmail.com China 2504 58
Henan Fengda Chemical Co., Ltd
+8613613820652 info@fdachem.com China 5085 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21700 55
ATK CHEMICAL COMPANY LIMITED
+undefined-21-51877795 ivan@atkchemical.com China 32480 60
career henan chemical co
+86-0371-86658258 sales@coreychem.com China 29914 58
Hubei Jusheng Technology Co.,Ltd.
18871490254 linda@hubeijusheng.com CHINA 28180 58
Casorganics US Corp
+17326109938 sales@casorganics.com CHINA 174 58
Standardpharm Co. Ltd.
86-714-3992388 overseasales1@yongstandards.com United States 14336 58
BOC Sciences
+1-631-485-4226 inquiry@bocsci.com United States 19553 58
Chongqing Chemdad Co., Ltd
+86-023-61398051 +8613650506873 sales@chemdad.com China 39916 58

View Lastest Price from R-(+)-Lansoprazole manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
R-(+)-Lansoprazole pictures 2024-03-23 R-(+)-Lansoprazole
138530-94-6
US $8.00-0.40 / KG 1KG 99% g-kg-tons, free sample is available Henan Fengda Chemical Co., Ltd
R-(+)-Lansoprazole pictures 2023-08-18 R-(+)-Lansoprazole
138530-94-6
US $200.00 / kg 1kg 99% 1000tons Henan Bao Enluo International TradeCo.,LTD
Dexlansoprazole pictures 2023-04-04 Dexlansoprazole
138530-94-6
US $0.00 / kg 1kg 99% 1ton Zhejiang Hengkang Pharmaceutical Co., Ltd.
  • R-(+)-Lansoprazole pictures
  • R-(+)-Lansoprazole
    138530-94-6
  • US $200.00 / kg
  • 99%
  • Henan Bao Enluo International TradeCo.,LTD
  • Dexlansoprazole pictures
  • Dexlansoprazole
    138530-94-6
  • US $0.00 / kg
  • 99%
  • Zhejiang Hengkang Pharmaceutical Co., Ltd.

R-(+)-Lansoprazole Spectrum

(R)-2-[[[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole 1H-Benzimidazole, 2-[(R)-[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]- (9CI) 1H-Benzimidazole, 2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-, (R)- R-(+)-Lansoprazole 2-[(R)-[[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole T 168390 TAK 390 2-[[3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl]-1H-benzoimidazole 2-[(R)-[[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]Methyl]sulfinyl]- (+)2-[(R)-{[3-METHYL-4-(2,2,2-TRIFLUOROETHOXY) PYRIDIN-2-YL-1H-BENZIMIDAZOLE T 168390,TAK 390 (R)-2-(((3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methyl)sulfinyl)-1H-benzo[d]imidazole Dexlansoprazole 22.5% enteric coated pellets Lansoprazole R-Isomer 1H-BenziMidazole,2-[(R)-[[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]Methyl]sulfinyl]- Lansoprazole Impurity 14 Dexlansoprazole related impurities 2 Dexlansoprazole / R-(+)-Lansoprazole Lansoprazole impurity 17/Lansoprazole R-Isomer/(R)-Lansoprazole/Dexlansoprazole/2-[(R)-[[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole R-(+)-Lansoprazole USP/EP/BP Dexlansaprazole DexlansoprazoleQ: What is Dexlansoprazole Q: What is the CAS Number of Dexlansoprazole Q: What is the storage condition of Dexlansoprazole Dexlansoprazole Dexlanzoprazole (+)-Lansoprazole D-lansoprazole 138530-94-6 DEXILANT APIs Chiral Reagents Intermediates & Fine Chemicals Pharmaceuticals Sulfur & Selenium Compounds