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945667-22-1

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945667-22-1 Usage

Description

While liraglutide targets the incretin system as a GLP-1 analog for therapeutic intervention in T2DM, saxagliptin enhances GLP-1 plasma concentrations by inhibiting the DPP-4 enzyme responsible for degradation of GLP-1 by cleavage of the two N-terminal amino acids adjacent to alanine (or proline), thereby rendering the hormone inactive. Similarto vildagliptin, saxagliptin is a cyanopyrrolidine substrate-based inhibitor. The proline mimetic occupies the small S1-pocket while the nitrile’s trajectory aligns with the scissile bond of the substrate. The slow dissociation kinetics of saxagliptin is attributed to a reversible, covalent reaction between the nitrile and the catalytically active serine hydroxyl (Ser630). The steric bulk provided by the adamantyl moiety and the constrained cyclopropyl ring stabilizes the trans-rotamer of the amide, thereby preventing the problematic intramolecular cyclization, via the amino group attacking the nitrile, which is favored in the cis-conformation. Since metabolism of saxagliptin is primarily mediated by CYP3A4/5, there is a potential for drug interactions with concomitant administration of strong inducers or inhibitors of these cytochrome P450 enzymes. The most common adverse events (>5% of patients) included upper respiratory tract infection, urinary tract infection, and headache.

Originator

Bristol-Myers-Squibb (US)

Uses

Saxagliptin Hydrate is a selective and reversible dipeptidyl peptidase-4 (DPP4) inhibitor that may be used to develop treatment for type 2 diabetes.

Definition

ChEBI: A hydrate that is the monohydrate form of anhydrous saxagliptin. Used for the treatment of Type II diabetes.

Brand name

Onglyza

Check Digit Verification of cas no

The CAS Registry Mumber 945667-22-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 9,4,5,6,6 and 7 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 945667-22:
(8*9)+(7*4)+(6*5)+(5*6)+(4*6)+(3*7)+(2*2)+(1*2)=211
211 % 10 = 1
So 945667-22-1 is a valid CAS Registry Number.
InChI:InChI:1S/C18H25N3O2.H2O/c19-8-13-2-12-3-14(12)21(13)16(22)15(20)17-4-10-1-11(5-17)7-18(23,6-10)9-17;/h10-15,23H,1-7,9,20H2;1H2

945667-22-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name saxagliptin hydrate

1.2 Other means of identification

Product number -
Other names Onglyza

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:945667-22-1 SDS

945667-22-1Synthetic route

3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester
709031-43-6

3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester

saxagliptin monohydrate
945667-22-1

saxagliptin monohydrate

Conditions
ConditionsYield
Stage #1: 3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester With hydrogenchloride In methanol; dichloromethane; water for 18h;
Stage #2: With sodium hydroxide; water In methanol; dichloromethane for 0.333333h; pH=9.0 - 10.5; Product distribution / selectivity;
81%
Stage #1: 3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester With hydrogenchloride In water; ethyl acetate at 23℃; for 4h;
Stage #2: With water; potassium carbonate In ethyl acetate at 16 - 20℃; for 2h; Product distribution / selectivity;
77%
Stage #1: 3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester With hydrogenchloride In water; isopropyl alcohol at 65℃; for 1.5h;
Stage #2: With sodium hydroxide; water; potassium carbonate In dichloromethane; isopropyl alcohol pH=~ 9; Product distribution / selectivity;
saxagliptin

saxagliptin

saxagliptin monohydrate
945667-22-1

saxagliptin monohydrate

Conditions
ConditionsYield
With water In ethyl acetate; isopropyl alcohol at 65℃;
saxagliptin monohydrate
945667-22-1

saxagliptin monohydrate

saxagliptin dihydrochloride dihydrate

saxagliptin dihydrochloride dihydrate

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane; ethanol at 20℃;
saxagliptin monohydrate
945667-22-1

saxagliptin monohydrate

saxagliptin

saxagliptin

Conditions
ConditionsYield
Stage #1: saxagliptin monohydrate In dichloromethane; isopropyl alcohol
Stage #2: In ethyl acetate

945667-22-1Relevant articles and documents

A sand geleg sandbank salt and its preparation method

-

Paragraph 0034; 0035, (2018/11/03)

The invention relates to a saxagliptin salt and a preparation method thereof. The saxagliptin salt has a structure represented by the formula II. Saxagliptin p-toluene sulfonate with a stable crystal form can be obtained through the salt-forming reactions between saxagliptin free alkali and p-toluene sulfonic acid under different solution systems. Stability researches show that saxagliptin p-toluene sulfonate has a better thermal stability than that of saxagliptin monohydrate and saxagliptin hydrochloride. Moreover, the preparation method of the saxagliptin salt is simple and is suitable for industrial production.

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