(1S,3S,5S)-2-[(2S)-2-amino-2-[(1r,3R,5R,7S)-3-hydroxyadamantan-1-yl]acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile

Base Information

Chemical Name:(1S,3S,5S)-2-[(2S)-2-amino-2-[(1r,3R,5R,7S)-3-hydroxyadamantan-1-yl]acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile
CAS No.:361442-04-8
Molecular Formula:C18H25N3O2
Molecular Weight:315.415
Hs Code.:29339900
Nikkaji Number:J2.484.876K
Wikipedia:Saxagliptin
Wikidata:Q76416837,Q27096685
NCI Thesaurus Code:C75983
Pharos Ligand ID:FUT699N3K4NG
ChEMBL ID:CHEMBL2298396
Mol file:361442-04-8.mol

Synonyms:3-hydroxyadamantylglycine-4,5-methanoprolinenitrile hydrate;BMS 477118;BMS-477118;BMS477118;Onglyza;saxagliptin

Suppliers and Price of (1S,3S,5S)-2-[(2S)-2-amino-2-[(1r,3R,5R,7S)-3-hydroxyadamantan-1-yl]acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

TRC
Saxagliptin
25mg
$ 680.00

DC Chemicals
Saxagliptin >98%
1 g
$ 900.00

DC Chemicals
Saxagliptin >98%
100 mg
$ 250.00

CSNpharm
Saxagliptin
10mg
$ 92.00

CSNpharm
Saxagliptin
5mg
$ 71.00

CSNpharm
Saxagliptin
50mg
$ 245.00

ChemScene
Saxagliptin 99.61%
10mg
$ 108.00

ChemScene
Saxagliptin 99.61%
100mg
$ 420.00

ChemScene
Saxagliptin 99.61%
50mg
$ 288.00

Biosynth Carbosynth
Saxagliptin
1 g
$ 350.00

Total 199 raw suppliers

Chemical Property of (1S,3S,5S)-2-[(2S)-2-amino-2-[(1r,3R,5R,7S)-3-hydroxyadamantan-1-yl]acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile

Chemical Property:

Appearance/Colour:White powder
Vapor Pressure:2.51E-14mmHg at 25°C
Refractive Index:1.64
Boiling Point:548.7 °C at 760 mmHg
PKA:15.12±0.40(Predicted)
Flash Point:285.6 °C
PSA：90.35000
Density:1.35 g/cm³
LogP:1.79618
Storage Temp.:2-8°C
Solubility.:DMSO (Slightly), Methanol (Sparingly)
XLogP3:0.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:315.19467705
Heavy Atom Count:23
Complexity:609

Purity/Quality:

99.0%min ^*data from raw suppliers

Saxagliptin ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:
Statements: 28-38-41-48
Safety Statements: 24/25-26-28-36/37/39

MSDS Files:: SDS file from LookChem

Useful:

Drug Classes:Antidiabetic Agents
Canonical SMILES:C1C2CC2N(C1C#N)C(=O)C(C34CC5CC(C3)CC(C5)(C4)O)N
Isomeric SMILES:C1[C@@H]2C[C@@H]2N([C@@H]1C#N)C(=O)[C@H](C34C[C@H]5C[C@@H](C3)CC(C5)(C4)O)N
Recent ClinicalTrials:Study to Evaluate Safety and Efficacy of Dapagliflozin and Saxagliptin in Patients With Type 2 Diabetes Mellitus Aged 10 to Below 18 Years Old
Recent EU Clinical Trials:A 26 Week, Multicenter, Randomized, Placebo-Controlled, Double-Blind, Parallel Group, Phase
Recent NIPH Clinical Trials:Effect of omarigliptin on glucose variability and oxidative stress in type 2 diabetes patients
Uses Saxagliptin is a potent and selective reversible inhibitor of dipeptidyl peptidase-4, which is being developed for the treatment of type 2 diabetes. It is absorbed rapidly after oral administration an d has a pharmacokinetic profile compatible with once daily dosing. Saxagliptin is a potent and selective reversible inhibitor of dipeptidyl peptidase-4, which is being developed for the treatment of type 2 diabetes. It is absorbed rapidly after oral administration and has a pharmacokinetic profile compatible with once daily dosing.
Clinical Use Saxagliptin, previously identified as BMS-477118, is an oral hypoglycemic of the dipeptidyl peptidase-4 (DPP-4) inhibitor class developed by Bristol-Myers Squibb for the treatment of type 2 diabetes. DPP-IV is the primary enzyme responsible for degradation of incretins, such as glucagon-like peptide-1 (GLP-1), which is a hormone responsible for the glucose-dependent stimulation of insulin in humans. Inhibitors of DPP-IV serve as effective glucose regulators by increasing the endogenous concentration of GLP-1.
Drug interactions Potentially hazardous interactions with other drugs None known

Technology Process of (1S,3S,5S)-2-[(2S)-2-amino-2-[(1r,3R,5R,7S)-3-hydroxyadamantan-1-yl]acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile

There total 9 articles about (1S,3S,5S)-2-[(2S)-2-amino-2-[(1r,3R,5R,7S)-3-hydroxyadamantan-1-yl]acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: saxaglipitin

: 361442-04-8,1564265-93-5
(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.1^3,7]dec-1-yl)-1-oxoethyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile

Guidance literature:: With sodium hydroxide; In dichloromethane; water; at 20 ℃; for 1h; pH=9;

Reference yield:

: [(1S)-2-[(1S,3S,5S)-3-cyano-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-2-oxoethyl]carbamic acid-1,1-dimethylethyl ester

: 361442-04-8,1564265-93-5
(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.1^3,7]dec-1-yl)-1-oxoethyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile

Guidance literature:: [(1S)-2-[(1S,3S,5S)-3-cyano-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-2-oxoethyl]carbamic acid-1,1-dimethylethyl ester; With hydrogenchloride; water; In methanol; dichloromethane; at 0 - 20 ℃; for 20.6667h;

With sodium hydroxide; In water; pH=> 11;

Reference yield:

: racemic N-boc-3-hydroxyadamant-1-yl glycine

: 361442-04-8,1564265-93-5
(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.1^3,7]dec-1-yl)-1-oxoethyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile

Guidance literature:: Multi-step reaction with 5 steps

1.1: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 3.33 h / 70 °C

2.1: hydrogenchloride; water / ethyl acetate; water / pH 3

3.1: 4-methyl-morpholine / ethyl acetate; acetic acid butyl ester / 0.08 h / 0 °C / Inert atmosphere

3.2: .(R).T₃P / 17.5 h / 0 - 25 °C

4.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 1.5 h / 0 °C

4.2: 20 - 25 °C / pH > 10

5.1: hydrogenchloride; water / dichloromethane; methanol / 20.67 h / 0 - 20 °C

5.2: pH > 11

With 4-methyl-morpholine; pyridine; hydrogenchloride; (1R,2S)-2-Amino-1,2-diphenylethanol; water; trifluoroacetic anhydride; In tetrahydrofuran; methanol; dichloromethane; acetic acid butyl ester; water; ethyl acetate;