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Home> Encyclopedia >Pharmaceutical Intermediates>Pharmaceutical>Organic Intermediate
Vildagliptin structure
Vildagliptin structure


Iupac Name:(2S)-1-[2-[(3-hydroxy-1-adamantyl)amino]acetyl]pyrrolidine-2-carbonitrile
CAS No.: 274901-16-5
Molecular Weight:303.406
Modify Date.: 2022-11-25 02:24
Introduction: Glyptins are class of oral anti-hyperglycemic agents that inhibit dipeptidyl peptidase 4 (DPP-4), which can act as a serine exopeptidase. Aside from their use in type 2 diabetes, gliptins have positive cardiovascular and anti-inflammtatory effects. Antidiabetic. View more+
1. Names and Identifiers
1.1 Name
1.2 Synonyms

(-)-(2S)-1-[[(3-Hydroxytricyclo[[3,7]]dec-1-yl)amino]acetyl]pyrrolidine-2-carbonitrile (2S)-1-[N-(3-Hydroxyadamantan-1-yl)glycyl]-2-pyrrolidinecarbonitrile (2S)-1-[N-(3-Hydroxyadamantan-1-yl)glycyl]pyrrolidine-2-carbonitrile (2S)-1-[N-(3-hydroxytricyclo[]dec-1-yl)glycyl]pyrrolidine-2-carbonitrile 2-Pyrrolidinecarbonitrile, 1-(((3-hydroxytricyclo(,7)dec-1-yl)amino)acetyl)-, (2S)- 2-Pyrrolidinecarbonitrile, 1-[2-[(3-hydroxytricyclo[]dec-1-yl)amino]acetyl]-, (2S)- Galvus Laf 237 Unii-I6B4B2U96p Vidagliptin (see vildagliptin) Vildagliptin (NVP-LAF 237)

1.3 CAS No.
1.4 CID
1.6 Molecular Formula
C17H25N3O2 (isomer)
1.7 Inchi
1.8 InChkey
1.9 Canonical Smiles
1.10 Isomers Smiles
2. Properties
2.1 Density
2.1 Melting point
2.1 Boiling point
531.3 °C at 760 mmHg
2.1 Flash Point
275.1 °C
2.1 Precise Quality
2.1 PSA
2.1 logP
2.1 Appearance
white crystalline powder
2.2 Storage
-20°C Freezer
2.3 Chemical Properties
White Solid
2.4 Color/Form
2.5 Physical
2.6 pKa
2.7 StorageTemp
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
3. Use and Manufacturing
3.1 GHS Classification
Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 9 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H302 (33.33%): Harmful if swallowed [Warning Acute toxicity, oral]
H312 (22.22%): Harmful in contact with skin [Warning Acute toxicity, dermal]
H332 (22.22%): Harmful if inhaled [Warning Acute toxicity, inhalation]
H373 (11.11%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]
H413 (55.56%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P260, P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P314, P322, P330, P363, and P501
3.2 Usage
Glyptins are class of oral anti-hyperglycemic agents that inhibit dipeptidyl peptidase 4 (DPP-4), which can act as a serine exopeptidase. Aside from their use in type 2 diabetes, gliptins have positive cardiovascular and anti-inflammtatory effects. Antidiabetic.
4. Safety and Handling
4.1 Risk Statements
4.1 Safety Statements

2.Hazard identification

2.1 Classification of the substance or mixture

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 4

2.2 GHS label elements, including precautionary statements

Pictogram(s) No symbol.
Signal word

No signal word.

Hazard statement(s)

H413 May cause long lasting harmful effects to aquatic life

Precautionary statement(s)

P273 Avoid release to the environment.






P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification


6. Synthesis Route
8. Other Information
8.0 Target
8.1 DPP-4 (Cell-free assay)
2.3 nM
8.2 Uses
Glyptins are class of oral anti-hyperglycemic agents that inhibit dipeptidyl peptidase 4 (DPP-4), which can act as a serine exopeptidase. Aside from their use in type 2 diabetes, gliptins have positive cardiovascular and anti-inflammtatory effects. Antidiabetic.
8.3 Indications and Usage
Vildagliptin (vildagliptin), developed by Novartis (Novartis) Pharmaceutical Co., Ltd, is another oral administrated inhibitor of Dipeptidyl peptidase-IV after sitagliptin (sitagliptin). In 2008, it is approved for marketing in the European Union for the treatment of type 2 diabetes.
Diabetes is a chronic metabolic disease with its prevalence being increased year by year. Type 2 diabetes is a complicated diseases caused with the combined action between polygenic genetic factors and environmental factors.
Dipeptidyl peptidase IV (DPP-IV) inhibitors are a new class of anti-diabetic drugs which induces and facilitate the biosynthesis and secretion of insulin. It plays a role in lowering the blood carbohydrate concentration through multiple mechanisms such as inhibiting the β cell apoptosis, inhibiting glucagon secretion and reducing food intake. During its lowering effect on reducing blood carbohydrate levels, it can also reverse the situation of deteriorating function of pancreas islet for diabetic patients at the same time. Vildagliptin is the representative of drugs among the dipeptidyl peptidase inhibitor. It exhibited a good anti-diabetic effects and tolerance no matter whether it is being administered alone or in combination with metformin and insulin medication in clinical studies.
8.4 Mechanisms of Action
Vildagliptin is a selective, competitive and reversible DPP-4 inhibitor. Glucose-dependent insulinotropic polypeptide (GIP) and glucagon-like peptide 21 (GLP21) are important hormones that regulate body glucose concentration and have the same functions as intestinal insulin. Type-2 diabetes patients suffer from GIP insulin secretion failure, so only their GLP21 can promote insulin secretion by affecting receptors on islet beta cell membranes. GLP21 can also inhibit glucagon secretion and inhibit gastric clearing to extend the feeling of fullness (control appetite). DPP-4 binds with proteins in many types of tissues, including tissue in the kidney, liver, small intestine brush border, pancreatic duct, lymph cells, and endothelial cells, and it can deactivate GLP21 by hydrolyzing its N-terminal position-2 alanine. Vildagliptin binds with DPP-4 to produce a DPP-4 compound and inhibit its activity. It increases GLP21 concentration and promotes islet beta cells to produce insulin, while also lowering glucagon concentration, thus lowering blood sugar. Vildagliptin has not noticeable effects on weight.
8.5 Adverse reactions
Most common adverse reactions include headache, nasopharyngitis, coughing, constipation, dizziness and excess sweating. There have been very rare cases of hypotension, but it is unclear if conditions are related to this drug. Almost all research shows that the hypoglycemia occurrence rate while using Vildagliptin is similar to the rate when using a placebo. Control trials showed that compared to thiazolidinediones, Vildagliptin causes a similar occurrence rate of headaches, rashes, and other adverse reactions, but Vildagliptin has a lower occurrence rate of adverse reactions forcing patients to cease treatment and of severe adverse reactions.
8.6 Description
Vildagliptin, a DPP-4 inhibitor, was launched for the oral treatment of type 2 diabetes. Vildagliptin is the second DPP-4 inhibitor to reach the market behind sitagliptin, which was introduced in 2006. DPP-4 inhibitors act by slowing the inactivation of incretins, which are endogenous peptides involved in the physiologic regulation of glucose homeostasis. When blood glucose concentrations are normal or elevated, GLP-1 and GIP increase the synthesis and release of insulin from pancreatic βcells via intracellular signaling pathways involving cAMP. GLP-1 also lowers glucagon secretion from pancreatic α cells, which leads to reduced hepatic glucose production. However, although GLP-1 and GIP effectively lower blood glucose, they are short-lived as a result of rapid inactivation by the ubiquitous serine protease DPP-4. By inhibiting DPP-4, vildagliptin increases the concentration and duration of active incretin levels, which in turn results in increased insulin release and decreased glucagon levels in a glucose-dependent manner. Both vildagliptin and sitagliptin are potent, competitive, reversible inhibitors of DPP- 4 (IC50=3.5 and 18 nM, respectively), and they both show slow, tight-binding inhibition kinetics.
8.7 Chemical Properties
White Solid
8.8 Originator
Novartis (US)
8.9 Uses
Vildagliptin (LAF-237) inhibits DPP?4 with IC50 of 2.3 nM
8.10 Uses
The major metabolite of Vildagliptin
8.11 Uses
Labelled Vildagliptin. It is a new oral anti-hyperglycemic agent of a new dipeptidyl peptidase-IV (DPP-IV) inhibitor class of drugs. Antidiabetic.
8.12 Uses
A metabolite of Vildagliptin
8.13 Brand name
8.14 Side effects
The most common adverse events reported in patients receiving vildagliptin included headache, nasopharyngitis, cough, constipation, dizziness, and increased sweating. Vildagliptin is not recommended for patients with liver impairment.
8.15 Chemical Synthesis
Vildagliptin is chemically derived in three steps starting from L-prolinamide via acylation with chloroacetyl chloride to produce 1-(chloroacetyl)-L-prolinamide, subsequent dehydration of the carboxamide group to the nitrile with trifluoroacetic anhydride, and condensation of the 1-(chloroacetyl)-L-prolinenitrile intermediate with 3-hydroxyadamantan-1-amine.
8.16 Mesh
Compounds that suppress the degradation of INCRETINS by blocking the action of DIPEPTIDYL-PEPTIDASE IV. This helps to correct the defective INSULIN and GLUCAGON secretion characteristic of TYPE 2 DIABETES MELLITUS by stimulating insulin secretion and suppressing glucagon release. (See all compounds classified as Dipeptidyl-Peptidase IV Inhibitors.)|Substances which lower blood glucose levels. (See all compounds classified as Hypoglycemic Agents.)
8.17 Mesh Entry Terms
8.18 Use Classification
Human drugs -> Galvus -> EMA Drug Category|Drugs used in diabetes -> Human pharmacotherapeutic group|Human drugs -> Xiliarx -> EMA Drug Category|Human drugs -> Eucreas -> EMA Drug Category|Drugs used in diabetes, Combinations of oral blood glucose lowering drugs -> Human pharmacotherapeutic group|Human drugs -> Zomarist -> EMA Drug Category|Human drugs -> Icandra (previously Vildagliptin / metformin hydrochloride Novartis) -> EMA Drug Category|Human drugs -> Jalra -> EMA Drug Category|Drugs used in diabetes, Dipeptidyl peptidase 4 (DPP-4) inhibitors -> Human pharmacotherapeutic group|Human Drugs -> EU pediatric investigation plans
9. Computational chemical data
  • Molecular Weight: 303.406g/mol
  • Molecular Formula: C17H25N3O2
  • Compound Is Canonicalized: True
  • XLogP3-AA: 0.9
  • Exact Mass: 303.19467705
  • Monoisotopic Mass: 303.19467705
  • Complexity: 523
  • Rotatable Bond Count: 3
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Topological Polar Surface Area: 76.4
  • Heavy Atom Count: 22
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count: 2
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
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