Physical and Chemical Properties Hypoglycemic agents Uses
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Nateglinide

Physical and Chemical Properties Hypoglycemic agents Uses
Product Name
Nateglinide
CAS No.
105816-04-4
Chemical Name
Nateglinide
Synonyms
STARLIX;N-(Trans-4-Isopropylcyclohexyl-1-Carbonyl)-D-Phenylalamine;ay4166;A-4166;Fastic;Glinate;DJN 608;Starsis;Natelide;Fastic-d5
CBNumber
CB9472923
Molecular Formula
C19H27NO3
Formula Weight
317.42
MOL File
105816-04-4.mol
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Nateglinide Property

Melting point:
137-141°C
alpha 
D20 -9.4° (c = 1 in methanol)
Boiling point:
527.6±39.0 °C(Predicted)
Density 
1.104±0.06 g/cm3(Predicted)
storage temp. 
room temp
solubility 
DMSO: >5mg/mL
pka
3.61±0.10(Predicted)
form 
solid
color 
white to off-white
Merck 
14,6428
CAS DataBase Reference
105816-04-4(CAS DataBase Reference)
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Safety

Hazard Codes 
Xn
Risk Statements 
22
Safety Statements 
24/25-36
WGK Germany 
3
RTECS 
SQ7318950
HS Code 
29242990
Toxicity
LD50 orally in rats: >2.0 g/kg (Hasegawa)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H361Suspected of damaging fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P281Use personal protective equipment as required.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
N3538
Product name
Nateglinide
Purity
≥98% (HPLC), solid
Packaging
10mg
Price
$105.2
Updated
2024/03/01
Sigma-Aldrich
Product number
1457607
Product name
Nateglinide
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$393
Updated
2024/03/01
TCI Chemical
Product number
N0912
Product name
Nateglinide
Purity
>98.0%(HPLC)(T)
Packaging
500mg
Price
$42
Updated
2024/03/01
TCI Chemical
Product number
N0912
Product name
Nateglinide
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$50
Updated
2024/03/01
Cayman Chemical
Product number
23320
Product name
Nateglinide
Purity
≥98%
Packaging
250mg
Price
$44
Updated
2024/03/01
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Nateglinide Chemical Properties,Usage,Production

Physical and Chemical Properties

White or almost white crystalline powder, odorless, bitter taste. It is soluble in methanol, ethanol, chloroform, dissolved in acetone, ethyl ether, almost insoluble in water. Valid form used in clinic is H-type, mp 137~141 ℃. [Α] D-37.5 °, the maximum UV absorption wavelength in methanol is 252,257,263nm.
The above information is edited by the chemicalbook of Tian Ye.

Hypoglycemic agents

Nateglinide and mitiglinide, repaglinide are three commonly used non-sulfonylurea oral hypoglycemic agents for insulin secretion,it is successfully developed for the first time by the Japanese company Ajomoto , its chemical structure belongs to carbamoylmethyl-benzoic acid (CMBA), it belongs to D-phenylalanine derivatives, it is a new generation of antidiabetic drugs having amino acid structure ,it is an amino acid derivative prompting insulin secretion, it is also currently the only non-sulfonylureas insulinotropic agent having amino acid structure. The mechanism is mainly through binding the pancreatic β cell sulfonylurea receptor, blocking islet cell ATP-sensitive potassium channels, leading to membrane depolarization, causing the calcium channe lopen to promote insulin secretion. This product is a new type of meal blood glucose regulator, which can effectively control the postprandial blood glucose levels, with rapid onset, short duration of action, low incidence of cardiovascular side effects and hypoglycemia and other characteristics.
Oral bioavailability is 72%, after 15min it can produce insulin secretion effect, Tmax is 0.5~0.9 h, 0.2 h insulin levels achieve peak ,after 1.5 h it is similar to placebo. The plasma protein binding rate is 99%. After reaching plasmapeak , plasma concentrations decline rapidly.T1/2 of oral administration of 120 mg and intravenous injection 60 mg of is 1.5 to 1.7 hours, and the plasma clearance is 7.4 hours. It is metabolized in the liver by isoenzyme CYP2C9 and CYP3A4 way. The main metabolites are products after isomeric oxidation,it can be hydroxyl, diastereomers, isopropyl isomer or unsaturated aliphatic isomers.The main metabolites in plasma and urine are metabolites after the hydroxylation of isopropyl methine family (me-thine carbon) . About 2/3 nateglinide is excreted from the fecal , and the rest is excreted in the urine. Such excretion way is beneficial to elderly Ⅱ diabetes mellitus with renal dysfunction. nateglinide eliminate T1/2 is 1.4 h, because nateglinide T1/2 is short, there is no report yet about the drug accumulation in the body . Long-term use of nateglinide does not produce drug-induced hypoglycemia caused by drug accumulation .It is used for the treatment of diet therapy, exercise therapy and mild to moderate non-insulin dependent (Ⅱ type) diabetes which taking α-glucosidase inhibitor can not control. The results show that: nateglinide can be used more physiologically for meal glucose control, there is less opportunity for contact with insulin and hypoglycemia which allows patients to flexibly plan scheduling mealtimes, which means there is medication while eating, not eating no medication.

Uses

It is used for the treatment of diabetes

Description

Nateglinide is a N-acylated D-phenylalanine marketed in Japan as novel orally active insulinotropic agent for the treatment of type-2 diabetes mellitus. It belongs to the class of nonsulfonylureas and shows some structural similarity to repaglinide, the only other representative in this family. In single pancreatic beta-cells isolated from rats, Nateglinide was found to specifically block the ATP-sensitive K+ channel resulting in an increase in intracellular calcium concentration. This primary action would underlie the mechanism by which Nateglinide markedly stimulates or potentiates, depending on glucose concentrations, insulin secretion from pancreatic beta-cells. Clinical studies demonstrated a good safety profile with a low potential for hypoglycemia. The pharmacokinetic profile was consistent with the changes of the blood glucose and plasma insulin level. Interestingly, Nateglinide exerts a rapid onset and short duration of action due to a rapid absorption and clearance. Unlike other similar agents, Nateglinide suppresses postprandial glucose elevations.

Chemical Properties

Cyrstalline Solid

Originator

Ajinomoto (Japan)

Uses

antidiabetic KATP channel blocker

Uses

An amino-acid derivative that stimulates insulin secretion. Used as an antidiabetic.

Definition

ChEBI: An N-acyl-D-phenylalanine resulting from the formal condensation of the amino group of D-phenylalanine with the carboxy group of trans-4-isopropylcyclohexanecarboxylic acid. An orally-ad inistered, rapidly-absorbed, short-acting insulinotropic agent, it is used for the treatment of type 2 diabetes mellitus.

brand name

Starlix (Novartis);Fastic;Starsis.

General Description

Although nateglinide, N-(4-isopropylcyclohexanecarbonyl)-D-phenylalanine (Starlix), belongs tothe metaglinides, it is a phenylalanine derivative and representsa novel drug in the management of type 2 diabetes.

General Description

Nateglinide (Starlix) is D-Phenylalanine, N-[[trans-4-(1-methylethyl)cyclohexyl]carbonyl]-; or (-)-N-[(trans-4-isopropylcyclohexyl)carbonyl]-D-phenylalanine. Itis noteworthy that, although nateglinide is much less potenton a dosage basis than is repaglinide and most of the sulfonylureas,this drug seems to exhibit unique molecularpharmacodynamics. Nateglinide closes ATP-sensitive K channels some threefold more rapidly than repaglinide, andexhibits an off-rate twice as fast as that of glyburide orglimepiride and five times faster than repaglinide. Thesecharacteristics are reflected by the systemic pharmacodynamicsof this drug, translating clinically to improvedsafety, among other apparent benefits.

Biochem/physiol Actions

Nateglinide is a Kir6.2/SUR1 channel inhibitor and antidiabetic. It is selective for the SUR1 subtype, which is found on pancreatic islet cells. Nateglinide evokes KATP channel-dependent insulin secretion (50-200 μM) in the absence and presence of insulin.

Mechanism of action

Approved in the United States in late 2000, nateglinide is a rapidly absorbed insulin secretagogue that has a mechanism of action similar to that of repaglinide, with effects appearing within 20 minutes following oral dosing. Bioavailability is 73%, and it is 98% protein bound, primarily to albumin. Nateglinide is tissue selective, with low affinity for cardiac and skeletal muscle.

Clinical Use

Treatment of type 2 diabetes in combination with metformin

Drug interactions

Potentially hazardous interactions with other drugs
Antibacterials: concentration reduced by rifampicin.
Antifungals: hypoglycaemic effect possibly enhanced by fluconazole.
Lipid-lowering agents: hypoglycaemic effect possibly enhanced by gemfibrozil.

Metabolism

It is metabolized in the liver, with 16% excreted in the urine unchanged. The major metabolites are hydroxyl derivatives (CYP2C9, 70%; CYP3A4, 30%) that are further conjugated to the glucuronide derivatives.

storage

Store at RT

Nateglinide Preparation Products And Raw materials

Raw materials

Preparation Products

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Nateglinide Suppliers

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View Lastest Price from Nateglinide manufacturers

HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
Nateglinide 105816-04-4
Price
US $999.00-800.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000
Release date
2024-08-21
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Nateglinide 105816-04-4
Price
US $0.00-0.00/Kg/Drum
Min. Order
1KG
Purity
99%min
Supply Ability
1000kg
Release date
2021-09-10
Hebei Weibang Biotechnology Co., Ltd
Product
Nateglinide 105816-04-4
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
500000kg
Release date
2024-11-01

105816-04-4, NateglinideRelated Search:

Phenyl salicylate Diphenyl ether PHENYL VALERATE D-Phenylalanine DL-Phenylalanine Propionic acid Phenprobamate Propane Bis(cyclohexanone)oxaldihydrazone Repaglinide Glimepiride PHENYL RESIN Phenylacetic acid N-ACETYL-D-PHENYLALANINE Mitiglinide calcium dihydrate (S)-3-Methyl-1-(2-piperidin-1-ylphenyl)butylamine REPAGLINIDE RELATED COMPOUND C (25 MG) ((S)-2-ETHOXY-4-[2-[[2-PHENYL-1 -[2-(1 -PIPERIDINYL)PHE-NYL]ETHYL]AMINO]-2-OXOETHYL] BENZOIC ACID) cis-Octahydroisoindole

  • (-)-n-(trans-4-isopropylcyclohexanecarbonyl)-d-phenylalanine
  • ay4166
  • Nateglinide(H)
  • trans-d-phenylalanin
  • N-(Trans-4-Isopropylcyclohexyl-1-Carbonyl)-D-Phenylalamine
  • trans-d-phenylalanine
  • NATAGLINIDE
  • Nateglinide (200 mg)
  • Glinate
  • Natelide
  • AY 4166-d5
  • DJN 608-d5
  • D-Nateglinide-d5
  • Fastic-d5
  • Glinate-d5
  • N-[[trans-4-(1-Methylethyl)cyclohexyl]carbonyl]-D-phenylalanine-d5
  • Natelide-d5
  • SDZ-DJN 608-d5
  • Senaglinide-d5
  • Starlix DS-d5
  • Starlix-d5
  • Starsis-d5
  • Nateglinide (Starlix)
  • Nateglinide(A-4166)
  • (R)-2-((1r,4R)-4-isopropylcyclohexanecarboxamido)-3-phenylpropanoic acid
  • Nateglinide(3-Phenyl-2-(4-propan-2-ylcyclohexyl)carbonylamino-propanoicacid)
  • Fastic, N-[(trans-4-Isopropylcyclohexyl)carbonyl]-D-phenylalanine, Starlix, Starsis
  • N-(4α-Isopropylcyclohexane-1β-yl)carbonyl-D-phenylalanine
  • N-[[4α-(1-Methylethyl)cyclohexan-1β-yl]carbonyl]-D-phenylalanine
  • N-[[4β-(1-Methylethyl)cyclohexan-1α-yl]carbonyl]-D-phenylalanine
  • Nateglinide Solution, 100ppm
  • N-[[4-(1-Methylethyl)cyclohexyl]carbonyl]-D-phenylalanine
  • (2R)-2-[[oxo-(4-propan-2-ylcyclohexyl)methyl]amino]-3-phenylpropanoic acid
  • trans-n-((4-(1-methylethyl)cyclohexyl)carbonyl)-d-phenylalanine
  • 3-phenyl-2-(4-propan-2-ylcyclohexyl)carbonylamino-propanoic acid
  • A-4166
  • STARLIX
  • N-[[TRANS-4-(1-METHYLETHYL)CYCLOHEXYL]CARBONYL]-D-PHENYLALANINE
  • NATEGLINIDE
  • Nagteglinide
  • Nagelienai nateglinide
  • Nateglinide intermediate
  • N-(trans-4-isopropylcyclohexylcarbonyl)-D-phenylamine
  • Starlix, A-4166, N-[[trans-4-(1-methylethyl)cyclohexyl]carbonyl]-D-phenylalanine,
  • H-TYPE NATEGLINIDE
  • N-(TRANE-4-ISO-PROPYLCYLOLOHEXYLCARBOXYL)-D-PHENYLPROPYLICACID(NATEGLINIDE)
  • DJN 608
  • D-Nateglinide
  • D-Phenylalanine, N-[[4-(1-methylethyl)cyclohexyl]carbonyl]-, trans-
  • D-Phenylalanine, N-[[trans-4-(1-methylethyl)cyclohexyl]carbonyl]- (9CI)
  • Fastic
  • SDZ-DJN 608
  • Senaglinide
  • Starlix DS
  • Starsis
  • n-(trans-4-Isopropylcylolohexylcarboxyl)-d-phenylpropylicacid
  • Nateglinide 105816-04-4 CAS NO.105816-04-4
  • Nateglinide, 98%, an insulin secretagog agent