Nateglinide

Modify Date: 2024-01-02 11:55:09

Nateglinide Structure
Nateglinide structure
 Common Name Nateglinide
CAS Number 105816-04-4 Molecular Weight 317.423
Density 1.1±0.1 g/cm3 Boiling Point 527.6±39.0 °C at 760 mmHg
Molecular Formula C19H27NO3 Melting Point 137-141ºC
MSDS Chinese USA Flash Point 272.9±27.1 °C

 Use of Nateglinide


Nateglinide is an insulin secretagog agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM).Target: OthersNateglinide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It belongs to the meglitinide class of short-acting insulin secretagogues, which act by binding to β cells of the pancreas to stimulate insulin release. Nateglinide is an amino acid derivative that induces an early insulin response to meals decreasing postprandial blood glucose levels. It should only be taken with meals and meal-time doses should be skipped with any skipped meal. Approximately one month of therapy is required before a decrease in fasting blood glucose is seen. Meglitnides may have a neutral effect on weight or cause a slight increase in weight. The average weight gain caused by meglitinides appears to be lower than that caused by sulfonylureas and insulin and appears to occur only in those na?ve to oral antidiabetic agents. Due to their mechanism of action, meglitinides may cause hypoglycemia although the risk is thought to be lower than that of sulfonylureas since their action is dependent on the presence of glucose. In addition to reducing postprandial and fasting blood glucose, meglitnides have been shown to decrease glycosylated hemoglobin (HbA1c) levels, which are reflective of the last 8-10 weeks of glucose control. Meglitinides appear to be more effective at lowering postprandial blood glucose than metformin, sulfonylureas and thiazolidinediones. Nateglinide is extensively metabolized in the liver and excreted in urine (83%) and feces (10%). The major metabolites possess less activity than the parent compound. One minor metabolite, the isoprene, has the same potency as its parent compound [1-3].

 Names

Name nateglinide
Synonym More Synonyms

 Nateglinide Biological Activity

Description Nateglinide is an insulin secretagog agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM).Target: OthersNateglinide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It belongs to the meglitinide class of short-acting insulin secretagogues, which act by binding to β cells of the pancreas to stimulate insulin release. Nateglinide is an amino acid derivative that induces an early insulin response to meals decreasing postprandial blood glucose levels. It should only be taken with meals and meal-time doses should be skipped with any skipped meal. Approximately one month of therapy is required before a decrease in fasting blood glucose is seen. Meglitnides may have a neutral effect on weight or cause a slight increase in weight. The average weight gain caused by meglitinides appears to be lower than that caused by sulfonylureas and insulin and appears to occur only in those na?ve to oral antidiabetic agents. Due to their mechanism of action, meglitinides may cause hypoglycemia although the risk is thought to be lower than that of sulfonylureas since their action is dependent on the presence of glucose. In addition to reducing postprandial and fasting blood glucose, meglitnides have been shown to decrease glycosylated hemoglobin (HbA1c) levels, which are reflective of the last 8-10 weeks of glucose control. Meglitinides appear to be more effective at lowering postprandial blood glucose than metformin, sulfonylureas and thiazolidinediones. Nateglinide is extensively metabolized in the liver and excreted in urine (83%) and feces (10%). The major metabolites possess less activity than the parent compound. One minor metabolite, the isoprene, has the same potency as its parent compound [1-3].
Related Catalog
References

[1]. http://205.193.93.51/dpdonline/searchRequest.dodin=2245439

[2]. http://www.drugs.com/cdi/nateglinide.html

[3]. http://www.drugbank.ca/drugs/DB00731

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 527.6±39.0 °C at 760 mmHg
Melting Point 137-141ºC
Molecular Formula C19H27NO3
Molecular Weight 317.423
Flash Point 272.9±27.1 °C
Exact Mass 317.199097
PSA 66.40000
LogP 4.21
Vapour Pressure 0.0±1.5 mmHg at 25°C
Index of Refraction 1.536
Storage condition Room temp

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
SQ7318950
CHEMICAL NAME :
D-Phenylalanine, N-((4-(1-methylethyl)cyclohexyl)carbonyl)-, trans-
CAS REGISTRY NUMBER :
105816-04-4
LAST UPDATED :
199806
DATA ITEMS CITED :
7

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - ptosis Behavioral - somnolence (general depressed activity) Gastrointestinal - hypermotility, diarrhea
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 25(Suppl 1),S5,1997
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Gastrointestinal - nausea or vomiting
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 25(Suppl 1),S9,1997 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
90 gm/kg/13W-I
TOXIC EFFECTS :
Endocrine - changes in adrenal weight Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 25(Suppl 1),S13,1997
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
182 gm/kg/52W-I
TOXIC EFFECTS :
Gastrointestinal - changes in structure or function of salivary glands Gastrointestinal - ulceration or bleeding from stomach Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 25(Suppl 1),S63,1997
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
27300 mg/kg/13W-I
TOXIC EFFECTS :
Gastrointestinal - changes in structure or function of salivary glands Liver - change in gall bladder structure or function Related to Chronic Data - death
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 25(Suppl 1),S35,1997
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
36400 mg/kg/52W-I
TOXIC EFFECTS :
Gastrointestinal - changes in structure or function of salivary glands
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 25(Suppl 1),S79,1997 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
27 gm/kg
SEX/DURATION :
female 17-22 day(s) after conception lactating female 1-21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 25(Suppl 1),S139,1997

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xn: Harmful;
Risk Phrases R22
Safety Phrases 24/25-36
RIDADR NONH for all modes of transport
RTECS SQ7318950
HS Code 2924299090

 Synthetic Route

 Customs

HS Code 2924299090
Summary 2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

 Articles50

More Articles
Formulation and in vitro evaluation of nateglinide microspheres using HPMC and carbopol-940 polymers by ionic gelation method.

Pak. J. Pharm. Sci. 26(6) , 1229-35, (2013)

This study involves the design and characterization of Nateglinide (NAT) microspheres to enhance patient compliance. Ionic gelation technique was used to prepare Nateglinide Microspheres by using rate...

From evidence assessments to coverage decisions?: the case example of glinides in Germany.

Health Policy 104(1) , 27-31, (2012)

In Germany, coverage decisions in the statutory health insurance (SHI) system are based on the principles of evidence-based medicine. Recently, an evidence assessment by the Institute for Quality and ...

Nateglinide--current and future role in the treatment of patients with type 2 diabetes mellitus.

Int. J. Clin. Pract. 59(10) , 1218-28, (2005)

Therapy for type 2 diabetes mellitus should aim to control not only fasting, but also postprandial glucose levels. Nateglinide, a d-phenylalanine derivative, restores postprandial early phase insulin ...

 Synonyms

Glinate
Starsis
SDZ DJN 608
Starlix
(2R)-2-{[(trans-4-Isopropylcyclohexyl)carbonyl]amino}-3-phenylpropanoic acid
N-{[trans-4-(1-methylethyl)cyclohexyl]carbonyl}-D-phenylalanine
(-)-N-(trans-4-Isopropylcyclohexanecarbonyl)-D-phenylalanine
(2R)-2-({[trans-4-(1-methylethyl)cyclohexyl]carbonyl}amino)-3-phenylpropanoic acid
DJN 608
Natelide
N-[[trans-4-(1-Methylethyl)cyclohexyl]carbonyl]-D-phenylalanine
N-{[trans-4-(Propan-2-yl)cyclohexyl]carbonyl}-D-phenylalanin
MFCD00875706
ay4166
Starlix DS
Fastic-d5
A-4166
Fastic
D-Phenylalanine, N-[[trans-4-(1-methylethyl)cyclohexyl]carbonyl]-
N-[(trans-4-Isopropylcyclohexyl)carbonyl]-D-phenylalanine
(-)-N-(trans-4-Isopropylcyclohexyl-1-carbonyl)-D-phenylalanine
Nateglinide
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Related Compounds: More...
Nateglinide
105746-37-0
L-Nateglinide
105816-05-5
Nateglinide-d5
1227666-13-8
Nateglinide Ethyl Ester
187728-85-4
Nateglinide Methyl Ester
105746-47-2
D-Phenylalanyl Nateglinide
944746-48-9
D-Phenylalanyl-d5 nateglinide
1356354-42-1
Nateglinide Related CoMpound C
105816-06-6
Nateglinide Acyl--D-glucuronide
183996-85-2
(1-Bromo-2-cyclohexylethyl)benzene
1339191-70-6
4-((Cyclohexylamino)methyl)benzoic acid hydrochloride
1158522-08-7
1-[(2,4-Dichlorophenyl)methyl]-N-(1,1-dimethylethyl)-2-methyl-1H-indole-3-methanamine
940364-43-2
Methyl 5-(4-morpholinylsulfonyl)-2-[(phenylmethyl)oxy]benzoate
1285516-72-4
2-(2,3-Dimethoxyphenyl)-5-methyl-1H-benzo[d]imidazole
1305744-46-0
2-Methoxy-6-(pyrazol-1-yl)-benzonitrile
134104-43-1
1H-3-Benzazepin-7-ol, 8-chloro-2,3,4,5-tetrahydro-5-(3-iodophenyl)-3-methyl-, (S)-
131615-57-1
{1-[(2-Methyl-1,3-thiazol-5-yl)methyl]cyclopropyl}methanamine
1464886-25-6
(4-Methyl-tetrahydro-furan-2-yl)-methanol
6906-52-1
N-(1-cyanocyclopentyl)-2-[4-(4-fluorobenzenesulfonyl)-1,4-diazepan-1-yl]acetamide
930439-75-1
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