Home Other Building Blocks Saxagliptin hydrate

Saxagliptin hydrate

CAS No.:
945667-22-1
Catalog Number:
AG003A9U
Molecular Formula:
C18H27N3O3
Molecular Weight:
333.4253
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Purity
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Product Description
Catalog Number:
AG003A9U
Chemical Name:
Saxagliptin hydrate
CAS Number:
945667-22-1
Molecular Formula:
C18H27N3O3
Molecular Weight:
333.4253
MDL Number:
MFCD26131254
IUPAC Name:
(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxy-1-adamantyl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile;hydrate
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/t10?,11?,12-,13+,14+,15-,17?,18?;/m1./s1
InChI Key:
AFNTWHMDBNQQPX-NHKADLRUSA-N
SMILES:
N#C[C@@H]1C[C@H]2[C@@H](N1C(=O)[C@H](C13CC4CC(C1)CC(C3)(C4)O)N)C2.O
UNII:
9GB927LAJW
Properties
Complexity:
609  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
2  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
0
Exact Mass:
333.205g/mol
Formal Charge:
0
Heavy Atom Count:
24  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
333.432g/mol
Monoisotopic Mass:
333.205g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
91.4A^2
Undefined Atom Stereocenter Count:
2  
Undefined Bond Stereocenter Count:
0
Literature
Title Journal
Saxagliptin: a novel antiparkinsonian approach. Neuropharmacology 20150201
Saxagliptin overview: special focus on safety and adverse effects. Expert opinion on drug safety 20130101
Development of a rapid UPLC-MS/MS method for quantification of saxagliptin in rat plasma and application to pharmacokinetic study. Biomedical chromatography : BMC 20121201
Safety of saxagliptin: rationale for and design of a series of postmarketing observational studies. Pharmacoepidemiology and drug safety 20121101
Quantitative model of the relationship between dipeptidyl peptidase-4 (DPP-4) inhibition and response: meta-analysis of alogliptin, saxagliptin, sitagliptin, and vildagliptin efficacy results. Journal of clinical pharmacology 20121001
Effects of saxagliptin and sitagliptin on glycaemic control and pancreatic β-cell mass in a streptozotocin-induced mouse model of type 2 diabetes. Diabetes, obesity & metabolism 20121001
Effects of saxagliptin added to sub-maximal doses of metformin compared with uptitration of metformin in type 2 diabetes: the PROMPT study. Current medical research and opinion 20121001
Overcoming bioanalytical challenges in an Onglyza(®) intravenous [(14)C]microdose absolute bioavailability study with accelerator MS. Bioanalysis 20120801
Cost-effectiveness of saxagliptin (Onglyza®) in type 2 diabetes in Sweden. Primary care diabetes 20120701
Characterization of the in vitro and in vivo metabolism and disposition and cytochrome P450 inhibition/induction profile of saxagliptin in human. Drug metabolism and disposition: the biological fate of chemicals 20120701
Pharmacokinetic study of saxagliptin in healthy Chinese subjects. Clinical drug investigation 20120701
Drug-induced hypoglycaemia in type 2 diabetes. Expert opinion on drug safety 20120701
Saxagliptin and sitagliptin in adult patients with type 2 diabetes: a systematic review and meta-analysis. Diabetes, obesity & metabolism 20120601
An update in incretin-based therapy: a focus on dipeptidyl peptidase--4 inhibitors. Current diabetes reviews 20120501
Adding saxagliptin to extended-release metformin vs. uptitrating metformin dosage. Diabetes, obesity & metabolism 20120401
DPP-4 inhibitors in the management of type 2 diabetes: a critical review of head-to-head trials. Diabetes & metabolism 20120401
Effect of saxagliptin as add-on therapy in patients with poorly controlled type 2 diabetes on insulin alone or insulin combined with metformin. Current medical research and opinion 20120401
Dipeptidyl peptidase-4 inhibitors: 3 years of experience. Diabetes technology & therapeutics 20120401
Liquid chromatography and tandem mass spectrometry method for the quantitative determination of saxagliptin and its major pharmacologically active 5-monohydroxy metabolite in human plasma: method validation and overcoming specific and non-specific binding at low concentrations. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20120315
Efficacy and safety of saxagliptin in drug-naïve Asian patients with type 2 diabetes mellitus: a randomized controlled trial. Diabetes/metabolism research and reviews 20120301
Saxagliptin for the treatment of type 2 diabetes mellitus: focus on recent studies. Annals of medicine 20120301
Cost effectiveness of saxagliptin and metformin versus sulfonylurea and metformin in the treatment of type 2 diabetes mellitus in Germany: a Cardiff diabetes model analysis. Clinical drug investigation 20120301
Saxagliptin plus metformin combination in patients with type 2 diabetes and renal impairment. Expert opinion on drug metabolism & toxicology 20120301
Saxagliptin: a review of its use as combination therapy in the management of type 2 diabetes mellitus in the EU. Drugs 20120122
The cost-effectiveness of saxagliptin versus NPH insulin when used in combination with other oral antidiabetes agents in the treatment of type 2 diabetes mellitus in Poland. Diabetes technology & therapeutics 20120101
Metformin + saxagliptin for type 2 diabetes. Expert opinion on pharmacotherapy 20120101
A pharmacometric approach to quantify the impact of chronic kidney disease and hemodialysis on systemic drug exposure: application to saxagliptin. Journal of clinical pharmacology 20120101
Saxagliptin for the treatment of type 2 diabetes mellitus: assessing cardiovascular data. Cardiovascular diabetology 20120101
A protocol for active surveillance of acute myocardial infarction in association with the use of a new antidiabetic pharmaceutical agent. Pharmacoepidemiology and drug safety 20120101
Potency, selectivity and prolonged binding of saxagliptin to DPP4: maintenance of DPP4 inhibition by saxagliptin in vitro and ex vivo when compared to a rapidly-dissociating DPP4 inhibitor. BMC pharmacology 20120101
Cost-effectiveness and budget impact of saxagliptine as additional therapy to metformin for the treatment of diabetes mellitus type 2 in the Brazilian private health system. Revista da Associacao Medica Brasileira (1992) 20120101
Kinetic and mechanistic insight into the thermodynamic degradation of saxagliptin. The Journal of organic chemistry 20111216
Long-term treatment with the dipeptidyl peptidase-4 inhibitor saxagliptin in patients with type 2 diabetes mellitus and renal impairment: a randomised controlled 52-week efficacy and safety study. International journal of clinical practice 20111201
[Incretin-based therapy for treating patients with type 2 diabetes]. Orvosi hetilap 20111127
Efficacy and safety of saxagliptin added to metformin in Asian people with type 2 diabetes mellitus: a randomized controlled trial. Diabetes research and clinical practice 20111101
The design and rationale of the saxagliptin assessment of vascular outcomes recorded in patients with diabetes mellitus-thrombolysis in myocardial infarction (SAVOR-TIMI) 53 study. American heart journal 20111101
[Dipeptidyl-peptidase-4 inhibitors (gliptins): a new class of oral antidiabetic drugs]. Orvosi hetilap 20110911
Effects of saxagliptin on β-cell stimulation and insulin secretion in patients with type 2 diabetes. Diabetes, obesity & metabolism 20110901
Efficacy of saxagliptin as an add-on to oral monotherapy in the phase 3 clinical development program: predictive factors of the treatment response in type 2 diabetes. Annales d'endocrinologie 20110901
Ongoing clinical trials evaluating the cardiovascular safety and efficacy of therapeutic approaches to diabetes mellitus. The American journal of cardiology 20110802
Saxagliptin: a clinical review in the treatment of type 2 diabetes mellitus. Clinical therapeutics 20110801
Saxagliptin, a potent, selective inhibitor of DPP-4, does not alter the pharmacokinetics of three oral antidiabetic drugs (metformin, glyburide or pioglitazone) in healthy subjects. Diabetes, obesity & metabolism 20110701
Effect of rifampicin on the pharmacokinetics and pharmacodynamics of saxagliptin, a dipeptidyl peptidase-4 inhibitor, in healthy subjects. British journal of clinical pharmacology 20110701
Efficacy and safety of saxagliptin combination therapy in US patients with type 2 diabetes. Postgraduate medicine 20110701
Saxagliptin improves glycaemic control and is well tolerated in patients with type 2 diabetes mellitus and renal impairment. Diabetes, obesity & metabolism 20110601
Initial combination therapy with saxagliptin and metformin provides sustained glycaemic control and is well tolerated for up to 76 weeks. Diabetes, obesity & metabolism 20110601
Place in therapy for liraglutide and saxagliptin for type 2 diabetes. Southern medical journal 20110601
Recent diabetes issues affecting the primary care clinician. Southern medical journal 20110601
Enzymatic preparation of 5-hydroxy-L-proline, N-Cbz-5-hydroxy-L-proline, and N-Boc-5-hydroxy-L-proline from (α-N-protected)-L-ornithine using a transaminase or an amine oxidase. Enzyme and microbial technology 20110506
An analysis of the impact of FDA's guidelines for addressing cardiovascular risk of drugs for type 2 diabetes on clinical development. Contemporary clinical trials 20110501
DPP-4 inhibitors: impact on glycemic control and cardiovascular risk factors. Diabetes care 20110501
Efficacy and safety of saxagliptin in older patients with type 2 diabetes mellitus. Current medical research and opinion 20110401
Influence of renal or hepatic impairment on the pharmacokinetics of saxagliptin. Clinical pharmacokinetics 20110401
FDA's first active medical product surveillance eyes antidiabetic-MI link. American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists 20110401
Safety and efficacy of saxagliptin added to thiazolidinedione over 76 weeks in patients with type 2 diabetes mellitus. Diabetes & vascular disease research 20110401
Safety and efficacy of saxagliptin in combination with submaximal sulphonylurea versus up-titrated sulphonylurea over 76 weeks. Diabetes & vascular disease research 20110401
Saxagliptin/metformin (kombiglyze XR) for type 2 diabetes. The Medical letter on drugs and therapeutics 20110321
Incretin therapies in the management of elderly patients with type 2 diabetes mellitus. Hospital practice (1995) 20110201
Saxagliptin. No more effective than other gliptins, but a high potential for drug interactions. Prescrire international 20110201
Focus on incretin-based therapies: targeting the core defects of type 2 diabetes. Postgraduate medicine 20110101
Effect of enhanced glycemic control with saxagliptin on endothelial nitric oxide release and CD40 levels in obese rats. Journal of atherosclerosis and thrombosis 20110101
Bioequivalence of saxagliptin/metformin extended-release (XR) fixed-dose combination tablets and single-component saxagliptin and metformin XR tablets in healthy adult subjects. Clinical drug investigation 20110101
DPP-4 inhibitors: what may be the clinical differentiators? Diabetes research and clinical practice 20101101
Saxagliptin is non-inferior to glipizide in patients with type 2 diabetes mellitus inadequately controlled on metformin alone: a 52-week randomised controlled trial. International journal of clinical practice 20101101
Effect of a high-fat meal on the pharmacokinetics of saxagliptin in healthy subjects. Journal of clinical pharmacology 20101001
Saxagliptin and metformin XR combination therapy provides glycemic control over 24 hours in patients with T2DM inadequately controlled with metformin. Current medical research and opinion 20101001
Efficacy and safety of saxagliptin in combination with metformin compared with sitagliptin in combination with metformin in adult patients with type 2 diabetes mellitus. Diabetes/metabolism research and reviews 20101001
Saxagliptin: a dipeptidyl peptidase-4 inhibitor for the treatment of type 2 diabetes mellitus. American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists 20100915
Dipeptidylpeptidase-4 inhibitors (gliptins): focus on drug-drug interactions. Clinical pharmacokinetics 20100901
Distinguishing among incretin-based therapies. Glucose-lowering effects of incretin-based therapies. The Journal of family practice 20100901
Distinguishing among incretin-based therapies. Safety, tolerability, and nonglycemic effects of incretin-based therapies. The Journal of family practice 20100901
Distinguishing among incretin-based therapies. Patient education and self-management. The Journal of family practice 20100901
Distinguishing among incretin-based therapies. Introduction. The Journal of family practice 20100901
Distinguishing among incretin-based therapies. Pathophysiology of type 2 diabetes mellitus: potential role of incretin-based therapies. The Journal of family practice 20100901
[Saxagliptin (Onglyza): new inhibitor of the dipeptidylpeptidase-4 for the oral treatment of type 2 diabetes]. Revue medicale de Liege 20100901
Managing type 2 diabetes in the primary care setting: beyond glucocentricity. The American journal of the medical sciences 20100801
Pharmacokinetics of dipeptidylpeptidase-4 inhibitors. Diabetes, obesity & metabolism 20100801
Saxagliptin efficacy. Diabetes, obesity & metabolism 20100801
Incretin-based therapies in the management of type 2 diabetes: rationale and reality in a managed care setting. The American journal of managed care 20100801
Saxagliptin: a new drug for the treatment of type 2 diabetes. Mini reviews in medicinal chemistry 20100701
Incretin physiology and its role in type 2 diabetes mellitus. The Journal of the American Osteopathic Association 20100701
Saxagliptin: a new dipeptidyl peptidase 4 inhibitor for type 2 diabetes. The Annals of pharmacotherapy 20100601
A systematic assessment of cardiovascular outcomes in the saxagliptin drug development program for type 2 diabetes. Postgraduate medicine 20100501
Choosing among the incretin agents and why it matters. The Journal of family practice 20100501
[New hypoglycemic agents in type 2 diabetes]. La Revue du praticien 20100420
[DPP-4 inhibitors in clinical use. Therapy without the risk of hypoglycaemia]. Pharmazie in unserer Zeit 20100301
The physiologic role of incretin hormones: clinical applications. The Journal of the American Osteopathic Association 20100301
Medicinal Chemistry of Incretin Mimetics and DPP-4 Inhibitors. ChemMedChem 20100201
Saxagliptin in type 2 diabetes. Drugs of today (Barcelona, Spain : 1998) 20100201
Reaching HbA1c goals with saxagliptin in combination with other oral antidiabetic drugs. Postgraduate medicine 20100101
Saxagliptin: a new dipeptidyl peptidase-4 inhibitor for type 2 diabetes. Cardiology in review 20100101
Saxagliptin added to a thiazolidinedione improves glycemic control in patients with type 2 diabetes and inadequate control on thiazolidinedione alone. The Journal of clinical endocrinology and metabolism 20091201
Exploration of the DPP-4 inhibitors with a focus on saxagliptin. Expert opinion on pharmacotherapy 20091201
Role of the incretin pathway in the pathogenesis of type 2 diabetes mellitus. Cleveland Clinic journal of medicine 20091201
Saxagliptin (Onglyza) for type 2 diabetes. The Medical letter on drugs and therapeutics 20091102
DPP-4 inhibitors in clinical practice. Postgraduate medicine 20091101
Effect of saxagliptin monotherapy in treatment-naïve patients with type 2 diabetes. Current medical research and opinion 20091001
Call for comparative effectiveness research: lowering A1c with sitagliptin, saxagliptin, or cinnamon. Journal of managed care pharmacy : JMCP 20091001
The efficacy and safety of saxagliptin when added to metformin therapy in patients with inadequately controlled type 2 diabetes with metformin alone. Diabetes care 20090901
Saxagliptin added to a submaximal dose of sulphonylurea improves glycaemic control compared with uptitration of sulphonylurea in patients with type 2 diabetes: a randomised controlled trial. International journal of clinical practice 20090901
FDA approves saxagliptin for type 2 diabetes. American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists 20090901
Defining the importance of daily glycemic control and implications for type 2 diabetes management. Postgraduate medicine 20090901
Clinical results of treating type 2 diabetic patients with sitagliptin, vildagliptin or saxagliptin--diabetes control and potential adverse events. Best practice & research. Clinical endocrinology & metabolism 20090801
Pharmacokinetics of the dipeptidyl peptidase 4 inhibitor saxagliptin in rats, dogs, and monkeys and clinical projections. Drug metabolism and disposition: the biological fate of chemicals 20090601
Saxagliptin given in combination with metformin as initial therapy improves glycaemic control in patients with type 2 diabetes compared with either monotherapy: a randomized controlled trial. Diabetes, obesity & metabolism 20090601
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DPP4 inhibitors: from sitagliptin monotherapy to the new alogliptin-pioglitazone combination therapy. Advances in therapy 20090301
Saxagliptin: a new DPP-4 inhibitor for the treatment of type 2 diabetes mellitus. Advances in therapy 20090301
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Prasugrel hydrochloride, dronedarone, and saxagliptin hydrochloride. Journal of the American Pharmacists Association : JAPhA 20090101
Saxagliptin, a dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes. IDrugs : the investigational drugs journal 20081201
Glucose-lowering activity of the dipeptidyl peptidase-4 inhibitor saxagliptin in drug-naive patients with type 2 diabetes. Diabetes, obesity & metabolism 20080501
Involvement of DPP-IV catalytic residues in enzyme-saxagliptin complex formation. Protein science : a publication of the Protein Society 20080201
DPP-4 inhibitors and their potential role in the management of type 2 diabetes. International journal of clinical practice 20061101
Biocatalytic ammonolysis of (5S)-4,5-dihydro-1H-pyrrole-1,5-dicarboxylic acid, 1-(1,1-dimethylethyl)-5-ethyl ester: preparation of an intermediate to the dipeptidyl peptidase IV inhibitor Saxagliptin. Bioorganic & medicinal chemistry letters 20060201
Mechanism of Gly-Pro-pNA cleavage catalyzed by dipeptidyl peptidase-IV and its inhibition by saxagliptin (BMS-477118). Archives of biochemistry and biophysics 20060101
Discovery and preclinical profile of Saxagliptin (BMS-477118): a highly potent, long-acting, orally active dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes. Journal of medicinal chemistry 20050728
Properties