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{{Short description|Diabetes medication}}
{{Infobox drug
| Watchedfields = changed
| verifiedrevid = 464392221
| image = Sitagliptin.svg
| width = 254
| alt =
| image2 = Sitagliptin 3D.png
| alt2 =
| caption =


| pronounce = {{IPAc-en|audio=En-us-Sitagliptin.ogg|s|ɪ|t|ə|ˈ|g|l|ɪ|p|t|ɪ|n}}
| tradename = Januvia, Zituvio, others
| Drugs.com = {{drugs.com|monograph|sitagliptin}}
| MedlinePlus = a606023
| DailyMedID = Sitagliptin
| pregnancy_AU = B3
| pregnancy_AU_comment =
| pregnancy_category=
| routes_of_administration = [[Oral administration|By mouth]]
| class =
| ATC_prefix = A10
| ATC_suffix = BH01
| ATC_supplemental =


| legal_AU = S4
| legal_AU_comment =
| legal_BR = 
| legal_BR_comment =
| legal_CA = 
| legal_CA_comment =
| legal_DE = 
| legal_DE_comment =
| legal_NZ = 
| legal_NZ_comment =
| legal_UK = POM
| legal_UK_comment =
| legal_US = Rx-only
| legal_US_comment =
| legal_EU = Rx-only
| legal_EU_comment =
| legal_UN = 
| legal_UN_comment =
| legal_status = 


| bioavailability = 87%
| protein_bound = 38%
| metabolism = [[Liver]] ([[CYP3A4]]- and [[CYP2C8]]-mediated)
| metabolites =
| onset =
| elimination_half-life = 8 to 14 h
| duration_of_action =
| excretion = [[Kidney]] (80%)


| index2_label = as salt
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 486460-32-6
| CAS_supplemental =
| PubChem = 4369359
| IUPHAR_ligand = 6286
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01261
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 3571948
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = QFP0P1DV7Z
| KEGG_Ref =
| KEGG = D08516
| KEGG2_Ref =
| KEGG2 = D06645
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 40237
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1422
| NIAID_ChemDB =
| PDB_ligand =
| synonyms =


| IUPAC_name = (''R'')-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-''a'']pyrazin-7(8''H'')-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine
| C=16 | H=15 | F=6 | N=5 | O=1
| SMILES = Fc1cc(c(F)cc1F)C[C@@H](N)CC(=O)N3Cc2nnc(n2CC3)C(F)(F)F
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C16H15F6N5O/c17-10-6-12(19)11(18)4-8(10)3-9(23)5-14(28)26-1-2-27-13(7-26)24-25-15(27)16(20,21)22/h4,6,9H,1-3,5,7,23H2/t9-/m1/s1
| StdInChI_comment =
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MFFMDFFZMYYVKS-SECBINFHSA-N
| density =
| density_notes =
| melting_point =
| melting_high =
| melting_notes =
| boiling_point =
| boiling_notes =
| solubility =
| sol_units =
| specific_rotation =
}}


'''Sitagliptin''', sold under the brand name '''Januvia''' among others, is an [[anti-diabetic medication]] used to treat [[type 2 diabetes]]. In the United Kingdom it is listed as less preferred than [[metformin]] or a [[sulfonylurea]]. It is taken [[Oral administration|by mouth]]. It is also available in the [[fixed-dose combination]] medication [[sitagliptin/metformin]] (Janumet, Janumet XR).


Common side effects include headaches, swelling of the legs, and [[upper respiratory tract infections]]. Serious side effects may include [[angioedema]], [[low blood sugar]], [[kidney problems]], [[pancreatitis]], and [[joint pain]]. Whether use in [[pregnancy]] or [[breastfeeding]] is safe is unclear. It is in the [[DPP-4 inhibitors|dipeptidyl peptidase-4 (DPP-4) inhibitor]] class and works by increasing the production of [[insulin]] and decreasing the production of [[glucagon]] by the pancreas.


Sitagliptin was developed by [[Merck & Co.]] and approved for medical use in the United States in 2006. In 2021, it was the 83rd most commonly prescribed medication in the United States, with more than 8{{nbsp}}million prescriptions. It is available as a [[generic medication]] in Canada but not the United States.

==Medical uses==
Sitagliptin is used to treat type 2 diabetes. It is generally less preferred than [[metformin]] or [[sulfonylureas]]. It is taken by mouth. It is also available as the [[fixed-dose combination]]s of [[sitagliptin/metformin]] (Janumet, Janumet XR) and [[sitagliptin/simvastatin]] (Juvisync).

Sitagliptin should not be used to treat type 1 diabetes. In December 2020, the U.S. [[Food and Drug Administration]] (FDA) approved labeling changes stating that Januvia (sitagliptin), Janumet (sitagliptin and metformin hydrochloride), and Janumet XR (sitagliptin and metformin hydrochloride extended-release) are not proven to improve glycemic (blood sugar) control in children aged 10 to 17 with type 2 diabetes. The drugs are approved to improve blood sugar control in adults aged 18 and older with type 2 diabetes.

==Adverse effects==
Adverse effects from sitagliptin are similar to [[placebo]], except for rare [[nausea]], [[common cold]]-like symptoms, and photosensitivity. It does not increase the risk of diarrhea. No [[statistical significance|significant]] difference exists in the occurrence of [[hypoglycemia]] between placebo and sitagliptin. In those taking [[sulphonylurea]]s, the risk of [[hypoglycemia|low blood sugar]] is increased.

The existence of rare case reports of [[kidney failure]] and hypersensitivity reactions is noted in the United States prescribing information, but a causative role for sitagliptin has not been established.

Several [[postmarketing surveillance|postmarketing reports]] of [[pancreatitis]] (some fatal) have been made in people treated with sitagliptin and other DPP-4 inhibitors, and the U.S. package insert carries a warning to this effect, although the causal link between sitagliptin and pancreatitis has not yet been fully substantiated. One study with lab rats published in 2009 concluded that some of the possible risks of pancreatitis or pancreatic cancer may be reduced when it is used with metformin. However, while DPP-4 inhibitors showed an increase in such risk factors, as of 2009, no increase in pancreatic cancer has been reported in individuals taking DPP-4 inhibitors.

In 2015, the U.S. Food and Drug Administration (FDA) added a new warning and precaution about the risk of "severe and disabling" joint pain to the labels of all DPP-4 inhibitor medicines.

==Mechanism of action==
{{see also|Dipeptidyl peptidase-4 inhibitors}}

Sitagliptin works to [[competitive inhibition|competitively inhibit]] the [[enzyme]] dipeptidyl peptidase 4 (DPP-4). This enzyme breaks down the [[incretin]]s [[GLP-1]] and GIP, [[gastrointestinal hormone]]s released in response to a meal. By preventing breakdown of GLP-1 and GIP, they are able to increase the secretion of insulin and suppress the release of glucagon by the alpha cells of the pancreas. This drives blood glucose levels towards normal. As the blood glucose level approaches normal, the amounts of insulin released and glucagon suppressed diminishes, thus tending to prevent an "overshoot" and subsequent low blood sugar (hypoglycemia), which is seen with some other oral hypoglycemic agents.

Sitagliptin has been shown to lower [[HbA1c]] level by about 0.7% points versus placebo. It is slightly less effective than metformin when used as a [[monotherapy]]. It does not cause weight gain and has less hypoglycemia compared to sulfonylureas. Sitagliptin is recommended as a second-line drug (in combination with other drugs) after the combination of diet/exercise and metformin fails.

==History==
{{see also|Development of dipeptidyl peptidase-4 inhibitors}}

Sitagliptin was approved by the U.S. [[Food and Drug Administration]] (FDA) in October 2006, and is marketed in the US as Januvia by [[Merck & Co.]] On April 2, 2007, the FDA approved an oral combination of [[sitagliptin/metformin]] sold in the US under the brand name Janumet. On October 7, 2011, the FDA approved an oral combination of [[sitagliptin/simvastatin]] marketed in the US as Juvisync.

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{{Oral hypoglycemics}}
{{Merck&Co}}
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{{二次利用|date=4 February 2024}}
[[Category:Wikipedia medicine articles ready to translate]]
[[Category:Dipeptidyl peptidase-4 inhibitors]]
[[Category:Carboxamides]]
[[Category:Trifluoromethyl compounds]]
[[Category:Fluoroarenes]]
[[Category:Triazoles]]
[[Category:Drugs developed by Merck & Co.]]

Sitagliptin/en - Revision history

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