Taspoglutide

{{short description|Chemical compound}}

{{Use dmy dates|date=June 2020}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 470477813

| tradename =

| pregnancy_AU =

| pregnancy_US =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| routes_of_administration = subcutaneous

| bioavailability = N/A

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 275371-94-3

| ATC_prefix = none

| PubChem = 56842233

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 2PHK27IP3B

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 32819947

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = D09723

| C=152 | H=232 | N=40 | O=45

| smiles = CC[C@H](C)[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(=O)O)NC(=O)C(C)(C)NC(=O)[C@@H](N)Cc1c[nH]cn1)[C@@H](C)O)[C@@H](C)O)C(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCCCN)C(=O)NC(C)(C)C(=O)N[C@@H](CCCNC(=N)N)C(N)=O)C(C)C

| StdInChI = 1S/C152H232N40O45/c1-20-78(10)119(145(233)168-81(13)125(213)174-105(63-87-66-162-92-39-28-27-38-90(87)92)134(222)176-101(59-75(4)5)135(223)187-117(76(6)7)143(231)173-95(41-30-32-56-154)142(230)192-152(18,19)148(236)184-93(122(157)210)42-33-57-161-150(158)159)189-136(224)103(60-84-34-23-21-24-35-84)177-131(219)99(50-54-115(206)207)172-130(218)94(40-29-31-55-153)170-124(212)80(12)166-123(211)79(11)167-129(217)98(47-51-110(156)199)169-111(200)68-163-127(215)96(48-52-113(202)203)171-132(220)100(58-74(2)3)175-133(221)102(62-86-43-45-89(198)46-44-86)178-139(227)107(70-193)181-141(229)109(72-195)182-144(232)118(77(8)9)188-138(226)106(65-116(208)209)179-140(228)108(71-194)183-147(235)121(83(15)197)190-137(225)104(61-85-36-25-22-26-37-85)180-146(234)120(82(14)196)186-112(201)69-164-128(216)97(49-53-114(204)205)185-149(237)151(16,17)191-126(214)91(155)64-88-67-160-73-165-88/h21-28,34-39,43-46,66-67,73-83,91,93-109,117-121,162,193-198H,20,29-33,40-42,47-65,68-72,153-155H2,1-19H3,(H2,156,199)(H2,157,210)(H,160,165)(H,163,215)(H,164,216)(H,166,211)(H,167,217)(H,168,233)(H,169,200)(H,170,212)(H,171,220)(H,172,218)(H,173,231)(H,174,213)(H,175,221)(H,176,222)(H,177,219)(H,178,227)(H,179,228)(H,180,234)(H,181,229)(H,182,232)(H,183,235)(H,184,236)(H,185,237)(H,186,201)(H,187,223)(H,188,226)(H,189,224)(H,190,225)(H,191,214)(H,192,230)(H,202,203)(H,204,205)(H,206,207)(H,208,209)(H4,158,159,161)/t78-,79-,80-,81-,82+,83+,91-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,117-,118-,119-,120-,121-/m0/s1

| StdInChIKey = WRGVLTAWMNZWGT-VQSPYGJZSA-N

| Jmol = none

}}

Taspoglutide is a former experimental drug, a glucagon-like peptide-1 agonist (GLP-1 agonist), that was under investigation for treatment of type 2 diabetes and being codeveloped by Ipsen and Roche.{{cite news |url=http://findarticles.com/p/articles/mi_m0EIN/is_2008_June_10/ai_n25492242 |title=Ipsen: Roche Moves Investigational Diabetes Drug, Taspoglutide, into Phase III Clinical Trials |date = June 2008| work=Business Wire}}

{{cite web |url=http://www.bio-medicine.org/medicine-technology-1/Roche-Moves-Investigational-Diabetes-Drug--Taspoglutide--Into-Phase-III-Clinical-Trials-2379-1/ |title=Roche Moves Investigational Diabetes Drug, Taspoglutide, Into Phase III Clinical Trials |date=June 2008 |access-date=13 January 2009 |archive-date=3 March 2016 |archive-url=https://web.archive.org/web/20160303191454/http://www.bio-medicine.org/medicine-technology-1/Roche-Moves-Investigational-Diabetes-Drug--Taspoglutide--Into-Phase-III-Clinical-Trials-2379-1/ |url-status=dead }}

Initially, phase II trials reported it was effective and well tolerated.{{cite web | vauthors = Baggio LL, Drucker DJ |url=http://www.medscape.com/viewarticle/578304 |title=Glucagon-like Peptide-1 Analogs Other Than Exenatide |year=2008 }}

Of the eight planned phase III clinical trials of weekly taspoglutide (four against exenatide, sitagliptin, insulin glargine, and pioglitazone), at least five were active in 2009.{{cite web |url= http://www.medicalnewstoday.com/articles/169171.php |title= Ipsen's Partner Roche Announces That Taspoglutide Meets Its Primary Endpoint in the First Phase III Clinical Trial |date= October 2009 |access-date= 12 February 2010 |archive-date= 1 March 2010 |archive-url= https://web.archive.org/web/20100301202923/http://www.medicalnewstoday.com/articles/169171.php |url-status= dead }} Preliminary results in early 2010 were favourable.{{cite web |url=http://www.genengnews.com/news/bnitem.aspx?name=75286047 |title=Roche Reports Positive Data from Five Phase III Trials of Type 2 Diabetes Therapy |date=February 2010}} (At least one of the eight planned phase III trials had not started recruiting by end 2009.{{ClinicalTrialsGov|NCT01051011|A Study to Compare Taspoglutide and Insulin Glargine in Insulin-Naïve Patients With Type 2 Diabetes Mellitus Inadequately Controlled on Metformin and Sulfonylurea Combination Therapy}})

In September 2010 Roche halted Phase III clinical trials due to instances of serious hypersensitivity reactions and gastrointestinal side effects.{{cite web |url=http://www.medpagetoday.com/Endocrinology/Diabetes/22139 |title=Roche Halts Trials of Taspoglutide |date=13 September 2010 }}{{cite web |url=http://www.medicalnewstoday.com/articles/200893.php |title=Experimental Diabetes Drug Taspoglutide Late-Stage Trials Suspended |date=13 September 2010 }}

{{As of|May 2022}} no new trials have been registered since 2010.[http://clinicaltrials.gov/ct2/results?term=taspoglutide&Search=Search Clinical studies of taspoglutide]