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Taspoglutide

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
Taspoglutide
Clinical data
Routes of
administration
subcutaneous
ATC code
  • none
Pharmacokinetic data
BioavailabilityN/A
Identifiers
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
Chemical and physical data
FormulaC152H232N40O45
Molar mass3339.763 g·mol−1
  • 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
  • InChI=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
  • Key:WRGVLTAWMNZWGT-VQSPYGJZSA-N
 ☒NcheckY (what is this?)  (verify)

Taspoglutide is a formerexperimental drug, aglucagon-like peptide-1 agonist (GLP-1 agonist), that was under investigation for treatment oftype 2 diabetes and being codeveloped byIpsen andRoche.[1][2]

Initially, phase II trials reported it was effective and well tolerated.[3]

Of the eight planned phase III clinical trials of weekly taspoglutide (four againstexenatide,sitagliptin,insulin glargine, andpioglitazone), at least five were active in 2009.[4] Preliminary results in early 2010 were favourable.[5] (At least one of the eight planned phase III trials had not started recruiting by end 2009.[6])

In September 2010 Roche halted Phase III clinical trials due to instances of serious hypersensitivity reactions and gastrointestinal side effects.[7][8]

As of May 2022[update] no new trials have been registered since 2010.[9]

Chemistry

[edit]

Taspoglutide is the peptide with the sequence His-Aib-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Lys-Glu-Phe-Ile-Ala-Trp-Leu-Val-Lys-Aib-Arg-NH2, where Aib is2-aminoisobutyric acid (2-methylalanine).

In other words, it is the 8-(2-methylalanine)-35-(2-methylalanine)-36-L-argininamide derivative of the amino acid sequence 7–36 of human glucagon-like peptide I.

See also

[edit]

References

[edit]
  1. ^"Ipsen: Roche Moves Investigational Diabetes Drug, Taspoglutide, into Phase III Clinical Trials".Business Wire. June 2008.
  2. ^"Roche Moves Investigational Diabetes Drug, Taspoglutide, Into Phase III Clinical Trials". June 2008. Archived fromthe original on 3 March 2016. Retrieved13 January 2009.
  3. ^Baggio LL, Drucker DJ (2008)."Glucagon-like Peptide-1 Analogs Other Than Exenatide".
  4. ^"Ipsen's Partner Roche Announces That Taspoglutide Meets Its Primary Endpoint in the First Phase III Clinical Trial". October 2009. Archived fromthe original on 1 March 2010. Retrieved12 February 2010.
  5. ^"Roche Reports Positive Data from Five Phase III Trials of Type 2 Diabetes Therapy". February 2010.
  6. ^Clinical trial numberNCT01051011 for "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" atClinicalTrials.gov
  7. ^"Roche Halts Trials of Taspoglutide". 13 September 2010.
  8. ^"Experimental Diabetes Drug Taspoglutide Late-Stage Trials Suspended". 13 September 2010.
  9. ^Clinical studies of taspoglutide
Oraldiabetes medication,insulins andinsulin analogues, and other drugs used in diabetes (A10)
Fast-acting
Short-acting
Long-acting
Ultra-long-acting
Inhalable
  • Exubera
  • Afrezza
Oral
Non-insulins
Insulin sensitizers
Biguanides
TZDs ("-glitazones") andPPAR agonists
Dual PPAR agonists
Amylin analogues andDACRAs
Secretagogues
K+ATP
Sulfonylureas
Meglitinides ("-glinides")
GLP-1 receptor agonists
GLP1 poly-agonist peptides
DPP-4 inhibitors ("-gliptins")
Other
Aldose reductase inhibitors
Alpha-glucosidase inhibitors
SGLT2 inhibitors ("-gliflozins")
Other
Combinations


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