teduglutide

{{Short description|Chemical compound}}

{{Use dmy dates|date=March 2024}}

{{cs1 config |name-list-style=vanc |display-authors=6}}

{{Infobox drug

| Watchedfields = changed

| verifiedrevid = 443663022

| image = Teduglutide.svg

| alt =

| pronounce =

| tradename = Revestive, Gattex

| Drugs.com = {{drugs.com|monograph|teduglutide}}

| MedlinePlus =

| DailyMedID = Teduglutide

| pregnancy_AU =

| pregnancy_AU_comment =

| pregnancy_category =

| routes_of_administration = Subcutaneous injection

| class =

| ATC_prefix = A16

| ATC_suffix = AX08

| ATC_supplemental =

| legal_AU = S4

| legal_AU_comment = {{cite web | title=Prescription medicines: registration of new chemical entities in Australia, 2017 | website=Therapeutic Goods Administration (TGA) | date=21 June 2022 | url=https://www.tga.gov.au/resources/publication/publications/prescription-medicines-registration-new-chemical-entities-australia-2017 | access-date=9 April 2023}}{{cite web | title=Prescription medicines and biologicals: TGA annual summary 2017 | website=Therapeutic Goods Administration (TGA) | date=21 June 2022 | url=https://www.tga.gov.au/resources/publication/publications/prescription-medicines-and-biologicals-tga-annual-summary-2017 | access-date=31 March 2024}}

| legal_BR =

| legal_BR_comment =

| legal_CA = Rx-only

| legal_CA_comment = {{cite web | title=Health Canada New Drug Authorizations: 2015 Highlights | website=Health Canada | date=4 May 2016 | url=https://www.canada.ca/en/health-canada/services/publications/drugs-health-products/health-canada-new-drug-authorizations-2015-highlights.html | access-date=7 April 2024}}

| legal_DE =

| legal_DE_comment =

| legal_NZ =

| legal_NZ_comment =

| legal_UK =

| 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 = 88%

| protein_bound =

| metabolism = Proteolysis

| metabolites =

| onset =

| elimination_half-life = 2h

| duration_of_action =

| excretion =

| CAS_number = 197922-42-2

| CAS_supplemental =

| PubChem = 16139605

| IUPHAR_ligand = 7049

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

| DrugBank =

| ChemSpiderID = 17296109

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

| UNII = 7M19191IKG

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D06053

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 72305

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL =

| NIAID_ChemDB =

| PDB_ligand =

| synonyms =

| IUPAC_name = L-histidylglycyl-L-α-aspartylglycyl-L-seryl-L-phenylalanyl-L-seryl-L-α-aspartyl-L-α-glutamyl-L-methionyl-L-asparaginyl-L-threonyl-L-isoleucyl-L-leucyl-L-α-aspartyl-L-asparaginyl-L-leucyl-L-alanyl-L-alanyl-L-arginyl-L-α-aspartyl-L-phenylalanyl-L-isoleucyl-L-asparaginyl-L-tryptophyl-L-leucyl-L-isoleucyl-L-glutaminyl-L-threonyl-L-lysyl-L-isoleucyl-L-threonyl-L-aspartic acid

| C=164 | H=252 | N=44 | O=55 |S=1

| SMILES = CC[C@H](C)[C@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)Cc1cnc[nH]1)[C@@H](C)O)[C@@H](C)CC)[C@@H](C)CC)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(O)=O)C(O)=O

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C164H252N44O55S/c1-21-77(11)126(156(255)187-95(44-46-114(167)214)141(240)206-130(83(17)211)160(259)186-93(42-33-34-49-165)140(239)202-129(80(14)24-4)159(258)208-131(84(18)212)161(260)200-111(163(262)263)66-125(230)231)203-151(250)100(54-76(9)10)189-145(244)103(57-88-67-175-92-41-32-31-40-90(88)92)192-147(246)105(60-116(169)216)199-157(256)127(78(12)22-2)204-152(251)102(56-87-38-29-26-30-39-87)190-149(248)109(64-123(226)227)195-137(236)94(43-35-50-174-164(171)172)183-134(233)82(16)179-133(232)81(15)180-142(241)98(52-74(5)6)188-146(245)104(59-115(168)215)194-150(249)110(65-124(228)229)196-143(242)99(53-75(7)8)198-158(257)128(79(13)23-3)205-162(261)132(85(19)213)207-153(252)106(61-117(170)217)193-139(238)97(48-51-264-20)185-138(237)96(45-47-120(220)221)184-148(247)108(63-122(224)225)197-155(254)113(72-210)201-144(243)101(55-86-36-27-25-28-37-86)191-154(253)112(71-209)182-119(219)70-177-136(235)107(62-121(222)223)181-118(218)69-176-135(234)91(166)58-89-68-173-73-178-89/h25-32,36-41,67-68,73-85,91,93-113,126-132,175,209-213H,21-24,33-35,42-66,69-72,165-166H2,1-20H3,(H2,167,214)(H2,168,215)(H2,169,216)(H2,170,217)(H,173,178)(H,176,234)(H,177,235)(H,179,232)(H,180,241)(H,181,218)(H,182,219)(H,183,233)(H,184,247)(H,185,237)(H,186,259)(H,187,255)(H,188,245)(H,189,244)(H,190,248)(H,191,253)(H,192,246)(H,193,238)(H,194,249)(H,195,236)(H,196,242)(H,197,254)(H,198,257)(H,199,256)(H,200,260)(H,201,243)(H,202,239)(H,203,250)(H,204,251)(H,205,261)(H,206,240)(H,207,252)(H,208,258)(H,220,221)(H,222,223)(H,224,225)(H,226,227)(H,228,229)(H,230,231)(H,262,263)(H4,171,172,174)/t77-,78-,79-,80-,81-,82-,83+,84+,85+,91-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,126-,127-,128-,129-,130-,131-,132-/m0/s1

| StdInChI_comment =

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = CILIXQOJUNDIDU-ASQIGDHWSA-N

| density =

| density_notes =

| melting_point =

| melting_high =

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| boiling_point =

| boiling_notes =

| solubility =

| sol_units =

| specific_rotation =

}}

Teduglutide, sold under the brand names Revestive (EU) and Gattex (US), is a 33-membered polypeptide and glucagon-like peptide-2 (GLP-2) analog that is used for the treatment of short bowel syndrome. It works by promoting mucosal growth and possibly restoring gastric emptying and secretion.{{cite journal | vauthors = Jeppesen PB | title = Teduglutide, a novel glucagon-like peptide 2 analog, in the treatment of patients with short bowel syndrome | journal = Therapeutic Advances in Gastroenterology | volume = 5 | issue = 3 | pages = 159–71 | date = May 2012 | pmid = 22570676 | pmc = 3342570 | doi = 10.1177/1756283X11436318 }} It was approved in both the European Union{{cite web | title=Revestive EPAR | website=European Medicines Agency (EMA) | date=11 December 2001 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/revestive | access-date=20 March 2024}} and the United States in 2012.{{cite web | title=Gattex- teduglutide injection, powder, lyophilized, for solution; Gattex- teduglutide kit | website=DailyMed | date=28 February 2024 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=66b69c1e-b25c-44d3-b5ff-1c1de9a516fa | access-date=20 March 2024}}