fbpx
Wikipedia

Teduglutide

January 01, 1970

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.[7] It was approved in both the European Union[5] and the United States in 2012.[4]

Teduglutide
Clinical data
Trade namesRevestive, Gattex
AHFS/Drugs.comMonograph
License data
Routes of
administration		Subcutaneous injection
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability88%
MetabolismProteolysis
Elimination half-life2h
Identifiers
  • 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
CAS Number
  • 197922-42-2
PubChem CID
  • 16139605
IUPHAR/BPS
  • 7049
ChemSpider
  • 17296109
UNII
  • 7M19191IKG
KEGG
  • D06053 Y
ChEBI
  • CHEBI:72305 Y
Chemical and physical data
FormulaC164H252N44O55S
Molar mass3752.13 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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
  • InChI=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 Y
  • Key:CILIXQOJUNDIDU-ASQIGDHWSA-N Y
  (verify)

Medical uses edit

Up to a certain point, the gut can adapt to partial resections that result in short bowel syndrome. Still, parenteral substitution of water, minerals and vitamins (depending on which part of the gut has been removed) is often necessary. Teduglutide may reduce or shorten the necessity of such infusions by improving the intestinal mucosa and possibly by other mechanisms.[8]

Adverse effects edit

Common adverse effects in clinical studies included abdominal discomfort (49% of patients), respiratory infections (28%), nausea (27%) and vomiting (14%), local reactions at the injection site (21%), and headache (17%).[8]

Chemistry and mechanism of action edit

Teduglutide differs from natural GLP-2 by a single amino acid: an alanine is replaced with a glycine. This blocks breaking down of the molecule by dipeptidyl peptidase and increases its half-life from seven minutes (GLP-2) to about two hours, while retaining its biological actions. These include maintenance of the intestinal mucosa, increasing intestinal blood flow, reducing gastrointestinal motility and secretion of gastric acid.[8]

Society and culture edit

Legal status edit

It was approved in both the European Union (brand name Revestive)[5][6] and the United States (brand name Gattex) in 2012.[4] It was granted orphan drug designation by the European Medicines Agency (EMA).[5][6]

References edit

  1. ^ "Prescription medicines: registration of new chemical entities in Australia, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 9 April 2023.
  2. ^ "Prescription medicines and biologicals: TGA annual summary 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 31 March 2024.
  3. ^ "Health Canada New Drug Authorizations: 2015 Highlights". Health Canada. 4 May 2016. Retrieved 7 April 2024.
  4. ^ a b c "Gattex- teduglutide injection, powder, lyophilized, for solution; Gattex- teduglutide kit". DailyMed. 28 February 2024. Retrieved 20 March 2024.
  5. ^ a b c d "Revestive EPAR". European Medicines Agency (EMA). 11 December 2001. Retrieved 20 March 2024.
  6. ^ a b c "Revestive Product information". Union Register of medicinal products. 4 September 2012. Retrieved 20 March 2024.
  7. ^ Jeppesen PB (May 2012). "Teduglutide, a novel glucagon-like peptide 2 analog, in the treatment of patients with short bowel syndrome". Therapeutic Advances in Gastroenterology. 5 (3): 159–71. doi:10.1177/1756283X11436318. PMC 3342570. PMID 22570676.
  8. ^ a b c Klement A (5 January 2015). "Das Kurzdarmsyndrom ist erstmals behandelbar: Revestive". Österreichische Apothekerzeitung (in German) (1/2015): 20f.

January 01, 1970
teduglutide, sold, under, brand, names, revestive, gattex, membered, polypeptide, glucagon, like, peptide, analog, that, used, treatment, short, bowel, syndrome, works, promoting, mucosal, growth, possibly, restoring, gastric, emptying, secretion, approved, bo. 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 7 It was approved in both the European Union 5 and the United States in 2012 4 TeduglutideClinical dataTrade namesRevestive GattexAHFS Drugs comMonographLicense dataUS DailyMed TeduglutideRoutes ofadministrationSubcutaneous injectionATC codeA16AX08 WHO Legal statusLegal statusAU S4 Prescription only 1 2 CA only 3 US only 4 EU Rx only 5 6 Pharmacokinetic dataBioavailability88 MetabolismProteolysisElimination half life2hIdentifiersIUPAC name L histidylglycyl L a aspartylglycyl L seryl L phenylalanyl L seryl L a aspartyl L a glutamyl L methionyl L asparaginyl L threonyl L isoleucyl L leucyl L a aspartyl L asparaginyl L leucyl L alanyl L alanyl L arginyl L a 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 acidCAS Number197922 42 2PubChem CID16139605IUPHAR BPS7049ChemSpider17296109UNII7M19191IKGKEGGD06053 YChEBICHEBI 72305 YChemical and physical dataFormulaC 164H 252N 44O 55SMolar mass3752 13 g mol 13D model JSmol Interactive imageSMILES 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 OInChI InChI 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 YKey CILIXQOJUNDIDU ASQIGDHWSA N Y verify Contents 1 Medical uses 2 Adverse effects 3 Chemistry and mechanism of action 4 Society and culture 4 1 Legal status 5 ReferencesMedical uses editUp to a certain point the gut can adapt to partial resections that result in short bowel syndrome Still parenteral substitution of water minerals and vitamins depending on which part of the gut has been removed is often necessary Teduglutide may reduce or shorten the necessity of such infusions by improving the intestinal mucosa and possibly by other mechanisms 8 Adverse effects editCommon adverse effects in clinical studies included abdominal discomfort 49 of patients respiratory infections 28 nausea 27 and vomiting 14 local reactions at the injection site 21 and headache 17 8 Chemistry and mechanism of action editTeduglutide differs from natural GLP 2 by a single amino acid an alanine is replaced with a glycine This blocks breaking down of the molecule by dipeptidyl peptidase and increases its half life from seven minutes GLP 2 to about two hours while retaining its biological actions These include maintenance of the intestinal mucosa increasing intestinal blood flow reducing gastrointestinal motility and secretion of gastric acid 8 Society and culture editLegal status edit It was approved in both the European Union brand name Revestive 5 6 and the United States brand name Gattex in 2012 4 It was granted orphan drug designation by the European Medicines Agency EMA 5 6 References edit Prescription medicines registration of new chemical entities in Australia 2017 Therapeutic Goods Administration TGA 21 June 2022 Retrieved 9 April 2023 Prescription medicines and biologicals TGA annual summary 2017 Therapeutic Goods Administration TGA 21 June 2022 Retrieved 31 March 2024 Health Canada New Drug Authorizations 2015 Highlights Health Canada 4 May 2016 Retrieved 7 April 2024 a b c Gattex teduglutide injection powder lyophilized for solution Gattex teduglutide kit DailyMed 28 February 2024 Retrieved 20 March 2024 a b c d Revestive EPAR European Medicines Agency EMA 11 December 2001 Retrieved 20 March 2024 a b c Revestive Product information Union Register of medicinal products 4 September 2012 Retrieved 20 March 2024 Jeppesen PB May 2012 Teduglutide a novel glucagon like peptide 2 analog in the treatment of patients with short bowel syndrome Therapeutic Advances in Gastroenterology 5 3 159 71 doi 10 1177 1756283X11436318 PMC 3342570 PMID 22570676 a b c Klement A 5 January 2015 Das Kurzdarmsyndrom ist erstmals behandelbar Revestive Osterreichische Apothekerzeitung in German 1 2015 20f Portal nbsp Medicine Retrieved from https en wikipedia org w index php title Teduglutide amp oldid 1217676704, wikipedia, wiki, book, books, library,

article

, read, download, free, free download, mp3, video, mp4, 3gp, jpg, jpeg, gif, png, picture, music, song, movie, book, game, games.