Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Terlipressin: Difference between pages

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+{{Short description|Chemical compound}}
-{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid [{{fullurl:Terlipressin|oldid=456622373}} 456622373] of page [[Terlipressin]] with values updated to verified values.}}
+{{cs1 config|name-list-style=vanc|display-authors=6}}
-{{Drugbox
+{{Infobox drug
-| Verifiedfields = changed
-| verifiedrevid = 419752440
+| verifiedrevid = 470602469
-| IUPAC_name = 1-{[(4''R'',7''S'',10''S'',13''S'',16''S'',19''R'')-19-{[({[(aminoacetyl)amino]acetyl}amino)acetyl]amino}-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-(4-hydroxybenzyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl]carbonyl}-<small>L</small>-prolyl-''N''-(2-amino-2-oxoethyl)-<small>L</small>-lysinamide
 | image = terlipressin.png
+| alt =
 <!--Clinical data-->
-| tradename =
+| tradename = Terlivaz
 | Drugs.com = {{drugs.com|international|terlipressin}}
 | pregnancy_category =
+| routes_of_administration = [[Intravenous]]
-| legal_status =
+| ATC_prefix = H01
-| routes_of_administration = [[intravenous|IV]]
+| ATC_suffix = BA04
+| ATC_supplemental =
+<!-- Legal status -->
+| legal_AU          = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled -->
+| legal_AU_comment  =
+| legal_BR          = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
+| legal_BR_comment  =
+| legal_CA          = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
+| legal_CA_comment  =
+| legal_DE          = <!-- Anlage I, II, III or Unscheduled -->
+| legal_DE_comment  =
+| legal_NZ          = <!-- Class A, B, C -->
+| legal_NZ_comment  =
+| legal_UK          = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->
+| legal_UK_comment  =
+| legal_US          = Rx-only
+| legal_US_comment  = <ref name="Terlivaz FDA label" /><ref>{{cite web | title=Drug Approval Package: Terlivaz | publisher=U.S. [[Food and Drug Administration]] (FDA) | date=7 October 2022 | url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/022231Orig1s000TOC.cfm | access-date=4 December 2022}}</ref>
+| legal_EU          =
+| legal_EU_comment  =
+| legal_UN          = <!-- N I, II, III, IV / P I, II, III, IV -->
+| legal_UN_comment  =
+| legal_status      = <!-- For countries not listed above -->
-<!--Pharmacokinetic data-->
+<!-- Pharmacokinetic data -->
 | bioavailability =
 | protein_bound = ~30%
 | metabolism =
 | elimination_half-life =
 <!--Identifiers-->
 | CAS_number_Ref = {{cascite|correct|??}}
 | CAS_number = 14636-12-5
-| ATC_prefix = H01
-| ATC_suffix = BA04
-| ATC_supplemental =
 | PubChem = 72081
 | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
@@ Line 30: / Line 50: @@
 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
 | ChemSpiderID = 65067
-| UNII_Ref = {{fdacite|changed|FDA}}
+| UNII_Ref = {{fdacite|correct|FDA}}
 | UNII = 7Z5X49W53P
 | KEGG_Ref = {{keggcite|correct|kegg}}
@@ Line 36: / Line 56: @@
 <!--Chemical data-->
+| IUPAC_name = 1-<nowiki/>{[(4''R'',7''S'',10''S'',13''S'',16''S'',19''R'')-19-<nowiki/>{[({[(aminoacetyl)amino]acetyl}amino)acetyl]amino}-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-(4-hydroxybenzyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl]carbonyl}-<small>L</small>-prolyl-''N''-(2-amino-2-oxoethyl)-<small>L</small>-lysinamide
 | C=52 | H=74 | N=16 | O=15 | S=2
-| molecular_weight = 1227.37 g/mol
 | smiles = O=C(N)CNC(=O)[C@@H](NC(=O)[C@H]4N(C(=O)[C@H]1NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)CN)CSSC1)Cc2ccc(O)cc2)Cc3ccccc3)CCC(=O)N)CC(=O)N)CCC4)CCCCN
-| InChI = 1/C52H74N16O15S2/c53-17-5-4-9-31(45(76)60-23-41(57)72)63-51(82)38-10-6-18-68(38)52(83)37-27-85-84-26-36(61-44(75)25-59-43(74)24-58-42(73)22-54)50(81)65-34(20-29-11-13-30(69)14-12-29)48(79)64-33(19-28-7-2-1-3-8-28)47(78)62-32(15-16-39(55)70)46(77)66-35(21-40(56)71)49(80)67-37/h1-3,7-8,11-14,31-38,69H,4-6,9-10,15-27,53-54H2,(H2,55,70)(H2,56,71)(H2,57,72)(H,58,73)(H,59,74)(H,60,76)(H,61,75)(H,62,78)(H,63,82)(H,64,79)(H,65,81)(H,66,77)(H,67,80)/t31-,32-,33-,34-,35-,36-,37-,38-/m0/s1
-| InChIKey = BENFXAYNYRLAIU-QSVFAHTRBE
 | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
 | StdInChI = 1S/C52H74N16O15S2/c53-17-5-4-9-31(45(76)60-23-41(57)72)63-51(82)38-10-6-18-68(38)52(83)37-27-85-84-26-36(61-44(75)25-59-43(74)24-58-42(73)22-54)50(81)65-34(20-29-11-13-30(69)14-12-29)48(79)64-33(19-28-7-2-1-3-8-28)47(78)62-32(15-16-39(55)70)46(77)66-35(21-40(56)71)49(80)67-37/h1-3,7-8,11-14,31-38,69H,4-6,9-10,15-27,53-54H2,(H2,55,70)(H2,56,71)(H2,57,72)(H,58,73)(H,59,74)(H,60,76)(H,61,75)(H,62,78)(H,63,82)(H,64,79)(H,65,81)(H,66,77)(H,67,80)/t31-,32-,33-,34-,35-,36-,37-,38-/m0/s1
@@ Line 46: / Line 64: @@
 | StdInChIKey = BENFXAYNYRLAIU-QSVFAHTRSA-N
 }}
+'''Terlipressin''', sold under the brand name '''Terlivaz ''' among others, is an [[analog (chemistry)|analogue]] of [[vasopressin]] used as a vasoactive [[Medication|drug]] in the management of [[hypotension|low blood pressure]].  It has been found to be effective when [[norepinephrine]] does not help. Terlipressin is a vasopressin receptor agonist.<ref name="Terlivaz FDA label" />
+Terlipressin was approved for medical use in the United States in 2022.<ref name="Terlivaz FDA label" /><ref>{{cite web | title=Drug Approval Package: Terlivaz | website=U.S. [[Food and Drug Administration]] (FDA) | date=7 October 2022 | url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/022231Orig1s000TOC.cfm | access-date=23 January 2023}}</ref><ref name="New Drug Therapy Approvals 2022" /> The US [[Food and Drug Administration]] (FDA) considers it to be a [[first-in-class medication]].<ref name="New Drug Therapy Approvals 2022">{{cite web | title=Advancing Health Through Innovation: New Drug Therapy Approvals 2022 | website=U.S. [[Food and Drug Administration]] (FDA) | date=10 January 2023 | url=https://www.fda.gov/drugs/new-drugs-fda-cders-new-molecular-entities-and-new-therapeutic-biological-products/new-drug-therapy-approvals-2022 | access-date=22 January 2023}} {{PD-notice}}</ref><ref>{{cite report | title=New Drug Therapy Approvals 2022 | website=U.S. [[Food and Drug Administration]] (FDA) | date=January 2024 | url=https://www.fda.gov/media/164429/download | format=PDF | access-date=14 January 2024 | archive-url=https://web.archive.org/web/20240114065648/https://www.fda.gov/media/164429/download | archive-date=14 January 2024 | url-status=live }} {{PD-notice}}</ref>
+== Medical uses ==
+Terlipressin is [[indicated]] to improve kidney function in adults with [[hepatorenal syndrome]] with rapid reduction in kidney function.<ref name="Terlivaz FDA label">{{cite web | title=Terlivaz- terlipressin injection, powder, lyophilized, for solution | website=DailyMed | date=19 September 2022 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3a35b86c-f451-4fac-8499-43019e4da354 | access-date=27 September 2022 | archive-date=28 September 2022 | archive-url=https://web.archive.org/web/20220928050107/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3a35b86c-f451-4fac-8499-43019e4da354 | url-status=live }}</ref>
+Indications for use include norepinephrine-resistant [[septic shock]]<ref name="OBrien">{{cite journal | vauthors = O'Brien A, Clapp L, Singer M | title = Terlipressin for norepinephrine-resistant septic shock | journal = Lancet | volume = 359 | issue = 9313 | pages = 1209–1210 | date = April 2002 | pmid = 11955542 | doi = 10.1016/S0140-6736(02)08225-9 | s2cid = 38463837 }}</ref> although, 2021 Surviving Sepsis Guidelines recommend against its use for adults with septic shock<ref>{{cite journal | vauthors = Evans L, Rhodes A, Alhazzani W, Antonelli M, Coopersmith CM, French C, Machado FR, Mcintyre L, Ostermann M, Prescott HC, Schorr C, Simpson S, Wiersinga WJ, Alshamsi F, Angus DC, Arabi Y, Azevedo L, Beale R, Beilman G, Belley-Cote E, Burry L, Cecconi M, Centofanti J, Coz Yataco A, De Waele J, Dellinger RP, Doi K, Du B, Estenssoro E, Ferrer R, Gomersall C, Hodgson C, Hylander Møller M, Iwashyna T, Jacob S, Kleinpell R, Klompas M, Koh Y, Kumar A, Kwizera A, Lobo S, Masur H, McGloughlin S, Mehta S, Mehta Y, Mer M, Nunnally M, Oczkowski S, Osborn T, Papathanassoglou E, Perner A, Puskarich M, Roberts J, Schweickert W, Seckel M, Sevransky J, Sprung CL, Welte T, Zimmerman J, Levy M | title = Surviving Sepsis Campaign: International Guidelines for Management of Sepsis and Septic Shock 2021 | language = en-US | journal = Critical Care Medicine | volume = 49 | issue = 11 | pages = e1063–e1143 | date = November 2021 | pmid = 34605781 | doi = 10.1097/CCM.0000000000005337 | doi-access = free }}</ref> and [[hepatorenal syndrome]].<ref name="Uriz">{{cite journal | vauthors = Uriz J, Ginès P, Cárdenas A, Sort P, Jiménez W, Salmerón JM, Bataller R, Mas A, Navasa M, Arroyo V, Rodés J | title = Terlipressin plus albumin infusion: an effective and safe therapy of hepatorenal syndrome | journal = Journal of Hepatology | volume = 33 | issue = 1 | pages = 43–48 | date = July 2000 | pmid = 10905585 | doi = 10.1016/S0168-8278(00)80158-0 }}</ref> In addition, it is used to treat bleeding [[esophageal varices]].<ref name="Ioannou">{{cite journal | vauthors = Ioannou G, Doust J, Rockey DC | title = Terlipressin for acute esophageal variceal hemorrhage | journal = The Cochrane Database of Systematic Reviews | issue = 1 | pages = CD002147 | year = 2003 | pmid = 12535432 | pmc = 7017851 | doi = 10.1002/14651858.CD002147 | veditors = Ioannou GN }}</ref>
+==Contraindications==
+Terlipressin is contraindicated in people experiencing hypoxia or worsening respiratory symptoms and in people with ongoing coronary, peripheral or mesenteric ischemia.<ref name="Terlivaz FDA label" /> Terlipressin may cause fetal harm when used during pregnancy.<ref name="Terlivaz FDA label" />
+== Society and culture ==
+Terlipressin is available in United States,<ref>{{cite journal |title=FDA approves treatment to improve kidney function in adults with hepatorenal syndrome |journal=FDA |date=14 September 2022 |url=https://www.fda.gov/drugs/news-events-human-drugs/fda-approves-treatment-improve-kidney-function-adults-hepatorenal-syndrome |url-status=live |archive-url=https://web.archive.org/web/20230210043353/https://www.fda.gov/drugs/news-events-human-drugs/fda-approves-treatment-improve-kidney-function-adults-hepatorenal-syndrome |archive-date=2023-02-10 |access-date=2023-02-21}}</ref> New Zealand,<ref>{{cite web | title = GLYPRESSIN 1mg/8.5mL Solution for Injection; Terlipressin acetate | work = Medsafe, New Zealand Medicines and Medical Devices Safety Authority | publisher = New Zeeland Ministry of Health | url = http://www.medsafe.govt.nz/profs/datasheet/g/Glypressin01mgmlFerringinj.pdf | archive-url = https://web.archive.org/web/20211220215013/https://www.medsafe.govt.nz/profs/Datasheet/g/Glypressin01mgmlFerringinj.pdf | archive-date=2021-12-20 }}</ref> Australia, the European Union,<ref>{{cite web|url=https://www.drugs.com/international/terlipressin.html|title=Terlipressin|access-date=2018-01-23|archive-date=2019-06-26|archive-url=https://web.archive.org/web/20190626082700/https://www.drugs.com/international/terlipressin.html|url-status=live | work = Drugs.com }}</ref> India, Pakistan & UAE. It is sold under various brand names including Glypressin and Terlivaz.
+== References ==
+{{Reflist}}
+== External links ==
+* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/terlipressin | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Terlipressin }}
+{{Oxytocin and vasopressin receptor modulators}}
+{{Portal bar | Medicine}}
+[[Category:Vasoconstrictors]]
+[[Category:Peptides]]
+[[Category:Vasopressin receptor agonists]]
+[[Category:Antidiuretics]]