{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,9]],"date-time":"2025-11-09T07:48:21Z","timestamp":1762674501023,"version":"3.44.0"},"reference-count":27,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2021,12,1]],"date-time":"2021-12-01T00:00:00Z","timestamp":1638316800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2021,12,1]],"date-time":"2021-12-01T00:00:00Z","timestamp":1638316800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"},{"start":{"date-parts":[[2021,12,1]],"date-time":"2021-12-01T00:00:00Z","timestamp":1638316800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-017"},{"start":{"date-parts":[[2021,12,1]],"date-time":"2021-12-01T00:00:00Z","timestamp":1638316800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2021,12,1]],"date-time":"2021-12-01T00:00:00Z","timestamp":1638316800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-012"},{"start":{"date-parts":[[2021,12,1]],"date-time":"2021-12-01T00:00:00Z","timestamp":1638316800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2021,12,1]],"date-time":"2021-12-01T00:00:00Z","timestamp":1638316800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-004"}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["Steroids"],"published-print":{"date-parts":[[2021,12]]},"DOI":"10.1016\/j.steroids.2021.108928","type":"journal-article","created":{"date-parts":[[2021,10,13]],"date-time":"2021-10-13T21:34:16Z","timestamp":1634160856000},"page":"108928","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":5,"special_numbering":"C","title":["Vecuronium bromide and its advanced intermediates: A crystallographic and spectroscopic study"],"prefix":"10.1016","volume":"176","author":[{"given":"Samuele","family":"Ciceri","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Diego","family":"Colombo","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Patrizia","family":"Ferraboschi","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Paride","family":"Grisenti","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Marco","family":"Iannone","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Matteo","family":"Mori","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Fiorella","family":"Meneghetti","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"78","reference":[{"issue":"1","key":"10.1016\/j.steroids.2021.108928_b0005","first-page":"2","article-title":"Pharmacology of neuromuscular blocking drugs","volume":"4","author":"Appiah-Ankam","year":"2004","journal-title":"BJA Educ."},{"issue":"23","key":"10.1016\/j.steroids.2021.108928_b0010","doi-asserted-by":"crossref","first-page":"2287","DOI":"10.1093\/ajhp\/58.23.2287","article-title":"Neuromuscular blockers in surgery and intensive care, part 1","volume":"58","author":"McManus","year":"2001","journal-title":"Am. J. Health Syst. Pharm."},{"issue":"16","key":"10.1016\/j.steroids.2021.108928_b0015","doi-asserted-by":"crossref","first-page":"1507","DOI":"10.2174\/0929867023369466","article-title":"Synthesis and structure-activity relationships of neuromuscular blocking agents","volume":"9","author":"Zoltan","year":"2002","journal-title":"Curr. Med. Chem."},{"issue":"5 Suppl","key":"10.1016\/j.steroids.2021.108928_b0020","doi-asserted-by":"crossref","first-page":"S2","DOI":"10.1097\/00000539-200005001-00002","article-title":"Neuromuscular blocking drugs for the new millennium: current practice, future trends\u2013comparative pharmacology of neuromuscular blocking drugs","volume":"90","author":"Donati","year":"2000","journal-title":"Anesth. Analg."},{"key":"10.1016\/j.steroids.2021.108928_b0025","unstructured":"C.L. Hewett, D.S. Savage, Improvements in or relating to new 2 \u03b2,16 \u03b2 -diamino-androstanes, (1965) GB1138605."},{"key":"10.1016\/j.steroids.2021.108928_b0030","doi-asserted-by":"crossref","unstructured":"Chapter 8 \u2013 Relaxation of the skeletal muscles, in: K.W. Clarke, C.M. Trim, L.W. Hall (Eds.), Veterinary Anaesthesia, eleventh ed., W.B. Saunders, Oxford, 2014, pp. 169\u2013194.","DOI":"10.1016\/B978-0-7020-2793-2.00008-6"},{"issue":"4","key":"10.1016\/j.steroids.2021.108928_b0035","doi-asserted-by":"crossref","first-page":"490","DOI":"10.1097\/ACO.0000000000000891","article-title":"The future of neuromuscular blocking agents","volume":"33","author":"Stauble","year":"2020","journal-title":"Curr. Opin. Anaesthesiol."},{"key":"10.1016\/j.steroids.2021.108928_b0040","unstructured":"World Health Organization Model List of Essential Medicines, 21st List, 2019, World Health Organization, Geneva. https:\/\/www.who.int\/publications\/i\/item\/WHOMVPEMPIAU2019.06, 2019. Accessed 05 July 2021."},{"issue":"10","key":"10.1016\/j.steroids.2021.108928_b0045","doi-asserted-by":"crossref","first-page":"1116","DOI":"10.1021\/jm00268a011","article-title":"Pancuronium bromide and other steroidal neuromuscular blocking agents containing acetylcholine fragments","volume":"16","author":"Buckett","year":"1973","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.steroids.2021.108928_b0050","doi-asserted-by":"crossref","unstructured":"H. Kooijman, V.J. Van Geerestein, P. Van der Sluis, J.A. Kanters, J. Kroon, C.W. Funke, J. Kelder, Molecular structure of vecuronium bromide, a neuromuscular blocking agent. Crystal structure, molecular mechanics and NMR investigations, J. Chem. Soc., Perkin Trans. 2 (10) (1991) 1581. 10.1039\/P29910001581.","DOI":"10.1039\/p29910001581"},{"issue":"6","key":"10.1016\/j.steroids.2021.108928_b0055","doi-asserted-by":"crossref","first-page":"387","DOI":"10.1002\/(SICI)1097-458X(199806)36:6<387::AID-OMR282>3.0.CO;2-2","article-title":"1H and 13C NMR studies of some steroidal neuromuscular blocking drugs: solution conformations and dynamics","volume":"36","author":"Fielding","year":"1998","journal-title":"Magn. Reson. Chem."},{"issue":"4","key":"10.1016\/j.steroids.2021.108928_b0060","first-page":"531","article-title":"Structure elucidation of androstane intermediate in the synthesis of vecuronium bromide","volume":"25","author":"Jiang","year":"2008","journal-title":"Bopuxue Zazhi"},{"key":"10.1016\/j.steroids.2021.108928_b0065","doi-asserted-by":"crossref","unstructured":"P. Ferraboschi, M. Chiara Sala, R. Stradi, L. Ragonesi, C. Gagliardi, P. Lanzarotti, E.M. Ragg, M. Mori, F. Meneghetti, Full spectroscopic characterization of two crystal pseudopolymorphic forms of the antiandrogen cortexolone 17 \u03b1 -propionate for topic application, Steroids 128 (2017) 95\u2013104. https:\/\/doi.org\/10.1016\/j.steroids.2017.09.003.","DOI":"10.1016\/j.steroids.2017.09.003"},{"key":"10.1016\/j.steroids.2021.108928_b0070","doi-asserted-by":"crossref","first-page":"137","DOI":"10.1016\/j.steroids.2015.09.007","article-title":"Crystallographic and spectroscopic study on a known orally active progestin","volume":"104","author":"Ferraboschi","year":"2015","journal-title":"Steroids"},{"issue":"2","key":"10.1016\/j.steroids.2021.108928_b0075","doi-asserted-by":"crossref","first-page":"331","DOI":"10.3390\/molecules25020331","article-title":"Crystallographic and NMR investigation of ergometrine and methylergometrine, two alkaloids from claviceps purpurea","volume":"25","author":"Meneghetti","year":"2020","journal-title":"Molecules"},{"key":"10.1016\/j.steroids.2021.108928_b0080","doi-asserted-by":"crossref","first-page":"542","DOI":"10.1021\/jo01122a018","article-title":"A synthesis of androsterone","volume":"20","author":"Iriarte","year":"1955","journal-title":"J. Org. Chem."},{"key":"10.1016\/j.steroids.2021.108928_b0085","doi-asserted-by":"crossref","unstructured":"Z. Tuba, Synthesis of 2 \u03b2,16 \u03b2 -bis-(4'-dimethyl-1'-piperazino)-3\u03b1,17 \u03b2 -diacetoxy-5 \u03b1 -androstane dibromide and related compounds, Arzneimittelforschung 30(2a) (1980) 342\u2013346.","DOI":"10.1002\/chin.198027271"},{"key":"10.1016\/j.steroids.2021.108928_b0090","unstructured":"Z. Tuba, S. Maho, G. Szabo, G. Galik, G. Balogh, Environmentally-Friendly Process for the Synthesis of Quaternary Ammonium-Steroids, 2006. WO2006038047."},{"key":"10.1016\/j.steroids.2021.108928_b0095","doi-asserted-by":"crossref","unstructured":"D.N. Kirk, S.J. Gaskell, B.A. Marples, Spectroscopic Methods of Steroid Analysis, Blackie, 1995, p. 25\u2013113. 10.1007\/978-94-017-3078-5_2.","DOI":"10.1007\/978-94-017-3078-5_2"},{"issue":"7","key":"10.1016\/j.steroids.2021.108928_b0100","doi-asserted-by":"crossref","first-page":"559","DOI":"10.1002\/bscb.19840930704","article-title":"Nitrogen-15 NMR spectroscopy \u2013 applications in heterocyclic chemistry","volume":"93","author":"Fritz","year":"1984","journal-title":"Bull. Soc. Chim. Belg."},{"issue":"1","key":"10.1016\/j.steroids.2021.108928_b0105","doi-asserted-by":"crossref","first-page":"306","DOI":"10.1107\/S1600576715001132","article-title":"Crystal structure determination and refinement via SIR2014","volume":"48","author":"Burla","year":"2015","journal-title":"J. Appl. Crystallogr."},{"issue":"1","key":"10.1016\/j.steroids.2021.108928_b0110","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","article-title":"Crystal structure refinement with SHELXL","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. C"},{"issue":"4","key":"10.1016\/j.steroids.2021.108928_b0115","doi-asserted-by":"crossref","first-page":"849","DOI":"10.1107\/S0021889812029111","article-title":"WinGX and ORTEP for Windows: an update","volume":"45","author":"Farrugia","year":"2012","journal-title":"J. Appl. Crystallogr."},{"issue":"5","key":"10.1016\/j.steroids.2021.108928_b0120","doi-asserted-by":"crossref","first-page":"659","DOI":"10.1107\/S0021889895007138","article-title":"PARST95 \u2013 an update to PARST: a system of Fortran routines for calculating molecular structure parameters from the results of crystal structure analyses","volume":"28","author":"Nardelli","year":"1995","journal-title":"J. Appl. Crystallogr."},{"key":"10.1016\/j.steroids.2021.108928_b0125","doi-asserted-by":"crossref","unstructured":"C.F. Macrae, I. Sovago, S.J. Cottrell, P.T.A. Galek, P. McCabe, E. Pidcock, M. Platings, G.P. Shields, J.S. Stevens, M. Towler, P.A. Wood, Mercury 4.0: from visualization to analysis, design and prediction, J. Appl. Crystallogr. 53 (1) (2020) 226\u2013235. 10.1107\/S1600576719014092.","DOI":"10.1107\/S1600576719014092"},{"key":"10.1016\/j.steroids.2021.108928_b0130","unstructured":"M.J. Turner, J.J. McKinnon, S.K. Wolff, D.J. Grimwood, P.R. Spackman, D. Jayatilaka, M.A. Spackman, CrystalExplorer17, University of Western Australia. http:\/\/crystalexplorer.scb.uwa.edu.au\/, 2017. Accessed on 05 July 2021."},{"key":"10.1016\/j.steroids.2021.108928_b0135","doi-asserted-by":"crossref","unstructured":"D. Cremer, J.A. Pople, Molecular orbital theory of the electronic structure of organic compounds. XXIII. Pseudorotation in saturated five-membered ring compounds, J. Am. Chem. Soc. 97 (6) (1975) 1358\u20131367. 10.1021\/ja00839a012.","DOI":"10.1021\/ja00839a012"}],"container-title":["Steroids"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0039128X21001409?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0039128X21001409?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2025,9,22]],"date-time":"2025-09-22T10:08:00Z","timestamp":1758535680000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0039128X21001409"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,12]]},"references-count":27,"alternative-id":["S0039128X21001409"],"URL":"https:\/\/doi.org\/10.1016\/j.steroids.2021.108928","relation":{},"ISSN":["0039-128X"],"issn-type":[{"type":"print","value":"0039-128X"}],"subject":[],"published":{"date-parts":[[2021,12]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Vecuronium bromide and its advanced intermediates: A crystallographic and spectroscopic study","name":"articletitle","label":"Article Title"},{"value":"Steroids","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.steroids.2021.108928","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2021 Elsevier Inc. All rights reserved.","name":"copyright","label":"Copyright"}],"article-number":"108928"}}