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MedKoo Cat#: 464490 | Name: Alvimopan-d5

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Alvimopan-d5 is intended for use as an internal standard for the quantification of alvimopan by GC- or LC-MS. Alvimopan is a μ-opioid receptor antagonist (Ki = 0.47 nM). It is selective over the κ- and δ-opioid receptors (Kis= 100 nM and 12 nM, respectively). Alvimopan inhibits μ-opioid receptor-mediated GTP binding to CHO cell membranes with an IC50 value of 1.7 nM. It inhibits morphine-induced slowing of colorectal transit in mice with an ED50 value of 0.41 mg/kg. Alvimopan (0.3 and 1 mg/kg, p.o.) reduces inhibition of gastrointestinal (GI) transit induced by morphine, but not apraclonidine, in rats. Formulations containing alvimopan have been used in the treatment of opioid-induced bowel dysfunction.

Chemical Structure

Alvimopan-d5
Alvimopan-d5
CAS#Alvimopan-d5

Theoretical Analysis

MedKoo Cat#: 464490

Name: Alvimopan-d5

CAS#: Alvimopan-d5

Chemical Formula: C25H27D5N2O4

Exact Mass: 429.2676

Molecular Weight: 429.57

Elemental Analysis: C, 69.90; H, 8.68; N, 6.52; O, 14.90

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Related CAS #
156053-89-3 (free acid) 170098-38-1 (dihydrate) 1383577-62-5 (monohydrate) Alvimopan-d5
Synonym
Alvimopan-d5; Alvimopan d5; ADL 8-2698-d5;
IUPAC/Chemical Name
(3-((3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl)-2-((phenyl-d5)methyl)propanoyl)glycine
InChi Key
UPNUIXSCZBYVBB-VZVPYXQSSA-N
InChi Code
InChI=1S/C25H32N2O4/c1-18-16-27(12-11-25(18,2)21-9-6-10-22(28)14-21)17-20(24(31)26-15-23(29)30)13-19-7-4-3-5-8-19/h3-10,14,18,20,28H,11-13,15-17H2,1-2H3,(H,26,31)(H,29,30)/t18-,20?,25+/m0/s1/i3D,4D,5D,7D,8D
SMILES Code
C[C@@]1([C@@H](C)CN(CC(CC2=C(C([2H])=C(C([2H])=C2[2H])[2H])[2H])C(NCC(O)=O)=O)CC1)C3=CC(O)=CC=C3
Appearance
Solid powder
Purity
>99% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 429.57 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Hamel JF, Sabbagh C, Alves A, Regimbeau JM, Vignaud T, Venara A. Comparison of treatment to improve gastrointestinal functions after colorectal surgery within enhanced recovery programmes: a systematic review and meta-analysis. Sci Rep. 2021 Apr 1;11(1):7423. doi: 10.1038/s41598-021-86699-w. PMID: 33795783; PMCID: PMC8016851. 2: Hanna P, Regmi S, Kalapara A, Mulpuri KS, Zabell J, Albersheim J, Wahr J, Randle D, Kaizer A, Patten L, Konety B, Weight C. Alvimopan as part of the Enhanced Recovery After Surgery protocol following radical cystectomy is associated with decreased hospital stay. Int J Urol. 2021 Mar 26. doi: 10.1111/iju.14546. Epub ahead of print. PMID: 33769634. 3: Anand NM, Liya DH, Pradhan AK, Tayal N, Bansal A, Donakonda S, Jainarayanan AK. A comprehensive SARS-CoV-2 genomic analysis identifies potential targets for drug repurposing. PLoS One. 2021 Mar 18;16(3):e0248553. doi: 10.1371/journal.pone.0248553. PMID: 33735271; PMCID: PMC7971693. 4: Baby K, Maity S, Mehta CH, Suresh A, Nayak UY, Nayak Y. SARS-CoV-2 entry inhibitors by dual targeting TMPRSS2 and ACE2: An in silico drug repurposing study. Eur J Pharmacol. 2021 Apr 5;896:173922. doi: 10.1016/j.ejphar.2021.173922. Epub 2021 Feb 2. PMID: 33539819. 5: Alhashemi M, Hamad R, El-Kefraoui C, Blouin MC, Amar-Zifkin A, Landry T, Lee L, Baldini G, Feldman LS, Fiore JF Jr. The association of alvimopan treatment with postoperative outcomes after abdominal surgery: A systematic review across different surgical procedures and contexts of perioperative care. Surgery. 2021 Apr;169(4):934-944. doi: 10.1016/j.surg.2020.11.025. Epub 2020 Dec 27. PMID: 33380353. 6: Wallace BK, Li G, McKiernan JM, DeCastro GJ, Anderson CB. Radical cystectomy in a cohort of octogenarians managed in the ERAS era. Urol Oncol. 2020 Sep 24:S1078-1439(20)30430-0. doi: 10.1016/j.urolonc.2020.09.009. Epub ahead of print. PMID: 32981848. 7: Richie JP. Re: Improving Postoperative Quality of Care in Germ Cell Tumor Patients: Does Scheduled Alvimopan, Acetaminophen, and Gabapentin Improve Short- Term Clinical Outcomes after Retroperitoneal Lymph Node Dissection? J Urol. 2020 Nov;204(5):1099-1100. doi: 10.1097/JU.0000000000001262.01. Epub 2020 Sep 8. PMID: 32897136. 8: Hensley P, Higgins M, Rasper A, Ziada A, Strup S, Coleman C, Ruf K, Gupta S. Efficacy and safety of alvimopan use in benign urinary tract reconstruction. Int Urol Nephrol. 2021 Jan;53(1):77-82. doi: 10.1007/s11255-020-02621-9. Epub 2020 Aug 31. PMID: 32869174. 9: Chamie K, Golla V, Lenis AT, Lec PM, Rahman S, Viscusi ER. Peripherally Acting μ-Opioid Receptor Antagonists in the Management of Postoperative Ileus: a Clinical Review. J Gastrointest Surg. 2021 Jan;25(1):293-302. doi: 10.1007/s11605-020-04671-x. Epub 2020 Aug 10. PMID: 32779081; PMCID: PMC7851096. 10: Ouyang R, Li Z, Huang S, Liu J, Huang J. Efficacy and Safety of Peripherally Acting Mu-Opioid Receptor Antagonists for the Treatment of Opioid-Induced Constipation: A Bayesian Network Meta-analysis. Pain Med. 2020 Nov 1;21(11):3224-3232. doi: 10.1093/pm/pnaa152. PMID: 32488259. 11: Huang JT, Cole AP, Mossanen M, Preston MA, Wang Y, Kibel AS, Chung BI, Huang WJ, Chang SL. Alvimopan Is Associated With a Reduction in Length of Stay and Hospital Costs for Patients Undergoing Radical Cystectomy. Urology. 2020 Jun;140:115-121. doi: 10.1016/j.urology.2020.01.049. Epub 2020 Apr 5. PMID: 32268172. 12: Wessels F, Lenhart M, Kowalewski KF, Braun V, Terboven T, Roghmann F, Michel MS, Honeck P, Kriegmair MC. Early recovery after surgery for radical cystectomy: comprehensive assessment and meta-analysis of existing protocols. World J Urol. 2020 Dec;38(12):3139-3153. doi: 10.1007/s00345-020-03133-y. Epub 2020 Mar 2. PMID: 32124020; PMCID: PMC7716903. 13: Faraj KS, Judge NZ, Rose KM, Eversman S, Richards J, Blodgett G, Singh V, DeLucia NM, Humphreys MR, Castle EP, Tyson MD 2nd. How the Beneficial Effects of Alvimopan Differ With Surgical Approach for Radical Cystectomy. Urology. 2020 Jun;140:107-114. doi: 10.1016/j.urology.2019.12.058. Epub 2020 Feb 27. PMID: 32113791. 14: Calaway AC, Foster RS, Tong Y, Masterson TA, Bihrle R, Cary C. Improving postoperative quality of care in germ cell tumor patients: Does scheduled alvimopan, acetaminophen, and gabapentin improve short-term clinical outcomes after retroperitoneal lymph node dissection? Urol Oncol. 2020 Apr;38(4):305-312. doi: 10.1016/j.urolonc.2019.12.016. Epub 2020 Jan 27. PMID: 32001197. 15: Hu KY, Peterson CY, Ludwig KA, Ridolfi TJ. Response to: "Alvimopan and outcome after colectomy?". Surgery. 2020 Mar;167(3):677. doi: 10.1016/j.surg.2019.10.007. Epub 2019 Nov 27. PMID: 31785823. 16: Ueland W, Walsh-Blackmore S, Nisiewicz M, Davenport DL, Plymale MA, Plymale M, Roth JS. The contribution of specific enhanced recovery after surgery (ERAS) protocol elements to reduced length of hospital stay after ventral hernia repair. Surg Endosc. 2020 Oct;34(10):4638-4644. doi: 10.1007/s00464-019-07233-8. Epub 2019 Nov 8. PMID: 31705287. 17: Kehlet H. Alvimopan and outcome after colectomy? Surgery. 2020 Mar;167(3):676-677. doi: 10.1016/j.surg.2019.08.005. Epub 2019 Sep 27. PMID: 31570148. 18: Jang J, Kwok B, Zhong H, Xia Y, Grucela A, Bernstein M, Remzi F, Hudesman D, Chen J, Axelrad J, Chang S. Alvimopan for the Prevention of Postoperative Ileus in Inflammatory Bowel Disease Patients. Dig Dis Sci. 2020 Apr;65(4):1164-1171. doi: 10.1007/s10620-019-05839-5. Epub 2019 Sep 14. PMID: 31522323. 19: Discussion. Surgery. 2019 Oct;166(4):488. doi: 10.1016/j.surg.2019.04.049. Epub 2019 Jul 22. PMID: 31345566. 20: Henning RE, Hu KY, Rein LE, Szabo A, Peterson CY, Ludwig KA, Ridolfi TJ. Alvimopan is associated with decreased length of stay for both open and laparoscopic segmental colectomy. Surgery. 2019 Oct;166(4):483-488. doi: 10.1016/j.surg.2019.04.035. Epub 2019 Jul 22. PMID: 31345565.