Alvimopan
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MedKoo CAT#: 326704

CAS#: 156053-89-3

Description: Alvimopan, also known as HSDB-7704 and LY246736, is a drug which behaves as a peripherally acting μ-opioid antagonist. With limited ability to cross the blood–brain barrier, many of the undesirable side-effects of the opioid agonists such as constipation are minimized without affecting analgesia or precipitating withdrawal. It was approved in 2008. Alvimopan is indicated in people to avoid postoperative ileus following partial large or small bowel resection with primary anastomosis. Alvimopan accelerates the gastrointestinal recovery period as defined by time to first bowel movement or flatus.


Chemical Structure

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Alvimopan
CAS# 156053-89-3

Theoretical Analysis

MedKoo Cat#: 326704
Name: Alvimopan
CAS#: 156053-89-3
Chemical Formula: C25H32N2O4
Exact Mass: 424.2362
Molecular Weight: 424.541
Elemental Analysis: C, 70.73; H, 7.60; N, 6.60; O, 15.07

Price and Availability

Size Price Availability Quantity
5.0mg USD 260.0 2 Weeks
10.0mg USD 435.0 2 Weeks
25.0mg USD 790.0 2 Weeks
100.0mg USD 1550.0 2 Weeks
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Synonym: HSDB 7704; HSDB7704; HSDB-7704; LY246736; LY246736; LY-246736; Alvimopan. trade name Entereg.

IUPAC/Chemical Name: ((S)-2-benzyl-3-((3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl)propanoyl)glycine

InChi Key: UPNUIXSCZBYVBB-JVFUWBCBSA-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

SMILES Code: O=C(O)CNC([C@H](CN1C[C@H](C)[C@](C)(C2=CC=CC(O)=C2)CC1)CC3=CC=CC=C3)=O

Appearance: Solid powder

Purity: >98% (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: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

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

Preparing Stock Solutions

The following data is based on the product molecular weight 424.541 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

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1: Adam MA, Sun Z, Kim J, Thacker JK. Reply to Letter: Alvimopan Is Associated With Improved Outcomes and Cost Savings in Enhanced Recovery Colorectal Surgery Protocols. Ann Surg. 2016 Jun 8. [Epub ahead of print] PubMed PMID: 27280513.

2: Keller DS, Flores-Gonzalez JR, Ibarra S, Mahmood A, Haas EM. Is there value in alvimopan in minimally invasive colorectal surgery? Am J Surg. 2016 May 10. pii: S0002-9610(16)30211-2. doi: 10.1016/j.amjsurg.2016.02.016. [Epub ahead of print] PubMed PMID: 27262754.

3: Kehlet H. Alvimopan in Enhanced Recovery Colorectal Surgery? Ann Surg. 2016 May 26. [Epub ahead of print] PubMed PMID: 27232255.

4: Colorectal Writing Group for the SCOAP-CERTAIN Collaborative, Ehlers AP, Simianu VV, Bastawrous AL, Billingham RP, Davidson GH, Fichera A, Florence MG, Menon R, Thirlby RC, Flum DR, Farjah F. Alvimopan Use, Outcomes, and Costs: A Report from the Surgical Care and Outcomes Assessment Program Comparative Effectiveness Research Translation Network Collaborative. J Am Coll Surg. 2016 May;222(5):870-7. doi: 10.1016/j.jamcollsurg.2016.01.051. Epub 2016 Feb 5. PubMed PMID: 27113517; PubMed Central PMCID: PMC4848460.

5: Shah KN, Waryasz G, DePasse JM, Daniels AH. Prevention of Paralytic Ileus Utilizing Alvimopan Following Spine Surgery. Orthop Rev (Pavia). 2015 Sep 28;7(3):6087. doi: 10.4081/or.2015.6087. eCollection 2015 Sep 28. PubMed PMID: 26605031; PubMed Central PMCID: PMC4592934.

6: Cui Y, Chen H, Qi L, Zu X, Li Y. Effect of alvimopan on accelerates gastrointestinal recovery after radical cystectomy: A systematic review and meta-analysis. Int J Surg. 2016 Jan;25:1-6. doi: 10.1016/j.ijsu.2015.11.013. Epub 2015 Nov 18. Review. PubMed PMID: 26596716.

7: Adam MA, Lee LM, Kim J, Shenoi M, Mallipeddi M, Aziz H, Stinnett S, Sun Z, Mantyh CR, Thacker JK. Alvimopan Provides Additional Improvement in Outcomes and Cost Savings in Enhanced Recovery Colorectal Surgery. Ann Surg. 2016 Jul;264(1):141-6. doi: 10.1097/SLA.0000000000001428. PubMed PMID: 26501697.

8: Brady JT, Dosokey EM, Crawshaw BP, Steele SR, Delaney CP. The use of alvimopan for postoperative ileus in small and large bowel resections. Expert Rev Gastroenterol Hepatol. 2015;9(11):1351-8. doi: 10.1586/17474124.2015.1095637. Epub 2015 Oct 21. PubMed PMID: 26488223.

9: Nguyen DL, Maithel S, Nguyen ET, Bechtold ML. Does alvimopan enhance return of bowel function in laparoscopic gastrointestinal surgery? A meta-analysis. Ann Gastroenterol. 2015 Oct-Dec;28(4):475-80. PubMed PMID: 26423597; PubMed Central PMCID: PMC4585395.

10: Earnshaw SR, Kauf TL, McDade C, Potashman MH, Pauyo C, Reese ES, Senagore A. Economic Impact of Alvimopan Considering Varying Definitions of Postoperative Ileus. J Am Coll Surg. 2015 Nov;221(5):941-50. doi: 10.1016/j.jamcollsurg.2015.08.004. Epub 2015 Aug 15. PubMed PMID: 26353904.

11: Berger NG, Ridolfi TJ, Ludwig KA. Delayed gastrointestinal recovery after abdominal operation - role of alvimopan. Clin Exp Gastroenterol. 2015 Aug 5;8:231-5. doi: 10.2147/CEG.S64029. eCollection 2015. Review. PubMed PMID: 26346889; PubMed Central PMCID: PMC4531031.

12: Manger JP, Nelson M, Blanchard S, Helo S, Conaway M, Krupski TL. Alvimopan: A cost-effective tool to decrease cystectomy length of stay. Cent European J Urol. 2014;67(4):335-41. doi: 10.5173/ceju.2014.04.art4. Epub 2014 Dec 5. PubMed PMID: 25667750; PubMed Central PMCID: PMC4310883.

13: McRae WH 3rd, Simpson-Camp L, Hammen PF, Al-Sayegh HK. The use of alvimopan in patients receiving epidural analgesia after large bowel resection. Am Surg. 2015 Feb;81(2):212-6. PubMed PMID: 25642887.

14: Simorov A, Thompson J, Oleynikov D. Alvimopan reduces length of stay and costs in patients undergoing segmental colonic resections: results from multicenter national administrative database. Am J Surg. 2014 Dec;208(6):919-25; discussion 925. doi: 10.1016/j.amjsurg.2014.08.011. Epub 2014 Sep 22. PubMed PMID: 25440479.

15: Lee CT. Reply to Santosh Kumar and Aditya Prakash Sharma's letter to the editor re: Cheryl T. Lee, Sam S. Chang, Ashish M. Kamat, et al. Alvimopan accelerates gastrointestinal recovery after radical cystectomy: a multicenter randomized placebo-controlled trial. Eur Urol 2014;66:265-72. Eur Urol. 2015 Feb;67(2):e30-1. doi: 10.1016/j.eururo.2014.09.051. Epub 2014 Oct 7. PubMed PMID: 25304758.

16: Kumar S, Sharma AP. Re: Cheryl T. Lee, Sam S. Chang, Ashish M. Kamat, et al. Alvimopan accelerates gastrointestinal recovery after radical cystectomy: a multicenter randomized placebo-controlled trial. Eur urol 2014;66:265-72. Eur Urol. 2015 Feb;67(2):e29. doi: 10.1016/j.eururo.2014.09.050. Epub 2014 Oct 3. PubMed PMID: 25288191.

17: Tobis S, Heinlen JE, Ruel N, Lau C, Kawachi M, Wilson T, Chan K. Effect of alvimopan on return of bowel function after robot-assisted radical cystectomy. J Laparoendosc Adv Surg Tech A. 2014 Oct;24(10):693-7. doi: 10.1089/lap.2014.0170. Epub 2014 Sep 2. PubMed PMID: 25180566.

18: Rodriguez RW. Off-label uses of alvimopan and methylnaltrexone. Am J Health Syst Pharm. 2014 Sep 1;71(17):1450-5. doi: 10.2146/ajhp130632. PubMed PMID: 25147168.

19: Vora A, Marchalik D, Nissim H, Kowalczyk K, Bandi G, McGeagh K, Lynch J, Venkatesan K, Ghasemian R, Hwang J, Hwang MV. Multi-institutional outcomes and cost effectiveness of using alvimopan to lower gastrointestinal morbidity after cystectomy and urinary diversion. Can J Urol. 2014 Apr;21(2):7222-7. PubMed PMID: 24775576.

20: Clyne M. Bladder cancer: faster recovery after radical cystectomy with alvimopan. Nat Rev Urol. 2014 Apr;11(4):186. doi: 10.1038/nrurol.2014.67. Epub 2014 Mar 18. PubMed PMID: 24637421.