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MedKoo Cat#: 461068 | Name: Loperamide oxide
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Description:

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

Loperamide oxide is a prodrug of the effective antidiarrheal loperamide.

Chemical Structure

Loperamide oxide
Loperamide oxide
CAS#106900-12-3

Theoretical Analysis

MedKoo Cat#: 461068

Name: Loperamide oxide

CAS#: 106900-12-3

Chemical Formula: C29H33ClN2O3

Exact Mass: 492.2180

Molecular Weight: 493.04

Elemental Analysis: C, 70.65; H, 6.75; Cl, 7.19; N, 5.68; O, 9.73

Price and Availability

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25mg USD 550.00 2 weeks
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Synonym
Loperamide oxide; R 58425; R-58425; R58425; Loperamide N-oxide
IUPAC/Chemical Name
(1r,4s)-4-(4-chlorophenyl)-1-(4-(dimethylamino)-4-oxo-3,3-diphenylbutyl)-4-hydroxypiperidine 1-oxide
InChi Key
KXVSBTJVTUVNPM-UKPNQBOSSA-N
InChi Code
InChI=1S/C29H33ClN2O3/c1-31(2)27(33)29(24-9-5-3-6-10-24,25-11-7-4-8-12-25)19-22-32(35)20-17-28(34,18-21-32)23-13-15-26(30)16-14-23/h3-16,34H,17-22H2,1-2H3/t28-,32-
SMILES Code
O=C(N(C)C)C(C1=CC=CC=C1)(C2=CC=CC=C2)CC[N@@+]3([O-])CC[C@](O)(C4=CC=C(Cl)C=C4)CC3
Appearance
Solid powder
Purity
>95% (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
Shelf Life
>3 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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Loperamide oxide is a prodrug of the effective antidiarrheal loperamide.
In vitro activity:
The effect of loperamide on tachykinin NK(2)- and NK(3)-receptor-mediated 5-HT outflow from guinea pig colonic mucosa was investigated in vitro. Loperamide concentration-dependently suppressed the senktide-evoked 5-HT outflow, but failed to affect the betaAla-NKA-evoked 5-HT outflow. Reference: J Pharmacol Sci. 2005 Jun;98(2):175-80. https://pubmed.ncbi.nlm.nih.gov/15942125/
In vivo activity:
Peripheral opioids act as analgesics in bone cancer pain in mice. The aim of this report was to characterize the analgesic responses obtained by activating peripheral opioid receptors in bone cancer pain. Loperamide, an opioid agonist unable to cross the blood-brain barrier, inhibits both thermal and mechanical hyperalgesia when s.c. injected, locally over the tibial tumoral mass (7.5-75 microg) or distantly, under the fur of the neck (4 mg/kg). Reference: Pharmacol Biochem Behav. 2005 May;81(1):114-21. https://pubmed.ncbi.nlm.nih.gov/15894068/

Preparing Stock Solutions

The following data is based on the product molecular weight 493.04 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
Formulation protocol:
1. Kojima S, Ikeda M, Kamikawa Y. Loperamide inhibits tachykinin NK3-receptor-triggered serotonin release without affecting NK2-receptor-triggered serotonin release from guinea pig colonic mucosa. J Pharmacol Sci. 2005 Jun;98(2):175-80. doi: 10.1254/jphs.fpj05011x. Epub 2005 Jun 8. PMID: 15942125. 2. Church J, Fletcher EJ, Abdel-Hamid K, MacDonald JF. Loperamide blocks high-voltage-activated calcium channels and N-methyl-D-aspartate-evoked responses in rat and mouse cultured hippocampal pyramidal neurons. Mol Pharmacol. 1994 Apr;45(4):747-57. PMID: 8183255. 3. Menéndez L, Lastra A, Meana A, Hidalgo A, Baamonde A. Analgesic effects of loperamide in bone cancer pain in mice. Pharmacol Biochem Behav. 2005 May;81(1):114-21. doi: 10.1016/j.pbb.2005.02.007. Epub 2005 Apr 25. PMID: 15894068. 4. DeHaven-Hudkins DL, Burgos LC, Cassel JA, Daubert JD, DeHaven RN, Mansson E, Nagasaka H, Yu G, Yaksh T. Loperamide (ADL 2-1294), an opioid antihyperalgesic agent with peripheral selectivity. J Pharmacol Exp Ther. 1999 Apr;289(1):494-502. PMID: 10087042.
In vitro protocol:
1. Kojima S, Ikeda M, Kamikawa Y. Loperamide inhibits tachykinin NK3-receptor-triggered serotonin release without affecting NK2-receptor-triggered serotonin release from guinea pig colonic mucosa. J Pharmacol Sci. 2005 Jun;98(2):175-80. doi: 10.1254/jphs.fpj05011x. Epub 2005 Jun 8. PMID: 15942125. 2. Church J, Fletcher EJ, Abdel-Hamid K, MacDonald JF. Loperamide blocks high-voltage-activated calcium channels and N-methyl-D-aspartate-evoked responses in rat and mouse cultured hippocampal pyramidal neurons. Mol Pharmacol. 1994 Apr;45(4):747-57. PMID: 8183255.
In vivo protocol:
1. Menéndez L, Lastra A, Meana A, Hidalgo A, Baamonde A. Analgesic effects of loperamide in bone cancer pain in mice. Pharmacol Biochem Behav. 2005 May;81(1):114-21. doi: 10.1016/j.pbb.2005.02.007. Epub 2005 Apr 25. PMID: 15894068. 2. DeHaven-Hudkins DL, Burgos LC, Cassel JA, Daubert JD, DeHaven RN, Mansson E, Nagasaka H, Yu G, Yaksh T. Loperamide (ADL 2-1294), an opioid antihyperalgesic agent with peripheral selectivity. J Pharmacol Exp Ther. 1999 Apr;289(1):494-502. PMID: 10087042.
1: Kamali F, Huang ML. Increased systemic availability of loperamide after oral administration of loperamide and loperamide oxide with cotrimoxazole. Br J Clin Pharmacol. 1996 Feb;41(2):125-8. PubMed PMID: 8838438. 2: Dettmer A. Loperamide oxide in the treatment of acute diarrhea in adults. Clin Ther. 1994 Nov-Dec;16(6):972-80. PubMed PMID: 7697694. 3: Stacher G, Steinringer H, Schneider C, Vacariu-Granser GV, Castiglione F, Gaupmann G, Weber U, Stacher-Janotta G. Effects of the prodrug loperamide oxide, loperamide, and placebo on jejunal motor activity. Dig Dis Sci. 1992 Feb;37(2):198-204. PubMed PMID: 1735336. 4: Dreverman JW, Van der Poel AJ. Loperamide oxide in acute diarrhoea: a double-blind, placebo-controlled trial. The Dutch Diarrhoea Trialists Group. Aliment Pharmacol Ther. 1995 Aug;9(4):441-6. PubMed PMID: 8527621. 5: van Outryve M, Toussaint J. Loperamide oxide for the treatment of chronic diarrhoea in Crohn's disease. J Int Med Res. 1995 Sep-Oct;23(5):335-41. PubMed PMID: 8529776. 6: Göke M, Ewe K, Donner K, Meyer zum Büschenfelde KH. Influence of loperamide and loperamide oxide on the anal sphincter. A manometric study. Dis Colon Rectum. 1992 Sep;35(9):857-61. PubMed PMID: 1511646. 7: Sun WM, Read NW, Verlinden M. Effects of loperamide oxide on gastrointestinal transit time and anorectal function in patients with chronic diarrhoea and faecal incontinence. Scand J Gastroenterol. 1997 Jan;32(1):34-8. PubMed PMID: 9018764. 8: Van Beijsterveldt LE, Geerts RJ, Wuyts K, Woestenborghs RJ, Meuldermans WE, Heykants JJ. Gastrointestinal distribution of the prodrug loperamide oxide and its active drug loperamide in the dog. Drug Metab Dispos. 1995 Feb;23(2):216-22. PubMed PMID: 7736914. 9: Hardcastle J, Hardcastle PT, Goldhill J. Comparison of the effects of loperamide and loperamide oxide on absorptive processes in rat small intestine. J Pharm Pharmacol. 1993 Oct;45(10):919-21. PubMed PMID: 7904634. 10: Beubler E, Badhri P. Comparison of the antisecretory effects of loperamide and loperamide oxide in the jejunum and the colon of rats in-vivo. J Pharm Pharmacol. 1990 Oct;42(10):689-92. PubMed PMID: 1982139. 11: Yeoh EK, Horowitz M, Russo A, Muecke T, Robb T, Chatterton BE. Gastrointestinal function in chronic radiation enteritis--effects of loperamide-N-oxide. Gut. 1993 Apr;34(4):476-82. PubMed PMID: 8491393; PubMed Central PMCID: PMC1374306. 12: Hughes IW. First-line treatment in acute non-dysenteric diarrhoea: clinical comparison of loperamide oxide, loperamide and placebo. UK Janssen Research Group of General Practitioners. Br J Clin Pract. 1995 Jul-Aug;49(4):181-5. PubMed PMID: 7547157. 13: Hardcastle J, Hardcastle PT, Goldhill J. The effect of loperamide oxide on prostaglandin-stimulated fluid transport in rat small intestine. J Pharm Pharmacol. 1990 May;42(5):364-6. PubMed PMID: 1976790. 14: Lavrijsen K, van Dyck D, van Houdt J, Hendrickx J, Monbaliu J, Woestenborghs R, Meuldermans W, Heykants J. Reduction of the prodrug loperamide oxide to its active drug loperamide in the gut of rats, dogs, and humans. Drug Metab Dispos. 1995 Mar;23(3):354-62. PubMed PMID: 7628301. 15: Stevens PJ, Dunbar F, Briscoe P. Potential of Loperamide Oxide in the Reduction of Ileostomy and Colostomy Output. Clin Drug Investig. 1995 Sep;10(3):158-64. doi: 10.2165/00044011-199510030-00004. PubMed PMID: 27519199. 16: Kamali F, Adriaens L, Huang ML, Woestenborghs R, Emanuel M, Rawlins MD. Dose proportionality study of loperamide following oral administration of loperamide oxide. Eur J Clin Pharmacol. 1992;42(6):693-4. PubMed PMID: 1623916. 17: Beubler E, Badhri P, Schirgi-Degen A. Antisecretory activities of orally administered loperamide and loperamide oxide on intestinal secretion in rats. J Pharm Pharmacol. 1993 Sep;45(9):803-6. PubMed PMID: 7903368. 18: Nikodem VC, Hofmeyr GJ. Secretion of the antidiarrhoeal agent loperamide oxide in breast milk. Eur J Clin Pharmacol. 1992;42(6):695-6. PubMed PMID: 1623917. 19: Ragnarsson G, Bodemar G. Treatment of irritable bowel syndrome with loperamide oxide. An open study to determine optimal dosage. J Intern Med. 2000 Aug;248(2):165-6. PubMed PMID: 10947896. 20: Megens AA, Canters LL, Awouters FH, Niemegeers CJ. Normalization of small intestinal propulsion with loperamide-like antidiarrheals in rats. Eur J Pharmacol. 1990 Mar 27;178(3):357-64. PubMed PMID: 2340864.