Rapacuronium Bromide | Org 9487 | CAS#156137-99-4 | 465499-11-0 | neuromuscular blocker

MedKoo Cat#: 326865 | Name: Rapacuronium Bromide

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Description:

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

Rapacuronium Bromide, also known as Org 9487, is a rapidly acting, non-depolarizing neuromuscular blocker formerly used in modern anaesthesia, to aid and enable endotracheal intubation, which is often necessary to assist in the controlled ventilation of unconscious patients during surgery and sometimes in intensive care. As a non-depolarizing agent it did not cause initial stimulation of muscles before weakening them. Due to risk of fatal bronchospasm it was withdrawn from the United States market by Organon on March 27, 2001, less than 2 years after its FDA approval in 1999.

Chemical Structure

Rapacuronium Bromide

CAS#156137-99-4 (bromide)

Theoretical Analysis

MedKoo Cat#: 326865

Name: Rapacuronium Bromide

CAS#: 156137-99-4 (bromide)

Chemical Formula: C37H61BrN2O4

Exact Mass: 0.0000

Molecular Weight: 677.81

Elemental Analysis: C, 65.57; H, 9.07; Br, 11.79; N, 4.13; O, 9.44

Price and Availability

Size	Price	Availability
5mg	USD 650.00	2 Weeks
10mg	USD 1,000.00	2 Weeks
25mg	USD 2,250.00	2 Weeks

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Related CAS #

156137-99-4 (bromide) 465499-11-0 (cation)

Synonym

Org 9487; Org9487; Org-9487; Rapacuronium Bromide, brand name Raplon.

IUPAC/Chemical Name

1-((2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-3-acetoxy-10,13-dimethyl-2-(piperidin-1-yl)-17-(propionyloxy)hexadecahydro-1H-cyclopenta[a]phenanthren-16-yl)-1-allylpiperidin-1-ium bromide

InChi Key

LVQTUXZKLGXYIU-GWSNJHLMSA-M

InChi Code

InChI=1S/C37H61N2O4.BrH/c1-6-20-39(21-12-9-13-22-39)32-24-30-28-15-14-27-23-33(42-26(3)40)31(38-18-10-8-11-19-38)25-37(27,5)29(28)16-17-36(30,4)35(32)43-34(41)7-2;/h6,27-33,35H,1,7-25H2,2-5H3;1H/q+1;/p-1/t27-,28+,29-,30-,31-,32-,33-,35-,36-,37-;/m0./s1

SMILES Code

C=CC[N+]1([C@H]2C[C@@]3([H])[C@]4([H])CC[C@@]5([H])C[C@H](OC(C)=O)[C@@H](N6CCCCC6)C[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@H]2OC(CC)=O)CCCCC1.[Br-]

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

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

Related CAS# 156137-99-4 (bromide) 465499-11-0 (cation)

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Rapacuronium bromide (Org 9487) is an allosteric modulator of muscarinic acetylcholine receptor (mAChR).

In vitro activity:

The dual detrimental interactions of rapacuronium with muscarinic receptors demonstrated in vitro correlate with in vivo muscarinic receptor mechanisms of bronchoconstriction and may account for the profound bronchoconstriction seen with its clinical use. Reference: Anesthesiology. 2007 Apr;106(4):763-72. https://pubmed.ncbi.nlm.nih.gov/17413914/

In vivo activity:

Rapacuronium accelerates the rate of ACh binding but decreases its affinity under equilibrium conditions. This results in potentiation of receptor activation at low concentrations of rapacuronium (1 microM) but not at high concentrations (10 microM). Reference: BMC Pharmacol. 2009 Dec 28;9:15. https://pubmed.ncbi.nlm.nih.gov/20038295/

Preparing Stock Solutions

The following data is based on the product molecular weight 677.81 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.

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. Jooste E, Zhang Y, Emala CW. Neuromuscular blocking agents' differential bronchoconstrictive potential in Guinea pig airways. Anesthesiology. 2007 Apr;106(4):763-72. doi: 10.1097/01.anes.0000264763.48920.c9. PMID: 17413914. 2. Jakubík J, Randáková A, El-Fakahany EE, Dolezal V. Divergence of allosteric effects of rapacuronium on binding and function of muscarinic receptors. BMC Pharmacol. 2009 Dec 28;9:15. doi: 10.1186/1471-2210-9-15. PMID: 20038295; PMCID: PMC2806265. 3. Jooste EH, Sharma A, Zhang Y, Emala CW. Rapacuronium augments acetylcholine-induced bronchoconstriction via positive allosteric interactions at the M3 muscarinic receptor. Anesthesiology. 2005 Dec;103(6):1195-203. doi: 10.1097/00000542-200512000-00014. PMID: 16306732.

In vitro protocol:

In vivo protocol:

1. Jakubík J, Randáková A, El-Fakahany EE, Dolezal V. Divergence of allosteric effects of rapacuronium on binding and function of muscarinic receptors. BMC Pharmacol. 2009 Dec 28;9:15. doi: 10.1186/1471-2210-9-15. PMID: 20038295; PMCID: PMC2806265. 2. Jooste EH, Sharma A, Zhang Y, Emala CW. Rapacuronium augments acetylcholine-induced bronchoconstriction via positive allosteric interactions at the M3 muscarinic receptor. Anesthesiology. 2005 Dec;103(6):1195-203. doi: 10.1097/00000542-200512000-00014. PMID: 16306732.

1: Plowman AN. Rapacuronium bromide (Organon Teknika). IDrugs. 1999 Jul;2(7):711-7. PMID: 16127642. 2: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2003 May;25(4):317-40. PMID: 12808477. 3: Wight WJ, Wright PM. Pharmacokinetics and pharmacodynamics of rapacuronium bromide. Clin Pharmacokinet. 2002;41(13):1059-76. doi: 10.2165/00003088-200241130-00004. PMID: 12403643. 4: Tuba Z, Maho S, Vizi ES. Synthesis and structure-activity relationships of neuromuscular blocking agents. Curr Med Chem. 2002 Aug;9(16):1507-36. doi: 10.2174/0929867023369466. PMID: 12171561. 5: Moore EW, Hunter JM. The new neuromuscular blocking agents: do they offer any advantages? Br J Anaesth. 2001 Dec;87(6):912-25. doi: 10.1093/bja/87.6.912. PMID: 11878696. 6: Sparr HJ, Beaufort TM, Fuchs-Buder T. Newer neuromuscular blocking agents: how do they compare with established agents? Drugs. 2001;61(7):919-42. doi: 10.2165/00003495-200161070-00003. PMID: 11434449. 7: Tobias JD, Johnson JO. Rapacuronium administration to patients receiving phenytoin or carbamazepine. J Neurosurg Anesthesiol. 2001 Jul;13(3):240-2. doi: 10.1097/00008506-200107000-00011. PMID: 11426100. 8: Stump L. Rapacuronium bromide. J Perianesth Nurs. 2000 Aug;15(4):258-9. doi: 10.1053/jpan.2000.9470. PMID: 11235463. 9: Frankowski GA, Johnson JO, Tobias JD. Rapacuronium administration to two children with Duchenne's muscular dystrophy. Anesth Analg. 2000 Jul;91(1):27-8. doi: 10.1097/00000539-200007000-00005. PMID: 10866881. 10: Onrust SV, Foster RH. Rapacuronium bromide: a review of its use in anaesthetic practice. Drugs. 1999 Nov;58(5):887-918. doi: 10.2165/00003495-199958050-00011. PMID: 10595867. 11: Proost JH, Schiere S, Beaufort TM, Wierda JM. Rapid onset/offset of rapacuronium bromide explained? Anesthesiology. 1999 Nov;91(5):1554-5; author reply 1555-6. doi: 10.1097/00000542-199911000-00058. PMID: 10551617. 12: Larijani GE, Zafeiridis A, Goldberg ME. Clinical pharmacology of rapacuronium bromide, a new short-acting neuromuscular blocking agent. Pharmacotherapy. 1999 Oct;19(10):1118-22. doi: 10.1592/phco.19.15.1118.30572. PMID: 10512060. 13: Atherton DP, Hunter JM. Clinical pharmacokinetics of the newer neuromuscular blocking drugs. Clin Pharmacokinet. 1999 Mar;36(3):169-89. doi: 10.2165/00003088-199936030-00001. PMID: 10223167. 14: Szenohradszky J, Caldwell JE, Wright PM, Brown R, Lau M, Luks AM, Fisher DM. Influence of renal failure on the pharmacokinetics and neuromuscular effects of a single dose of rapacuronium bromide. Anesthesiology. 1999 Jan;90(1):24-35. doi: 10.1097/00000542-199901000-00006. PMID: 9915309. 15: Wright PM, Brown R, Lau M, Fisher DM. A pharmacodynamic explanation for the rapid onset/offset of rapacuronium bromide. Anesthesiology. 1999 Jan;90(1):16-23. doi: 10.1097/00000542-199901000-00005. PMID: 9915308.