Tapentadol HCl

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

MedKoo CAT#: 100803

CAS#: 175591-09-0 (HCl)

Description: Tapentadol is a centrally acting opioid analgesic of the benzenoid class with a dual mode of action as an agonist of the μ-opioid receptor and as a norepinephrine reuptake inhibitor (NRI).[3] Its analgesic properties come into effect within thirty-two minutes of oral administration, and last for 4–6 hours. This agent may be effective in the management of pain, cancer-related and other.


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Tapentadol HCl is not available. Tapentadol HCl is a controlled substance.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 100803
Name: Tapentadol HCl
CAS#: 175591-09-0 (HCl)
Chemical Formula: C14H24ClNO
Exact Mass:
Molecular Weight: 257.802
Elemental Analysis: C, 65.23; H, 9.38; Cl, 13.75; N, 5.43; O, 6.21


Related CAS #: 175591-23-8 (free base)   175591-09-0 (HCl)    

Synonym: CG5503; CG-5503; CG 5503; Tapentadol; brand names: Nucynta, Palexia and Tapal.

IUPAC/Chemical Name: 3-((2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl)phenol hydrochloride

InChi Key: ZELFLGGRLLOERW-YECZQDJWSA-N

InChi Code: InChI=1S/C14H23NO.ClH/c1-5-14(11(2)10-15(3)4)12-7-6-8-13(16)9-12;/h6-9,11,14,16H,5,10H2,1-4H3;1H/t11-,14+;/m0./s1

SMILES Code: OC1=CC=CC([C@H](CC)[C@@H](C)CN(C)C)=C1.[H]Cl


Technical Data

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).

Harmonized System Code:
293490


Additional Information

Tapentadol (trade name Nucynta, Palexia, In India - ZYNTAP)  is a centrally acting analgesic with a dual mode of action as an agonist at the μ-opioid receptor and as a norepinephrine reuptake inhibitor. While its analgesic actions have been compared to tramadol and oxycodone, its general potency is somewhere between tramadol and morphine in effectiveness. Tapentadol is a new molecular entity that is structurally similar to Tramadol (Tramal). It has opioid and nonopioid acitivity in a single compound. In the US, Tapentadol is FDA approved for the treatment of moderate to severe acute pain. Due to the dual mechanism of action as an opioid agonist and norepinephrine reuptake inhibitor, there is potential for off label use in chronic pain. (source: http://en.wikipedia.org/wiki/Tapentadol).
 
Grunenthal (Achen, Germany) and Johnson & Johnson Pharmaceutical Research & Development (Raritan, NL)  are currently developing tapentadol hydrochloride (controlled release) for cancer pain.
Grunenthal (Achen, Germany) and Johnson & Johnson Pharmaceutical Research & Development (Raritan, NL)  are currently developing


References

 1: Cepeda MS, Sutton A, Weinstein R, Kim M. Effect of Tapentadol Extended Release on Productivity: Results From an Analysis Combining Evidence From Multiple Sources. Clin J Pain. 2011 Jun 3. [Epub ahead of print] PubMed PMID: 21646907.

2: Etropolski M, Kelly K, Okamoto A, Rauschkolb C. Comparable efficacy and superior gastrointestinal tolerability (nausea, vomiting, constipation) of tapentadol compared with oxycodone hydrochloride. Adv Ther. 2011 May;28(5):401-17. Epub 2011 Apr 13. PubMed PMID: 21494892.

3: Guay DR. Oral hydromorphone extended-release. Consult Pharm. 2010 Dec;25(12):816-28. Review. PubMed PMID: 21172762.

4: Schwartz S, Etropolski M, Shapiro DY, Okamoto A, Lange R, Haeussler J, Rauschkolb C. Safety and efficacy of tapentadol ER in patients with painful diabetic peripheral neuropathy: results of a randomized-withdrawal, placebo-controlled trial. Curr Med Res Opin. 2011 Jan;27(1):151-62. PubMed PMID: 21162697.

5: Schwartz S, Etropolski M, Shapiro DY, Okamoto A, Lange R, Haeussler J, Rauschkolb C. Safety and efficacy of tapentadol ER in patients with painful diabetic peripheral neuropathy: results of a randomized-withdrawal, placebo-controlled trial. Curr Med Res Opin. 2010 Dec 2. [Epub ahead of print] PubMed PMID: 21126106.

6: Oh C, Rengelshausen J, Mangold B, Etropolski M, Rauschkolb C, Wang SS, Upmalis D, Häufel T. A thorough QT/QTc study of multiple doses of tapentadol immediate release in healthy subjects. Int J Clin Pharmacol Ther. 2010 Oct;48(10):678-87. PubMed PMID: 20875374.

7: Vorsanger G, Xiang J, Okamoto A, Upmalis D, Moskovitz B. Evaluation of study discontinuations with tapentadol inmmediate release and oxycodone immediate release in patients with low back or osteoarthritis pain. J Opioid Manag. 2010 May-Jun;6(3):169-79. PubMed PMID: 20642246.

8: Wild JE, Grond S, Kuperwasser B, Gilbert J, McCann B, Lange B, Steup A, Häufel T, Etropolski MS, Rauschkolb C, Lange R. Long-term safety and tolerability of tapentadol extended release for the management of chronic low back pain or osteoarthritis pain. Pain Pract. 2010 Sep-Oct;10(5):416-27. doi: 10.1111/j.1533-2500.2010.00397.x. PubMed PMID: 20602712.

9: Afilalo M, Etropolski MS, Kuperwasser B, Kelly K, Okamoto A, Van Hove I, Steup A, Lange B, Rauschkolb C, Haeussler J. Efficacy and safety of Tapentadol extended release compared with oxycodone controlled release for the management of moderate to severe chronic pain related to osteoarthritis of the knee: a randomized, double-blind, placebo- and active-controlled phase III study. Clin Drug Investig. 2010;30(8):489-505. doi: 10.2165/11533440-000000000-00000. PubMed PMID: 20586515.

10: Buynak R, Shapiro DY, Okamoto A, Van Hove I, Rauschkolb C, Steup A, Lange B, Lange C, Etropolski M. Efficacy and safety of tapentadol extended release for the management of chronic low back pain: results of a prospective, randomized, double-blind, placebo- and active-controlled Phase III study. Expert Opin Pharmacother. 2010 Aug;11(11):1787-804. Erratum in: Expert Opin Pharmacother. 2010 Nov;11(16):2773. PubMed PMID: 20578811.