Dapitant

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

MedKoo CAT#: 206099

CAS#: 153438-49-4

Description: Dapitant, also known as RPR100893, is potent and selective NK1 receptor antagonist both in vitro and in vivo, and exhibits high affinity for guinea pig and human NK1 receptor . Dapitant was developed as a potential drug for the acute treatment of migraine. However, in clinical trials, it was not effective.


Price and Availability

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Dapitant is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 206099
Name: Dapitant
CAS#: 153438-49-4
Chemical Formula: C37H39NO4
Exact Mass: 561.28791
Molecular Weight: 561.70986
Elemental Analysis: C, 79.11; H, 7.00; N, 2.49; O, 11.39


Synonym: RPR100893; RPR 100893; RPR-100893; Erispant; Dapitant.

IUPAC/Chemical Name: (S)-1-((3aS,4S,7aS)-4-hydroxy-4-(2-methoxyphenyl)-7,7-diphenylhexahydro-1H-isoindol-2(3H)-yl)-2-(2-methoxyphenyl)propan-1-one

InChi Key: CCIWVEMVBWEMCY-RCFOMQFPSA-N

InChi Code: InChI=1S/C37H39NO4/c1-26(29-18-10-12-20-33(29)41-2)35(39)38-24-31-32(25-38)37(40,30-19-11-13-21-34(30)42-3)23-22-36(31,27-14-6-4-7-15-27)28-16-8-5-9-17-28/h4-21,26,31-32,40H,22-25H2,1-3H3/t26-,31-,32+,37+/m0/s1

SMILES Code: C[C@@H](C1=CC=CC=C1OC)C(N2C[C@]3([H])C(C4=CC=CC=C4)(C5=CC=CC=C5)CC[C@](C6=CC=CC=C6OC)(O)[C@]3([H])C2)=O


Technical Data

Appearance:
white 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

  
 
 
 


References

1: Diener HC; RPR100893 Study Group. RPR100893, a substance-P antagonist, is not effective in the treatment of migraine attacks. Cephalalgia. 2003 Apr;23(3):183-5. PubMed PMID: 12662184.

2: Campbell EA, Gentry C, Patel S, Kidd B, Cruwys S, Fox AJ, Urban L. Oral anti-hyperalgesic and anti-inflammatory activity of NK(1) receptor antagonists in models of inflammatory hyperalgesia of the guinea-pig. Pain. 2000 Sep;87(3):253-63. PubMed PMID: 10963905.

3: Kerdelhué B, Williams RF, Lenoir V, Fardin V, Kolm P, Hodgen GD, Jones GS, Scholler R, Jones HW Jr. Variations in plasma levels of substance P and effects of a specific substance P antagonist of the NK(1) receptor on preovulatory LH and FSH surges and progesterone secretion in the cycling cynomolgus monkey. Neuroendocrinology. 2000 Apr;71(4):228-36. PubMed PMID: 10773742.

4: Dapitant. RPR 100893. Drugs R D. 1999 Dec;2(6):383-4. PubMed PMID: 10763446.

5: Kerr KP, Mitchelson F, Coupar IM. Tachykinins play a minor role in mediating the third phase of the contractile response to vagal nerve stimulation of the guinea-pig oesophagus. Neuropeptides. 2000 Feb;34(1):12-7. PubMed PMID: 10688963.

6: Campbell EA, Gentry CT, Patel S, Panesar MS, Walpole CS, Urban L. Selective neurokinin-1 receptor antagonists are anti-hyperalgesic in a model of neuropathic pain in the guinea-pig. Neuroscience. 1998 Dec;87(3):527-32. PubMed PMID: 9758219.

7: Alia S, Azérad J, Pollin B. Effects of RPR 100893, a potent NK1 antagonist, on the jaw-opening reflex in the guinea pig. Brain Res. 1998 Mar 16;787(1):99-106. PubMed PMID: 9518568.

8: Suzuki N. [Migraine and neurotransmitters]. Nihon Naika Gakkai Zasshi. 1998 Feb 10;87(2):365-72. Review. Japanese. PubMed PMID: 9549335.

9: Kerdelhué B, Gordon K, Williams R, Lenoir V, Fardin V, Chevalier P, Garret C, Duval P, Kolm P, Hodgen G, Jones H, Jones GS. Stimulatory effect of a specific substance P antagonist (RPR 100893) of the human NK1 receptor on the estradiol-induced LH and FSH surges in the ovariectomized cynomolgus monkey. J Neurosci Res. 1997 Oct 1;50(1):94-103. PubMed PMID: 9379497.

10: Floch A, Thiry C, Cavero I. Pharmacological evidence that NK-2 tachykinin receptors mediate hypotension in the guinea pig but not in the rat. Fundam Clin Pharmacol. 1996;10(4):337-43. PubMed PMID: 8871132.