ABT 102

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

MedKoo CAT#: 524104

CAS#: 808756-71-0

Description: ABT 102 is a potent and selective antagonist of transient receptor potential vanilloid 1 (TRPV1) receptors under clinical trials. It is a very promising approach for pain management.


Price and Availability

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ABT 102, purity > 98%, is not in stock, may be available through custom synthesis. Minimum 1 gram order is requested. Current shipping out time is about 70 days after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 524104
Name: ABT 102
CAS#: 808756-71-0
Chemical Formula: C21H24N4O
Exact Mass: 348.19501
Molecular Weight: 348.44
Elemental Analysis: C, 72.39; H, 6.94; N, 16.08; O, 4.59


Synonym: ABT 102; ABT-102; ABT102; CHEMBL398338;

IUPAC/Chemical Name: Urea, N-((1R)-5-(1,1-dimethylethyl)-2,3-dihydro-1H-inden-1-yl)-N'-1H-indazol-4-yl-

InChi Key: TYOYXJNGINZFET-GOSISDBHSA-N

InChi Code: InChI=1S/C21H24N4O/c1-21(2,3)14-8-9-15-13(11-14)7-10-18(15)24-20(26)23-17-5-4-6-19-16(17)12-22-25-19/h4-6,8-9,11-12,18H,7,10H2,1-3H3,(H,22,25)(H2,23,24,26)/t18-/m1/s1

SMILES Code: O=C(NC1=CC=CC2=C1C=NN2)N[C@@H]3CCC4=C3C=CC(C(C)(C)C)=C4


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


References

1: Jog R, Kumar S, Shen J, Jugade N, Tan DC, Gokhale R, Burgess DJ. Formulation design and evaluation of amorphous ABT-102 nanoparticles. Int J Pharm. 2016 Feb 10;498(1-2):153-69. doi: 10.1016/j.ijpharm.2015.12.033. Epub 2015 Dec 15. PubMed PMID: 26705150.
2: Frank KJ, Westedt U, Rosenblatt KM, Hölig P, Rosenberg J, Mägerlein M, Fricker G, Brandl M. What is the mechanism behind increased permeation rate of a poorly soluble drug from aqueous dispersions of an amorphous solid dispersion? J Pharm Sci. 2014 Jun;103(6):1779-86. doi: 10.1002/jps.23979. Epub 2014 Apr 24. PubMed PMID: 24764046.
3: Leys LJ, Chu KL, Xu J, Pai M, Yang HS, Robb HM, Jarvis MF, Radek RJ, McGaraughty S. Disturbances in slow-wave sleep are induced by models of bilateral inflammation, neuropathic, and postoperative pain, but not osteoarthritic pain in rats. Pain. 2013 Jul;154(7):1092-102. doi: 10.1016/j.pain.2013.03.019. Epub 2013 Mar 15. PubMed PMID: 23664655.
4: Frank KJ, Westedt U, Rosenblatt KM, Hölig P, Rosenberg J, Mägerlein M, Fricker G, Brandl M. The amorphous solid dispersion of the poorly soluble ABT-102 forms nano/microparticulate structures in aqueous medium: impact on solubility. Int J Nanomedicine. 2012;7:5757-68. doi: 10.2147/IJN.S36571. Epub 2012 Nov 12. PubMed PMID: 23166440; PubMed Central PMCID: PMC3500034.
5: Othman AA, Nothaft W, Awni WM, Dutta S. Effects of the TRPV1 antagonist ABT-102 on body temperature in healthy volunteers: pharmacokinetic/ pharmacodynamic analysis of three phase 1 trials. Br J Clin Pharmacol. 2013 Apr;75(4):1029-40. doi: 10.1111/j.1365-2125.2012.04405.x. PubMed PMID: 22966986; PubMed Central PMCID: PMC3612721.
6: Frank KJ, Rosenblatt KM, Westedt U, Hölig P, Rosenberg J, Mägerlein M, Fricker G, Brandl M. Amorphous solid dispersion enhances permeation of poorly soluble ABT-102: true supersaturation vs. apparent solubility enhancement. Int J Pharm. 2012 Nov 1;437(1-2):288-93. doi: 10.1016/j.ijpharm.2012.08.014. Epub 2012 Aug 20. PubMed PMID: 22951865.
7: Schaffler K, Reeh P, Duan WR, Best AE, Othman AA, Faltynek CR, Locke C, Nothaft W. An oral TRPV1 antagonist attenuates laser radiant-heat-evoked potentials and pain ratings from UV(B)-inflamed and normal skin. Br J Clin Pharmacol. 2013 Feb;75(2):404-14. doi: 10.1111/j.1365-2125.2012.04377.x. PubMed PMID: 22775239; PubMed Central PMCID: PMC3579255.
8: Frank KJ, Westedt U, Rosenblatt KM, Hölig P, Rosenberg J, Mägerlein M, Brandl M, Fricker G. Impact of FaSSIF on the solubility and dissolution-/permeation rate of a poorly water-soluble compound. Eur J Pharm Sci. 2012 Aug 30;47(1):16-20. doi: 10.1016/j.ejps.2012.04.015. Epub 2012 May 1. PubMed PMID: 22579958.
9: Kort ME, Kym PR. TRPV1 antagonists: clinical setbacks and prospects for future development. Prog Med Chem. 2012;51:57-70. doi: 10.1016/B978-0-12-396493-9.00002-9. Review. PubMed PMID: 22520471.
10: Othman AA, Nothaft W, Awni WM, Dutta S. Pharmacokinetics of the TRPV1 antagonist ABT-102 in healthy human volunteers: population analysis of data from 3 phase 1 trials. J Clin Pharmacol. 2012 Jul;52(7):1028-41. doi: 10.1177/0091270011407497. Epub 2011 May 12. PubMed PMID: 21566201.
11: Rowbotham MC, Nothaft W, Duan WR, Wang Y, Faltynek C, McGaraughty S, Chu KL, Svensson P. Oral and cutaneous thermosensory profile of selective TRPV1 inhibition by ABT-102 in a randomized healthy volunteer trial. Pain. 2011 May;152(5):1192-200. doi: 10.1016/j.pain.2011.01.051. Epub 2011 Mar 4. PubMed PMID: 21377273.
12: Kym PR, Kort ME, Hutchins CW. Analgesic potential of TRPV1 antagonists. Biochem Pharmacol. 2009 Aug 1;78(3):211-6. doi: 10.1016/j.bcp.2009.02.014. Epub 2009 Mar 5. PubMed PMID: 19481638.
13: Honore P, Chandran P, Hernandez G, Gauvin DM, Mikusa JP, Zhong C, Joshi SK, Ghilardi JR, Sevcik MA, Fryer RM, Segreti JA, Banfor PN, Marsh K, Neelands T, Bayburt E, Daanen JF, Gomtsyan A, Lee CH, Kort ME, Reilly RM, Surowy CS, Kym PR, Mantyh PW, Sullivan JP, Jarvis MF, Faltynek CR. Repeated dosing of ABT-102, a potent and selective TRPV1 antagonist, enhances TRPV1-mediated analgesic activity in rodents, but attenuates antagonist-induced hyperthermia. Pain. 2009 Mar;142(1-2):27-35. doi: 10.1016/j.pain.2008.11.004. Epub 2009 Jan 9. PubMed PMID: 19135797.
14: Surowy CS, Neelands TR, Bianchi BR, McGaraughty S, El Kouhen R, Han P, Chu KL, McDonald HA, Vos M, Niforatos W, Bayburt EK, Gomtsyan A, Lee CH, Honore P, Sullivan JP, Jarvis MF, Faltynek CR. (R)-(5-tert-butyl-2,3-dihydro-1H-inden-1-yl)-3-(1H-indazol-4-yl)-urea (ABT-102) blocks polymodal activation of transient receptor potential vanilloid 1 receptors in vitro and heat-evoked firing of spinal dorsal horn neurons in vivo. J Pharmacol Exp Ther. 2008 Sep;326(3):879-88. doi: 10.1124/jpet.108.138511. Epub 2008 May 30. PubMed PMID: 18515644.
15: Gomtsyan A, Bayburt EK, Schmidt RG, Surowy CS, Honore P, Marsh KC, Hannick SM, McDonald HA, Wetter JM, Sullivan JP, Jarvis MF, Faltynek CR, Lee CH. Identification of (R)-1-(5-tert-butyl-2,3-dihydro-1H-inden-1-yl)-3-(1H-indazol-4-yl)urea (ABT-102) as a potent TRPV1 antagonist for pain management. J Med Chem. 2008 Feb 14;51(3):392-5. doi: 10.1021/jm701007g. Epub 2008 Jan 10. PubMed PMID: 18183945.