Synonym
EMA400; EMA 400; EMA-400; PD-126055; PD126055; PD 126055
IUPAC/Chemical Name
5-Benzyloxy-2-diphenylacetyl-6-methoxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid
InChi Key
GHBCIXGRCZIPNQ-UHFFFAOYSA-N
InChi Code
InChI=1S/C32H29NO5/c1-37-28-18-17-25-20-33(31(34)29(23-13-7-3-8-14-23)24-15-9-4-10-16-24)27(32(35)36)19-26(25)30(28)38-21-22-11-5-2-6-12-22/h2-18,27,29H,19-21H2,1H3,(H,35,36)
SMILES Code
O=C(C1N(C(C(C2=CC=CC=C2)C3=CC=CC=C3)=O)CC4=C(C(OCC5=CC=CC=C5)=C(OC)C=C4)C1)O
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
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).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
507.59
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 |
1: Anand U, Yiangou Y, Sinisi M, Fox M, MacQuillan A, Quick T, Korchev YE, Bountra C, McCarthy T, Anand P. Mechanisms underlying clinical efficacy of Angiotensin II type 2 receptor (AT2R) antagonist EMA401 in neuropathic pain: clinical tissue and in vitro studies. Mol Pain. 2015 Jun 26;11:38. doi: 10.1186/s12990-015-0038-x. PubMed PMID: 26111701; PubMed Central PMCID: PMC4482278.
2: Rice AS, Smith MT. Angiotensin II type 2-receptor: new clinically validated target in the treatment of neuropathic pain. Clin Pharmacol Ther. 2015 Feb;97(2):128-30. doi: 10.1002/cpt.29. Epub 2014 Dec 20. PubMed PMID: 25670516.
3: McCarthy T. Development of EMA401 as an orally-administered, highly-selective angiotensin II type 2 receptor antagonist for the treatment of neuropathic pain. J Peripher Nerv Syst. 2014 Oct;19 Suppl 2:S13-4. doi: 10.1111/jns.12080_4. Review. PubMed PMID: 25269730.
4: Smith MT, Wyse BD, Edwards SR. Small molecule angiotensin II type 2 receptor (AT₂R) antagonists as novel analgesics for neuropathic pain: comparative pharmacokinetics, radioligand binding, and efficacy in rats. Pain Med. 2013 May;14(5):692-705. doi: 10.1111/pme.12063. Epub 2013 Mar 14. PubMed PMID: 23489258.
5: New drug treatment reduces chronic pain following shingles. J Pain Palliat Care Pharmacother. 2014 Jun;28(2):180-1. PubMed PMID: 25011130.
6: Anand U, Facer P, Yiangou Y, Sinisi M, Fox M, McCarthy T, Bountra C, Korchev YE, Anand P. Angiotensin II type 2 receptor (AT2 R) localization and antagonist-mediated inhibition of capsaicin responses and neurite outgrowth in human and rat sensory neurons. Eur J Pain. 2013 Aug;17(7):1012-26. doi: 10.1002/j.1532-2149.2012.00269.x. Epub 2012 Dec 17. PubMed PMID: 23255326; PubMed Central PMCID: PMC3748799.
7: Keppel Hesselink JM, Schatman ME. EMA401: an old antagonist of the AT2R for a new indication in neuropathic pain. J Pain Res. 2017 Feb 20;10:439-443. doi: 10.2147/JPR.S128520. eCollection 2017. PubMed PMID: 28255254; PubMed Central PMCID: PMC5325092.
