Synonym
AY-30,715; AY 30,715; AY30,715; AY-30715; AY 30715; AY30715; pemedolac; WAY-PEM-420; Dexpemedolac
IUPAC/Chemical Name
(1S,4R)-4-Benzyl-1-ethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetic acid
InChi Key
BUUODSZYUAZDIF-AOMKIAJQSA-N
InChi Code
InChI=1S/C22H23NO3/c1-2-22(13-19(24)25)21-20(17-10-6-7-11-18(17)23-21)16(14-26-22)12-15-8-4-3-5-9-15/h3-11,16,23H,2,12-14H2,1H3,(H,24,25)/t16-,22-/m0/s1
SMILES Code
CC[C@@]1(CC(=O)O)OC[C@H](Cc2ccccc2)c3c1[nH]c4ccccc34
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).
HS Tariff Code
2934.99.9001
More Info
In acute anti-inflammatory tests, pemedolac exhibited only weak activity as evidenced by an ED50 approximately 100 mg/kg p.o. in the carrageenan paw edema procedure. This demonstrates for pemedolac a separation of at least 50-fold between the acute analgesic and anti-inflammatory activities, which was greater than that observed with reference NSAIDs. The compound also had a low ulcerogenic liability with an acute UD50 = 107 mg/kg p.o. and a subacute UD50 estimated to be 140 mg/kg/day p.o.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
349.42
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: Catalano A, Iacopetta D, Ceramella J, Saturnino C, Sinicropi MS. A Comprehensive Review on Pyranoindole-containing Agents. Curr Med Chem. 2022;29(21):3667-3683. doi: 10.2174/0929867328666211206111058. PMID: 34872472.
2: Chau T, Walter T, Zimmerman J, Hartman D, Ochalski S, Weichman B. Analgesic activities of PEM-420, the active eutomer of pemedolac. Agents Actions. 1993;39 Spec No:C27-9. doi: 10.1007/BF01972710. PMID: 8273576.
3: Chau TT, Weichman BM. Pemedolac: a novel and long-acting non-narcotic analgesic. J Pharmacol Exp Ther. 1989 Mar;248(3):907-15. PMID: 2703977.
4: Mobilio D, Humber LG, Katz AH, Demerson CA, Hughes P, Brigance R, Conway K, Shah U, Williams G, Labbadia F, et al. Structure-activity relationships among analogues of pemedolac, cis-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)pyrano[3,4-b]indo le-1-a cetic acid, a potent analgesic agent. J Med Chem. 1988 Nov;31(11):2211-7. doi: 10.1021/jm00119a024. PMID: 3263504.
5: Katz AH, Demerson CA, Shaw CC, Asselin AA, Humber LG, Conway KM, Gavin G, Guinosso C, Jensen NP, Mobilio D, et al. Synthesis and analgesic activity of pemedolac (cis-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)pyrano[3,4-b]ind ole-1- acetic acid). J Med Chem. 1988 Jun;31(6):1244-50. doi: 10.1021/jm00401a029. PMID: 3373493.
