Synonym
CRS3123 2HCl; REP-3123 Dihydrochloride; REP 3123 Dihydrochloride; REP3123 Dihydrochloride
IUPAC/Chemical Name
(R)-(+)-5-[[3-[(6,8-Dibromochroman-4-yl)amino]propyl]amino]-4H-thieno[3,2-b]pyridin-7-one dihydrochloride
InChi Key
HZJABMYSJSDCBO-FMOMHUKBSA-N
InChi Code
InChI=1S/C19H19Br2N3O2S.2ClH/c20-11-8-12-14(2-6-26-18(12)13(21)9-11)22-4-1-5-23-17-10-16(25)19-15(24-17)3-7-27-19;;/h3,7-10,14,22H,1-2,4-6H2,(H2,23,24,25);2*1H/t14-;;/m1../s1
SMILES Code
O=C1C2=C(C=CS2)NC(NCCCN[C@@H]3CCOC4=C3C=C(Br)C=C4Br)=C1.[H]Cl.[H]Cl
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
>3 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
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
586.16
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: Mercaldi GF, Andrade MO, Zanella JL, Cordeiro AT, Benedetti CE. Molecular basis for diaryldiamine selectivity and competition with tRNA in a type 2 methionyl-tRNA synthetase from a Gram-negative bacterium. J Biol Chem. 2021 Jan- Jun;296:100658. doi: 10.1016/j.jbc.2021.100658. Epub 2021 Apr 12. PMID: 33857480; PMCID: PMC8165550.
2: Kullar R, Tran MN, Goldstein EJC. Investigational Treatment Agents for Recurrent Clostridioides difficile Infection (rCDI). J Exp Pharmacol. 2020 Oct 9;12:371-384. doi: 10.2147/JEP.S242959. PMID: 33116952; PMCID: PMC7553590.
3: Hussain T, Yogavel M, Sharma A. Inhibition of protein synthesis and malaria parasite development by drug targeting of methionyl-tRNA synthetases. Antimicrob Agents Chemother. 2015 Apr;59(4):1856-67. doi: 10.1128/AAC.02220-13. Epub 2015 Jan 12. PMID: 25583729; PMCID: PMC4356764.
4: Al-Moubarak E, Simons C. A homology model for Clostridium difficile methionyl tRNA synthetase: active site analysis and docking interactions. J Mol Model. 2011 Jul;17(7):1679-93. doi: 10.1007/s00894-010-0871-9. Epub 2010 Nov 2. PMID: 21042822.
5: Johnson AP. New antibiotics for selective treatment of gastrointestinal infection caused by Clostridium difficile. Expert Opin Ther Pat. 2010 Oct;20(10):1389-99. doi: 10.1517/13543776.2010.511177. PMID: 20698814.
6: Critchley IA, Green LS, Young CL, Bullard JM, Evans RJ, Price M, Jarvis TC, Guiles JW, Janjic N, Ochsner UA. Spectrum of activity and mode of action of REP3123, a new antibiotic to treat Clostridium difficile infections. J Antimicrob Chemother. 2009 May;63(5):954-63. doi: 10.1093/jac/dkp041. Epub 2009 Mar 3. PMID: 19258353.
7: Ochsner UA, Bell SJ, O'Leary AL, Hoang T, Stone KC, Young CL, Critchley IA, Janjic N. Inhibitory effect of REP3123 on toxin and spore formation in Clostridium difficile, and in vivo efficacy in a hamster gastrointestinal infection model. J Antimicrob Chemother. 2009 May;63(5):964-71. doi: 10.1093/jac/dkp042. Epub 2009 Feb 26. PMID: 19251726.
8: Citron DM, Warren YA, Tyrrell KL, Merriam V, Goldstein EJ. Comparative in vitro activity of REP3123 against Clostridium difficile and other anaerobic intestinal bacteria. J Antimicrob Chemother. 2009 May;63(5):972-6. doi: 10.1093/jac/dkp037. Epub 2009 Feb 24. PMID: 19240076.
9: Guiles J, Critchley I, Sun X. New agents for Clostridium difficile-associated disease. Expert Opin Investig Drugs. 2008 Nov;17(11):1671-83. doi: 10.1517/13543784.17.11.1671. PMID: 18922104.
