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MedKoo Cat#: 530253 | Name: Pomaglumetad methionil HCl

Description:

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

Pomaglumetad methionil, also known as LY2140023, is a prodrug of LY-404039 and a a novel metabotropic glutamate 2/3 receptor agonist peptide prodrug. Pomaglumetad methionil is currently in clinical development as a potential new treatment for schizophrenia. LY2140023 is generally well tolerated and appears to have a low association with adverse events related to dopamine D2 receptor antagonism and with weight gain, which are commonly seen with current antipsychotics.

Chemical Structure

Pomaglumetad methionil HCl
Pomaglumetad methionil HCl
CAS#635318-26-2 (HCl)

Theoretical Analysis

MedKoo Cat#: 530253

Name: Pomaglumetad methionil HCl

CAS#: 635318-26-2 (HCl)

Chemical Formula: C12H19ClN2O7S2

Exact Mass:

Molecular Weight: 402.86

Elemental Analysis: C, 35.78; H, 4.75; Cl, 8.80; N, 6.95; O, 27.80; S, 15.92

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
635318-26-2 (HCl) 635318-55-7 (free base) 635318-56-8 (tosylate) 635318-57-9 (mseylate) 956385-05-0 (hydrate)
Synonym
Pomaglumetad methionil HCl; LY2140023; LY-2140023; LY 2140023; LY2140023 monohydrate; Prodrug of LY-404039;
IUPAC/Chemical Name
(1R,4S,5S,6S)-4-(L-Methionylamino)-2-thiabicyclo(3.1.0)hexane-4,6-dicarboxylic acid 2,2-dioxide hydrochloride
InChi Key
KTYRTJLEXFSWRJ-LBMFEJOUSA-N
InChi Code
InChI=1S/C12H18N2O7S2.ClH/c1-22-3-2-5(13)9(15)14-12(11(18)19)4-23(20,21)8-6(7(8)12)10(16)17;/h5-8H,2-4,13H2,1H3,(H,14,15)(H,16,17)(H,18,19);1H/t5-,6+,7+,8-,12-;/m0./s1
SMILES Code
O=C([C@]1(NC([C@H](CCSC)N)=O)CS([C@@]2([H])[C@H](C(O)=O)[C@@]12[H])(=O)=O)O.[H]Cl
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
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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 402.86 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.

Recalculate based on batch purity %
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: Mehta MA, Schmechtig A, Kotoula V, McColm J, Jackson K, Brittain C, Tauscher-Wisniewski S, Kinon BJ, Morrison PD, Pollak T, Mant T, Williams SCR, Schwarz AJ. Group II metabotropic glutamate receptor agonist prodrugs LY2979165 and LY2140023 attenuate the functional imaging response to ketamine in healthy subjects. Psychopharmacology (Berl). 2018 Jul;235(7):1875-1886. doi: 10.1007/s00213-018-4877-9. Epub 2018 Mar 21. PubMed PMID: 29564482. 2: Pak YA, Long AJ, Annes WF, Witcher JW, Knadler MP, Ayan-Oshodi MA, Mitchell MI, Leese P, Hillgren KM. In Vitro and Clinical Evaluations of the Drug-Drug Interaction Potential of a Metabotropic Glutamate 2/3 Receptor Agonist Prodrug with Intestinal Peptide Transporter 1. Drug Metab Dispos. 2017 Feb;45(2):137-144. doi: 10.1124/dmd.116.071118. Epub 2016 Nov 28. PubMed PMID: 27895114; PubMed Central PMCID: PMC5267515. 3: Nisenbaum LK, Downing AM, Zhao F, Millen BA, Munsie L, Kinon BJ, Adams DH, Gomez JC, Penny MA. Serotonin 2A Receptor SNP rs7330461 Association with Treatment Response to Pomaglumetad Methionil in Patients with Schizophrenia. J Pers Med. 2016 Feb 5;6(1). pii: E9. doi: 10.3390/jpm6010009. PubMed PMID: 26861400; PubMed Central PMCID: PMC4810388. 4: Su P, Lu JY, Seeman P, Liu F. Glutamate drug reduces dopamine inhibition of phosphorylation. Synapse. 2016 Feb;70(2):45-8. doi: 10.1002/syn.21874. Epub 2015 Dec 2. PubMed PMID: 26583745. 5: Marek GJ. When is a Proof-of-Concept (POC) not a POC? Pomaglumetad (LY2140023) as a Case Study for Antipsychotic Efficacy. Curr Pharm Des. 2015;21(26):3788-96. PubMed PMID: 26044978. 6: Kinon BJ, Millen BA, Zhang L, McKinzie DL. Exploratory analysis for a targeted patient population responsive to the metabotropic glutamate 2/3 receptor agonist pomaglumetad methionil in schizophrenia. Biol Psychiatry. 2015 Dec 1;78(11):754-62. doi: 10.1016/j.biopsych.2015.03.016. Epub 2015 Mar 19. PubMed PMID: 25890643. 7: Zhang W, Mitchell MI, Knadler MP, Long A, Witcher J, Walling D, Annes W, Ayan-Oshodi M. Effect of pomaglumetad methionil on the QT interval in subjects with schizophrenia. Int J Clin Pharmacol Ther. 2015 Jun;53(6):462-70. doi: 10.5414/CP202289. PubMed PMID: 25881753. 8: Moulton RD, Ruterbories KJ, Bedwell DW, Mohutsky MA. In vitro characterization of the bioconversion of pomaglumetad methionil, a novel metabotropic glutamate 2/3 receptor agonist peptide prodrug. Drug Metab Dispos. 2015 May;43(5):756-61. doi: 10.1124/dmd.114.062893. Epub 2015 Mar 9. PubMed PMID: 25755052. 9: Deutschenbaur L, Beck J, Kiyhankhadiv A, Mühlhauser M, Borgwardt S, Walter M, Hasler G, Sollberger D, Lang UE. Role of calcium, glutamate and NMDA in major depression and therapeutic application. Prog Neuropsychopharmacol Biol Psychiatry. 2016 Jan 4;64:325-33. doi: 10.1016/j.pnpbp.2015.02.015. Epub 2015 Mar 4. Review. PubMed PMID: 25747801. 10: Downing AM, Kinon BJ, Millen BA, Zhang L, Liu L, Morozova MA, Brenner R, Rayle TJ, Nisenbaum L, Zhao F, Gomez JC. A Double-Blind, Placebo-Controlled Comparator Study of LY2140023 monohydrate in patients with schizophrenia. BMC Psychiatry. 2014 Dec 10;14:351. doi: 10.1186/s12888-014-0351-3. PubMed PMID: 25539791; PubMed Central PMCID: PMC4276262. 11: Annes WF, Long A, Witcher JW, Ayan-Oshodi MA, Knadler MP, Zhang W, Mitchell MI, Cornelissen K, Hall SD. Relative contributions of presystemic and systemic peptidases to oral exposure of a novel metabotropic glutamate 2/3 receptor agonist (LY404039) after oral administration of prodrug pomaglumetad methionil (LY2140023). J Pharm Sci. 2015 Jan;104(1):207-14. doi: 10.1002/jps.24226. Epub 2014 Nov 7. PubMed PMID: 25382826. 12: Patel MX, Collins S, Hellier J, Bhatia G, Murray RM. The quality of reporting of phase II and III trials for new antipsychotics: a systematic review. Psychol Med. 2015 Feb;45(3):467-79. doi: 10.1017/S0033291714001214. Epub 2014 Jun 2. Review. PubMed PMID: 25065545. 13: Stauffer VL, Baygani SK, Kinon BJ, Krikke-Workel JO. A short-term, multicenter, placebo-controlled, randomized withdrawal study of a metabotropic glutamate 2/3 receptor agonist using an electronic patient-reported outcome device in patients with schizophrenia. J Clin Psychopharmacol. 2014 Oct;34(5):552-8. doi: 10.1097/JCP.0000000000000187. PubMed PMID: 25006819; PubMed Central PMCID: PMC4165473. 14: Adams DH, Zhang L, Millen BA, Kinon BJ, Gomez JC. Pomaglumetad Methionil (LY2140023 Monohydrate) and Aripiprazole in Patients with Schizophrenia: A Phase 3, Multicenter, Double-Blind Comparison. Schizophr Res Treatment. 2014;2014:758212. doi: 10.1155/2014/758212. Epub 2014 Mar 19. PubMed PMID: 24772351; PubMed Central PMCID: PMC3977437. 15: Stauffer VL, Millen BA, Andersen S, Kinon BJ, Lagrandeur L, Lindenmayer JP, Gomez JC. Pomaglumetad methionil: no significant difference as an adjunctive treatment for patients with prominent negative symptoms of schizophrenia compared to placebo. Schizophr Res. 2013 Nov;150(2-3):434-41. doi: 10.1016/j.schres.2013.08.020. Epub 2013 Sep 12. PubMed PMID: 24035403. 16: Adams DH, Kinon BJ, Baygani S, Millen BA, Velona I, Kollack-Walker S, Walling DP. A long-term, phase 2, multicenter, randomized, open-label, comparative safety study of pomaglumetad methionil (LY2140023 monohydrate) versus atypical antipsychotic standard of care in patients with schizophrenia. BMC Psychiatry. 2013 May 22;13:143. doi: 10.1186/1471-244X-13-143. PubMed PMID: 23694720; PubMed Central PMCID: PMC3666887. 17: Hopkins CR. Is there a path forward for mGlu(2) positive allosteric modulators for the treatment of schizophrenia? ACS Chem Neurosci. 2013 Feb 20;4(2):211-3. doi: 10.1021/cn400023y. PubMed PMID: 23421671; PubMed Central PMCID: PMC3582287. 18: Kinon BJ, Gómez JC. Clinical development of pomaglumetad methionil: a non-dopaminergic treatment for schizophrenia. Neuropharmacology. 2013 Mar;66:82-6. doi: 10.1016/j.neuropharm.2012.06.002. Epub 2012 Jun 18. PubMed PMID: 22722029.

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