Kelatorphan

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

MedKoo CAT#: 558234

CAS#: 92175-57-0

Description: Kelatorphan is a Inhibitor of enkephalin metabolism.

Chemical Structure

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Kelatorphan
CAS# 92175-57-0
Instruction

Theoretical Analysis

MedKoo Cat#: 558234
Name: Kelatorphan
CAS#: 92175-57-0
Chemical Formula: C14H18N2O5
Exact Mass: 294.12
Molecular Weight: 294.300
Elemental Analysis: C, 57.14; H, 6.16; N, 9.52; O, 27.18

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Kelatorphan;

IUPAC/Chemical Name: ((R)-2-benzyl-4-(hydroxyamino)-4-oxobutanoyl)-L-alanine

InChi Key: OJCFZTVYDSKXNM-GXSJLCMTSA-N

InChi Code: InChI=1S/C14H18N2O5/c1-9(14(19)20)15-13(18)11(8-12(17)16-21)7-10-5-3-2-4-6-10/h2-6,9,11,21H,7-8H2,1H3,(H,15,18)(H,16,17)(H,19,20)/t9-,11+/m0/s1

SMILES Code: C[C@@H](C(O)=O)NC([C@H](CC1=CC=CC=C1)CC(NO)=O)=O

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: >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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 294.30 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Tholander F, Roques BP, Fournié-Zaluski MC, Thunnissen MM, Haeggström JZ. Crystal structure of leukotriene A4 hydrolase in complex with kelatorphan, implications for design of zinc metallopeptidase inhibitors. FEBS Lett. 2010 Aug 4;584(15):3446-51. doi: 10.1016/j.febslet.2010.06.044. Epub 2010 Jul 4. PubMed PMID: 20609366.

2: Crain SM, Shen KF. Low doses of cyclic AMP-phosphodiesterase inhibitors rapidly evoke opioid receptor-mediated thermal hyperalgesia in naïve mice which is converted to prominent analgesia by cotreatment with ultra-low-dose naltrexone. Brain Res. 2008 Sep 22;1231:16-24. doi: 10.1016/j.brainres.2008.07.015. Epub 2008 Jul 12. PubMed PMID: 18656459.

3: Crain SM, Shen KF. Naloxone rapidly evokes endogenous kappa opioid receptor-mediated hyperalgesia in naïve mice pretreated briefly with GM1 ganglioside or in chronic morphine-dependent mice. Brain Res. 2007 Sep 5;1167:31-41. Epub 2007 Jul 14. PubMed PMID: 17692296.

4: Yamamoto Y, Ono H, Ueda A, Shimamura M, Nishimura K, Hazato T. Spinorphin as an endogenous inhibitor of enkephalin-degrading enzymes: roles in pain and inflammation. Curr Protein Pept Sci. 2002 Dec;3(6):587-99. Review. PubMed PMID: 12470213.

5: Clarke RW, Bhandari RN, Leggett J. Opioid and GABA receptors involved in mediation and modulation of tonic and stimulus-evoked inhibition of a spinal reflex in the decerebrated and spinalized rabbit. Neuropharmacology. 2001 Sep;41(3):311-20. PubMed PMID: 11522322.

6: Penning TD. Inhibitors of leukotriene A4 (LTA4) hydrolase as potential anti-inflammatory agents. Curr Pharm Des. 2001 Feb;7(3):163-79. Review. PubMed PMID: 11311111.

7: Boudinot E, Morin-Surun M, Foutz AS, Fournié-Zaluski M, Roques BP, Denavit-Saubié M. Effects of the potent analgesic enkephalin-catabolizing enzyme inhibitors RB101 and kelatorphan on respiration. Pain. 2001 Feb 1;90(1-2):7-13. PubMed PMID: 11166965.

8: Peyroux J, Beslot F, Claperon N, Fournie-Zaluski MC, Roques BP. Effect of endopeptidase-24.11 inhibitors and C-ANP receptor ligand on responses evoked in arterioles of rat cremaster muscle by atrial natriuretic peptide. Br J Pharmacol. 1995 Dec;116(8):3117-24. PubMed PMID: 8719785; PubMed Central PMCID: PMC1909177.

9: Bedecs K, Langel U, Bartfai T. Metabolism of galanin and galanin (1-16) in isolated cerebrospinal fluid and spinal cord membranes from rat. Neuropeptides. 1995 Sep;29(3):137-43. PubMed PMID: 8538874.

10: Churchill L, Roques BP, Kalivas PW. Dopamine depletion augments endogenous opioid-induced locomotion in the nucleus accumbens using both mu 1 and delta opioid receptors. Psychopharmacology (Berl). 1995 Aug;120(3):347-55. PubMed PMID: 8524983.

11: Matsumura Y, Tsukahara Y, Kojima T, Murata S, Murakami A, Takada K, Takaoka M, Morimoto S. Effects of phosphoramidon on endothelin-1 and big endothelin-1 production in human aortic endothelial cells. Biol Pharm Bull. 1995 Mar;18(3):401-6. PubMed PMID: 7550091.

12: Cronin A, Keifer JC, Baghdoyan HA, Lydic R. Opioid inhibition of rapid eye movement sleep by a specific mu receptor agonist. Br J Anaesth. 1995 Feb;74(2):188-92. PubMed PMID: 7696070.

13: Lee SH, Kayser V, Guilbaud G. Antinociceptive effect of systemic kelatorphan, in mononeuropathic rats, involves different opioid receptor types. Eur J Pharmacol. 1994 Oct 13;264(1):61-7. PubMed PMID: 7828644.

14: Fujita K, Matsumura Y, Kita S, Hisaki K, Takaoka M, Morimoto S. Phosphoramidon-sensitive conversion of big endothelin-1 and degradation of endothelin-1 in rat kidney. Hypertension. 1994 Aug;24(2):227-33. PubMed PMID: 8039848.

15: Floch A, Fardin V, Cavero I. Characterization of NK1 and NK2 tachykinin receptors in guinea-pig and rat bronchopulmonary and vascular systems. Br J Pharmacol. 1994 Mar;111(3):759-68. PubMed PMID: 7517328; PubMed Central PMCID: PMC1910082.

16: Stanfa LC, Dickenson AH. Electrophysiological studies on the spinal roles of endogenous opioids in carrageenan inflammation. Pain. 1994 Feb;56(2):185-91. PubMed PMID: 7911987.

17: Tölle TR, Schadrack J, Castro-Lopes JM, Evan G, Roques BP, Zieglgänsberger W. Effects of Kelatorphan and morphine before and after noxious stimulation on immediate-early gene expression in rat spinal cord neurons. Pain. 1994 Jan;56(1):103-12. PubMed PMID: 8159434.

18: Sellami S, de Beaurepaire R. Medial diencephalic sites involved in calcitonin-induced hyperthermia and analgesia. Brain Res. 1993 Jul 9;616(1-2):307-10. PubMed PMID: 8358621.

19: Daugé V, Kalivas PW, Duffy T, Roques BP. Effect of inhibiting enkephalin catabolism in the VTA on motor activity and extracellular dopamine. Brain Res. 1992 Dec 25;599(2):209-14. PubMed PMID: 1291031.

20: Ruiz-Gayo M, Durieux C, Fournié-Zaluski MC, Roques BP. Stimulation of delta-opioid receptors reduces the in vivo binding of the cholecystokinin (CCK)-B-selective agonist [3H]pBC 264: evidence for a physiological regulation of CCKergic systems by endogenous enkephalins. J Neurochem. 1992 Nov;59(5):1805-11. PubMed PMID: 1357099.