Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C40H50N8O10 |
| Molecular Weight | 802.8726 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@H](NC(=O)[C@@H](N)CC1=CC=C(O)C=C1)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)NCC(=O)N[C@@H](CC3=CC=C(O)C=C3)C(=O)N4CCC[C@H]4C(=O)N[C@@H](CO)C(N)=O
InChI
InChIKey=FHZPGIUBXYVUOY-VWGYHWLBSA-N
InChI=1S/C40H50N8O10/c1-23(44-37(55)29(41)18-25-9-13-27(50)14-10-25)36(54)46-30(19-24-6-3-2-4-7-24)38(56)43-21-34(52)45-31(20-26-11-15-28(51)16-12-26)40(58)48-17-5-8-33(48)39(57)47-32(22-49)35(42)53/h2-4,6-7,9-16,23,29-33,49-51H,5,8,17-22,41H2,1H3,(H2,42,53)(H,43,56)(H,44,55)(H,45,52)(H,46,54)(H,47,57)/t23-,29+,30+,31+,32+,33+/m1/s1
| Molecular Formula | C40H50N8O10 |
| Molecular Weight | 802.8726 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Approval Year
Doses
| Dose | Population | Adverse events |
|---|---|---|
20 ug single, intrathecal (unknown) Studied dose Dose: 20 ug Route: intrathecal Route: single Dose: 20 ug Sources: |
unhealthy n = 50 Health Status: unhealthy Condition: pain Sex: M+F Food Status: UNKNOWN Population Size: 50 Sources: |
Other AEs: Headache, Nausea... Other AEs: Headache (6%) Sources: Nausea (22%) vomiting (22%) Urinary retention (26%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Nausea | 22% | 20 ug single, intrathecal (unknown) Studied dose Dose: 20 ug Route: intrathecal Route: single Dose: 20 ug Sources: |
unhealthy n = 50 Health Status: unhealthy Condition: pain Sex: M+F Food Status: UNKNOWN Population Size: 50 Sources: |
| vomiting | 22% | 20 ug single, intrathecal (unknown) Studied dose Dose: 20 ug Route: intrathecal Route: single Dose: 20 ug Sources: |
unhealthy n = 50 Health Status: unhealthy Condition: pain Sex: M+F Food Status: UNKNOWN Population Size: 50 Sources: |
| Urinary retention | 26% | 20 ug single, intrathecal (unknown) Studied dose Dose: 20 ug Route: intrathecal Route: single Dose: 20 ug Sources: |
unhealthy n = 50 Health Status: unhealthy Condition: pain Sex: M+F Food Status: UNKNOWN Population Size: 50 Sources: |
| Headache | 6% | 20 ug single, intrathecal (unknown) Studied dose Dose: 20 ug Route: intrathecal Route: single Dose: 20 ug Sources: |
unhealthy n = 50 Health Status: unhealthy Condition: pain Sex: M+F Food Status: UNKNOWN Population Size: 50 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Blood-brain barrier permeability of novel [D-arg2]dermorphin (1-4) analogs: transport property is related to the slow onset of antinociceptive activity in the central nervous system. | 2004 Jul |
|
| [Thermoregulatory activity of dermorphin fragments]. | 2004 Sep-Oct |
|
| Synthesis of dermorphin-(1-4) derivatives catalyzed by proteases in organic solvents. | 2005 Jan |
|
| New tris-alkoxycarbonyl arginine derivatives for peptide synthesis. | 2005 Jan |
|
| [Study of thermoregulatory activity of a fragment of natural dermorphin precursor Arg-dermorphin and its analogs]. | 2005 Jan-Feb |
|
| Distinguishing and quantifying peptides and proteins containing D-amino acids by tandem mass spectrometry. | 2005 Jul 15 |
|
| Abbreviated nomenclature for cyclic and branched homo- and hetero-detic peptides. | 2005 Jun |
|
| [Analgesic activity of dermorphin and its proline analogs]. | 2005 Mar-Apr |
|
| 6-Hydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid mimics active conformation of tyrosine in opioid peptides. | 2005 May 16 |
|
| [Comparative study of the physical dependence on proline analog of dermorphin and morphine]. | 2005 May-Jun |
|
| Synthesis and biological evaluation of constrained analogues of the opioid peptide H-Tyr-D-Ala-Phe-Gly-NH2 using the 4-amino-2-benzazepin-3-one scaffold. | 2005 Nov |
|
| [Comparative study of the antiarrhythmic activity of mu- and delta-opioid receptor agonists during acute cardiac ischemia and reperfusion models in rats]. | 2005 Nov-Dec |
|
| Inhibitory control of the acute mu-withdrawal response by indirectly activated adenosine A1 and kappa-opioid systems in the Guinea-pig ileum; reversal by cholecystokinin. | 2005 Oct |
|
| Cyclic dermorphin tetrapeptide analogues obtained via ring-closing metathesis. | 2006 |
|
| Effects of the intravenous administration of [Lys7]dermorphin on local cerebral glucose utilization in the rat. | 2006 Aug 21 |
|
| Targeted drug delivery crossing cytoplasmic membranes of intended cells via ligand-grafted sterically stabilized liposomes. | 2006 Feb 21 |
|
| Involvement of spinal mu1-opioid receptors on the Tyr-d-Arg-Phe-sarcosine-induced antinociception. | 2006 Jul 1 |
|
| Descending facilitation from the rostral ventromedial medulla maintains nerve injury-induced central sensitization. | 2006 Jul 21 |
|
| Involvement of endogenous opioid peptides in the antinociception induced by the novel dermorphin tetrapeptide analog amidino-TAPA. | 2007 Apr 10 |
|
| Ureido group containing cyclic dermorphin(1-7) analogues: synthesis, biology and conformation. | 2007 Aug |
|
| Receptor binding properties and antinociceptive effects of chimeric peptides consisting of a micro-opioid receptor agonist and an ORL1 receptor antagonist. | 2007 Jul |
|
| Supranodose vagotomy eliminates respiratory depression evoked by dermorphin in anaesthetized rats. | 2007 Jun 1 |
|
| Novel glycosylated [Lys(7)]-dermorphin analogues: synthesis, biological activity and conformational investigations. | 2007 Mar |
|
| [The relationship between the structure of dermorphines and their thermoregulatory activity]. | 2007 Nov-Dec |
|
| Dependence of the analgesic activities of dermorphin, metenkephalin, and dynorphin A on the ambient temperature. | 2007 Nov-Dec |
|
| [Synthesis, pharmacokinetics, and metabolism of the C-terminal tripeptide of dermorphin and its diastereomer]. | 2007 Nov-Dec |
|
| Effect of sedatin (synthetic dermorphin analog) on the development of Acipenser schrenckii young fish. | 2007 Oct |
|
| Effect of synthetic dermorphin analogues on tissue homeostasis in the myocardium of newborn albino rats. | 2007 Oct |
|
| Mechanisms for the effect of arginine-containing dermorphin analogue on proliferative processes in the gastric mucosa of albino rats. | 2007 Sep |
|
| [Comparative analysis of analgesic activities of dermorphin, [DPro6]-dermorphin, and their C-terminal tripeptides]. | 2007 Sep-Oct |
|
| Methylnaltrexone in the treatment of opioid-induced constipation. | 2008 |
|
| Multiple ligands in opioid research. | 2008 |
|
| Blood-brain barrier penetration by two dermorphin tetrapeptide analogues: role of lipophilicity vs structural flexibility. | 2008 Apr 24 |
|
| Conformation-activity relationships of cyclo-constrained micro/delta opioid agonists derived from the N-terminal tetrapeptide segment of dermorphin/deltorphin. | 2008 Aug |
|
| Amygdala intercalated neurons are required for expression of fear extinction. | 2008 Jul 31 |
|
| The use of tritium-labeled dermorphin for studying the interactions of C-terminal dermorphin fragment Tyr-Pro-Ser-NH2 and its stereoisomer Tyr-D-Pro-Ser-NH2 with opioid receptors. | 2008 Mar-Apr |
|
| Conformation-activity relationships of cyclo-constrained mu/delta opioid agonists derived from the N-terminal tetrapeptide segment of dermorphin/deltorphin. | 2009 |
|
| Discovery of dermorphin-based affinity labels with subnanomolar affinity for mu opioid receptors. | 2009 Dec 10 |
|
| Protective effect of dermorphin analogue sedatin on indomethacin-induced injury to the gastric mucosa. | 2009 Jul |
|
| [Significance of opioid receptors in regulation of cardiac tolerance in pathogenic impact of long-term ischemia-reperfusion in vivo]. | 2009 Jun |
|
| D-amino acid detection in peptides by MALDI-TOF-TOF. | 2009 Jun 1 |
|
| Neuropathic pain is maintained by brainstem neurons co-expressing opioid and cholecystokinin receptors. | 2009 Mar |
|
| Synthesis and receptor binding of opioid peptide analogues containing beta3-homo-amino acids. | 2009 Nov |
|
| Evaluation of side effects through selective ablation of the mu opioid receptor expressing descending nociceptive facilitatory neurons in the rostral ventromedial medulla with dermorphin-saporin. | 2009 Nov |
|
| Purification and functional reconstitution of monomeric mu-opioid receptors: allosteric modulation of agonist binding by Gi2. | 2009 Sep 25 |
|
| Partial ablation of mu-opioid receptor rich striosomes produces deficits on a motor-skill learning task. | 2009 Sep 29 |
|
| AntiBP2: improved version of antibacterial peptide prediction. | 2010 Jan 18 |
|
| Analytical characterization and comparison of the blood-brain barrier permeability of eight opioid peptides. | 2010 Jul |
|
| Opioid receptor internalization contributes to dermorphin-mediated antinociception. | 2010 Jun 30 |
|
| Synthesis, biological evaluation, and automated docking of constrained analogues of the opioid peptide H-Dmt-D-Ala-Phe-Gly-NH₂ using the 4- or 5-methyl substituted 4-amino-1,2,4,5-tetrahydro-2-benzazepin-3-one scaffold. | 2011 Oct 13 |
Patents
Sample Use Guides
In a clinical trial, dermorphin was given at a dose of 20 uM intrathecally.
Route of Administration:
Other
Rat neurons were treated with dermorphin. The drug caused the inhibition of spontaneous firing of all neurons of the locus coeruleus tested, with an IC50 of 7 nM. Larger concentrations of dermorphin (30-100 nM) further hyperpolarized the neurons of the locus coeruleus and simultaneously caused a reduction in input resistance. These effects were antagonized by naloxone, with a dissociation equilibrium constant of 0.8 nM.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 04:51:19 UTC 2023
by
admin
on
Sat Dec 16 04:51:19 UTC 2023
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| Record UNII |
2SEC01B703
|
| Record Status |
Validated (UNII)
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| Record Version |
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-
Download
| Name | Type | Language | ||
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Common Name | English |
| Code System | Code | Type | Description | ||
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77614-16-5
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DERMORPHIN
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2SEC01B703
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DTXSID40228281
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C030058
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5485199
Created by
admin on Sat Dec 16 04:51:19 UTC 2023 , Edited by admin on Sat Dec 16 04:51:19 UTC 2023
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| Related Record | Type | Details | ||
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OFF TARGET->NON-INHIBITOR |
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TARGET->WEAK AGONIST |
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TARGET -> AGONIST |
Ki
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TARGET -> AGONIST |
IC50
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ACTIVE MOIETY |
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