DERMORPHIN

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

Structure Search

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

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3831962 | https://www.ncbi.nlm.nih.gov/pubmed/26756519

Dermorphin is a selective mu-opioid receptor agonist. It was isolated from isolated from skin extracts of frogs belonging to the genus Phyllomedusa and was shown to relife pain in patients with postoperative pain syndrome.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mu-type opioid receptor 61 Target ID: P35372\|\|\|G8XRH8\|\|\|Q5TDA1\|\|\|Q9UN57 Gene ID: 4988.0 Gene Symbol: OPRM1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26756519	Agonist 2752		8.8 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Postoperative pain 22 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3831962	Primary		Phase II 1147	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
20 ug single, intrathecal Studied dose Dose: 20 ug Route: intrathecal Route: single Dose: 20 ug Sources: https://pubmed.ncbi.nlm.nih.gov/3831962	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3831962	Other AEs: Nausea, vomiting... Other AEs: Nausea (22%) vomiting (22%) Urinary retention (26%) Headache (6%) Sources: https://pubmed.ncbi.nlm.nih.gov/3831962

AEs

AE	Significance	Dose	Population
Nausea	22%	20 ug single, intrathecal Studied dose Dose: 20 ug Route: intrathecal Route: single Dose: 20 ug Sources: https://pubmed.ncbi.nlm.nih.gov/3831962	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3831962
vomiting	22%	20 ug single, intrathecal Studied dose Dose: 20 ug Route: intrathecal Route: single Dose: 20 ug Sources: https://pubmed.ncbi.nlm.nih.gov/3831962	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3831962
Urinary retention	26%	20 ug single, intrathecal Studied dose Dose: 20 ug Route: intrathecal Route: single Dose: 20 ug Sources: https://pubmed.ncbi.nlm.nih.gov/3831962	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3831962
Headache	6%	20 ug single, intrathecal Studied dose Dose: 20 ug Route: intrathecal Route: single Dose: 20 ug Sources: https://pubmed.ncbi.nlm.nih.gov/3831962	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3831962

Sourcing

Vendor/Aggregator	ID	URL
AbovChem LLC	HY-P0244
Alfa Chemistry	232577	http://www.alfa-chemistry.com/search.aspx?q=232577
Alfa Chemistry	ACM77614165	http://www.alfa-chemistry.com/search.aspx?q=ACM77614165
Bachem	H-2565	https://shop.bachem.com/catalogsearch/result/?q=H-2565
BOC Sciences	77614-16-5	http://www.bocsci.com/description.asp?cas=77614-16-5
Chem Scene	CS-7103	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-7103
Compound Cloud	5485199
eMolecules	43477173	https://orderbb.emolecules.com/search/#?query=43477173
Hangzhou Yuhao Chemical Technology	RT5660
mcule	MCULE-3764930303	https://mcule.com/MCULE-3764930303/
MedChem Express	HY-P0244	https://www.medchemexpress.com/search.html?q=HY-P0244&ft=&fa=&fp=
MolPort	MolPort-016-581-003	https://www.molport.com/shop/molecule-link/MolPort-016-581-003
MolPort	MolPort-046-689-305	https://www.molport.com/shop/molecule-link/MolPort-046-689-305
Toronto Research Chemicals	D281940	https://www.trc-canada.com/product-detail/?CatNum=D281940
Toronto Research Chemicals	M264630	https://www.trc-canada.com/product-detail/?CatNum=M264630

PubMed

Title	Date	PubMed
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.	2011-10-13	21870874
Analytical characterization and comparison of the blood-brain barrier permeability of eight opioid peptides.	2010-07	20347901
Opioid receptor internalization contributes to dermorphin-mediated antinociception.	2010-06-30	20394808
AntiBP2: improved version of antibacterial peptide prediction.	2010-01-18	20122190
Discovery of dermorphin-based affinity labels with subnanomolar affinity for mu opioid receptors.	2009-12-10	19621878
Synthesis and receptor binding of opioid peptide analogues containing beta3-homo-amino acids.	2009-11	19787815
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.	2009-11	19559047
Partial ablation of mu-opioid receptor rich striosomes produces deficits on a motor-skill learning task.	2009-09-29	19463902
Purification and functional reconstitution of monomeric mu-opioid receptors: allosteric modulation of agonist binding by Gi2.	2009-09-25	19542234
[The relationship between the structure of dermorphines and their thermoregulatory activity].	2009-09-23	19768965
Protective effect of dermorphin analogue sedatin on indomethacin-induced injury to the gastric mucosa.	2009-07	19902098
D-amino acid detection in peptides by MALDI-TOF-TOF.	2009-06-01	19476389
[Significance of opioid receptors in regulation of cardiac tolerance in pathogenic impact of long-term ischemia-reperfusion in vivo].	2009-06	19639880
Neuropathic pain is maintained by brainstem neurons co-expressing opioid and cholecystokinin receptors.	2009-03	19050032
Conformation-activity relationships of cyclo-constrained mu/delta opioid agonists derived from the N-terminal tetrapeptide segment of dermorphin/deltorphin.	2009	19400278
Conformation-activity relationships of cyclo-constrained micro/delta opioid agonists derived from the N-terminal tetrapeptide segment of dermorphin/deltorphin.	2008-08	18338322
Amygdala intercalated neurons are required for expression of fear extinction.	2008-07-31	18615014
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.	2008-06-10	18536274
Blood-brain barrier penetration by two dermorphin tetrapeptide analogues: role of lipophilicity vs structural flexibility.	2008-04-24	18370374
Dependence of the analgesic activities of dermorphin, metenkephalin, and dynorphin A on the ambient temperature.	2008-02-16	18274480
[Synthesis, pharmacokinetics, and metabolism of the C-terminal tripeptide of dermorphin and its diastereomer].	2008-01-05	18173119
Methylnaltrexone in the treatment of opioid-induced constipation.	2008	21677823
Multiple ligands in opioid research.	2008	18782061
[Comparative analysis of analgesic activities of dermorphin, [DPro6]-dermorphin, and their C-terminal tripeptides].	2007-11-28	18038625
Effect of sedatin (synthetic dermorphin analog) on the development of Acipenser schrenckii young fish.	2007-10	18642708
Effect of synthetic dermorphin analogues on tissue homeostasis in the myocardium of newborn albino rats.	2007-10	18642706
Mechanisms for the effect of arginine-containing dermorphin analogue on proliferative processes in the gastric mucosa of albino rats.	2007-09	18457022
Ureido group containing cyclic dermorphin(1-7) analogues: synthesis, biology and conformation.	2007-08	17605130
Receptor binding properties and antinociceptive effects of chimeric peptides consisting of a micro-opioid receptor agonist and an ORL1 receptor antagonist.	2007-07	17603164
Supranodose vagotomy eliminates respiratory depression evoked by dermorphin in anaesthetized rats.	2007-06-01	17362918
Involvement of endogenous opioid peptides in the antinociception induced by the novel dermorphin tetrapeptide analog amidino-TAPA.	2007-04-10	17307162
Novel glycosylated [Lys(7)]-dermorphin analogues: synthesis, biological activity and conformational investigations.	2007-03	17177323
Effects of the intravenous administration of [Lys7]dermorphin on local cerebral glucose utilization in the rat.	2006-08-21	16831415
Descending facilitation from the rostral ventromedial medulla maintains nerve injury-induced central sensitization.	2006-07-21	16650614
Involvement of spinal mu1-opioid receptors on the Tyr-d-Arg-Phe-sarcosine-induced antinociception.	2006-07-01	16730704
Targeted drug delivery crossing cytoplasmic membranes of intended cells via ligand-grafted sterically stabilized liposomes.	2006-02-21	16356575
[Comparative study of the antiarrhythmic activity of mu- and delta-opioid receptor agonists during acute cardiac ischemia and reperfusion models in rats].	2006-01-13	16405030
Cyclic dermorphin tetrapeptide analogues obtained via ring-closing metathesis.	2006	16496038
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.	2005-11	16218989
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.	2005-10	15894374
[Comparative study of the physical dependence on proline analog of dermorphin and morphine].	2005-07-29	16047673
Distinguishing and quantifying peptides and proteins containing D-amino acids by tandem mass spectrometry.	2005-07-15	16013875
[Analgesic activity of dermorphin and its proline analogs].	2005-06-07	15934358
Abbreviated nomenclature for cyclic and branched homo- and hetero-detic peptides.	2005-06	15885114
Cyclic enkephalin and dermorphin analogues containing a carbonyl bridge.	2005-06	15635652
6-Hydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid mimics active conformation of tyrosine in opioid peptides.	2005-05-16	15863298
[Study of thermoregulatory activity of a fragment of natural dermorphin precursor Arg-dermorphin and its analogs].	2005-03-17	15768633
Synthesis of dermorphin-(1-4) derivatives catalyzed by proteases in organic solvents.	2005-01	15686545
New tris-alkoxycarbonyl arginine derivatives for peptide synthesis.	2005-01	15635728
[Thermoregulatory activity of dermorphin fragments].	2004-11-24	15559135

Patents

Sample Use Guides

In Vivo Use Guide

In a clinical trial, dermorphin was given at a dose of 20 uM intrathecally.

Route of Administration: Other

In Vitro Use Guide

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 `Mon Mar 31 21:24:15 GMT 2025` Edited by `admin` on `Mon Mar 31 21:24:15 GMT 2025`
Record UNII	2SEC01B703
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

L-SERINAMIDE, L-TYROSYL-D-ALANYL-L-PHENYLALANYLGLYCYL-L-TYROSYL-L-PROLYL-

Preferred Name

English

DERMORPHIN

Common Name

English

TYR-D-ALA-PHE-GLY-TYR-PRO-SER-NH2

Common Name

English

Code System Code Type Description

CAS

77614-16-5