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Details

Stereochemistry ABSOLUTE
Molecular Formula C30H34FN5O5
Molecular Weight 563.6199
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FRAKEFAMIDE

SMILES

C[C@@H](NC(=O)[C@@H](N)CC1=CC=C(O)C=C1)C(=O)N[C@@H](CC2=CC=C(F)C=C2)C(=O)N[C@@H](CC3=CC=CC=C3)C(N)=O

InChI

InChIKey=GTPHQORJKFJIRB-JTQLPTLWSA-N
InChI=1S/C30H34FN5O5/c1-18(34-29(40)24(32)15-20-9-13-23(37)14-10-20)28(39)36-26(17-21-7-11-22(31)12-8-21)30(41)35-25(27(33)38)16-19-5-3-2-4-6-19/h2-14,18,24-26,37H,15-17,32H2,1H3,(H2,33,38)(H,34,40)(H,35,41)(H,36,39)/t18-,24+,25+,26+/m1/s1

HIDE SMILES / InChI

Molecular Formula C30H34FN5O5
Molecular Weight 563.6199
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Frakefamide is a tetrapeptide with an amide function at the C-terminus. The amino acid sequence of frakefamide is L-tyrosyl-D-alanyl-p-fluoro-L-phenylalanyl-Lphenylalaninamide. Hence, it contains both natural and unnatural R-amino acids. Frakefamide has shown interesting properties for use in acute and chronic pain treatment. It acts as a selective agonist on mu-opioid receptors and belongs to the dermorphin peptide family. It has been shown to be a potent peripherally acting analgesic in rats and humans. However, frakefamide had been found to have "unexpected results" in Phase II trials and AstraZeneca offered to hand the drug back.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
1.22 mg/kg single, intravenous (total)
Studied dose
Dose: 1.22 mg/kg
Route: intravenous
Route: single
Dose: 1.22 mg/kg
Sources:
healthy, ADULT
n = 12
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Population Size: 12
Sources:
Other AEs: myalgia, Rhinitis...
Other AEs:
myalgia (12 patients)
Rhinitis (6 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
myalgia 12 patients
1.22 mg/kg single, intravenous (total)
Studied dose
Dose: 1.22 mg/kg
Route: intravenous
Route: single
Dose: 1.22 mg/kg
Sources:
healthy, ADULT
n = 12
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Population Size: 12
Sources:
Rhinitis 6 patients
1.22 mg/kg single, intravenous (total)
Studied dose
Dose: 1.22 mg/kg
Route: intravenous
Route: single
Dose: 1.22 mg/kg
Sources:
healthy, ADULT
n = 12
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Population Size: 12
Sources:
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

1 nmol · kg(-1) · min(-1) during the first 15 min, followed by another 15 min of 3 nmol · kg(-1) · min(-1) and thereafter 6 nmol · kg(-1) · min(-1) up to 6 h. This corresponds to a total dose of 1.22 mg/kg.
Route of Administration: Intravenous
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:44:02 UTC 2023
Edited
by admin
on Wed Jul 05 23:44:02 UTC 2023
Record UNII
DM32B4GU70
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FRAKEFAMIDE
INN  
INN  
Official Name English
frakefamide [INN]
Common Name English
SPD-759
Code English
LEF-576
Code English
Classification Tree Code System Code
NCI_THESAURUS C67413
Created by admin on Wed Jul 05 23:44:03 UTC 2023 , Edited by admin on Wed Jul 05 23:44:03 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID701030318
Created by admin on Wed Jul 05 23:44:03 UTC 2023 , Edited by admin on Wed Jul 05 23:44:03 UTC 2023
PRIMARY
PUBCHEM
9829352
Created by admin on Wed Jul 05 23:44:03 UTC 2023 , Edited by admin on Wed Jul 05 23:44:03 UTC 2023
PRIMARY
WIKIPEDIA
Frakefamide
Created by admin on Wed Jul 05 23:44:03 UTC 2023 , Edited by admin on Wed Jul 05 23:44:03 UTC 2023
PRIMARY
FDA UNII
DM32B4GU70
Created by admin on Wed Jul 05 23:44:03 UTC 2023 , Edited by admin on Wed Jul 05 23:44:03 UTC 2023
PRIMARY
NCI_THESAURUS
C77290
Created by admin on Wed Jul 05 23:44:03 UTC 2023 , Edited by admin on Wed Jul 05 23:44:03 UTC 2023
PRIMARY
MESH
C497770
Created by admin on Wed Jul 05 23:44:03 UTC 2023 , Edited by admin on Wed Jul 05 23:44:03 UTC 2023
PRIMARY
INN
7852
Created by admin on Wed Jul 05 23:44:03 UTC 2023 , Edited by admin on Wed Jul 05 23:44:03 UTC 2023
PRIMARY
ChEMBL
CHEMBL2105081
Created by admin on Wed Jul 05 23:44:03 UTC 2023 , Edited by admin on Wed Jul 05 23:44:03 UTC 2023
PRIMARY
SMS_ID
300000034253
Created by admin on Wed Jul 05 23:44:03 UTC 2023 , Edited by admin on Wed Jul 05 23:44:03 UTC 2023
PRIMARY
CAS
188196-22-7
Created by admin on Wed Jul 05 23:44:03 UTC 2023 , Edited by admin on Wed Jul 05 23:44:03 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY