FRAKEFAMIDE

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16368813 | doi: 10.1021/op020060k | http://www.telegraph.co.uk/finance/2727217/Shire-shares-fall-after-drugs-setback.html | http://en.pharmacodia.com/web/drug/1_5948.html

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Opioid receptors; mu & delta 1 Target ID: CHEMBL2095149 Sources: Bountra, C. et al. (2003) 'Pain: Current Understanding, Emerging Therapies, and Novel Approaches to Drug Discovery', p.400 Retrieved from https://books.google.ru/books?id=anRzslvfcUwC	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 619 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16368813	Primary		Phase II 1147	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
1.22 mg/kg single, intravenous Studied dose Dose: 1.22 mg/kg Route: intravenous Route: single Dose: 1.22 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/16368813	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/16368813	Other AEs: myalgia, Rhinitis... Other AEs: myalgia (12 patients) Rhinitis (6 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/16368813

AEs

AE	Significance	Dose	Population
myalgia	12 patients	1.22 mg/kg single, intravenous Studied dose Dose: 1.22 mg/kg Route: intravenous Route: single Dose: 1.22 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/16368813	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/16368813
Rhinitis	6 patients	1.22 mg/kg single, intravenous Studied dose Dose: 1.22 mg/kg Route: intravenous Route: single Dose: 1.22 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/16368813	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/16368813

Sourcing

Vendor/Aggregator	ID	URL
Alfa Chemistry	ACM188196227	http://www.alfa-chemistry.com/search.aspx?q=ACM188196227
BOC Sciences	188196-22-7	http://www.bocsci.com/description.asp?cas=188196-22-7
Chem Scene	CS-0122452	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0122452
MedChem Express	HY-106147B	https://www.medchemexpress.com/search.html?q=HY-106147B&ft=&fa=&fp=

PubMed

Title	Date	PubMed
A novel molecule (frakefamide) with peripheral opioid properties: the effects on resting ventilation compared with morphine and placebo.	2005 Mar	15728057
A novel molecule with peripheral opioid properties: the effects on hypercarbic and hypoxic ventilation at steady-state compared with morphine and placebo.	2006 Jan	16368813

Patents

Sample Use Guides

In Vivo Use Guide

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 `Mon Mar 31 18:23:57 GMT 2025` Edited by `admin` on `Mon Mar 31 18:23:57 GMT 2025`
Record UNII	DM32B4GU70
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FRAKEFAMIDE

Official Name

English

LEF-576

Preferred Name

English

frakefamide [INN]

Common Name

English

SPD-759

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C67413