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Details

Stereochemistry ABSOLUTE
Molecular Formula C33H43FN10O6.2C2HF3O2
Molecular Weight 922.803
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NEMIFITIDE DITRIFLUTATE

SMILES

OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.[H][C@]1(C[C@@H](O)CN1C(=O)[C@@H](N)CC2=CC=C(F)C=C2)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC3=CNC4=C3C=CC=C4)C(N)=O

InChI

InChIKey=QXCFOJXOLMOPRK-QOXNQHIRSA-N
InChI=1S/C33H43FN10O6.2C2HF3O2/c34-20-9-7-18(8-10-20)12-23(35)32(50)44-17-21(45)14-27(44)31(49)43-25(6-3-11-39-33(37)38)30(48)41-16-28(46)42-26(29(36)47)13-19-15-40-24-5-2-1-4-22(19)24;2*3-2(4,5)1(6)7/h1-2,4-5,7-10,15,21,23,25-27,40,45H,3,6,11-14,16-17,35H2,(H2,36,47)(H,41,48)(H,42,46)(H,43,49)(H4,37,38,39);2*(H,6,7)/t21-,23+,25+,26+,27+;;/m1../s1

HIDE SMILES / InChI

Molecular Formula C33H43FN10O6
Molecular Weight 694.7563
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C2HF3O2
Molecular Weight 114.0233
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Nemifitide is a peptide analog of melanocyte-inhibiting factor (MIF) that has been reported to relieve depressive symptoms in a very short period. Tetragenex (formerly Innapharma) was developing nemifitide with potential in the treatment of depression. Clinical data obtained from two pilot clinical studies, double-blind, placebo-controlled, parallel-design, in-patient and outpatient, suggested that nemifitide may have the following advantages over current therapies: rapid onset of action (3–5 d), short period of administration (5–10 doses over a 1–2 wk period), and a relatively long duration of treatment effect (3–6 months). The mechanism of action of nemifitide was investigated by evaluating its in-vitro receptor binding and in-vivo localization in the rat brain as well as its interactions with psychoprobes indicative of specific neurotransmitter pathways in acute studies in rats. The results of these studies indicate that nemifitide readily crosses the blood–brain barrier and is localized mainly in the amygdala, hippocampus and frontal cortex of the rat brain. Its in-vitro binding to several receptors including 5-HT-2A, as well as its significant interaction with d-fenfluramine in the rat, suggest the participation of the serotonergic pathway in its mode of action in a different way than that observed with SSRI antidepressants.

Approval Year

PubMed

PubMed

TitleDatePubMed
Clinical pharmacokinetic studies with INN 00835 (nemifitide), a novel pentapeptide antidepressant.
2002 Jan

Sample Use Guides

Doses of 18, 36, 54 and 72 mg/d showed almost equal clinical effect of duration between retreatment doses, the 36 mg/d dose being the most reproducible. The range of dose from 18 to 72 mg/d looks promising for the future clinical trials. Nemifitide was administered subcutaneously.
Route of Administration: Other
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:11:15 GMT 2023
Edited
by admin
on Fri Dec 15 16:11:15 GMT 2023
Record UNII
27454M5E8Z
Record Status Validated (UNII)
Record Version
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Name Type Language
NEMIFITIDE DITRIFLUTATE
USAN  
USAN  
Official Name English
4-FLUORO-L-PHENYLALANYL-TRANS-4-HYDROXY-L-PROLYL-L-ARGINYLGLYCYL-L-TRYPTOPHANAMIDE BIS(TRIFLUOROACETATE) (SALT)
Common Name English
NEMIFITIDE DITRIFLUTATE [USAN]
Common Name English
INN-00835
Code English
NEMIFITIDE BIS(TRIFLUOROACETATE) [MI]
Common Name English
L-TRYPTOPHANAMIDE, 4-FLUORO-L-PHENYLALANYL-(4R)-4-HYDROXY-L-PROLYL-L-ARGINYLGLYCYL-BIS(TRIFLUOROACETATE) (SALT)
Common Name English
NEMIFITIDE BIS(TRIFLUOROACETATE)
MI  
Common Name English
INN 00835
Code English
Code System Code Type Description
NCI_THESAURUS
C166549
Created by admin on Fri Dec 15 16:11:15 GMT 2023 , Edited by admin on Fri Dec 15 16:11:15 GMT 2023
PRIMARY
USAN
MM-75
Created by admin on Fri Dec 15 16:11:15 GMT 2023 , Edited by admin on Fri Dec 15 16:11:15 GMT 2023
PRIMARY
PUBCHEM
6918347
Created by admin on Fri Dec 15 16:11:15 GMT 2023 , Edited by admin on Fri Dec 15 16:11:15 GMT 2023
PRIMARY
CAS
204992-09-6
Created by admin on Fri Dec 15 16:11:15 GMT 2023 , Edited by admin on Fri Dec 15 16:11:15 GMT 2023
PRIMARY
FDA UNII
27454M5E8Z
Created by admin on Fri Dec 15 16:11:15 GMT 2023 , Edited by admin on Fri Dec 15 16:11:15 GMT 2023
PRIMARY
MERCK INDEX
m7800
Created by admin on Fri Dec 15 16:11:15 GMT 2023 , Edited by admin on Fri Dec 15 16:11:15 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL2107761
Created by admin on Fri Dec 15 16:11:15 GMT 2023 , Edited by admin on Fri Dec 15 16:11:15 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY