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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H17ClN2O
Molecular Weight 300.783
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETIFOXINE, (S)-

SMILES

CCNC1=NC2=CC=C(Cl)C=C2[C@@](C)(O1)C3=CC=CC=C3

InChI

InChIKey=IBYCYJFUEJQSMK-KRWDZBQOSA-N
InChI=1S/C17H17ClN2O/c1-3-19-16-20-15-10-9-13(18)11-14(15)17(2,21-16)12-7-5-4-6-8-12/h4-11H,3H2,1-2H3,(H,19,20)/t17-/m0/s1

HIDE SMILES / InChI

Molecular Formula C17H17ClN2O
Molecular Weight 300.783
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

(S)-Etifoxine is a first in class pain-relieving drug candidate, with the power of morphine and oxycodone, but without the addictive, sedative and GI side effects. (S)-etifoxine is an isomer, chemically isolated from Etifoxine (Stresam), an approved racemic drug (off patent) prescribed in Europe. Preclinical studies determined that the (S)-isomer of Stresam® ((S)-etifoxine) is a non-sedating anxiolytic. It was also discovered that (S)-etifoxine possesses highly potent analgesic activity comparable to morphine (the gold standard) which is consistent with Stresam®’s TSPO-mediated effects on chemotherapy-induced neuropathy and peripheral nerve injury. However, (S)-etifoxine does not display any of the negative side-effects associated with morphine. Even more notably, Stresam® has demonstrated peripheral nerve regeneration and functional recovery. It is believed that (S)-etifoxine will retain these same properties.

CNS Activity

Curator's Comment: Data for R/S-Etifoxine

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Patents

Patents

Sample Use Guides

50 mg tid as etifoxine
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:55:26 GMT 2023
Edited
by admin
on Sat Dec 16 09:55:26 GMT 2023
Record UNII
963E1X3T2S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ETIFOXINE, (S)-
Common Name English
4H-3,1-BENZOXAZIN-2-AMINE, 6-CHLORO-N-ETHYL-4-METHYL-4-PHENYL-, (4S)-
Systematic Name English
S-ETIFOXINE
Common Name English
Code System Code Type Description
CAS
950513-31-2
Created by admin on Sat Dec 16 09:55:26 GMT 2023 , Edited by admin on Sat Dec 16 09:55:26 GMT 2023
PRIMARY
PUBCHEM
135564604
Created by admin on Sat Dec 16 09:55:26 GMT 2023 , Edited by admin on Sat Dec 16 09:55:26 GMT 2023
PRIMARY
FDA UNII
963E1X3T2S
Created by admin on Sat Dec 16 09:55:26 GMT 2023 , Edited by admin on Sat Dec 16 09:55:26 GMT 2023
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER