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Details

Stereochemistry ACHIRAL
Molecular Formula C16H17BrN2
Molecular Weight 317.224
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ZIMELDINE

SMILES

CN(C)C\C=C(\C1=CC=C(Br)C=C1)C2=CN=CC=C2

InChI

InChIKey=OYPPVKRFBIWMSX-SXGWCWSVSA-N
InChI=1S/C16H17BrN2/c1-19(2)11-9-16(14-4-3-10-18-12-14)13-5-7-15(17)8-6-13/h3-10,12H,11H2,1-2H3/b16-9-

HIDE SMILES / InChI

Molecular Formula C16H17BrN2
Molecular Weight 317.224
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Zimeldine was one of the first selective serotonin reuptake inhibitors to be marketed as an antidepressant under the brand names Zimeldine, Normud, and Zelmid. Zimelidine was developed in the late 1970s and early 1980s by Arvid Carlsson, who was then working for the Swedish company Astra AB. While zimelidine had a very favorable safety profile, within a year and a half of its introduction, rare case reports of Guillain–Barré syndrome emerged that appeared to be caused by the drug, prompting its withdrawl from the market.

CNS Activity

Originator

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
zimeldine
Primary
zimeldine
Primary
zimeldine

PubMed

Sample Use Guides

In Vivo Use Guide
Eleven narcoleptic patients were studied before and one month after treatment with 100 mg daily oral dose of zimelidine. All patients improved with zimelidine. Ten patients had complete suppression of cataplexy.
Route of Administration: Oral
In Vitro Use Guide
Human PC-3, DU-145, and LNCaP cells were each maintained in Leibovitz's L-medium containing 5% fetal bovine serum and antibiotics. Cells were plated in serum-supplemented growth medium at 10,000 cells per well and treated with zimelidine 24 hours later. After 3 days, cell numbers were determined using the MTT assay. Zimelidine demonstrated concentration dependent inhibition against all three prostate carcinoma cell lines. The half maximal concentration for growth inhibition was reported as 15.0, 25.0, and 65.0 micro-M for PC-3, DU-145, and LNCaP respectively.
Substance Class Chemical
Record UNII
3J928617DW
Record Status Validated (UNII)
Record Version