Structure via PubChem · Public domain (PubChem)
zimelidine
Sign in to saveAlso known as (z)-zimelidine, (Z)-3-[1-(p-bromophenyl)-3-(dimethylamino)propenyl]pyridine, (Z)-3-(4'-bromophenyl)-3-(3''-pyridyl)dimethylallylamine, cis-zimelidine, zimeldine
Zimelidine (INN, BAN; brand names Zimeldine, Normud, Zelmid), is an antidepressant medication of the selective serotonin reuptake inhibitor (SSRI) class, and the first SSRI antidepressant to be marketed. It is a pyridylallylamine, and is structurally different from other antidepressants.
Key facts
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 470635867
- Drug.Verifiedfields
- changed
- Drug.IUPAC_name
- (Z)-3-(4-Bromophenyl)-N,N-dimethyl-3-(pyridin-3-yl)prop-2-en-1-amine
- Drug.image
- Zimelidine.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 222
- Drug.tradename
- Zelmid, Normud
- Drug.legal_status
- Withdrawn worldwide
- Drug.routes_of_administration
- Oral
- Drug.elimination_half life
- 8.4±2 hours (parent compound) 19.4±3.6 hours (norzimelidine)
- Drug.CAS_number
- 56775-88-3
- Drug.CAS_supplemental
- 60525-15-7 (anhydrous dihydrochloride), 61129-30-4 (dihydrochloride monohydrate)
- Drug.ATC_prefix
- N06
- Drug.ATC_suffix
- AB02
- Drug.PubChem
- 5365247
- Drug.DrugBank
- DB04832
- Drug.ChemSpiderID
- 4517305
via Wikipedia infobox
Chemical data
- Formula
- C16H17BrN2
- Molecular weight
- 317.22 g/mol
- IUPAC name
- (Z)-3-(4-bromophenyl)-N,N-dimethyl-3-pyridin-3-ylprop-2-en-1-amine
- SMILES
- CN(C)C/C=C(/C1=CC=C(C=C1)Br)\C2=CN=CC=C2
- InChIKey
- OYPPVKRFBIWMSX-SXGWCWSVSA-N
- XLogP
- 3.9
- Polar surface area
- 16.1 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
Withdrawn- Max clinical phase
- Approved
- Molecule type
- Small molecule
- Indications
- major depressive disorder
via ChEMBL · EBI
Research
685 papers- Zimelidine: a review of its pharmacological properties and therapeutic efficacy in depressive illness.Drugs · 1982
- Zimelidine: a placebo-controlled trial in depression.Psychiatry research · 1983
- Antidepressant overdosage.Drugs · 1982
- Cardiovascular and anticholinergic effects of zimelidine.Progress in neuro-psychopharmacology & biological psychiatry · 1982
- Maprotiline, nomifensine, mianserin, zimelidine: a review of antidepressant efficacy in in-patients.Neuropharmacology · 1980
via PubMed
Wikidata facts
- Has part
- bromine
- Mass
- 316.057511
- Has use
- medication
Show 6 more facts
- chemical formula
- C₁₆H₁₇BrN₂
- isomeric SMILES
- CN(C)C/C=C(/C1=CC=C(C=C1)Br)\C2=CN=CC=C2
- canonical SMILES
- CN(C)CC=C(C1=CC=C(C=C1)Br)C2=CN=CC=C2
- defined daily dose
- 0.2
- subject has role
- selective serotonin reuptake inhibitor
- Commons category
- Zimelidine
via Wikidata · CC0
~3 min read
Encyclopedic overview
6 sectionsContents
- Other uses
- Mechanism of action
- Side effects
- Interactions
- See also
- References
Zimelidine (INN, BAN; brand names Zimeldine, Normud, Zelmid), is an antidepressant medication of the selective serotonin reuptake inhibitor (SSRI) class, and the first SSRI antidepressant to be marketed. It is a pyridylallylamine, and is structurally different from other antidepressants.
Zimelidine was developed in the late 1970s and early 1980s by Arvid Carlsson, Hans Corrodi and Peter Berntsson, who were then collaborating with the Swedish company Astra AB. Their work began with a series of antihistamines known as pheniramines that were found to block both serotonin and noradrenaline reuptake, and among these, brompheniramine was identified as the most potent serotonin reuptake blocker and was therefore selected as the starting point for their synthesis program, ultimately leading to the invention of zimelidine as a derivative of brompheniramine. Zimelidine was first sold in 1982.
Excerpted from Wikipedia’s “zimelidine” article, available under the CC BY-SA 4.0 licence.