cyprolidol

{{Short description|1960s experimental antidepressant drug}}

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{{Infobox drug

| drug_name = Cyprolidol

| image = Cyprolidol.svg

| width = 250px

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| CAS_number = 7433-09-2

| CAS_supplemental =
[2364-72-9] (hydrochloride),
[4904-00-1]
(±)-trans/(1RS,2SR)

| PubChem = 23287

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| DrugBank =

| ChemSpiderID = 21778

| UNII = 7UQN2OJ7SM

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| ChEMBL = 2110906

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| synonyms = IN 1060

| IUPAC_name = diphenyl-(2-pyridin-4-ylcyclopropyl)methanol

| C=21 | H=19 | N=1 | O=1

| SMILES = C1C(C1C(C2=CC=CC=C2)(C3=CC=CC=C3)O)C4=CC=NC=C4

| StdInChI = 1S/C21H19NO/c23-21(17-7-3-1-4-8-17,18-9-5-2-6-10-18)20-15-19(20)16-11-13-22-14-12-16/h1-14,19-20,23H,15H2

| StdInChIKey = KPUSUIKQQCFQCX-UHFFFAOYSA-N

}}

Cyprolidol is an experimental antidepressant drug that was developed by Neisler Laboratories in the 1960s.{{cite web | title = Cyprolidol hydrochloride | work = Inxight Drugs | publisher = National Center for Advancing Translational Sciences (NCATS), U.S. National Institutes of Health | url = https://drugs.ncats.io/drug/7UQN2OJ7SM }} It was never approved for human use.

In preclinical studies, cyprolidol demonstrated antidepressant effects in animal models that were qualitatively similar to those of imipramine, a well-established tricyclic antidepressant.{{cite journal | vauthors = Brown ML, Gershon S, Korol B | title = Some pharmacological effects of a new potential antidepressant cyprolidol (IN-1060) compared with imipramine | journal = Medicina et Pharmacologia Experimentalis. International Journal of Experimental Medicine | volume = 15 | issue = 4 | pages = 329–43 | date = 1966 | pmid = 6012765 | doi = 10.1159/000135886 }}{{cite journal | vauthors = Miller L, Napoli M, O'Dell TB | title = Pharmacological evaluation of a potential psychotherapeutic agent: cyprolidol, a pyridylcyclopropane derivative | journal = Archives Internationales de Pharmacodynamie et de Therapie | volume = 166 | issue = 2 | pages = 313–323 | date = April 1967 | pmid = 4963240 }} However, clinical observations indicated that cyprolidol was less effective than imipramine in humans.{{cite journal | vauthors = Hekimian LJ, Gershon S, Floyd A | title = Cyprolidol and imipramine: a double-blind controlled study in endogenous depression | journal = Arzneimittel-Forschung | volume = 19 | issue = 6 | pages = 955–956 | date = June 1969 | pmid = 4896165 }} Pharmacologically, cyprolidol also exhibited cardiovascular effects, such as blocking the tyramine-induced rise in blood pressure in anesthetized dogs while potentiating this response in conscious dogs, suggesting a complex interaction with adrenergic systems.{{cite journal | vauthors = Korol B, Brown ML, Sletten IW | title = Effects of a new antidepressant cyprolidol (IN-1060) upon the blood pressure responses to autonomic drugs in conscious dogs | journal = Current Therapeutic Research, Clinical and Experimental | volume = 8 | issue = 11 | pages = 543–548 | date = November 1966 | pmid = 4963159 }}

Its synthesis is similar to tranylcypromine, a monoamine oxidase inhibitor.