Anipamil: Difference between revisions

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 443439957

| ImageFile = Anipamil.svg

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageSize = 200

| ImageName = Skeletal formula of Anipamil

| IUPACName = 2-(3-methoxyphenyl)-2-[3-[2-(3-methoxyphenyl)ethyl-methylamino]propyl]tetradecanenitrile

|Section1 = {{Chembox Identifiers

| CASNo = 83200-10-6

| CASNo_Ref = {{cascite|correct|??}}

| PubChem = 54966

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 2104548

| ChemSpiderID = 49636

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| EINECS = 280-213-5

| MeSHName = Anipamil

| SMILES = CCCCCCCCCCCCC(CCCN(C)CCC1=CC(OC)=CC=C1)(C#N)C1=CC(OC)=CC=C1

| SMILES1 = N#CC(c1cc(OC)ccc1)(CCCCCCCCCCCC)CCCN(CCc2cccc(OC)c2)C

| StdInChI = 1S/C34H52N2O2/c1-5-6-7-8-9-10-11-12-13-14-23-34(29-35,31-19-16-21-33(28-31)38-4)24-17-25-36(2)26-22-30-18-15-20-32(27-30)37-3/h15-16,18-21,27-28H,5-14,17,22-26H2,1-4H3

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| InChI = 1/C34H52N2O2/c1-5-6-7-8-9-10-11-12-13-14-23-34(29-35,31-19-16-21-33(28-31)38-4)24-17-25-36(2)26-22-30-18-15-20-32(27-30)37-3/h15-16,18-21,27-28H,5-14,17,22-26H2,1-4H3

| StdInChIKey = PHFDAOXXIZOUIX-UHFFFAOYSA-N

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| InChIKey = PHFDAOXXIZOUIX-UHFFFAOYAP

|Section2 = {{Chembox Properties

| C=34 | H=52 | N=2 | O=2

'''Anipamil''' is a [[calcium channel blocker]],<ref>{{Cite journal|last1=Raddino|first1=Riccardo|last2=Poli|first2=Enzo|last3=Pasini|first3=Evasio|last4=Ferrari|first4=Roberto|date=1992-09-01|title=Effects of the novel calcium channel blocker, anipamil, on the isolated rabbit heart|journal=Naunyn-Schmiedeberg's Archives of Pharmacology|language=en|volume=346|issue=3|pages=339–344|doi=10.1007/BF00173549|pmid=1383837|s2cid=20915840|issn=0028-1298}}</ref> specifically of the [[phenylalkylamine]] type. This type is separate from its more common cousin [[Dihydropyridine]]. Anipamil is an analog of the more common drug [[verapamil]], which is the most common type of [[phenylalkylamine]] style calcium channel blocker. Anipamil has been shown to be a more effective antiarrhythmic medication<ref name=":0">{{Cite journal|title=Effects of anipamil, a long acting analog of verapamil, in pigs subjected to myocardial ischemia |language=en|doi=10.1016/0024-3205(95)02070-Y|volume=57|issue=12|journal=Life Sciences|pages=1219–1231 | last1 = Pugsley | first1 = M.K.|date=1995-08-11 |pmid=7674811}}</ref> than [[verapamil]] because it does not cause hypertension as seen in [[verapamil]].<ref>{{Cite journal|last1=Lefrandt|first1=J. D.|last2=Heitmann|first2=J.|last3=Sevre|first3=K.|last4=Castellano|first4=M.|last5=Hausberg|first5=M.|last6=Fallon|first6=M.|last7=Fluckiger|first7=L.|last8=Urbigkeit|first8=A.|last9=Rostrup|first9=M.|date=2001-11-01|title=The effects of dihydropyridine and phenylalkylamine calcium antagonist classes on autonomic function in hypertension: the VAMPHYRE study|journal=American Journal of Hypertension|volume=14|issue=11 Pt 1|pages=1083–1089|issn=0895-7061|pmid=11724204|doi=10.1016/S0895-7061(01)02218-X|doi-access=free}}</ref> It is able to do this by bonding to the [[myocardium]] tighter than [[verapamil]].<ref name=":0" />

== Study of Effects in Rabbits ==

Anipamil is used to prevent the thickening of aortic muscles in rabbits with hypertension . A study was done by the American Journal of Hypertension to understand the effects anipamil may have on the smooth muscle cell in hypertensive rabbits.<ref name=":1">{{Cite journal |last1=Pauletto |first1=Paolo |last2=Santina Da Ros |first2=Marta |date=1996-07-01 |title=Anipamil Prevents Intimal Thickening in the Aorta of Hypertensive Rabbits Through Changes in Smooth Muscle Cell Phenotype |journal=American Journal of Hypertension |volume=9 |issue=7 |pages=687–694 |doi=10.1016/0895-7061(96)00032-5|pmid=8806982 |doi-access=free }}</ref> After using monoclonal antimyosin antibodies to recognize smooth muscle, nonmuscle myosin heavy chains and identify various aortic smooth muscle types, twenty four rabbits with hypertension were studied over a period of 2.5-4 months.<ref name=":1" /> The rabbits were split into two groups of 12, and six rabbits from each group received a 40 mg oral dose of anipamil daily while the remaining received an oral placebo daily.<ref name=":1" /> Cryosections of primary and secondary smooth aortic muscle were then taken for morphometry and immunocytochemical studies to understand the potential change in phenotype after the addition of anipamil.<ref name=":1" /> The study revealed that smooth aortic muscle treated with anipamil demonstrates less thickening of the muscle and an increase in differentiated cell phenotype . The results of this study showed anipamil has a direct effect on smooth muscle cell phenotypes .

Another study occurred at the Institute of Pharmacological Sciences at the University of Milan to understand the antiatherosclerotic effects of anipamil in Cholesterol-Fed Rabbits.<ref name=":2">{{Cite journal |last1=Catapano |first1=A. L. |last2=Maggi |first2=F. M. |last3=Cicerano |first3=U. |date=1988-03-01 |title=The Antiatherosclerotic Effect of Anipamil in Cholesterol-Fed Rabbits |url=https://onlinelibrary.wiley.com/doi/10.1111/j.1749-6632.1988.tb33391.x |journal=Annals of the New York Academy of Sciences |language=en |volume=522 |issue=1 Calcium Antag |pages=519–521 |doi=10.1111/j.1749-6632.1988.tb33391.x |bibcode=1988NYASA.522..519C |s2cid=83705020 |issn=0077-8923}}</ref> In this study, there were three groups of 18 rabbits: control group, cholesterol-fed group, and a cholesterol-fed group receiving the drug.<ref name=":2" /> The control group received a standard pelleted show of 120 grams daily. The cholesterol-fed group received 1.6 grams of cholesterol per day.<ref name=":2" /> The cholesterol-red group receiving the drug received 1.6 grams of cholesterol per day along with an anipamil dose of 10 milligrams per day.<ref name=":2" /> During the two week, four week, and eight week mark, the amount of plasma cholesterol, triglycerides, and high density lipoprotein cholesterol were measured.<ref name=":2" /> The results showed that HDL cholesterol increased at 2-fold and plasma cholesterol increased at a 25-fold.<ref name=":2" /> Anipamil had no effect on the plasma cholesterol levels or HDL cholesterol and a decrease in the amount of aortic surface covered by plaque in the cholesterol-fed groups.<ref name=":2" /> The study showed that the consumption of anipamil at 10 milligrams per kilogram reduced the amount of plaque covering aortic surface and the amount of cholesterol in the aorta in cholesterol-fed rabbits.<ref name=":2" /> This study also showed that the antiatherosclerotic effects of anipamil has no effect on plasma cholesterol levels.<ref name=":2" />

==References==

<references />

[[Category:Calcium channel blockers]]

[[Category:Nitriles]]

[[Category:O-methylated phenols]]