{{위키데이터 속성 추적}}
{{Infobox drug
| Watchedfields = changed
| verifiedrevid = 461939027
| image = Verapamil structure.svg
| width = 
| alt               =
| image2 = Verapamil-from-xtal-Mercury-3D-bs.png
| width2 = 200
| chirality = [[라세미 혼합물]]
| caption           =

<!-- Clinical data -->
| pronounce = {{IPAc-en|v|ɛ|ˈ|r|æ|p|ə|m|ɪ|l}}<br />{{respell|ve|RAP|ə|mil}}
| tradename = 이솝틴(Isoptin), 칼란(Calan) 등<ref name=Names2016/>
| Drugs.com = {{drugs.com|monograph|verapamil-hydrochloride}}
| MedlinePlus       = a684030
| DailyMedID        = Verapamil
| pregnancy_AU      = C
| pregnancy_AU_comment =<ref name="Drugs.com pregnancy">{{웹 인용| title=Verapamil Use During Pregnancy | website=Drugs.com | date=18 November 2019 | url=https://www.drugs.com/pregnancy/verapamil.html | access-date=26 March 2020}}</ref>
| pregnancy_category=
| routes_of_administration = [[경구 투여]], [[정맥 주사]]
| class = [[칼슘 통로 차단제]]
| ATC_prefix = C08
| ATC_suffix = DA01
| ATC_supplemental  =

<!-- Legal status -->
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_AU_comment =
| legal_BR =  <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F-->
| legal_BR_comment =
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA_comment =
| legal_DE = <!-- Anlage I, II, III or Unscheduled-->
| legal_DE_comment =
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment =
| legal_UK = POM
| legal_UK_comment =<ref>{{웹 인용| title=Securon SR - Summary of Product Characteristics (SmPC) | website=(emc) | date=17 May 2017 | url=https://www.medicines.org.uk/emc/product/6243/smpc | access-date=26 March 2020}}</ref>
| legal_US = Rx-only
| legal_US_comment =<ref name="Calan FDA label">{{웹 인용| title=Calan- verapamil hydrochloride tablet, film coated | website=DailyMed | date=17 December 2019 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=55d5f933-42ff-4c80-a102-0ccb7f76b082 | access-date=26 March 2020}}</ref>
| legal_EU = Rx-only
| legal_EU_comment =<ref>{{웹 인용| author = Human Medicines Evaluation Division | title = Active substance(s): verapamil | work = List of nationally authorised medicinal products | publisher = European Medicines Agency | date = 14 October 2020 | url = https://www.ema.europa.eu/documents/psusa/verapamil-list-nationally-authorised-medicinal-products-psusa/00003105/202001_en.pdf }}</ref>
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV-->
| legal_UN_comment =
| legal_status = Rx-only

<!-- Pharmacokinetic data -->
| bioavailability = 35.1%
| protein_bound     =
| metabolism = [[간]]
| metabolites       =
| onset             =
| elimination_half-life = 2.8~7.4시간<ref name="Schroeder Frishman Parker Angiolillo 2013 pp. 83–130">{{서적 인용| vauthors = Schroeder JS, Frishman WH, Parker JD, Angiolillo DJ, Woods C, Scirica BM | title=Cardiovascular Therapeutics: A Companion to Braunwald's Heart Disease | chapter=Pharmacologic Options for Treatment of Ischemic Disease | publisher=Elsevier | year=2013 | isbn=978-1-4557-0101-8 | doi=10.1016/b978-1-4557-0101-8.00007-2 | pages=83–130 | quote=The elimination half-life of standard verapamil tablets is usually 3 to 7 hours,... }}</ref>
| duration_of_action =
| excretion = [[콩팥]]: 11%

<!-- Identifiers -->
| index2_label = as HCl
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 52-53-9
| CAS_supplemental  =
| PubChem = 2520
| IUPHAR_ligand = 2406
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00661
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2425
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = CJ0O37KU29
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D02356
| KEGG2_Ref = {{keggcite|correct|kegg}}
| KEGG2 = D00619
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 9948
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 6966
| NIAID_ChemDB      =
| PDB_ligand        =
| synonyms          =

<!-- Chemical and physical data -->
| IUPAC_name = (''RS'')-2-(3,4-Dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile
| C = 27 | H = 38 | N = 2 | O = 4
| SMILES = N#CC(c1cc(OC)c(OC)cc1)(CCCN(CCc2ccc(OC)c(OC)c2)C)C(C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C27H38N2O4/c1-20(2)27(19-28,22-10-12-24(31-5)26(18-22)33-7)14-8-15-29(3)16-13-21-9-11-23(30-4)25(17-21)32-6/h9-12,17-18,20H,8,13-16H2,1-7H3
| StdInChI_comment  =
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SGTNSNPWRIOYBX-UHFFFAOYSA-N
| density           =
| density_notes     =
| melting_point     =
| melting_high      =
| melting_notes     =
| boiling_point     =
| boiling_notes     =
| solubility        =
| sol_units         =
| specific_rotation =
}}

<!-- Definition and medical uses -->
'''베라파밀'''(Verapamil)은 '''이솝틴'''(Isoptin) 등의 상품명으로 판매되는 약물로,<ref name=Names2016>{{웹 인용|title=Verapamil |url=https://www.drugs.com/international/verapamil.html|website=www.drugs.com|access-date=14 December 2016|url-status=live|archive-url=https://web.archive.org/web/20170801162330/https://www.drugs.com/international/verapamil.html|archive-date=1 August 2017}}</ref> [[고혈압]], [[협심증]], [[심실상성 빈맥]] 등의 치료에 쓰이는 [[칼슘 통로 차단제]]이다.<ref name=AHFS2016>{{웹 인용|title=Verapamil Hydrochloride|url=https://www.drugs.com/monograph/verapamil-hydrochloride.html|publisher=The American Society of Health-System Pharmacists|access-date=8 December 2016|url-status=live|archive-url=https://web.archive.org/web/20161221004213/https://www.drugs.com/monograph/verapamil-hydrochloride.html|archive-date=21 December 2016}}</ref> [[편두통]]이나 [[군발두통]] 예방에 쓰이는 경우도 있다.<ref>{{저널 인용| vauthors = Tfelt-Hansen PC, Jensen RH | title = Management of cluster headache | journal = CNS Drugs | volume = 26 | issue = 7 | pages = 571–580 | date = July 2012 | pmid = 22650381 | doi = 10.2165/11632850-000000000-00000 | s2cid = 22522914 }}</ref><ref>{{저널 인용| vauthors = Merison K, Jacobs H | title = Diagnosis and Treatment of Childhood Migraine | journal = Current Treatment Options in Neurology | volume = 18 | issue = 11 | pages = 48 | date = November 2016 | pmid = 27704257 | doi = 10.1007/s11940-016-0431-4 | s2cid = 28302667 }}</ref> [[경구 투여]]와 [[정맥 주사]]용 약제가 존재한다.<ref name=AHFS2016/>

<!-- Side effects and mechanisms -->
흔한 부작용에는 [[두통]], [[저혈압]], [[구역질]], [[변비]]가 있다.<ref name=AHFS2016/> 다른 부작용에는 [[알레르기]] 반응과 [[근육통]] 등이 있다.<ref name=WHO2008/> 맥박이 느린 [[서맥]]이나 [[심부전]] 환자에서는 사용을 권고하지 않는다.<ref name=WHO2008/> [[임신]] 중 사용 시 태아에 문제가 생길 수 있다.<ref name="Drugs.com pregnancy" /> 작용 기전상 비-디히드로피리딘 칼슘 통로 차단제(non-DHP CCB)에 속하며,<ref name=AHFS2016/> 따라서 [[본 윌리엄스 분류]]상으로는 클래스 4 [[항부정맥제]]로 분류된다.<ref>{{서적 인용| vauthors = Milne GW |title=Gardner's Commercially Important Chemicals: Synonyms, Trade Names, and Properties |date=2005 |publisher=John Wiley & Sons |isbn=978-0-471-73661-5 |page=665 |url=https://books.google.com/books?id=oWdc2qcb3QsC&pg=PA223 |access-date=28 December 2018 }}</ref>

<!-- Society and culture -->
베라파밀은 1981년 미국에서 사용이 승인되었다.<ref name=AHFS2016/><ref>{{웹 인용| title=Isoptin: FDA-Approved Drugs | website=U.S. [[Food and Drug Administration]] (FDA) | url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=018485 | access-date=26 March 2020}}</ref> [[WHO 필수 의약품 목록]]에 등재되어 있다.<ref name="WHO21st">{{서적 인용| vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref><ref name="WHO22nd">{{서적 인용| vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 22nd list (2021) | year = 2021 | hdl = 10665/345533 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2021.02 | hdl-access=free }}</ref> [[복제약]]으로도 이용 가능하다.<ref name=AHFS2016/> 지속작용 제제도 존재한다.<ref name=WHO2008>{{서적 인용| title = WHO Model Formulary 2008 | year = 2009 | isbn = 9789241547659 | vauthors = ((World Health Organization)) | veditors = Stuart MC, Kouimtzi M, Hill SR | hdl = 10665/44053 | author-link = World Health Organization | publisher = World Health Organization | hdl-access=free }}</ref> 2021년 한 해 동안 200만 건 이상 처방되어, 196번째로 많이 처방된 약물로 기록되었다.<ref>{{웹 인용| title=The Top 300 of 2021 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=14 January 2024 | archive-date=15 January 2024 | archive-url=https://web.archive.org/web/20240115223848/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{웹 인용| title = Verapamil - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Verapamil | access-date = 14 January 2024}}</ref>

== 각주 ==
{{각주}}

[[분류:항부정맥제]]
[[분류:칼슘 통로 차단제]]
[[분류:카테콜 에터]]
[[분류:나이트릴]]
[[분류:펜에틸아민]]
[[분류:아이소프로필 화합물]]
[[분류:CYP3A4 억제제]]
[[분류:글라이신 수용체 대항제]]
[[분류:간독소]]
[[분류:세계 보건 기구 필수 의약품]]