Amodiaquine

{{Short description|Chemical compound}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{Drugbox

| verifiedrevid = 456692175

| IUPAC_name = 4-[(7-chloroquinolin-4-yl)amino]-2-[(diethylamino)methyl]phenol

| image = Amodiaquine.svg

| image_class = skin-invert-image

| width = 250

| tradename = Amdaquine, Amobin, Camoquin, others{{cite web|title=Amodiaquine|url=https://www.drugs.com/international/amodiaquine.html|website=drugs.com|access-date=27 November 2016|url-status=live|archive-url=https://web.archive.org/web/20161127154249/https://www.drugs.com/international/amodiaquine.html|archive-date=27 November 2016}}

| Drugs.com = {{drugs.com|international|amodiaquine}}

| pregnancy_AU =

| pregnancy_US =

| legal_AU =

| legal_UK =

| legal_US =

| elimination_half-life =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 86-42-0

| ATC_prefix = P01

| ATC_suffix = BA06

| PubChem = 2165

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB00613

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

| ChemSpiderID = 2080

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 220236ED28

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D02922

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 2674

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 682

| C=20 | H=22 | Cl=1 | N=3 | O=1

| smiles = Clc1cc2nccc(c2cc1)Nc3cc(c(O)cc3)CN(CC)CC

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

| StdInChI = 1S/C20H22ClN3O/c1-3-24(4-2)13-14-11-16(6-8-20(14)25)23-18-9-10-22-19-12-15(21)5-7-17(18)19/h5-12,25H,3-4,13H2,1-2H3,(H,22,23)

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

| StdInChIKey = OVCDSSHSILBFBN-UHFFFAOYSA-N

}}

Amodiaquine (ADQ) is a medication used to treat malaria, including Plasmodium falciparum malaria when uncomplicated.{{cite journal | vauthors = Nair A, Abrahamsson B, Barends DM, Groot DW, Kopp S, Polli JE, Shah VP, Dressman JB | title = Biowaiver monographs for immediate release solid oral dosage forms: amodiaquine hydrochloride | journal = Journal of Pharmaceutical Sciences | volume = 101 | issue = 12 | pages = 4390–4401 | date = December 2012 | pmid = 22949374 | doi = 10.1002/jps.23312 }}{{cite journal | vauthors = Olliaro P, Mussano P | title = Amodiaquine for treating malaria | journal = The Cochrane Database of Systematic Reviews | issue = 2 | pages = CD000016 | date = 2003 | pmid = 12804382 | pmc = 6532704 | doi = 10.1002/14651858.CD000016 }} It is recommended to be given with artesunate to reduce the risk of resistance. Due to the risk of rare but serious side effects, it is not generally recommended to prevent malaria. Though, the World Health Organization (WHO) in 2013 recommended use for seasonal preventive in children at high risk in combination with sulfadoxine and pyrimethamine.{{cite book |author= |title=Seasonal malaria chemoprevention with sulfadoxine–pyrimethamine plus amodiaquine in children: a field guide. |url=https://apps.who.int/iris/bitstream/handle/10665/85726/9789241504737_eng.pdf |location=Geneva |publisher=The World Health Organization |date=August 2013 |isbn=978-92-4-150473-7}}

Amodiaquine is a 4-aminoquinoline compound related to chloroquine. The side effects of amodiaquine are generally minor to moderate and are similar to those of chloroquine. Rarely liver problems or low blood cell levels may occur. When taken in excess headaches, trouble seeing, seizures, and cardiac arrest may occur. The WHO recommends its use for pregnant women during the second and third trimester as well as during lactation, but reports that evidence for use in the first trimester is still insufficient.{{Cite web |title=WHO Guidelines for malaria |url=https://www.who.int/publications-detail-redirect/guidelines-for-malaria |access-date=2024-01-22 |website=www.who.int |language=en}}

Amodiaquine was first made in 1948.{{cite book | vauthors = Ahmad I, Ahmad T, Usmanghani K | chapter = Amodiaquine hydrochloride |title=Profiles of Drug Substances, Excipients and Related Methodology| series = Analytical Profiles of Drug Substances and Excipients |date=1992| volume = 21 |publisher=Academic Press|isbn=978-0-08-086116-6 | doi = 10.1016/S0099-5428(08)60388-3 |page=45|chapter-url=https://books.google.com/books?id=3mP9TYffnewC&pg=PA44|language=en|url-status=live|archive-url=https://web.archive.org/web/20170908213921/https://books.google.com/books?id=3mP9TYffnewC&pg=PA44|archive-date=2017-09-08}} It is on the World Health Organization's List of Essential Medicines.{{cite book | 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 }}{{cite book | 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 }} While not available in the United States,{{cite journal|title=Amodiaquine|url=https://livertox.nih.gov/Amodiaquine.htm|website=Livertox|date=2012 |pmid=31643176 |access-date=27 November 2016|url-status=live|archive-url=https://web.archive.org/web/20161127154244/https://livertox.nih.gov/Amodiaquine.htm|archive-date=27 November 2016}} it is widely available in Africa.{{cite journal | title = Revised recommendations for preventing malaria in travelers to areas with chloroquine-resistant Plasmodium falciparum | journal = MMWR. Morbidity and Mortality Weekly Report | volume = 34 | issue = 14 | pages = 185–90, 195 | date = April 1985 | pmid = 3156271 | author1 = Centers for Disease Control (CDC) }}