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{{Short description|Chemical compound}} |
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{{Drugbox |
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{{Drugbox |
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| IUPAC_name = (11b''S'')-2-<nowiki>methyl]-3-ethyl-9,10-dimethoxy-4,6,7,11b-tetrahydro-1''H''-pyridoisoquinoline |
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| Watchedfields = changed |
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| image = dehydroemetine.png |
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| verifiedrevid = 405800522 |
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| CAS_number = 4914-30-1 |
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| IUPAC_name = (11b''S'')-2-<nowiki>methyl]-3-ethyl-9,10-dimethoxy-4,6,7,11b-tetrahydro-1''H''-pyridoisoquinoline |
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| ATC_prefix = P01 |
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| image = dehydroemetine.png |
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| ATC_suffix = AX09 |
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| PubChem = 21022 |
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<!--Clinical data--> |
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| DrugBank = |
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| KEGG = D00828 |
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| tradename = |
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| Drugs.com = {{drugs.com|international|dehydroemetine}} |
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| C=29|H=38|N=2|O=4 |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| molecular_weight = 478.62 g/mol |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| bioavailability = |
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| protein_bound = |
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| pregnancy_category = |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| metabolism = |
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| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| elimination_half-life = |
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| elimination_half-life = |
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| excretion = |
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| excretion = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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<!--Identifiers--> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| CAS_number_Ref = {{cascite|correct|CAS}} |
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| pregnancy_category= |
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| CAS_number = 4914-30-1 |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| ATC_prefix = P01 |
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| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| ATC_suffix = AX09 |
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| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
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| PubChem = 21022 |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| legal_status = |
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| DrugBank = |
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| routes_of_administration = |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = 7S79QT1T91 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D00828 |
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| ChEBI = 4363 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 547470 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 19773 |
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| smiles = O(c1cc2c(cc1OC)(NCC2)CC\5=C(/CC)CN4(c3c(cc(OC)c(OC)c3)CC4)C/5)C |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C29H38N2O4/c1-6-18-17-31-10-8-20-14-27(33-3)29(35-5)16-23(20)25(31)12-21(18)11-24-22-15-28(34-4)26(32-2)13-19(22)7-9-30-24/h13-16,24-25,30H,6-12,17H2,1-5H3/t24-,25+/m1/s1 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = XXLZPUYGHQWHRN-RPBOFIJWSA-N |
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<!--Chemical data--> |
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| C=29 | H=38 | N=2 | O=4 |
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}} |
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}} |
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'''Dehydroemetine''' is a synthetically produced ] similar to ] in its anti-amoebic properties and structure (they differ only in a double bond next to the ethyl radical), but it produces fewer side effects. In the United States, it is manufactured by ]. |
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'''Dehydroemetine''' is a synthetically produced ] similar to ] in its anti-amoebic properties and structure (they differ only in a double bond next to the ethyl substituent), but it produces fewer side effects. In the United States, it is manufactured by ].{{cn|date=September 2023}} |
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==Mechanism== |
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==Mechanism== |
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Its exact mechanism is not known, but '']'' it inhibits translocation.<ref name="isbn0-7484-0168-7">{{cite book |author=Abdi, Y. A. |title=Handbook of drugs for tropical parasitic infections |publisher=Taylor & Francis |location=Washington, DC |year=1995 |pages=47 |isbn=0-7484-0168-7 |oclc= |doi= |accessdate=}}</ref> |
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Its exact mechanism is not known, but '']'' it inhibits translocation.<ref name="isbn0-7484-0168-7">{{cite book | vauthors = Abdi YA |title=Handbook of drugs for tropical parasitic infections |publisher=Taylor & Francis |location=Washington, DC |year=1995 |pages=47 |isbn=0-7484-0168-7 }}</ref> |
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==Uses== |
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==Uses== |
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It is distributed by the ] on a ] basis as an ] for the treatment of ]-resistant amoebiasis. <ref name="CDC_EMETINE"> {{cite web |
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It was at one-time, but is no longer distributed by the ] on a ] basis as an ] for the treatment of ]-resistant amoebiasis.<ref name="CDC_EMETINE">{{cite web |
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| title = Center for Disease Control NCID Formulary |
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| title = Center for Disease Control NCID Formulary |
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| url=http://www.cdc.gov/ncidod/srp/drugs/formulary.html |
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| url=https://www.cdc.gov/ncidod/srp/drugs/formulary.html | archive-url = https://web.archive.org/web/20060209095558/https://www.cdc.gov/ncidod/srp/drugs/formulary.html | archive-date = 9 February 2006 |
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| accessdate = 2007-09-09 }} </ref> |
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| access-date = 2007-09-09 | publisher = Centers for Disease Control and Prevention }}</ref> |
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===Amoebic infections=== |
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===Amoebic infections=== |
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Some examples of the use of dehydroemetine in the treatment of amoebic infections include: |
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Some examples of the use of dehydroemetine in the treatment of amoebic infections include: |
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# In 1993, the successful treatment of ] in a 7-year old girl with dehydroemetine and metronidazole in Mexico. <ref name="pmid8302738">{{cite journal |author=Magaña-García M, Arista-Viveros A |title=Cutaneous amebiasis in children |journal=Pediatric dermatology |volume=10 |issue=4 |pages=352–5 |year=1993 |pmid=8302738 |doi=10.1111/j.1525-1470.1993.tb00397.x}}</ref> |
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# In 1993, the successful treatment of ] in a 7-year-old girl with dehydroemetine and metronidazole in Mexico.<ref name="pmid8302738">{{cite journal | vauthors = Magaña-García M, Arista-Viveros A | title = Cutaneous amebiasis in children | journal = Pediatric Dermatology | volume = 10 | issue = 4 | pages = 352–355 | date = December 1993 | pmid = 8302738 | doi = 10.1111/j.1525-1470.1993.tb00397.x | s2cid = 41438097 }}</ref> |
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# A double-blind study of oral dehydroemetine in the treatment of amoebiasis performed at St. Mary's Hospital, Catholic Medical College, Seoul, Republic of Korea in 1973-1974 showed dehydroemetine treatment was effective. A total of 60 patients were treated, 20 with dehydroemetine, 20 with Tiberal, and 20 with metronidazole. One-fourth of the patients treated with dehydroemetine reported adverse reactions, compared to 20% with other drugs, but no patient discontinued therapy due to the reaction. In all three cases, the drug therapy resulted in clearance of the infection, defined as negative results through an O&P exam, in all but 1-2 patients.<ref name="pmid538815">{{cite journal |author=Chun, Chong |title=Amoebic Comparative Double Blind Trials of Tiberal Compared with Metronidazole and Oral dehydroemetine in Oligosymptomatic Amoebiasis|journal=Korean Medical Database| url=http://kmbase.medric.or.kr/Main.aspx?d=KMBASE&m=VIEW&i=0351219740060010097}}</ref> |
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# A double-blind study of oral dehydroemetine in the treatment of amoebiasis performed at St. Mary's Hospital, Catholic Medical College, Seoul, Republic of Korea in 1973-1974 showed dehydroemetine treatment was effective. A total of 60 patients were treated, 20 with dehydroemetine, 20 with Tiberal, and 20 with metronidazole. One-fourth of the patients treated with dehydroemetine reported adverse reactions, compared to 20% with other drugs, but no patient discontinued therapy due to the reaction. In all three cases, the drug therapy resulted in clearance of the infection, defined as negative results through an O&P exam, in all but 1-2 patients.<ref name=Chong>{{cite journal | vauthors = Chun CH, Park PW, Lee OJ, Pak SY |title=Amoebic Comparative Double Blind Trials of Tiberal Compared with Metronidazole and Oral Dehydroemetine in Oligosymptomatie Amoebiasis |url=http://journal.icjournal.org/articles/view.php?code=ava&year=1974&vol=6&no=1&page=97 |journal=Korean Medical Database |publisher=The Korean Society of Infectious Diseases & Korean Society for Chemotherapy |volume=6 |issue=1 |pages=97–104 |access-date=November 9, 2015}}</ref> |
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# A 1979 study of 27 patients treated with dehydroemetine and various other drugs suggested all drug combinations were successful at treating amoebic liver abscesses. <ref name="pmid538815">{{cite journal |author=Peters M, Dietrich M, Bienzle U, Kern P, Mannweiler E |title=Amoebic liver abscess: a retrospective clinical evaluation of twenty-seven cases |journal=Tropenmedizin und Parasitologie |volume=30 |issue=4 |pages=409–16 |year=1979 |pmid=538815 |doi=}}</ref> |
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# A 1986 in vitro study compared the effects of dehydroemetine, metronidazole, ornidazole, and secnidazole on '']''. Metronidazole was found to be most effective, and the other three drugs were of similar effectiveness. <ref name="pmid2883732">{{cite journal |author=Chintana T, Sucharit P, Mahakittikun V, Siripanth C, Suphadtanaphongs W |title=In vitro studies on the sensitivity of local Entamoeba histolytica to anti-amoebic drugs |journal=Southeast Asian J. Trop. Med. Public Health |volume=17 |issue=4 |pages=591–4 |year=1986 |pmid=2883732 |doi=}}</ref> |
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# A 1979 study of 27 patients treated with dehydroemetine and various other drugs suggested all drug combinations were successful at treating amoebic liver abscesses.<ref name="pmid538815">{{cite journal | vauthors = Peters M, Dietrich M, Bienzle U, Kern P, Mannweiler E | title = Amoebic liver abscess: a retrospective clinical evaluation of twenty-seven cases | journal = Tropenmedizin und Parasitologie | volume = 30 | issue = 4 | pages = 409–416 | date = December 1979 | pmid = 538815 }}</ref> |
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# A 1986 in vitro study compared the effects of dehydroemetine, metronidazole, ornidazole, and secnidazole on '']''. Metronidazole was found to be most effective, and the other three drugs were of similar effectiveness.<ref name="pmid2883732">{{cite journal | vauthors = Chintana T, Sucharit P, Mahakittikun V, Siripanth C, Suphadtanaphongs W | title = In vitro studies on the sensitivity of local Entamoeba histolytica to anti-amoebic drugs | journal = The Southeast Asian Journal of Tropical Medicine and Public Health | volume = 17 | issue = 4 | pages = 591–594 | date = December 1986 | pmid = 2883732 }}</ref> |
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===In other diseases=== |
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===In other diseases=== |
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A 2020 ''in-vitro'' study found dehydroemetine to be effective in ].<ref name="pmid31964796">{{cite journal | vauthors = Panwar P, Burusco KK, Abubaker M, Matthews H, Gutnov A, Fernández-Álvaro E, Bryce RA, Wilkinson J, Nirmalan N | display-authors = 6 | title = Lead Optimization of Dehydroemetine for Repositioned Use in Malaria | journal = Antimicrobial Agents and Chemotherapy | volume = 64 | issue = 4 | date = March 2020 | pmid = 31964796 | pmc = 7179302 | doi = 10.1128/AAC.01444-19 | at = e01444-19 | doi-access = free }}</ref> |
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A 1980 report described the use of dehydroemetine in treatment of ], a condition which can produce painful neurological symptoms. The study involved 40 patients, all of whom were over 60, and compared dehydroemetine treatment to another drug. The study reported patients treated with dehydroemetine experienced relief of neuralgia with no changes in cardiovascular functions. <ref name="pmid6102504">{{cite journal |author=Hernandez-Perez E |title=Dehydroemetine therapy for herpes zoster. A comparison with corticosteroids |journal=Cutis; cutaneous medicine for the practitioner |volume=25 |issue=4 |pages=424–6 |year=1980 |pmid=6102504 |doi=}}</ref> |
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A 1980 report described the use of dehydroemetine in treatment of ], a condition which can produce painful neurological symptoms. The study involved 40 patients, all of whom were over 60, and compared dehydroemetine treatment to another drug. The study reported patients treated with dehydroemetine experienced relief of neuralgia with no changes in cardiovascular functions.<ref name="pmid6102504">{{cite journal | vauthors = Hernandez-Perez E | title = Dehydroemetine therapy for herpes zoster. A comparison with corticosteroids | journal = Cutis | volume = 25 | issue = 4 | pages = 424–426 | date = April 1980 | pmid = 6102504 }}</ref> |
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Dehydroemetine has been investigated as a treatment for '']'' infection. <ref name="pmid16732">{{cite journal |author=Al-Khateeb GH, Al-Jeboori TI, Al-Janabi KA |title=In vitro efficacy of some drugs on promastigotes of Leishmania donovani |journal=Chemotherapy |volume=23 |issue=4 |pages=267–75 |year=1977 |pmid=16732 |doi=10.1159/000221994}}</ref> |
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Dehydroemetine has been investigated as a treatment for '']'' infection.<ref name="pmid16732">{{cite journal | vauthors = Al-Khateeb GH, Al-Jeboori TI, Al-Janabi KA | title = In vitro efficacy of some drugs on promastigotes of Leishmania donovani | journal = Chemotherapy | volume = 23 | issue = 4 | pages = 267–275 | year = 1977 | pmid = 16732 | doi = 10.1159/000221994 }}</ref> |
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==References== |
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== References == |
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{{reflist|2}} |
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{{reflist|2}} |
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{{Agents against amoebozoa}} |
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{{Agents against amoebozoa}} |
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