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Dehydroemetine is a synthetically produced antiprotozoal agent similar to emetine 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 Roche.

Mechanism

Its exact mechanism is not known, but in vitro it inhibits translocation.^[1]

Uses

It is distributed by the Center for Disease Control on a compassionate use basis as an investigational drug for the treatment of metronidazole-resistant amoebiasis. ^[2]

Amoebic infections

Some examples of the use of dehydroemetine in the treatment of amoebic infections include:

In 1993, the successful treatment of cutaneous amebiasis in a 7-year old girl with dehydroemetine and metronidazole in Mexico. ^[3]
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.^[4]
A 1979 study of 27 patients treated with dehydroemetine and various other drugs suggested all drug combinations were successful at treating amoebic liver abscesses. ^[4]
A 1986 in vitro study compared the effects of dehydroemetine, metronidazole, ornidazole, and secnidazole on Entamoeba histolytica. Metronidazole was found to be most effective, and the other three drugs were of similar effectiveness. ^[5]

In other diseases

A 1980 report described the use of dehydroemetine in treatment of herpes zoster, 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. ^[6]

Dehydroemetine has been investigated as a treatment for Leishmania infection. ^[7]

References

^ Abdi, Y. A. (1995). Handbook of drugs for tropical parasitic infections. Washington, DC: Taylor & Francis. pp. 47. ISBN 0-7484-0168-7.
^ "Center for Disease Control NCID Formulary". http://www.cdc.gov/ncidod/srp/drugs/formulary.html. Retrieved 2007-09-09.
^ Magaña-García M, Arista-Viveros A (1993). "Cutaneous amebiasis in children". Pediatric dermatology 10 (4): 352–5. doi:10.1111/j.1525-1470.1993.tb00397.x. PMID 8302738.
^ ^a ^b Chun, Chong. "Amoebic Comparative Double Blind Trials of Tiberal Compared with Metronidazole and Oral dehydroemetine in Oligosymptomatic Amoebiasis". Korean Medical Database. http://kmbase.medric.or.kr/Main.aspx?d=KMBASE&m=VIEW&i=0351219740060010097.
^ Chintana T, Sucharit P, Mahakittikun V, Siripanth C, Suphadtanaphongs W (1986). "In vitro studies on the sensitivity of local Entamoeba histolytica to anti-amoebic drugs". Southeast Asian J. Trop. Med. Public Health 17 (4): 591–4. PMID 2883732.
^ Hernandez-Perez E (1980). "Dehydroemetine therapy for herpes zoster. A comparison with corticosteroids". Cutis; cutaneous medicine for the practitioner 25 (4): 424–6. PMID 6102504.
^ Al-Khateeb GH, Al-Jeboori TI, Al-Janabi KA (1977). "In vitro efficacy of some drugs on promastigotes of Leishmania donovani". Chemotherapy 23 (4): 267–75. doi:10.1159/000221994. PMID 16732.

UpToDate Contents

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1. 赤痢アメーバによる腸菅アメーバ症 intestinal entamoeba histolytica amebiasis

English Journal

Development of a pharmacodynamic screening model with Entamoeba histolytica.

Tasanor O, Brem B, Leitsch D, Binder M, Duchêne M, Greger H, Wernsdorfer WH.Author information Institute for Specific Prophylaxis und Tropical Medicine, Center for Physiology und Pathophysiology, Medical University of Vienna, Vienna, Austria. tasanor@yahoo.comErratum inWien Klin Wochenschr. 2009 Oct;121 Suppl 3:following 56. AbstractHuman amoebiasis caused by Entamoeba histolytica is widely distributed in the tropics and subtropics, but also occurring in neighbouring parts of the temperate zones. Invasive amoebiasis causes dysentery and, by haematogenous spread, also extra-intestinal hepatic, pulmonary or cerebral abscesses, not rarely fatal conditions. The available anti-amoebic drugs have shortcomings regarding tolerability and efficacy. To facilitate the screening of candidate material, an in vitro system has been developed that permits the determination of specific anti-amoebic activity. PYE medium, supplemented with bovine serum, proved to be suitable for the maintenance of the stock cultures of Entamoeba histolytica strain HM1:1MSS. For sensitivity testing, Waymouth medium and cultivation under aerobic conditions were most reliable. After adapting the system to the use of 96-well (8 x 12) tissue culture plates, sensitivity tests were carried out with metronidazole, dehydroemetine and dihydroartemisinin as active control drugs, and seven extracts from Stemona tuberosa, Aglaia edulis, Aglaia elaeagnoidea and Aglaia odorata. Stem bark extract from Aglaia elaeagnoidea was the most active material with an IC(99) of 496 ng/ml and a slope S of 1.1325, followed by leaf extract from Stemona tuberosa with an IC(99) of 638 ng/ml and a slope S of 1.5648. All seven extracts showed full activity at concentrations <4000 ng/ml and qualified for further investigation.
Wiener klinische Wochenschrift.Wien Klin Wochenschr.2007;119(19-20 Suppl 3):88-95.
Human amoebiasis caused by Entamoeba histolytica is widely distributed in the tropics and subtropics, but also occurring in neighbouring parts of the temperate zones. Invasive amoebiasis causes dysentery and, by haematogenous spread, also extra-intestinal hepatic, pulmonary or cerebral abscesses, no
PMID 17987365

[Hepatic fasciolasis diagnosed in state phase].

Cruz López O, Adán Pimentel A, Tamariz Cruz OJ, Muñoz López A, Cruz López MC, Cruz López ME, Muñoz López S.Author information Departamento de Ciencias de la Salud de la Universidad Autónoma de Tlaxcala. othoncruz@yahoo.comAbstractINTRODUCTION: Hepatic fasciolosis is a zoonosis that accidentally can invade the human.
Revista de gastroenterología de México.Rev Gastroenterol Mex.2006 Jan-Mar;71(1):59-62.
INTRODUCTION: Hepatic fasciolosis is a zoonosis that accidentally can invade the human.REPORT OF A CASE: 62 years old male, farmer, lives in a rural community in Tehuacan, Puebla, Mexico. His living space is not provided with running water nor drainage. He has contact with sheep and bovines. Started
PMID 17061480

Histopathology of cutaneous amebiasis.

Magaña M, Magaña ML, Alcántara A, Pérez-Martín MA.Author information Hospital General de México/Universidad Nacional Autónoma de México, Mexico City, Mexico. dermatopatologia@att.net.mxAbstractCutaneous amebiasis (CA) is the manifestation in the skin and underlying soft tissues of the pathogenic properties of Entamoeba histolytica, which may be the only expression of the infection or may be associated with disease in other organs. So far, there have been only isolated case reports on this disease. We herein report the histopathologic findings on a series of seven cases, six adults and one child, of CA. The most common findings include ulcers, areas of necrosis, mixed inflammatory infiltrates, and the presence of trophozoites, the invasive form of the parasite. CA is a very rare and severe disease, it is progressive and destructive; erythrophagocytosis, a microscopic sign of pathogenicity, is always seen in CA.
The American Journal of dermatopathology.Am J Dermatopathol.2004 Aug;26(4):280-4.
Cutaneous amebiasis (CA) is the manifestation in the skin and underlying soft tissues of the pathogenic properties of Entamoeba histolytica, which may be the only expression of the infection or may be associated with disease in other organs. So far, there have been only isolated case reports on this
PMID 15249857

Japanese Journal

A CASE OF AMEBIC LIVER ABSCESS RUPTURED INTO THE DUODENUM

新国恵也,岩谷昭,角田和彦,西村淳,河内保之,清水武昭
日本臨床外科学会雑誌 65(9), 2435-2439, 2004
… Trophozoites of Entamoeba histlytica were detected in the necrotizing tissue within the abscess cavity microscopically.The abscess cavity diminished and he was recovered consequently after administration of dehydroemetine followed by metronidazole. …
NAID 130003604211

Management and utilization of orphan drugs against parasitic infections in recent 7 years in Japan.

田辺清勝,尾辻義人,中林敏夫,大友弘士,田中寛
Ｊａｐａｎｅｓｅ　Ｊｏｕｒｎａｌ　ｏｆ　Ｔｒｏｐｉｃａｌ　Ｍｅｄｉｃｉｎｅ　ａｎｄ　Ｈｙｇｉｅｎｅ 17(3), 229-236, 1989
… chloroquine, Fansidar, Fansimef, quinine (iv), primaquine, mebendazole, praziquantel, thiabendazole, quinacrine, dehydroemetine (iv), pentamidine, Pentostam, suramin, stibophen, nifurtimox and pyrimethamine. …
NAID 130003795724

IN VITRO ASSAY OF CYTOGENETIC DAMAGE INDUCED IN BONE MARROW CELLS IN VIVO BY CHEMICAL CARCINOGENS

SHUBBER Esmail Kodhom,KRAM David,WILLIAMS Jerry
Japanese Journal of Medical Science and Biology 38(5-6), 207-216, 1985
… Dehydroemetine, known as a nonmutagenic drug, was negative in this assay. …
NAID 130003778431

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★リンクテーブル★

リンク元	「デヒドロエメチン」

「デヒドロエメチン」

Dehydroemetine
Systematic (IUPAC) name
	(11bS)-2-[[(1R)-6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]-3-ethyl-9,10-dimethoxy-4,6,7,11b-tetrahydro-1H-pyrido[2,1-a]isoquinoline
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	4914-30-1
ATC code	P01AX09
PubChem	CID 21022
ChemSpider	19773
UNII	7S79QT1T91
KEGG	D00828
ChEMBL	CHEMBL547470
Chemical data
Formula	C29H38N2O4
Mol. mass	478.62 g/mol
	SMILES O(c1cc2c(cc1OC)[C@H](NCC2)CC\5=C(/CC)CN4[C@H](c3c(cc(OC)c(OC)c3)CC4)C/5)C;
	InChI InChI=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; Key:XXLZPUYGHQWHRN-RPBOFIJWSA-N ;
(what is this?) (verify);

　　[★]

英: dehydroemetine
商: Mebadin

[isbn0-7484-0168-7-1] Abdi, Y. A. (1995). Handbook of drugs for tropical parasitic infections. Washington, DC: Taylor & Francis. pp. 47. ISBN 0-7484-0168-7.

[CDC_EMETINE-2] "Center for Disease Control NCID Formulary". http://www.cdc.gov/ncidod/srp/drugs/formulary.html. Retrieved 2007-09-09.

[pmid8302738-3] Magaña-García M, Arista-Viveros A (1993). "Cutaneous amebiasis in children". Pediatric dermatology 10 (4): 352–5. doi:10.1111/j.1525-1470.1993.tb00397.x. PMID 8302738.

[pmid538815-4] Chun, Chong. "Amoebic Comparative Double Blind Trials of Tiberal Compared with Metronidazole and Oral dehydroemetine in Oligosymptomatic Amoebiasis". Korean Medical Database. http://kmbase.medric.or.kr/Main.aspx?d=KMBASE&m=VIEW&i=0351219740060010097.

[pmid2883732-5] Chintana T, Sucharit P, Mahakittikun V, Siripanth C, Suphadtanaphongs W (1986). "In vitro studies on the sensitivity of local Entamoeba histolytica to anti-amoebic drugs". Southeast Asian J. Trop. Med. Public Health 17 (4): 591–4. PMID 2883732.

[pmid6102504-6] Hernandez-Perez E (1980). "Dehydroemetine therapy for herpes zoster. A comparison with corticosteroids". Cutis; cutaneous medicine for the practitioner 25 (4): 424–6. PMID 6102504.

[pmid16732-7] Al-Khateeb GH, Al-Jeboori TI, Al-Janabi KA (1977). "In vitro efficacy of some drugs on promastigotes of Leishmania donovani". Chemotherapy 23 (4): 267–75. doi:10.1159/000221994. PMID 16732.

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dehydroemetine