ジヒドロエメチン
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2012/11/10 00:33:53」(JST)
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Dehydroemetine
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| 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 Y |
| ATC code |
P01AX09 |
| PubChem |
CID 21022 |
| ChemSpider |
19773 |
| UNII |
7S79QT1T91 N |
| KEGG |
D00828 Y |
| ChEMBL |
CHEMBL547470 N |
| 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
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InChI
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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
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N (what is this?) (verify)
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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.
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Contents
- 1 Mechanism
- 2 Uses
- 2.1 Amoebic infections
- 2.2 In other diseases
- 3 References
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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.
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Antiparasitics – antiprotozoal agents – agents against amoebozoa/amebicide (P01)
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| Entamoeba |
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Tissue amebicides
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Nitroimidazole derivatives
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- Metronidazole#
- Tinidazole
- Ornidazole
- Nimorazole
- Secnidazole
- Azanidazole
- Propenidazole
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Other
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- isoquinoline (Emetine/Dehydroemetine)
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Luminal amebicides
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Hydroxyquinoline derivatives
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- Cl (Chlorquinaldol)
- Br (Tilbroquinol
- Broxyquinoline)
- I (Diiodohydroxyquinoline)
- I,Cl (Clioquinol)
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Dichloroacetamide derivatives
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- Diloxanide#
- Clefamide
- Etofamide
- Teclozan
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Aminoglycoside
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Other/ungrouped
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- arsenic (Arsthinol
- Difetarsone
- Glycobiarsol)
- phenanthroline (Phanquinone)
- aminoacridine (Mepacrine)
- quinazoline (Trimetrexate)
- thiazole (Tenonitrozole)
- sesquiterpene (Fumagillin)
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| Acanthamoeba |
- Propamidine
- Chlorhexidine
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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English Journal
- Nakajima Y.SourceDepartment of Parasitology and Immunology, Yamanashi Medical University.
- Nihon rinsho. Japanese journal of clinical medicine.Nihon Rinsho.2003 Feb;61 Suppl 2:774-9.
- PMID 12722315
- Hepatopulmonary amoebiasis. Efficacy of various treatment regimens containing dehydroemetine and/or metronidazole.
- Jain NK, Madan A, Sharma TN, Sharma DK, Mandhana RG.SourceHospital for Chest Diseases and Tuberculosis, Sawai Man Singh Medical College, Jaipur.
- The Journal of the Association of Physicians of India.J Assoc Physicians India.1990 Apr;38(4):269-71.
- Thirty three patients with hepatopulmonary amoebiasis were studied. Pulmonary involvement was observed in 55%, pleuro-pulmonary lesions in 30%. Typical chocolate coloured sputum was obtained in 24% and pleural fluid in 21% of patients. Entamoeba histolytica were demonstrable in the sputum in only 6%
- PMID 2202709
Related Links
- More on Emetine Definition: The principal alkaloid of ipecac, from the ground roots of Uragoga (or Cephaelis) ipecacuanha or U. acuminata, of the Rubiaceae. It is used as an amebicide in many different preparations and may cause ...
- DIHYDROEMETINE HYDROCHLORIDE - chemical information, properties, structures, articles, patents and more chemical data. ... Richest Group Limited Manufacturer China Started from 1996,Richest Group is global manufacturer ...
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