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Dehydroemetine

Dehydroemetine structure

CAS No:
4914-30-1
Formula:
C29H38N2O4
Chemical Name:
Dehydroemetine
Synonyms:
4H-Benzo[a]quinolizine,3-ethyl-1,6,7,11b-tetrahydro-9,10-dimethoxy-2-[[(1R)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-isoquinolinyl]methyl]-,(11bS)-;Emetine,2,3-didehydro-;Emetan,2,3-didehydro-6′,7′,10,11-tetramethoxy-;Emetine,dehydro-;Emetine,2-dehydro-;(11bS)-3-Ethyl-1,6,7,11b-tetrahydro-9,10-dimethoxy-2-[[(1R)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-isoquinolinyl]methyl]-4H-benzo[a]quinolizine;2-Dehydroemetine;3-Ethyl-9,10-dimethoxy-1,6,7,11b-tetrahydro-2-[(1,2,3,4-tetrahydro-6,7-dimethoxy-1-isoquinolyl)methyl]-4H-benzo[a]quinolizine;2,3-Dehydroemetine;Dehydroemetine;(-)-2,3-Dehydroemetine;Mebadin;Ro 1-9334;Ro 1-9334/19;7679-25-6;20978-07-8
Categories:
Active Pharmaceutical Ingredients > Antiparasitic Drugs

Description

Dehydroemetine, a synthetic analogue of emetine dihydrochloride, is used for visceral leishmaniasis. Dehydroemetine used for anti-parasites[1].

Dehydroemetine is a pyridoisoquinoline which was developed in response to the cardiovascular toxicity associated with emetine and results from the dehydrogenation of the heterotricylic ring of emetine. It is an antiprotozoal agent and displays antimalarial, antiamoebic, and antileishmanial properties. It has a role as an antiprotozoal drug, an antimalarial and an antileishmanial agent. It is a member of isoquinolines, an aromatic ether and a pyridoisoquinoline. It derives from a hydride of an emetan.|Dehydroemetine is a synthetic derivative of emetine; used in the treatment of intestinal amoebiasis.

Dehydroemetine Basic Attributes

Molecular Weight：

478.629

Exact Mass：

478.62

EC Number：

225-542-7

UNII：

7S79QT1T91

NSC Number：

131546

NCI Thesaurus Code：

C418

ATC Code：

P - Antiparasitic products, insecticides and repellents

Characteristics

PSA：

52.2

XLogP3：

5.27430

Density：

1.19g/cm3

Melting Point：

95 °C

Boiling Point：

604.7ºC at 760mmHg

Flash Point：

319.5ºC

Refractive Index：

1.606

Specific rotation：

D -183°

Drug Information

MeSH Entry Terms：

dehydroemetine

Dehydroemetine Use and Manufacturing

The synthetic racemic derivative of the plant alkaloid emetine. Formulated as the hydrochloride for intramuscular administration. Like the parent compound, emetine, it inhibits E. histolytica at concentrations of 1–10 mg/L in vitro, but it is more active than the parent in animal models. Drugresistance in E. histolytica is rare.
No human pharmacokinetic data are available. A halflife of 2 days, compared with 5 days for emetine, has been reported. There is selective tissue binding and accumulation in the liver, lung, spleen and kidney.
It is considerably less toxic than emetine, possibly because it is more rapidly eliminated. Nevertheless, nausea, vomiting, diarrhea and abdominal cramps frequently occur. Neuromuscular effects have also been reported. More serious cardiotoxic effects can lead to electrocardiogram (EGG) changes, tachycardia and a drop in blood pressure.
It was formerly used as a second-line treatment in severe intestinal or hepatic amebiasis, but is no longer recommended for use.

Computed Properties

Molecular Weight:478.6
XLogP3:3.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:7
Exact Mass:478.28315770
Monoisotopic Mass:478.28315770
Topological Polar Surface Area:52.2
Heavy Atom Count:35
Complexity:744
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Recommended Suppliers of Dehydroemetine

Shaanxi Dideu Medichem Co. Ltd Contact Supplier

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dehydroemetine

CAS No.: 4914-30-1

Grade: Industrial Grade

Content: 99.0%

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