(-)-Emetine

480.649

480.64

207-592-1

X8D5EPO80M

DTXSID5022980|DTXSID4041024|DTXSID80424947

WHITE AMORPHOUS POWDER

P - Antiparasitic products, insecticides and repellents

52.2

6.01210

1.17g/cm3

74 °C

600.3ºC at 760mmHg

316.9ºC

SPARINGLY SOL IN WATER, PETROLEUM ETHER, IN SOLN OF POTASSIUM OR SODIUM HYDROXIDE; FREELY SOL IN METHANOL, ETHYL ACETATE

-20°C Freezer

LD50 i.p. in rats: 12.1 mg/kg (Radomski)

D20 -50° (c = 2 in CHCl3)

Very bitter taste

STRONG ALKALINE REACTION

PK1 5.77; PK2 6.64|DIACIDIC BASE: K1 = 1.7X10-6; K2 = 2.3X10-7

219.6 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Contains water of crystallization varying from 3 to 8 H2O; clusters of needles after drying at 105 °C, MP: 235-255 °C (decomposition); specific optical rotation: +11 deg (concentration by volume = 1 g in 100 ml water); 1 g of the hydrated salt dissolves in about 7 ml water; pH of aq soln (1 g in 50 ml) 5.6; sol in alcohol. /Emetine dihydrochloride/

III

6.1(b)

1544

DK1750000

Darkens on exposure to light.

P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501

H300

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

MANNO BR, MANNO JE; TOXICOLOGY OF IPECAC: REVIEW; CLIN TOXICOL; 10 (2): 221 (1977). THE TOXICOLOGY OF IPECAC IS REVIEWED.|DHEW/NCI; Bioassay of Emetine for Possible Carcinogenicity (1978) Technical Rpt Series No. 43 DHEW Pub No. (NIH) 78-843 /Emetine hydrochloride/

IN ISOLATED RAT FUNDUS SMOOTH MUSCLE, PRETREATMENT FOR 10 MIN WITH 5-15 UG EMETINE ANTAGONIZED THE INCREASED CONTRACTIONS INDUCED BY PROSTAGLANDIN E2. MAX INHIBITION WAS OBTAINED WITH 10 AND 15 UG EMETINE.

Groups of 35 Sprague Dawley rats of each sex were administered emetine at one of two doses, either 0. 5 or 1 mg/kg body weight, three times per week for 52 weeks, and then observed for an additional 31 or 32 weeks. Control groups of each sex consisted of 10 untreated rats (untreated controls) and 10 rats injected with buffered saline (vehicle controls). ... All surviving rats were killed at 83 or 84 weeks. ...Emetine was toxic to male rats at the high dose ...as shown by the low survival in these groups. Twenty six percent of the high-dose male rats and 69% of the high-dose female rats ... survived to the end of the study. No tumors occurred at a statistically significant incidence in treated rats ... compared with controls; however, it should be noted that in this study, treatment ... was stopped at week 52 and the studies were terminated by week 83, which is earlier than in current bioassays where animals are treated until termination of the studies at 2 years. It is concluded that the results of this study do not allow evaluation of the possible carcinogenicity of emetine.|Groups of 35 B6C3F1 mice of each sex were administered emetine at one of two doses, either 3.2 or 6.4 mg/kg body weight (mid and high dose), three times per wk. Control groups of each sex consisted of 15 untreated mice (untreated controls) and 15 mice injected with buffered saline (vehicle controls). Due to high mortality rates in the initial treated groups, additional groups of 35 mice of each sex were later put on study at 1.6 mg/kg (low dose), together with 10 untreated-control and 10 vehicle control mice of each sex. The high-dose males were treated for 28 wk and the mid and high dose females for 40 and 33 wk, respectively. Mid- and low dose male mice and low-dose female mice were treated for 52 wk, and then observed for an additional 20 or 26 weeks. All surviving mice were killed at 78-83 wk. Emetine was toxic to ... to both sexes of mice at the high and mid doses and to a lesser extent at the low dose, as shown by the low survival in these groups. ... None of the high and mid dose mice of either sex, survived to the end of the study. In the low dose mice, 30/35 males and 21/35 females lived at least 1 yr, and the median time on study was 72 wk for males and 59 weeks for females. No tumors occurred at a statistically significant incidence in treated ... mice compared with controls; however, it should be noted that in this study, treatment ... was stopped at wk 52 and the studies were terminated by wk 83, which is earlier than in current bioassays where animals aretreated until termination of the studies at 2 yr. In addition, there was poor survival among the treated mice. It is concluded that the results of this study do not allow evaluation of the possible carcinogenicity of emetine.

IT IS CONTRAINDICATED IN PATIENTS WITH CARDIAC DISEASE, KIDNEY OR LIVER DAMAGE, IN AGED OR DEBILITATED INDIVIDUALS, IN PREGNANCY, OR IN CHILDREN UNLESS THERE IS SEVERE DYSENTERY.|IN PATIENTS WITH ORGANIC HEART DISEASE, EMETINE SHOULD NOT BE USED UNLESS ... ABSOLUTELY NECESSARY, AS IN CASES OF AMEBIC HEPATITIS OR ABSCESS NOT CONTROLLED BY METRONIDAZOLE OR CHLOROQUINE.

/IT IS/ PRINCIPAL ALKALOID ... OF IPECAC.|By extraction from root of Cephalis ipecacuanha (ipecac) or synthetically.|Principal alkaloid of ipecac, the ground roots of Uragoga ipecacuanha (Brot.) Baill. Rubiaceae.

Amebicides; Antinematodal Agents; Protein Synthesis Inhibitors|... /IT/ IS USED IN THE TREATMENT OF ACUTE AMEBIC DYSENTERY, AMEBIC HEPATITIS, AND AMEBIC ABSCESSES OF THE LIVER AND OTHER ORGANS. ... /IT/ HAS NO EFFECT ON CYSTS.|IN AMEBIC HEPATITIS TOTAL AMT OF EMETINE /GIVEN/ IS LARGER /THAN THAT FOR AMEBIASIS/ ... REST PERIOD OF 1 WEEK, TOGETHER WITH ORAL THERAPY OF DIIODOHYDROXYQUIN OR GLYCOBIARSOL (MILIBIS) OR ANOTHER SIMILAR AGENT.|VALID USES OF EMETINE IN INTESTINAL AMEBIASIS ARE FOR SEVERE CASES OF AMEBIC DIARRHEA & ACUTE AMEBIC DYSENTERY, THAT IS WHEN TROPHOZOITES ARE FOUND IN THE STOOL.|For more Therapeutic Uses (Complete) data for EMETINE (10 total), please visit the HSDB record page.

Patients ... should remain sedentary, they require close medical supervision (including electrocardiographic monitoring).|EMETINE-INDUCED DIARRHEA MAY BE MISTAKEN FOR EXACERBATION OF AMEBIC DYSENTERY, FROM WHICH IT CAN ... BE DIFFERENTIATED BY THE FACT THAT PERIOD OF IMPROVEMENT ... OFTEN PRECEDES DIARRHEA.|PRECORDIAL PAIN CAUSED BY EMETINE MAY RESEMBLE THAT OF CORONARY THROMBOSIS, FROM WHICH IT REQUIRES DIFFERENTIATION. ... TACHYCARDIA ... FREQUENTLY PRECEDES ... ECG ABNORMALITIES. EMETINE SHOULD BE DISCONTINUED AS SOON AS /IT/ ... IS EVIDENT.|DRUG SHOULD BE STOPPED UPON APPEARANCE OF ... NEUROMUSCULAR SYMPTOMS, MARKED GI EFFECTS, OR CONSIDERABLE WEAKNESS.|For more Drug Warnings (Complete) data for EMETINE (17 total), please visit the HSDB record page.

/Emetine/ is considered to be a cumulative toxin the ingestion of which should not exceed 1 mg/kg/day.

Agents which are destructive to amebae, especially the parasitic species causing AMEBIASIS in man and animal. (See all compounds classified as Amebicides.)|Agents that cause vomiting. They may act directly on the gastrointestinal tract, bringing about emesis through local irritant effects, or indirectly, through their effects on the chemoreceptor trigger zone in the postremal area near the medulla. (See all compounds classified as Emetics.)|Substances used in the treatment or control of nematode infestations. They are used also in veterinary practice. (See all compounds classified as Antinematodal Agents.)|Agents that are used to stimulate evacuation of the bowels. (See all compounds classified as Cathartics.)|Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)

EMETINE IS ABSORBED FROM PARENTERAL SITES OF ADMINISTRATION & IS EXCRETED ... SLOWLY.|ALTHOUGH DRUG APPEARS IN URINE 20-40 MIN AFTER INJECTION, EMETINE CAN STILL BE FOUND THERE 40-60 DAYS AFTER TREATMENT HAS BEEN DISCONTINUED. ... HIGHEST CONCN OF ALKALOID IS FOUND IN LIVER ... APPRECIABLE AMT ARE ALSO FOUND IN LUNG, KIDNEY, & SPLEEN.|... EMETINE SHOWS A PREDILECTION FOR ACCUMULATING IN MUSCULAR ORGANS ... .

AMINOACYLATION OF EMETINE|Emetine undergoes slow hepatic metabolism, with urine metabolites detectable for 40-60 days ... .

EMETINE PREVENTED PROTEIN SYNTHESIS /IN ANIMAL CELLS/ BY INHIBITING TRANSLOCATION OF PEPTIDYL-TRNA FROM ACCEPTOR SITE TO DONOR SITE ON RIBOSOME. EMETINE ... INHIBITS PROTEIN SYNTHESIS IN EUKARYOTES BUT NOT IN PROCARYOTES.|Emetine is a direct myotoxin that inhibits protein synthesis, disrupts mitochondrial oxidative phosphorylation, and produces both skeletal and cardiac myopathies.|EMETINE CAUSES DEGENERATION OF NUCLEUS & RETICULATION OF CYTOPLASM OF AMEBAE; IT IS THOUGHT TO ERADICATE PARASITES BY INTERFERING WITH MULTIPLICATION OF TROPHOZOITES.

CARDIOVASCULAR REACTIONS ARE THE MOST SERIOUS AND INCLUDE PRECORDIAL PAIN, DYSPNEA, TACHYCARDIA, HYPOTENSION, GALLOP RHYTHM, CARDIAC DILATATION, CONGESTIVE FAILURE AND DEATH. /EMETINE FORMULATIONS/|ADVERSE REACTIONS /FOLLOWING SC OR IM INJECTION/ ARE OBSERVED IN 50-75% OF INDIVIDUALS TREATED WITH EMETINES. /EMETINE FORMULATIONS/|ELECTROCARDIOGRAPHIC CHANGES ARE THOSE OF CODUCTION DELAY AND CAN BE OF LONG DURATION (AVG, 6 WEEKS). ALTERATIONS INCLUDE WIDENING OF QRS COMPLEX, PROLONGATION OF P-R AND Q-T INTERVALS, CHANGES IN S-T SEGMENT AND FLATTENING OR INVERSION OF T WAVE. ... INJURY TO MYOCARDIUM AND OTHER ORGANS MAY OCCUR.|NAUSEA, VOMITING, & DIARRHEA ... HEADACHE, SKELETAL MUSCLE WEAKNESS, STIFFNESS, PAIN AND MUSCLE WEAKNESS AT SITE OF INJECTION, AS WELL AS ECZEMATOUS, URTICARIAL, OR PURPURIC LESIONS ALSO HAVE BEEN OBSERVED.|For more Human Toxicity Excerpts (Complete) data for EMETINE (10 total), please visit the HSDB record page.

Dihydrochloride, Emetine

Ampules, 65 mg. /Emetine hydrochloride/|... Emetine account/s/ for 0.7 mg/ml of syrup /of ipecac/ ... .|GENERIC: SOLUTION /FOR INJECTION/: SOLN 65 MG/ML IN 1 ML CONTAINERS. /EMETINE HYDROCHLORIDE/

Principal alkaloid of ipecac, the ground roots of Uragoga ipecacuanha (Brot.) Baill. Rubiaceae.

A METHOD FOR THE DETERMINATION OF EMETINE AND CEPHAELINE IN IPECACUANHA ROOT USING UV AND IR SPECTROMETRY IS DESCRIBED.|EMETINE WITH DANSYL CHLORIDE WAS STUDIED WITH THE AIM OF DEVELOPING A SENSITIVE AND SPECIFIC LC METHOD FOR THESE SUBSTANCES IN COMPLEX PHARMACEUTICAL DOSAGE FORMS.|A UV SPECTROPHOTOMETRIC METHOD WAS USED FOR THE DETERMINATION OF EMETINE.|Corn kernels treated with emetine were removed from the ears, blended, and extracted with methanol. The extract was analyzed by HPLC. For detection, a fluorescence detector set at excitation of 285 and emission at 316 nm was used. The recoveries of samples fortified between 0.1 ppm to 20 ppm with emetine ranged from 95.5-103.3%.

EMETINE WAS DETERMINED IN PLASMA BY HPLC AFTER OXIDATIVE ACTIVATION TO A FLUORESCENT PRODUCT.|EMETINE AND 2-DEHYDROEMETINE WERE DETERMINED IN BIOLOGICAL MATERIALS BY SPECTROFLUORIMETRY.