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Emetin, seine Salze undVerbindungen

Emetine

HCID 10219
NotizenReaktionen
GrundinformationenNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
483-18-1
Standard-SMILES
CC[C@H]1CN2CCc3cc(OC)c(OC)cc3[C@@H]2C[C@@H]1C[C@H]1NCCc2cc(OC)c(OC)cc21
InChIKey
AUVVAXYIELKVAI-CKBKHPSWSA-N
Summenformel
C29H40N2O4
Durchschnittliche Molmasse
480,6 g/mol
Monoisotopische Masse
480,29880776

Namen und Bezeichner

Bevorzugter Name
Emetine
IUPAC
(2S,3R,11bS)-2-[[(1R)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizine
Lokaler Name
Emetin, seine Salze undVerbindungen
Englischer Name
Emetine
Summenformel
C29H40N2O4
Molmasse
480.64

Namen und Synonyme

EMETINE483-18-1EmetinCephaeline methyl ether(-)-EmetineMethyl cephaeline6',7',10,11-TetramethoxyemetanCephaline-O-methyl etherEmetinumEmetan, 6',7',10,11-tetramethoxy-NSC-33669DTXSID5022980
Weitere Namen anzeigen
C09421Emetine (>Ipecac alkaliEMetine (>90%)EMETINE USP/EP/BPEmetine HCL BP/USP6',7',10,11-Tetramethoxymetan
X8D5EPO80M(2S,3R,11bS)-2-[[(1R)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizineCHEBI:4781DTXCID402980IpecineMethylcephaeline(2S,3R,11bS)-2-(((1R)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo(a)quinolizineRefChem:136683

Datenbank-Bezeichner

CAS
483-18-1、7083-71-8
PubChem CID
10219
DTXSID
DTXSID5022980

Eigenschaften

Berechnete Struktureigenschaften

XLogP
4,7
Polarare Oberfläche (TPSA)
52,2 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
7
Schwere Atome
35
Formalladung
0
Komplexität
679

Experimentelle und physikochemische Eigenschaften

pHSTRONG ALKALINE REACTION
TasteVery bitter taste
Color/FormWHITE AMORPHOUS POWDER
Solubility · 2 Einträge

MODERATELY SOL IN DILUTE AMMONIUM HYDROXIDE; SOL IN ETHER, ALCOHOL, ACETONE; SLIGHTLY SOL IN CHLOROFORM, BENZENE; INSOL IN GLACIAL ACETIC ACID; SOL IN 80% ACETIC ACID

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

DecompositionWhen heated to decomposition it emits highly toxic fumes of /nitrogen oxides/.
Melting Point74 °C
Optical RotationSPECIFIC OPTICAL ROTATION: -50 DEG @ 20 °C/D (CHLOROFORM, 2%)
Stability/Shelf Life · 3 Einträge

TURNS YELLOW ON EXPOSURE TO LIGHT AND HEAT.

Solid and solutions turn yellow on exposure to light or heat. /Emetine dihydrochloride/

Darkens on exposure to light.

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

Danger

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral];H315 (97.4%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (97.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (97.4%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Gefahrenhinweise

FDA Requirements · 1 Eintrag

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).

Special Reports · 2 Einträge

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/

Hazard Classes and CategoriesAcute Tox. 1 (100%);Skin Irrit. 2 (97.4%);Eye Irrit. 2 (97.4%);STOT SE 3 (97.4%)

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

P - Antiparasitic products, insecticides and repellents;P01 - Antiprotozoals;P01A - Agents against amoebiasis and other protozoal diseases;P01AX - Other agents against amoebiasis and other protozoal diseases;P01AX02 - Emetine

QP - Antiparasitic products, insecticides and repellents;QP51 - Antiprotozoals;QP51A - Agents against protozoal diseases;QP51AX - Other antiprotozoal agents;QP51AX02 - Emetine

Mechanism of Action · 3 Einträge

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.

Metabolism/Metabolites · 2 Einträge

AMINOACYLATION OF EMETINE

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

MeSH Pharmacological Classification · 5 Einträge

Agents which are destructive to amebae, especially the parasitic species causing AMEBIASIS in man and animal.

Substances used in the treatment or control of nematode infestations. They are used also in veterinary practice.

Agents that are used to stimulate evacuation of the bowels.

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.

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.

Zugehörige Reaktionen

1
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 1267097
HRID 1267097als Produktuspto-grants-2003_04

Notizen zur Verbindung

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Auf dieser SeiteGrundinformationenNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
ChEMBL
CHEMBL1255782、CHEMBL50588
ChEBI
CHEBI:4781
UNII
X8D5EPO80M
EC Number
207-592-1、809-653-3
Nikkaji
J9.377G
Dissociation Constants · 2 Einträge

PK1 5.77; PK2 6.64

DIACIDIC BASE: K1 = 1.7X10-6; K2 = 2.3X10-7

Collision Cross Section · 2 Einträge

213.01 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];215.97 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];219.86 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];204.45 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

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

Other Experimental Properties · 1 Eintrag

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/

Physikochemische Eigenschaften

Schmelzpunkt
89 · 89-96°C
Siedepunkt
578.63 °C · 578.63°C (rough estimate)
Dichte
1.1174 · 1.1174 (rough estimate)
Brechungsindex
1.58 · 1.5800 (estimate)
storage temp.
-20 °C · -20°C Freezer
Löslichkeit
Soluble in Water (100 mg/ml)
pka
5.77 · 5.77, 6.64(at 25℃)
Aggregatzustand
solid
Farbe
White
Wasserlöslichkeit
961.3 mg/L · 961.3mg/L(15 ºC)
Stabilität
2 years · Stable for 2 years from date of purchase as supplied. Solutions in water may be stored at -20°C for up to 3 months.

Toxikologische Informationen

InteractionsIN 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.
Ongoing Test Status · 1 Eintrag

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. /Emetine hydrochloride/ [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=316-42-7]

Medical SurveillanceSRP: Physical exam of workers exposed to emetine should emphasize evaluation and monitoring of cardiac, liver and kidney function.
Natural Pollution Sources · 3 Einträge

/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.

Human Toxicity Excerpts · 5 Einträge

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.

Non-Human Toxicity Excerpts · 5 Einträge

DIRECT TOXIC EFFECT OF EMETINE ON CARDIAC MUSCLE HAS BEEN REPEATEDLY DEMONSTRATED IN ANIMALS.

IN ... ANIMALS ... LARGE DOSES PRODUCE ACUTE LESIONS IN HEART, LIVER, KIDNEY, INTESTINAL TRACT, & SKELETAL MUSCLES.

OF THE MAJOR ALKALOIDS OF IPECAC, CEPHAELINE IS SAID TO BE TWICE AS TOXIC AS EMETINE WHEN GIVEN SC IN WHITE RATS ... . /IPECAC/

THE CUMULATIVE NATURE OF EMETINE POISONING WAS NOTED WHEN CATS & RABBITS WERE FOUND TO TOLERATE DOSES OF 1.5-4 MG/KG FOR A FEW DAYS EVEN THOUGH THIS REGIMEN INVARIABLY ENDED FATALLY ... .

For more Non-Human Toxicity Excerpts (Complete) data for EMETINE (10 total), please visit the HSDB record page.

Populations at Special Risk · 2 Einträge

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.

National Toxicology Program Studies · 2 Einträge

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.

Regulatorische Informationen

FDA Requirements · 1 Eintrag

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).

Sicherheitsdaten

ridadr
1544
Toxizität
LD50 i.p. in rats: 12.1 mg/kg (Radomski)
hazard_class
6.1(b)
packing_group
III
Giftige Stoffe Daten
483-18-1(Hazardous Substances Data)
Absorption, Distribution and Excretion · 3 Einträge

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 ... .

Verwendung und Herstellung

Uses · 2 Einträge

MEDICATION (VET)

MEDICATION

Methods of Manufacturing · 3 Einträge

... GROUND IPECAC ... MIXED WITH AMMONIA ... EXTRACTED WITH ETHER ... ALKALOIDS ARE EXTRACTED WITH DILUTE ACID ... NEUTRALIZED WITH SODIUM HYDROXIDE ... EMETINE ... /EXTRACTED/ WITH ETHER ... .

SYNTHESIS FROM HEXAHYDROGALLIC ACID; FROM 2-OXOBENZO[A]QUINOLIZINE.

By extraction from root of Cephalis ipecacuanha (ipecac) or synthetically.

Formulations/Preparations · 3 Einträge

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/

General Manufacturing InformationPrincipal alkaloid of ipecac, the ground roots of Uragoga ipecacuanha (Brot.) Baill. Rubiaceae.

Anwendungen

VerwendenEmetine is the principal alkaloid of ipecac, the ground roots of Uragoga ipecacuanha.

Anbieter30 Anbieter

南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
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成都健腾生物技术有限公司028-85159085 18080455027 · [email protected]
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武汉市皇臻生物化工有限公司13795480948 · [email protected]
Aktin Chemicals, Inc.028-85159085 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
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风咏生物(AbMole)021-10000000 13000000000 · [email protected]
西安天广源生物科技有限公司17391627434 · [email protected]
杭州洁汉化工有限公司+86-571-86217390; +8618058761490 · [email protected]
上海易恩化学技术有限公司400-400-1332688 18019345275 · [email protected]
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Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: Emetine is a pyridoisoquinoline comprising emetam having methoxy substituents at the 6'-, 7'-, 10- and 11-positions. It is an antiprotozoal agent and emetic. It inhibits SARS-CoV2, Zika and Ebola virus replication and displays antimalarial, antineoplastic and antiamoebic properties. It has a role as an antiprotozoal drug, a plant metabolite, an antiviral agent, an emetic, a protein synthesis inhibitor, an antimalarial, an antineoplastic agent, an autophagy inhibitor, an antiinfective agent, an expectorant, an anticoronaviral agent and an antiamoebic agent. It is a pyridoisoquinoline and an isoquinoline alkaloid. It is functionally related to a cephaeline. It is a conjugate base of an emetine(2+). It derives from a hydride of an emetan.