Ipecac
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Identification
- Summary
Ipecac is an emetic agent used to induce vomiting in poisoning.
- Generic Name
- Ipecac
- DrugBank Accession Number
- DB13293
- Background
Ipecac is obtained from the plant Cephaelis ipecacuanha and contains a number of emetic alkaloids including emetine and cephaeline.9 Ipecac was approved by Health Canada as an OTC but all those products are now discontinued.7 The FDA does not have currently any approved product containing ipecac, however, ipecac as an ingredient is accepted to be sold over the counter in packages of 1 fluid ounce (30 ml) for the emergency use to cause vomiting in poisoning.8
- Type
- Small Molecule
- Groups
- Approved, Withdrawn
- Synonyms
- Ipecac
- Ipecac syrup
- Ipecacuanha
- Ipsatol
Pharmacology
- Indication
Ipecac is indicated as an emetic agent for the induction of vomiting in poisoning victims who ingested systemic poison in order to prevent absorption of the chemicals through the gastrointestinal tract. In low doses, ipecac was also used as an expectorant.9
Reports have suggested that ipecac was vastly used in patients with eating disorders to produce vomiting.5
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Allergic cough Combination Product in combination with: Ammonium chloride (DB06767), Potassium citrate (DB09125), Diphenhydramine (DB01075) •••••••••••• ••••• Used in combination to treat Bronchitis Combination Product in combination with: Diphenhydramine (DB01075), Ammonium chloride (DB06767), Potassium citrate (DB09125) •••••••••••• ••••• Used in combination to treat Cough caused by common cold Combination Product in combination with: Diphenhydramine (DB01075), Potassium citrate (DB09125), Ammonium chloride (DB06767) •••••••••••• ••••• Used in combination to treat Coughing Combination Product in combination with: Glycyrrhiza glabra (DB14312), Ammonium bicarbonate (DB15925), Dextromethorphan (DB00514) •••••••••••• ••••• Used in combination to treat Coughing Combination Product in combination with: Diphenhydramine (DB01075), Ammonium chloride (DB06767), Potassium citrate (DB09125) •••••••••••• ••••• - Associated Therapies
- Contraindications & Blackbox Warnings
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- Pharmacodynamics
An effective and safe dose of ipecac may cause vomiting within 20 minutes of the administration.9 In prospective studies with children, the mean time to vomit was reported to be of 21.7 minutes.10
- Mechanism of action
The emetic components of ipecac, emetine and cephaeline, act centrally and locally in the gastrointestinal tract to cause vomiting.9 The mechanism by which ipecac performs his effect is by irritating the stomach lining and chemically stimulating the chemoreceptor trigger zone.6
- Absorption
The main components of ipecac are rapidly absorbed from the GI tract, this absorption depends on the amount of emesis produced by the administered dose. The peak plasma concentration of 10-16 ng/ml is attained 20 minutes after first administration.5 The bioavailability of ipecac is reduced over time from 67-11% after 5-60 minutes of administration.3
- Volume of distribution
The volume of distribution is thought to be large based on the prolonged excretion.5
- Protein binding
This pharmacokinetic property is not relevant as the absorbed dose of ipecac is minimal.
- Metabolism
The main components of ipecac have been shown in microsomal enzyme systems that emetine is converted to cephaeline and 9-O-demethylemetine by CYP2D6. On the other hand, CYP3A4 produces the transformation of emetine to 9-O-demethylemetine and 10-O-demethylemetine. In preclinical studies, it was shown that cephaline is conjugated with glucuronice to form cephaeline-6'-O-glucuronide for biliary excretion whereas emetine gets demethylated to cephaline and 9-O-demethylemetine before glucuronidation.5
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- Route of elimination
Due to the emetic function, even 76% of the administered dose is vomited. From the absorbed dose, the elimination from plasma is relatively rapid. In some clinical trials, the alkaloids were not observed in plasma 6 hours after administration. When the patient does not vomit any part of the administered dose, there could be traces in plasma after 24 hours. The component alkaloids are eliminated via the bile and urine as it has been observed a persistence in urine after chronic administration.5 Biliary and urinary excretion of ipecac corresponds to 57.5% and 16.5% of the administered dose respectively. From the excreted dose, unchanged cephaeline accountd for 42.4% of the eliminated dose in feces.4
- Half-life
The effect of ipecac is done in about 20 minutes and the elimination of the little-absorbed dose is reported to be very rapid. Thus, the half-life is thought to be of about 0.5-1 hour.5
- Clearance
The urinary excretion of the main components of ipecac accounts for 75% of the administered dose 48 hours after initial administration.6
- Adverse Effects
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- Toxicity
An overdose of an ipecac preparation may cause serious poisoning. If emesis is not provoked after two doses of ipecac, a gastric lavage is recommended.9 The overdose of the components such as emetine is reported to cause the onset of myopathy. Chronic use of this drug has been indicated to produce muscle weakness, waddling gait, dyspnea, left atrial enlargement and reduced left ventricular ejection fraction.5
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of Ipecac which could result in a higher serum level. Abametapir The serum concentration of Ipecac can be increased when it is combined with Abametapir. Abatacept The metabolism of Ipecac can be increased when combined with Abatacept. Abiraterone The metabolism of Ipecac can be decreased when combined with Abiraterone. Acebutolol The metabolism of Ipecac can be decreased when combined with Acebutolol. - Food Interactions
- No interactions found.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ipecac Syrup Syrup 140 mg / 100 mL Oral D.C. Labs Limited 1964-12-31 2003-07-11 Canada Ipecac Syrup 1.8gm/30ml USP Syrup 1.8 g / 30 mL Oral Meta Pharmaceuticals Inc. 1991-12-31 1998-11-05 Canada PMS-ipecac Syrup Syrup 7 % Oral Pharmascience Inc 1988-12-31 2009-12-02 Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image MEZINEX Ipecac (3 mg/5mL) + Guaifenesin (45 mg/5mL) + Promethazine hydrochloride (5 mg/5mL) Syrup Oral Ifars Pharmaceutical Laboratories 2014-12-29 2024-11-23 Indonesia Robol Tab Ipecac (4.32 mg / tab) + Alloin (16.2 mg / tab) + Belladonna (5.4 mg / tab) + Phenolphthalein (64.8 mg / tab) Tablet Oral Labs Anglo French 1979-12-31 1997-08-05 Canada Trousse Antipoison Pour Enfants Liq Ipecac (30 mL / vial) + Activated charcoal (120 mL / vial) Liquid Oral Prodemdis Enr. 1988-12-31 2010-07-15 Canada ZENIREX Ipecac (4 mg/5mL) + Guaifenesin (50 mg/5mL) + Promethazine hydrochloride (5 mg/5mL) Syrup Oral Pabrik Pharmasi Zenith 2019-04-12 2024-02-28 Indonesia ยาธาตุน้ำแดง Ipecac (2 ml/100ml) + Gentiana lutea extract (6.67 ml/100ml) + Peppermint oil (2 ml/100ml) + Rhubarb (10.67 ml/100ml) + Sodium bicarbonate (4 g/100ml) Solution องค์การเภสัชกรรม 2002-09-13 Not applicable Thailand
Categories
- ATC Codes
- R05CA04 — Ipecacuanha
- R05CA — Expectorants
- R05C — EXPECTORANTS, EXCL. COMBINATIONS WITH COUGH SUPPRESSANTS
- R05 — COUGH AND COLD PREPARATIONS
- R — RESPIRATORY SYSTEM
- Drug Categories
- Agents Causing Muscle Toxicity
- Antidotes
- Autonomic Agents
- Biological Products
- Central Nervous System Agents
- Complex Mixtures
- Cough and Cold Preparations
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Drugs that are Mainly Renally Excreted
- Emetics
- Expectorants
- Gastrointestinal Agents
- Peripheral Nervous System Agents
- Plant Extracts
- Plant Preparations
- Classification
- Not classified
- Affected organisms
- Humans
Chemical Identifiers
- UNII
- 62I3C8233L
- CAS number
- 8012-96-2
References
- General References
- Lee MR: Ipecacuanha: the South American vomiting root. J R Coll Physicians Edinb. 2008 Dec;38(4):355-60. [Article]
- Axelsson P, Thorn SE, Wattwil M: Betamethasone does not prevent nausea and vomiting induced by ipecacuanha. Acta Anaesthesiol Scand. 2004 Nov;48(10):1283-6. [Article]
- Saincher A, Sitar DS, Tenenbein M: Efficacy of ipecac during the first hour after drug ingestion in human volunteers. J Toxicol Clin Toxicol. 1997;35(6):609-15. [Article]
- Asano T, Watanabe J, Sadakane C, Ishihara K, Hirakura K, Wakui Y, Yanagisawa T, Kimura M, Kamei H, Yoshida T, Fujii Y, Yamashita M: Biotransformation of the ipecac alkaloids cephaeline and emetine from ipecac syrup in rats. Eur J Drug Metab Pharmacokinet. 2002 Jan-Mar;27(1):29-35. [Article]
- Barceloux D.G. (2012). Medical toxicology of drug abuse: Synthesized chemicals and psychoactive plants.. Wiley.
- Benzoni T. and Gossman W. (2017). Ipecac. Treasure Island: StatPearls Publishing.
- Health Canada [Link]
- FDA code of federal regulations [Link]
- FDA federal register [Link]
- FDA Poisonous Plant Database [Link]
- External Links
- PubChem Substance
- 347911447
- 5975
- ChEMBL
- CHEMBL2108372
- Wikipedia
- Ipecacuanha
- MSDS
- Download (46.5 KB)
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Stick Not applicable 50 kg/50kg Syrup Oral 140 mg / 100 mL Syrup Oral 1.8 g / 30 mL Syrup Oral Syrup Oral 7 % Tablet Oral Liquid Oral Syrup Oral Solution - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Liquid
- Experimental Properties
Property Value Source water solubility Soluble 'MSDS' logP 5.0 Barceloux D. Medical Toxicology of Drug Abuse. (2012) pKa 6.64-6.77 Purich D. The inhibitor index. (2017) - Predicted Properties
- Not Available
- Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
- Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
- Specific Function
- anandamide 11,12 epoxidase activity
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Barceloux D.G. (2012). Medical toxicology of drug abuse: Synthesized chemicals and psychoactive plants.. Wiley.
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Asano T, Kushida H, Sadakane C, Ishihara K, Wakui Y, Yanagisawa T, Kimura M, Kamei H, Yoshida T: Metabolism of ipecac alkaloids cephaeline and emetine by human hepatic microsomal cytochrome P450s, and their inhibitory effects on P450 enzyme activities. Biol Pharm Bull. 2001 Jun;24(6):678-82. [Article]
- Barceloux D.G. (2012). Medical toxicology of drug abuse: Synthesized chemicals and psychoactive plants.. Wiley.
Drug created at June 23, 2017 20:39 / Updated at October 17, 2024 17:20