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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Approved, Withdrawn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
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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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatAllergic coughCombination Product in combination with: Ammonium chloride (DB06767), Potassium citrate (DB09125), Diphenhydramine (DB01075)•••••••••••••••••
Used in combination to treatBronchitisCombination Product in combination with: Diphenhydramine (DB01075), Ammonium chloride (DB06767), Potassium citrate (DB09125)•••••••••••••••••
Used in combination to treatCough caused by common coldCombination Product in combination with: Diphenhydramine (DB01075), Potassium citrate (DB09125), Ammonium chloride (DB06767)•••••••••••••••••
Used in combination to treatCoughingCombination Product in combination with: Glycyrrhiza glabra (DB14312), Ammonium bicarbonate (DB15925), Dextromethorphan (DB00514)•••••••••••••••••
Used in combination to treatCoughingCombination 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
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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.
DrugInteraction
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AbacavirAbacavir may decrease the excretion rate of Ipecac which could result in a higher serum level.
AbametapirThe serum concentration of Ipecac can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Ipecac can be increased when combined with Abatacept.
AbirateroneThe metabolism of Ipecac can be decreased when combined with Abiraterone.
AcebutololThe metabolism of Ipecac can be decreased when combined with Acebutolol.
Food Interactions
No interactions found.

Products

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ipecac SyrupSyrup140 mg / 100 mLOralD.C. Labs Limited1964-12-312003-07-11Canada flag
Ipecac Syrup 1.8gm/30ml USPSyrup1.8 g / 30 mLOralMeta Pharmaceuticals Inc.1991-12-311998-11-05Canada flag
PMS-ipecac SyrupSyrup7 %OralPharmascience Inc1988-12-312009-12-02Canada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
MEZINEXIpecac (3 mg/5mL) + Guaifenesin (45 mg/5mL) + Promethazine hydrochloride (5 mg/5mL)SyrupOralIfars Pharmaceutical Laboratories2014-12-292024-11-23Indonesia flag
Robol TabIpecac (4.32 mg / tab) + Alloin (16.2 mg / tab) + Belladonna (5.4 mg / tab) + Phenolphthalein (64.8 mg / tab)TabletOralLabs Anglo French1979-12-311997-08-05Canada flag
Trousse Antipoison Pour Enfants LiqIpecac (30 mL / vial) + Activated charcoal (120 mL / vial)LiquidOralProdemdis Enr.1988-12-312010-07-15Canada flag
ZENIREXIpecac (4 mg/5mL) + Guaifenesin (50 mg/5mL) + Promethazine hydrochloride (5 mg/5mL)SyrupOralPabrik Pharmasi Zenith2019-04-122024-02-28Indonesia flag
ยาธาตุน้ำแดงIpecac (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)Solutionองค์การเภสัชกรรม2002-09-13Not applicableThailand flag

Categories

ATC Codes
R05CA04 — IpecacuanhaV03AB01 — Ipecacuanha
Drug Categories
Classification
Not classified
Affected organisms
  • Humans

Chemical Identifiers

UNII
62I3C8233L
CAS number
8012-96-2

References

General References
  1. Lee MR: Ipecacuanha: the South American vomiting root. J R Coll Physicians Edinb. 2008 Dec;38(4):355-60. [Article]
  2. 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]
  3. 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]
  4. 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]
  5. Barceloux D.G. (2012). Medical toxicology of drug abuse: Synthesized chemicals and psychoactive plants.. Wiley.
  6. Benzoni T. and Gossman W. (2017). Ipecac. Treasure Island: StatPearls Publishing.
  7. Health Canada [Link]
  8. FDA code of federal regulations [Link]
  9. FDA federal register [Link]
  10. FDA Poisonous Plant Database [Link]
PubChem Substance
347911447
RxNav
5975
ChEMBL
CHEMBL2108372
Wikipedia
Ipecacuanha
MSDS
Download (46.5 KB)

Clinical Trials

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Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
StickNot applicable50 kg/50kg
SyrupOral140 mg / 100 mL
SyrupOral1.8 g / 30 mL
SyrupOral
SyrupOral7 %
TabletOral
LiquidOral
SyrupOral
Solution
Prices
Not Available
Patents
Not Available

Properties

State
Liquid
Experimental Properties
PropertyValueSource
water solubilitySoluble'MSDS'
logP5.0Barceloux D. Medical Toxicology of Drug Abuse. (2012)
pKa6.64-6.77Purich 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

Details1. Cytochrome P450 2D6
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
  1. Barceloux D.G. (2012). Medical toxicology of drug abuse: Synthesized chemicals and psychoactive plants.. Wiley.
Details2. Cytochrome P450 3A4
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
  1. 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]
  2. 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