Tegaserod

Identification

Name

Tegaserod

Accession Number

DB01079  (APRD00096)

Type

Small Molecule

Groups

Approved, Investigational, Withdrawn

Description

Novartis' brand name Zelnorm (tegaserod) had originally received approval from the US FDA in 2002 for the treatment of irritable bowel syndrome with constipation (IBS-C).^5,8 It was, however, voluntarily withdrawn from widespread use in the US market in 2007 after concerns arose over the possibility that tegaserod could potentially cause dangerous cardiovascular events in patients.^5,8 Since then, closer evaluations of the original data suggesting such cardiovascular risk have resulted in the limited reintroduction or 're-approval' of tegaserod for treatment of IBS-C specifically in female patients less than 65 years of age and whom are considered to be at a lower risk of a cardiovascular event than the broader population.^5,8 Zelnorm (tegaserod) by Sloan Pharma subsequently gained re-approval in April of 2019.⁵ Nevertheless, tegaserod remains un-approved in certain regions.⁷

Despite the relative complications involved in its history of regulatory approval, ever since its first introduction in 2002 tegaserod remains the only therapy for IBS-C that possesses the unique mechanism of action of acting on serotonin-4 (5-HT(4)) receptors in smooth muscle cells and in the gastrointestinal wall to facilitate actions like esophageal relaxation, peristaltic gut movement, and natural secretions in the gut, among others.^5,1,3,8,6

Structure

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MOLSDFPDBSMILESInChI

Similar Structures

Structure for Tegaserod (DB01079)

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Synonyms

• 1-(((5-Methoxyindol-3-yl)methylene)amino)-3-pentylguanidine
• Tégasérod
• Tegaserod
• Tegaserodum

External IDs

HTF 919 / HTF-919 / SDZ HTF 919 / SDZ-HTF-919

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Tegaserod maleate	E5XNT3RF5A	189188-57-6	CPDDZSSEAVLMRY-FEQFWAPWSA-N

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Zelnorm	Tablet	6 mg/1	Oral	Novartis	2002-07-24	2009-01-31
Zelnorm	Tablet	6 mg/1	Oral	Novartis	2002-07-24	2008-06-30
Zelnorm	Tablet	2 mg/1	Oral	Novartis	2002-07-24	2010-05-31
Zelnorm	Tablet	6 mg/1	Oral	Alfasigma USA, Inc.	2019-08-01	Not applicable
Zelnorm	Tablet	6 mg/1	Oral	US WorldMeds, LLC	2019-07-29	Not applicable

Additional Data Available

Application Number
Application Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
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Product Code
Product Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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International/Other Brands

Zelmac

Categories

• Alimentary Tract and Metabolism
• BCRP/ABCG2 Substrates
• Cytochrome P-450 CYP1A2 Inhibitors
• Cytochrome P-450 CYP1A2 Inhibitors (strength unknown)
• Cytochrome P-450 CYP2C8 Inhibitors
• Cytochrome P-450 CYP2C8 Inhibitors (weak)
• Cytochrome P-450 CYP2D6 Inhibitors
• Cytochrome P-450 CYP2D6 Inhibitors (moderate)
• Cytochrome P-450 CYP2D6 Substrates
• Cytochrome P-450 CYP2E1 Inhibitors
• Cytochrome P-450 CYP2E1 Inhibitors (weak)
• Cytochrome P-450 Enzyme Inhibitors
• Cytochrome P-450 Substrates
• Drugs for Constipation
• Gastrointestinal Agents
• Heterocyclic Compounds, Fused-Ring
• Laxatives
• P-glycoprotein substrates
• Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome

UNII

458VC51857

CAS number

145158-71-0

Weight

Average: 301.394
Monoisotopic: 301.190260381

Chemical Formula

C₁₆H₂₃N₅O

InChI Key

IKBKZGMPCYNSLU-RGVLZGJSSA-N

InChI

InChI=1S/C16H23N5O/c1-3-4-5-8-18-16(17)21-20-11-12-10-19-15-7-6-13(22-2)9-14(12)15/h6-7,9-11,19H,3-5,8H2,1-2H3,(H3,17,18,21)/b20-11+

IUPAC Name

N'-[(E)-[(5-methoxy-1H-indol-3-yl)methylidene]amino]-N-pentylguanidine

SMILES

CCCCCNC(=N)N\N=C\C1=CNC2=C1C=C(OC)C=C2

Pharmacology

Indication

Tegaserod is a serotonin-4 (5-HT4) receptor agonist indicated for the treatment of adult women less than 65 years of age with irritable bowel syndrome with constipation (IBS-C) ^6,8. The safety and effectiveness of tegaserod in men with IBS-C have not been established ^6,8.

Associated Conditions

• Constipation-predominant Irritable Bowel Syndrome (IBS-C)

Pharmacodynamics

In general, it has been determined that tegaserod is an agonist of serotonin type-4 (5-HT(4)) receptors, an antagonist at 5-HT(2B) receptors, but is expected to possess minimal binding to 5-HT(1) receptors, and virtually no affinity for 5-HT(3) or dopamine receptors ^1,3,6.

In clinical trials with tegaserod, centrally analyzed ECGs were recorded in 4,605 male and female patients receiving tegaserod 6 mg twice daily or placebo for IBS-C and other related motility disorders ^6,8. No subject receiving the agent had an absolute QTcF above 480 ms ^6,8. An increase in QTcF of 30 to 60 ms was observed in 7% of patients receiving tegaserod and 8% receiving placebo ^6,8. An increase in QTcF of greater than 60 ms was observed in 0.3% and 0.2% of subjects, respectively ^6,8. The effects of tegaserod on the QTcF interval were ultimately not considered to be clinically meaningful ^6,8.

Furthermore, it was determined that there is a potential for tegaserod and its main metabolite (the M29 metabolite) to increase platelet aggregation in vitro ^6,8. In one in vitro study, at concentrations up to 10-times the maximum plasma concentration (Cmax) at the recommended dose, tegaserod significantly increased platelet aggregation in a concentration-dependent manner up to 74% (range 11% to 74%) compared to a control vehicle (with potentiation by various agonists) ^6,8. In another in vitro study, the M29 metabolite, at concentrations up to 0.6-times the Cmax of M29 also showed a 5% to 16% increase in platelet aggregation compared to the control vehicle ^6,8. The clinical implications of these in vitro platelet aggregation results remain unclear ^6,8.

Mechanism of action

Irritable bowel syndrome (IBS) is a complex functional disorder comprised of various abnormal and discomforting effects on the gastrointestinal tract and bowel function ^2,6,7,8. Although the cause of IBS has yet to be formally elucidated, patient experience has demonstrated that the disorder is typically associated with abdominal pain, abdominal distension, cramping or bloating, variations in urgency for bowel movements, feelings of incomplete evacuation, gastroesophageal reflux, and various other effects ^2,6,7,8. In particular, IBS that features constipation as a predominant effect is categorized as constipation-predominant IBS, or IBS-C ^6,8.

Concurrently, 5-Hydroxytryptamine (5-HT, or serotonin) has demonstrated the ability to elicit significant regulatory actions on gastrointestinal motility ¹. Specifically, it has been shown that the activation of 5-HT(4) receptors located on motor neurons and interneurons in the gastrointestinal wall can cause the release of acetylcholine, substance P, and calcitonin gene-related peptide that can all facilitate the propulsion of material through the gut ¹. Moreover, when 5-HT(4) receptors located in smooth muscle cells are also activated, activities that may alleviate symptoms of IBS-C like esophageal relaxation and the inhibition of human colonic circular muscle contraction can also occur ¹. Additionally, activating 5-HT(4) on enteric neurons and enterocytes also cause natural fluid secretion in the gut - an action which also strongly assists in promoting the movement of content along the gastrointestinal tract ¹.

Alternatively, it has also been observed that 5-HT may participate in generating visceral hyperalgesia in IBS, an observation supported in part by the finding of increased amounts of 5-HT and its metabolites in the plasma of patients experiencing IBS ³ It has therefore also been proposed that antagonism of 5-HT(2B) receptors can lead to inhibition of both 5-HT mediated gastrointestinal motility and visceral hypersensitivity ¹.

Subsequently, because tegaserod is considered to be an agonist of the 5-HT(4) receptor and an antagonist of the 5-HT(2B) receptor at clinically relevant levels, it is believed that tegaserod may elicit its mechanism of action by facilitating activities associated with the activation and antagonism of the 5-HT(4) and 5-HT(2B) receptors, like stimulating peristaltic gastrointestinal reflexes and intestinal secretion, inhibiting visceral sensitivity, enhancing basal motor activity, and normalizing impaired motility throughout the gastrointestinal tract, among other actions ^1,3,6,7,8.

Target	Actions	Organism
A5-hydroxytryptamine receptor 4	antagonist partial agonist	Humans
U5-hydroxytryptamine receptor 2B	antagonist	Humans
U5-hydroxytryptamine receptor 2C	antagonist	Humans
U5-hydroxytryptamine receptor 2A	antagonist	Humans

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Absorption

The absolute bioavailability of tegaserod is approximately 10% when administered to fasting subjects. The median time of peak tegaserod plasma concentration (Tmax) is approximately one hour (range 0.7 to 2 hours) ⁶.

Nevertheless, when tegaserod was given to individuals thirty minutes before a meal of high-fat and high-calorie content (about 150 calories from protein, 250 calories from carbohydrates, and 500 calories from fat), the AUC was reduced by 40% to 65%, the Cmax was reduced by approximately 20% to 40%, and the median Tmax was 0.7 hours ⁶. Additionally, plasma concentrations were similar when tegaserod was administered within thirty minutes before a meal or even two and a half hours after a meal ⁶.

Volume of distribution

Although tegaserod is not approved for intravenous administration, data regarding the mean volume of distribution of tegaserod at steady-state is recorded as 368 ± 223 L following research of tegaserod administered intravenously ⁶.

Protein binding

The protein binding recorded for tegaserod is about 98% ⁶.

Metabolism

Tegaserod is ultimately metabolized by way of hydrolysis and direct glucuronidation ^6,4. The substance is firstly hydrolyzed in the stomach ^6,4. It then undergoes oxidization and then conjugation to produce the main circulating tegaserod metabolite in human plasma, the so-called M29 metabolite, or 5-methoxyindole-3-carboxylic acid ^6,4. Nevertheless, it has been determined that this main circulating metabolite has negligible affinity for 5-HT(4) receptors in vitro ^6,4. Furthermore, tegaserod can also experience direct N-glucuronidation at each of its three guanidine nitrogens which leads to the generation of three isomeric N-glucuronides - the so-called M43.2, M43.8, and M45.3 metabolites ⁴.

• Tegaserod
  5-methoxyindole-3-carboxylic acid

Route of elimination

Approximately two-thirds of an orally administered dose of tegaserod is excreted unchanged in the feces, with the remaining one-third excreted in the urine as metabolites ⁶.

Half life

The mean terminal elimination half-life documented for tegaserod ranges from 4.6 to 8.1 hours following oral administration ⁶.

Clearance

Although tegaserod is not approved for intravenous administration, data regarding the mean plasma clearance of tegaserod is documented as 77 ± 15 L/h following research of tegaserod administered intravenously ⁶.

Toxicity

Single oral doses of 120 mg (which is 20 times the recommended dose) of tegaserod were administered to three healthy subjects in one study ⁶. All three subjects developed diarrhea and headache. Two of these subjects also reported intermittent abdominal pain and one developed orthostatic hypotension ⁶. In 28 healthy subjects exposed to 90 to 180 mg per day of tegaserod (which is 7.5 to 15 times the recommended daily dosage) for several days, adverse reactions were diarrhea (100%), headache (57%), abdominal pain (18%), flatulence (18%), nausea (7%), and vomiting (7%) ⁶.

Although available data from case reports with tegaserod use in pregnant women have not identified a drug-associated risk of major birth defects, miscarriage, or adverse maternal or fetal outcomes, animal studies involving maternal dietary administration of tegaserod with doses 45 to 71 times the recommended dose demonstrated decreased body weight, delays in developmental landmarks, and decreased survival in rat pups ⁶. Caution and careful consideration of risks versus benefits are recommended before administering tegaserod to a pregnant woman.

Despite there being little if any data available regarding the presence of tegaserod in human milk, the effects on the breastfed infant, or the effects on milk production, tegaserod and its metabolites are present in rat milk and the milk to plasma concentration ratio is very high in rats ⁶. Subsequently, because of the potential for serious reactions in the breastfed infant, including tumorigenicity, breastfeeding is not recommended during treatment with tegaserod ⁶.

The safety and effectiveness of tegaserod in pediatric patients has not yet been established ⁶.

Tegaserod is not indicated in patients that are aged 65 years or older ⁶.

Tegaserod was not carcinogenic in rats given oral dietary doses up to 180 mg/kg/day (approximately 93 to 111 times the recommended dose based on AUC) for 110 to 124 weeks ⁶. In mice, dietary administration of tegaserod for 104 weeks produced mucosal hyperplasia and adenocarcinoma of the small intestine at 600 mg/kg/day (approximately 83 to 110 times the recommended dose based on AUC) ⁶. There was no evidence of carcinogenicity at lower doses (3 to 35 times the recommended dose based on AUC) ⁶. Tegaserod was not genotoxic in the in vitro Chinese hamster lung fibroblast (CHL/V79) cell chromosomal aberration and forward mutation test, the in vitro rat hepatocyte unscheduled DNA synthesis (UDS) test or the in vivo mouse micronucleus test ⁶. The results of the Ames test for mutagenicity were equivocal. Tegaserod at oral (dietary) doses up to 240 mg/kg/day (approximately 57 times the recommended dose based on AUC) in male rats and 150 mg/kg/day (approximately 42 times the recommended dose based on AUC) in female rats was found to have no effect on fertility and reproductive performance ⁶.

Inhibition of the hERG (human Ether-a-go-go-Related Gene) channel was evident only in the micromolar concentration range with an IC50 of 13 micromolar (approximately 1300 times the Cmax in humans at the recommended dose) ⁶. In in vitro studies, tegaserod had no effects on impulse conduction in isolated guinea pig papillary muscle at up to 100 times the Cmax in humans, Langendorff-perfused isolated rabbit heart (QT interval) at up to 1000 times the Cmax in humans, or human atrial myocytes at multiples up to 10 times the Cmax in humans ⁶. The major metabolite, M29, had no effect on QT in the Langendorff-perfused isolated rabbit heart at multiples up to 323 times the Cmax in humans ⁶.

In anesthetized and conscious dogs, tegaserod at doses up to 92 to 134 times the recommended dose based on Cmax did not alter heart rate, QRS interval duration, QTc or other ECG parameters ⁶. In chronic toxicology studies in rats and dogs, there were no treatment-related changes in cardiac morphology after tegaserod administration at doses up to 660 times the recommended dose based on AUC ⁶.

Although tegaserod is expected to bind to 5-HT2B receptors in humans at the recommended dose, there does not appear to be any potential for heart valve injury based on functional evidence of 5-HT2B receptor antagonism ⁶.

Studies with isolated coronary and mesenteric blood vessels from non-human primates and humans showed no vasoconstrictor effect at concentrations approximately 100 times the human Cmax ⁶. Tegaserod exhibited antagonism of 5-HT-mediated vasoconstriction via 5-HT1B receptors ⁶. In rat thoracic aortic rings that were pre-constricted with phenylephrine or norepinephrine, tegaserod produced vasorelaxation, with IC50 values 6 and 64 times the Cmax plasma concentrations in humans, respectively ⁶. No effects were observed in the basal tone of aortic rings at concentrations up to 1000 times the human Cmax ⁶.

In studies with an anesthetized rat model for measuring macro- and micro-circulation of the colon, intraduodenal dosing with tegaserod (approximately 7 times the recommended dose based on Cmax) produced no clinically relevant effect on blood pressure, heart rate, or vascular conductance ⁶.

Affected organisms

• Humans and other mammals

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.

• All Drugs
• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental

Drug	Interaction
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(R)-warfarin	The metabolism of (R)-warfarin can be decreased when combined with Tegaserod.
(S)-Warfarin	The metabolism of (S)-Warfarin can be decreased when combined with Tegaserod.
1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine	The metabolism of Tegaserod can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine.
2,5-Dimethoxy-4-ethylamphetamine	The risk or severity of serotonin syndrome can be increased when Tegaserod is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamine	The risk or severity of serotonin syndrome can be increased when Tegaserod is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
4-Bromo-2,5-dimethoxyamphetamine	The risk or severity of serotonin syndrome can be increased when Tegaserod is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-Methoxyamphetamine	The metabolism of 4-Methoxyamphetamine can be decreased when combined with Tegaserod.
5-methoxy-N,N-dimethyltryptamine	The metabolism of 5-methoxy-N,N-dimethyltryptamine can be decreased when combined with Tegaserod.
6-O-benzylguanine	The metabolism of 6-O-benzylguanine can be decreased when combined with Tegaserod.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline	The risk or severity of serotonin syndrome can be increased when Tegaserod is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.

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Severity
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Food Interactions

• Take before a meal. To increase absorption, take 30 minutes before a meal.

References

Synthesis Reference

Sundaram Venkataraman, Srinivasulu Gudipati, Brahmeshwararao Mandava Venkata Naga, Goverdhan Banda, Radhakrishna Singamsetty, "Process for preparing form I of tegaserod maleate." U.S. Patent US20050272802, issued December 08, 2005.

US20050272802

General References

1. Beattie DT, Smith JA, Marquess D, Vickery RG, Armstrong SR, Pulido-Rios T, McCullough JL, Sandlund C, Richardson C, Mai N, Humphrey PP: The 5-HT4 receptor agonist, tegaserod, is a potent 5-HT2B receptor antagonist in vitro and in vivo. Br J Pharmacol. 2004 Nov;143(5):549-60. Epub 2004 Oct 4. [PubMed:15466450]
2. Talley NJ: Irritable bowel syndrome. Intern Med J. 2006 Nov;36(11):724-8. doi: 10.1111/j.1445-5994.2006.01217.x. [PubMed:17040359]
3. Borman RA, Tilford NS, Harmer DW, Day N, Ellis ES, Sheldrick RL, Carey J, Coleman RA, Baxter GS: 5-HT(2B) receptors play a key role in mediating the excitatory effects of 5-HT in human colon in vitro. Br J Pharmacol. 2002 Mar;135(5):1144-51. doi: 10.1038/sj.bjp.0704571. [PubMed:11877320]
4. Vickers AE, Zollinger M, Dannecker R, Tynes R, Heitz F, Fischer V: In vitro metabolism of tegaserod in human liver and intestine: assessment of drug interactions. Drug Metab Dispos. 2001 Oct;29(10):1269-76. [PubMed:11560869]
5. FDA approves the reintroduction of Zelnorm™ (tegaserod) for Irritable Bowel Syndrome with Constipation (IBS-C) in women under 65 [Link]
6. Tegaserod 2019 FDA Label [File]
7. EMA Refusal Assessment Report for Zelnorm (Tegaserod) [File]
8. FDA Joint Meeting of the Gastrointestinal Drugs Advisory Committee and Drug Safety and Risk Management Advisory Committee Briefing Document for Zelnorm (tegaserod maleate) [File]

External Links

KEGG Drug

D06056

PubChem Compound

5362436

PubChem Substance

46506519

ChemSpider

10609889

BindingDB

79022

RxNav

139778

ChEBI

51043

ChEMBL

CHEMBL76370

ZINC

ZINC000001545565

Therapeutic Targets Database

DAP001526

PharmGKB

PA130413154

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

Wikipedia

Tegaserod

ATC Codes

A06AX06 — Tegaserod

• A06AX — Other drugs for constipation
• A06A — DRUGS FOR CONSTIPATION
• A06 — DRUGS FOR CONSTIPATION
• A — ALIMENTARY TRACT AND METABOLISM

FDA label

Download (634 KB)

MSDS

Download (58.1 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
2	Completed	Treatment	Symptomatic Gastroespohageal Reflux Disease	1
2	Terminated	Not Available	Diabetic Gastropathy	1
2, 3	Terminated	Treatment	Constipation	1
3	Completed	Treatment	Chronic Constipation	1
3	Completed	Treatment	Constipation	1
3	Completed	Treatment	Dyspepsia	5
3	Completed	Treatment	Dyspepsia / Heartburn	1
3	Completed	Treatment	Gastro-esophageal Reflux Disease (GERD)	2
3	Terminated	Treatment	Constipation Predominant / Irritable Bowel Syndrome (IBS-C)	1
3	Terminated	Treatment	Opioid Induced Constipation (OIC)	2
4	Completed	Treatment	Chronic Constipation	1
4	Completed	Treatment	Constipation	1
4	Completed	Treatment	IBS-C and IBS With Mixed Bowel Habits	1
4	Terminated	Treatment	Chronic Constipation	1
4	Terminated	Treatment	Diabetes / Gastroparesis	1
Not Available	No Longer Available	Not Available	Chronic idiopathic constipation (CIC) / Constipation-predominant Irritable Bowel Syndrome (IBS-C)	1
Not Available	Terminated	Treatment	Constipation / Disease, Chronic	1
Not Available	Unknown Status	Treatment	Constipation	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

• Murfreesboro Pharmaceutical Nursing Supply
• Novartis AG

Dosage forms

Form	Route	Strength
Tablet	Oral	2 mg/1
Tablet	Oral	6 mg/1

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
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US5510353	No	1996-04-23	2013-04-26

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Filed On
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Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	155 °C	Not Available
logP	2.6	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0288 mg/mL	ALOGPS
logP	2.76	ALOGPS
logP	2.95	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	15.24	ChemAxon
pKa (Strongest Basic)	8.5	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	85.29 Å2	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	110.25 m3·mol-1	ChemAxon
Polarizability	34.96 Å3	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.9973
Blood Brain Barrier	+	0.7842
Caco-2 permeable	-	0.5939
P-glycoprotein substrate	Substrate	0.921
P-glycoprotein inhibitor I	Non-inhibitor	0.8978
P-glycoprotein inhibitor II	Non-inhibitor	0.959
Renal organic cation transporter	Inhibitor	0.5488
CYP450 2C9 substrate	Non-substrate	0.8522
CYP450 2D6 substrate	Non-substrate	0.5492
CYP450 3A4 substrate	Non-substrate	0.6565
CYP450 1A2 substrate	Non-inhibitor	0.53
CYP450 2C9 inhibitor	Non-inhibitor	0.7096
CYP450 2D6 inhibitor	Non-inhibitor	0.7807
CYP450 2C19 inhibitor	Non-inhibitor	0.6372
CYP450 3A4 inhibitor	Non-inhibitor	0.8954
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.7654
Ames test	Non AMES toxic	0.5434
Carcinogenicity	Non-carcinogens	0.7783
Biodegradation	Not ready biodegradable	0.9972
Rat acute toxicity	2.6038 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.5123
hERG inhibition (predictor II)	Non-inhibitor	0.8334

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Taxonomy

Description

This compound belongs to the class of organic compounds known as indoles. These are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

Indoles

Alternative Parents

Anisoles / Alkyl aryl ethers / Substituted pyrroles / Heteroaromatic compounds / Guanidines / Carboximidamides / Azacyclic compounds / Organopnictogen compounds / Imines / Hydrocarbon derivatives

Substituents

Indole / Anisole / Alkyl aryl ether / Substituted pyrrole / Benzenoid / Pyrrole / Heteroaromatic compound / Guanidine / Azacycle / Ether

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

guanidines, indoles, carboxamidine, hydrazines (CHEBI:51043)

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Drug created on June 13, 2005 07:24 / Updated on March 01, 2020 23:40