A1IVL

1-[(~{E})-(5-methoxy-1~{H}-indol-3-yl)methylideneamino]-3-pentyl-guanidine

Created:	2024-12-02
Last modified:	2025-05-21

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1 entries where A1IVL is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	45
Chiral Atom Count	0
Bond Count	46
Aromatic Bond Count	10

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Chemical Component Summary
Name	1-[(~{E})-(5-methoxy-1~{H}-indol-3-yl)methylideneamino]-3-pentyl-guanidine
Systematic Name (OpenEye OEToolkits)	1-[(~{E})-(5-methoxy-1~{H}-indol-3-yl)methylideneamino]-3-pentyl-guanidine
Formula	C₁₆ H₂₃ N₅ O
Molecular Weight	301.387
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	CACTVS	3.385	CCCCCNC(=N)NN=Cc1c[nH]c2ccc(OC)cc12
SMILES	OpenEye OEToolkits	2.0.7	CCCCCNC(=N)NN=Cc1c[nH]c2c1cc(cc2)OC
Canonical SMILES	CACTVS	3.385	CCCCCNC(=N)N/N=C/c1c[nH]c2ccc(OC)cc12
Canonical SMILES	OpenEye OEToolkits	2.0.7	[H]/N=C(/NCCCCC)\N/N=C/c1c[nH]c2c1cc(cc2)OC
InChI	InChI	1.06	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+
InChIKey	InChI	1.06	IKBKZGMPCYNSLU-RGVLZGJSSA-N

Drug Info: DrugBank

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License

DrugBank ID	DB01079 ?
Name	Tegaserod
Groups	withdrawn investigational approved
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2002 for the treatment of irritable bowel syndrome with constipation (IBS-C).[L5918,F4229] It was, however, voluntarily withdrawn from widespread use in the US market in 2007 after concerns arose over the possibility that tegaserod could potentially cause dangerous cardiovascular events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.[L5918,F4229] 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.[L5918,F4229] Zelnorm (tegaserod) by Sloan Pharma subsequently gained re-approval in April of 2019.[L5918] Nevertheless, tegaserod remains un-approved in certain regions.[F4226] 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.[L5918,A11044,A176762,F4229,F4223]
Synonyms	Tégasérod Tegaserod maleate Tegaserodum 1-(((5-Methoxyindol-3-yl)methylene)amino)-3-pentylguanidine Tegaserod
Brand Names	Zelnorm
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) [F4223, F4229]. The safety and effectiveness of tegaserod in men with IBS-C have not been established [F4223, F4229].
Categories	Alimentary Tract and Metabolism Antidepressive Agents BCRP/ABCG2 Substrates Central Nervous System Depressants 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 Serotonin 4 Receptor Agonists Serotonin 5-HT2 Receptor Antagonists Serotonin 5-HT2A Receptor Antagonists Serotonin 5-HT2C Receptor Antagonists Serotonin Agents Serotonin Receptor Antagonists Serotonin-4 Receptor Agonist
ATC-Code	A06AX06
CAS number	145158-71-0

Drug Targets

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License

Name	Target Sequence	Pharmacological Action	Actions
5-hydroxytryptamine receptor 4	MDKLDANVSSEEGFGSVEKVVLLTFLSTVILMAILGNLLVMVAVCWDRQL...	unknown	antagonist,partial agonist
5-hydroxytryptamine receptor 2C	MVNLRNAVHSFLVHLIGLLVWQSDISVSPVAAIVTDIFNTSDGGRFKFPD...	unknown	antagonist
5-hydroxytryptamine receptor 2A	MDILCEENTSLSSTTNSLMQLNDDTRLYSNDFNSGEANTSDAFNWTVDSE...	unknown	antagonist
5-hydroxytryptamine receptor 2B	MALSYRVSELQSTIPEHILQSTFVHVISSNWSGLQTESIPEEMKQIVEEQ...	unknown	antagonist
Cytochrome P450 1A2	MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...	unknown	inhibitor
Cytochrome P450 2C8	MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI...	unknown	inhibitor
Cytochrome P450 2D6	MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...	unknown	substrate,inhibitor
Cytochrome P450 2E1	MSALGVTVALLVWAAFLLLVSMWRQVHSSWNLPPGPFPLPIIGNLFQLEL...	unknown	inhibitor
Sodium-dependent serotonin transporter	METTPLNSQKQLSACEDGEDCQENGVLQKVVPTPGDKVESGQISNGYSAV...	unknown	substrate,inhibitor
Broad substrate specificity ATP-binding cassette transporter ABCG2	MSSSNVEVFIPVSQGNTNGFPATASNDLKAFTEGAVLSFHNICYRVKLKS...	unknown	substrate
ATP-dependent translocase ABCB1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682