Basic information
- CAS
152811-62-6- Standard SMILES
CCCCN1CCC(CNC(=O)c2c3n(c4ccccc24)CCCO3)CC1- InChIKey
KVCSJPATKXABRQ-UHFFFAOYSA-N- Molecular formula
- C22H31N3O2
- Average molar mass
- 369.5 g/mol
- Monoisotopic mass
- 369.24162723
Overview
Piboserod (SB 207266) is a selective 5-HT(4) receptor antagonist.
Names & identifiers
- Preferred name
- Piboserod
- IUPAC
- N-[(1-butylpiperidin-4-yl)methyl]-3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxamide
- English name
- PIBOSEROD,2H-(1,3)OXAZINO(3,2-A)INDOLE-10-CARBOXAMIDE, N-((1-BUTYL-4-PIPERIDINYL)METHYL)-3,4-DIHYDRO-
- Molecular formula
- C22H31N3O2
- Molecular weight
- 369.5
Names & synonyms
Piboserod152811-62-6N-[(1-butylpiperidin-4-yl)methyl]-3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxamideN-((1-butylpiperidin-4-yl)methyl)-3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxamideSB2072564UQ3S81B25DTXSID60165129N-[(1-BUTYLPIPERIDIN-4-YL)METHYL]-2H,3H,4H-[1,3]OXAZINO[3,2-A]INDOLE-10-CARBOXAMIDEpiboserodumN-((1-butylpiperidin-4-yl)methyl)-2H,3H,4H-(1,3)oxazino(3,2-a)indole-10-carboxamideN-((1-butylpiperidin-4-yl)methyl)-3,4-dihydro-2H-(1,3)oxazino(3,2-a)indole-10-carboxamideRefChem:174124
Show more names
CS-2135Unii-4uq3S81B25SB207266(Piboserod)Piboserod(SB-207266)SB-207266 >=98% (HPLC)Piboserod, 10 mM in DMSO
DTXCID8087620110-127-4SB-207266MFCD00923681SB 207266N-[(1-butyl-4-piperidinyl)methyl]-3,4-dihydro-2H-[1,3]-oxazino[3,2-a]indole-10-carboxamidePiboserod [INN]PIBOSEROD,2H-(1,3)OXAZINO(3,2-A)INDOLE-10-CARBOXAMIDE, N-((1-BUTYL-4-PIPERIDINYL)METHYL)-3,4-DIHYDRO-
Properties
Computed structural properties
- XLogP
- 3.7
- Topological polar surface area
- 46.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 6
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 492
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 110 · 110-113°
- Boiling point
- 570.3 · 570.3±35.0 °C(Predicted)
- Density
- 1.22 · 1.22±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 30 mg/mL; · DMF: 30 mg/mL; DMSO: 20 mg/mL; Ethanol: 30 mg/mL; Ethanol:PBS (pH7.2)(1:20): 0.05 mg/mL
- form
- powder
- pka
- 13.86 · 13.86±0.20(Predicted)
- color
- white to beige
- InChI
- 1S/C22H31N3O2/c1-2-3-11-24-13-9-17(10-14-24)16-23-21(26)20-18-7-4-5-8-19(18)25-12-6-15-27-22(20)25/h4-5,7-8,17H,2-3,6,9-16H2,1H3,(H,23,26)
- InChIKey
- KVCSJPATKXABRQ-UHFFFAOYSA-N
- SMILES
- O=C(NCC1CCN(CCCC)CC1)C2=C3N(CCCO3)C4=C2C=CC=C4
- FDA UNII
- 4 UQ3S81B25 · 4UQ3S81B25
Safety & regulation
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Safety data
- wgk
- WGK 3
- ridadr
- UN 2811 6.1 / PGIII
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard statements
- H301
- Hazard Classifications
- Acute Tox. 3 Oral
- Precautionary statements
- P301+P310+P330
Chemistry & industry
Pharmacology
Pharmacodynamics
GlaxoSmithKline was investigating piboserod, a 5HT4 antagonist, for the treatment of atrial fibrillation. Phase II trials were ongoing in March 2004, but by December of that year, development had been discontinued. Piboserod had previously being investigated for the treatment of irritable bowel syndrome (IBS), but development for this indication was terminated in 1999.
Mechanism of Action
Piboserod appears to act as a specific antagonist of one of the receptors for 5-hydroxytryptamine, the 5-HT4 receptor. The 5-HT4 receptor antagonists are thought to antagonize both the ability of serotonin to sensitize the peristaltic reflex and 5-HT-induced defecation, at least in animal studies. As 5-HT4 receptors are present in human atrial cells and when stimulated may cause atrial arrhythmias, piboserod was under investigation in clinical trials for atrial fibrillation.
Applications
UsesTreatment of irritable bowel syndrome (selective 5HT4receptor antagonist).
UsesPiboserod is a 5-HT4 receptor antagonist which has shown positive results as a Hepatitis C virus (HCV) entry inhibtor.
Suppliers58 total
北京华美互利生物化工010-56205725 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
湖北科乐精细化工有限公司027-59101668 19945030958 · [email protected]
上海波以尔化工有限公司[email protected]
Related reactions
2 records
Compound notes
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