Ici-118551
Basic information
- CAS
72795-19-8- Standard SMILES
Cc1ccc(OC[C@H](O)[C@H](C)NC(C)C)c2c1CCC2- InChIKey
VFIDUCMKNJIJTO-BBRMVZONSA-N- Molecular formula
- C17H27NO2
- Average molar mass
- 277.4 g/mol
- Monoisotopic mass
- 277.2041791
Overview
ICI 118551 is an indane substituted at position 7 by a methyl group and at position 4 by a 3-(isopropylamino)-2-hydroxybutoxy group (the 2R,3S-diastereomer). It has a role as a beta-adrenergic antagonist. It is an aromatic ether, a secondary alcohol, a member of indanes and a secondary amino compound.
Names & identifiers
- Preferred name
- Ici-118551
- IUPAC
- (2R,3S)-1-[(7-methyl-2,3-dihydro-1H-inden-4-yl)oxy]-3-(propan-2-ylamino)butan-2-ol
- English name
- ICI-118,551
- Molecular formula
- C17H27NO2
- Molecular weight
- 277.4
Names & synonyms
ICI-118551Ici 118551CHEBI:73289(2R,3S)-3-(isopropylamino)-1-((7-methyl-2,3-dihydro-1H-inden-4-yl)oxy)butan-2-ol(2R,3S)-3-(isopropylamino)-1-[(7-methyl-2,3-dihydro-1H-inden-4-yl)oxy]butan-2-olRefChem:923280(2S,3S)-1-((7-methyl-2,3-dihydro-1H-inden-4-yl)oxy)-3-(propan-2-ylamino)butan-2-olICI 118,55172795-19-8(2R,3S)-1-[(7-methyl-2,3-dihydro-1H-inden-4-yl)oxy]-3-(propan-2-ylamino)butan-2-olCHEMBL198059(2R,3S)-1-[(7-methyl-2,3-dihydro-1H-inden-4-yl)oxy]-3-[(propan-2-yl)amino]butan-2-ol
Show more names
Ici 111,581ICI-118,551ICI118551HClICI 118,551 HYDROCHLORIDEICI 118551 Hydrochloride ((±ICI-118-551 HYDROCHLORIDE HIGHLY SELECTI VE B2 AErythro-DL-1-(7-methylindan-4-yloxy)-3-isopropylaminobutan-2-olerythro-DL-1-(7-Methylindan-4-yloxy)-3-isopropylamino-2-butanol(2R,3S)-rel-1-[(2,3-Dihydro-7-methyl-1H-inden-4-yl)oxy]-3-[(1-methylethyl)amino]-2-butanol
72795-20-1ICI1185512-Butanol, 1-((2,3-dihydro-7-methyl-1H-inden-4-yl)oxy)-3-((1-methylethyl)amino)-, (2R,3S)-rel-2-Butanol, 1-[(2,3-dihydro-7-methyl-1H-inden-4-yl)oxy]-3-[(1-methylethyl)amino]-, (2R,3S)-rel-Tocris-0821Lopac-I-127Pertuzumab (anti-HER2)5GST9PQ295
Properties
Computed structural properties
- XLogP
- 3.3
- Topological polar surface area
- 41.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 6
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 295
Physicochemical properties
- Melting point
- 217 · 217-219°C
- Boiling point
- 439.3 · 439.3±45.0 °C(Predicted)
- Density
- 1.045 · 1.045±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
- solubility
- 7.3 mg/mL · ethanol: 7.3 mg/mL
- form
- powder
- pka
- 13.87 · 13.87±0.20(Predicted)
- color
- white
- InChI
- 1S/C17H27NO2/c1-11(2)18-13(4)16(19)10-20-17-9-8-12(3)14-6-5-7-15(14)17/h8-9,11,13,16,18-19H,5-7,10H2,1-4H3/t13-,16-/m0/s1
- InChIKey
- VFIDUCMKNJIJTO-BBRMVZONSA-N
- SMILES
- N([C@H]([C@@H](O)COc1c2c(c(cc1)C)CCC2)C)C(C)C
- EWG's Food Scores
- 1 · 1
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- WGK Germany
- 3 · 3
- Storage Class
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Drugs that bind to but do not activate beta-adrenergic receptors thereby blocking the actions of beta-adrenergic agonists. Adrenergic beta-antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches, and anxiety.
Applications
UsesThe (R,R)-enantiomer of ICI 118551 as highly selective β2-adrenoceptor antagonist. The S,S-enantiomer is the most potent.
Additional notes
DefinitionChEBI: ICI 118551 is an indane substituted at position 7 by a methyl group and at position 4 by a 3-(isopropylamino)-2-hydroxybutoxy group (the 2R,3S-diastereomer). It has a role as a beta-adrenergic antagonist. It is a member of indanes, an aromatic ether, a secondary alcohol and a secondary amino compound.
Related reactions
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Compound notes
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