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26921-17-5 molecular structure
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(2Z)-but-2-enedioic acid; tert-butyl[(2S)-2-hydroxy-3-{[4-(morpholin-4-yl)-1,2,5-thiadiazol-3-yl]oxy}propyl]amine

ChemBase ID: 131071
Molecular Formular: C17H28N4O7S
Molecular Mass: 432.49182
Monoisotopic Mass: 432.16787026
SMILES and InChIs

SMILES:
CC(C)(C)NC[C@@H](COc1c(nsn1)N1CCOCC1)O.C(=C\C(=O)O)\C(=O)O
Canonical SMILES:
O[C@H](COc1nsnc1N1CCOCC1)CNC(C)(C)C.OC(=O)/C=C\C(=O)O
InChI:
InChI=1S/C13H24N4O3S.C4H4O4/c1-13(2,3)14-8-10(18)9-20-12-11(15-21-16-12)17-4-6-19-7-5-17;5-3(6)1-2-4(7)8/h10,14,18H,4-9H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t10-;/m0./s1
InChIKey:
WLRMANUAADYWEA-NWASOUNVSA-N

Cite this record

CBID:131071 http://www.chembase.cn/molecule-131071.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2Z)-but-2-enedioic acid; tert-butyl[(2S)-2-hydroxy-3-{[4-(morpholin-4-yl)-1,2,5-thiadiazol-3-yl]oxy}propyl]amine
IUPAC Traditional name
maleic acid; timolol
(2Z)-but-2-enedioic acid; tert-butyl[(2S)-2-hydroxy-3-{[4-(morpholin-4-yl)-1,2,5-thiadiazol-3-yl]oxy}propyl]amine
Synonyms
S-(-)-1-(t-Butylamino)-3-[(4-morpholino-1,2,5-thiadiazol-3-yl)oxy]-2-propanol maleate salt
Timolol maleate salt
Betimol
Betime
Blocadren
Istalol
Timoptic
Timoptol
Optimol
(s)-Timolol maleate
(2S)-1-[(1,1-Dimethylethyl)amino]-3-[[4-(4-morpholinyl)-1,2,5-thiadiazol-3-yl]oxy]-2-propanol (2Z)-2-Butenedioate Salt
(S)-(-)-3-Morpholino-4-(3-tert-butylamino-2-hydroxypropoxy)-1,2,5-thiadiazole Hydrogen Maleate
(S)-(-)-Timolol Maleate
CAS Number
26921-17-5
EC Number
248-111-5
MDL Number
MFCD00058356
PubChem SID
24277810
162225349
PubChem CID
5281056

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 5281056 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 14.084203  H Acceptors
H Donor LogD (pH = 5.5) -1.86655 
LogD (pH = 7.4) -0.97262925  Log P 1.335706 
Molar Refractivity 83.92 cm3 Polarizability 31.508581 Å3
Polar Surface Area 79.74 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
ethanol: soluble expand Show data source
H2O: soluble expand Show data source
Apperance
White Solid expand Show data source
white to off-white powder expand Show data source
Melting Point
202-203 °C(lit.) expand Show data source
205-207°C expand Show data source
Optical Rotation
[α]25/D -5.4°, c = 4.9 in 1 M HCl(lit.) expand Show data source
Absorption Wavelength
ε1M/294 nm 8,700 expand Show data source
Storage Condition
Refrigerator expand Show data source
RTECS
UA8475000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
63-22 expand Show data source
Safety Statements
36 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H361 expand Show data source
GHS Precautionary statements
P281 expand Show data source
Personal Protective Equipment
Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
Gene Information
human ... ADRB1(153), ADRB2(154), ADRB3(155) expand Show data source
Mechanism of Action
Non-selective beta-adrenergic antagonist expand Show data source
Purity
≥98% (TLC) expand Show data source
Salt Data
Maleic Acid expand Show data source
Certificate of Analysis
Download expand Show data source
Application(s)
Anti-arrhythmia agent expand Show data source
Antihypertensive agent expand Show data source
Ophthalmic use (reduces intraocular pressure) expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - T6394 external link
Biochem/physiol Actions
Non-selective β-adrenoceptor antagonist; vasodilator; class II anti-arrhythmic; anti-glaucoma agent
Toronto Research Chemicals - T443710 external link
Antihypertensive; antiarrhythmic (class II); antianginal; antiglaucoma agent.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Wasson, et al.: J. Med. Chem., 15, 651 (1972)
  • • Franciosa, et al.: Clin. Pharmacol. Ther., 13, 138 (1972)
  • • Heel, R.C., et al.: Drugs, 17, 38 (1972)
  • • Rofman, B.A., et al.: Hypertension, 2, 643 (1972)
  • • Mazzo, D.J., et al.: Anal. Profiles Drug Subs., 16, 641
  • • Merck Index 12 9585. Karhuvaara et al (1989) b-Adrenoceptor antagonist activities and binding affinities of timolol enantiomers in rat atria. J.Pharm.Pharmacol. 41 649.
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PATENTS

PATENTS

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INTERNET

INTERNET

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