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Details

Stereochemistry ACHIRAL
Molecular Formula C28H52O7P2
Molecular Weight 562.6558
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TETRAISOPROPYL 2-(3,5-DI-TERT-BUTYL-4-HYDROXYPHENYL)ETHYL-1,1-BIPHOSPHONATE

SMILES

CC(C)OP(=O)(OC(C)C)C(CC1=CC(=C(O)C(=C1)C(C)(C)C)C(C)(C)C)P(=O)(OC(C)C)OC(C)C

InChI

InChIKey=YLJOVCWVJCDPLN-UHFFFAOYSA-N
InChI=1S/C28H52O7P2/c1-18(2)32-36(30,33-19(3)4)25(37(31,34-20(5)6)35-21(7)8)17-22-15-23(27(9,10)11)26(29)24(16-22)28(12,13)14/h15-16,18-21,25,29H,17H2,1-14H3

HIDE SMILES / InChI

Molecular Formula C28H52O7P2
Molecular Weight 562.6558
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Tetraisopropyl 2-(3,5-Di-Tert-Butyl-4-Hydroxyphenyl)Ethyl-1,1-Biphosphonate (also known as SR-9223I and SR 45023A) is a gem-diphosphonate derivative patented by Symphar S. A. as an antihypertensive and anti-inflammatory agent. Tetraisopropyl 2-(3,5-Di-Tert-Butyl-4-Hydroxyphenyl)Ethyl-1,1-Biphosphonate acts as 3-hydroxy-3-methylglutaryl reductase inhibitor, besides that SR-9223I suppresses acyl-CoA: cholesterol acyltransferase activity and prevents the oxidation of plasma lipoproteins. In preclinical studies, SR-9223i reduces blood cholesterol concentrations in mice, hamsters, dogs, and monkeys. SR-9223i inhibits the growth of a wide variety of tumor cell lines in vitro and triggered apoptosis in HL60 cells in less than 2 h. SR-9223i induces caspase-3 activity at concentrations similar to it’s IC(50) values for cell proliferation. Unfortunately, in clinical trials SR-9223I failed to demonstrate efficacy in patients with refractory melanoma and further development was discontinued.

Approval Year

PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

human: 200 mg per day continuously for 28 days mice, hamsters: 200 mg/kg/day dogs: 25-75 mg/kg/day monkeys: 25 mg/kg/day
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:53:23 GMT 2023
Edited
by admin
on Fri Dec 15 15:53:23 GMT 2023
Record UNII
JQ95208805
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TETRAISOPROPYL 2-(3,5-DI-TERT-BUTYL-4-HYDROXYPHENYL)ETHYL-1,1-BIPHOSPHONATE
Common Name English
SR-9223I
Code English
SR-45023A
Code English
SR 9223I
Code English
TETRAISOPROPYL 2-(3,5-DI-TERT-BUTYL-4-HYDROXYPHENYL)ETHYL-1,1-DIPHOSPHONATE
Common Name English
Code System Code Type Description
CAS
126411-13-0
Created by admin on Fri Dec 15 15:53:23 GMT 2023 , Edited by admin on Fri Dec 15 15:53:23 GMT 2023
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EPA CompTox
DTXSID80925540
Created by admin on Fri Dec 15 15:53:23 GMT 2023 , Edited by admin on Fri Dec 15 15:53:23 GMT 2023
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PUBCHEM
176405
Created by admin on Fri Dec 15 15:53:23 GMT 2023 , Edited by admin on Fri Dec 15 15:53:23 GMT 2023
PRIMARY
FDA UNII
JQ95208805
Created by admin on Fri Dec 15 15:53:23 GMT 2023 , Edited by admin on Fri Dec 15 15:53:23 GMT 2023
PRIMARY
NCI_THESAURUS
C1873
Created by admin on Fri Dec 15 15:53:23 GMT 2023 , Edited by admin on Fri Dec 15 15:53:23 GMT 2023
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