SB-423557

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C28H36N2O4
Molecular Weight	464.5964
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CCOC(=O)CCC1=CC=C(OC[C@H](O)CNC(C)(C)CC2CC3=C(C2)C=CC=C3)C(=C1)C#N

InChI

InChIKey=WOOHSVAEAZCDLR-RUZDIDTESA-N

InChI=1S/C28H36N2O4/c1-4-33-27(32)12-10-20-9-11-26(24(13-20)17-29)34-19-25(31)18-30-28(2,3)16-21-14-22-7-5-6-8-23(22)15-21/h5-9,11,13,21,25,30-31H,4,10,12,14-16,18-19H2,1-3H3/t25-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C28H36N2O4
Molecular Weight	464.5964
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

Substance Class	Chemical
Record UNII	VQF6R9B69W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SB-423557

Common Name

English

NPSP-790

Preferred Name

English

ETHYL 3-(3-CYANO-4-((2R)-2-HYDROXY-3-((2-INDAN-2-YL-1,1-DIMETHYL-ETHYL)AMINO)PROPOXY)PHENYL)PROPANOATE

Systematic Name

English

BENZENEPROPANOIC ACID, 4-CYANO-3-((2R)-3-((2-(2,3-DIHYDRO-1H-INDEN-2-YL)-1,1-DIMETHYLETHYL)AMINO)-2-HYDROXYPROPOXY)-, ETHYL ESTER

Systematic Name

English

SB-423557-A

Code

English

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Code System

Code

Type

Description

CAS

351490-26-1

PRIMARY

PUBCHEM

121596630

PRIMARY

FDA UNII

VQF6R9B69W

PRIMARY

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Related Record

Type

Details


					615K7YBS59

SB-423562

METABOLITE ACTIVE -> PRODRUG

Comments:

Here we describe two novel, short-acting calcium-sensing receptor antagonists (SB-423562 and its orally bioavailable precursor, SB-423557) that elicit transient PTH release from the parathyroid gland in several preclinical species and in humans. In an ovariectomized rat model of bone loss, daily oral administration of SB-423557 promoted bone formation and improved parameters of bone strength at lumbar spine, proximal tibia and midshaft femur. Chronic administration of SB-423557 did not increase parathyroid cell proliferation in rats. In healthy human volunteers, single doses of intravenous SB-423562 and oral SB-423557 elicited transient elevations of endogenous PTH concentrations in a profile similar to that observed with subcutaneously administered PTH. Both agents were well tolerated in humans. Transient increases in serum calcium, an expected effect of increased parathyroid hormone concentrations, were observed post-dose at the higher doses of SB-423557 studied.

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