LUNACALCIPOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C28H42O4S
Molecular Weight	474.696
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	3
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC=C([C@H](C)C\C=C\S(=O)(=O)C(C)(C)C)[C@@]1(C)CCC\C2=C/C=C3/C[C@@H](O)C[C@H](O)C3=C

InChI

InChIKey=RFQHCLMGLJGZNV-UXXOMSPDSA-N

InChI=1S/C28H42O4S/c1-19(9-8-16-33(31,32)27(3,4)5)24-13-14-25-21(10-7-15-28(24,25)6)11-12-22-17-23(29)18-26(30)20(22)2/h8,11-13,16,19,23,25-26,29-30H,2,7,9-10,14-15,17-18H2,1,3-6H3/b16-8+,21-11+,22-12-/t19-,23-,25+,26+,28-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C28H42O4S
Molecular Weight	474.696
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	3
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/30286109 | https://www.ncbi.nlm.nih.gov/pubmed/20347976 | http://www.opkorenal.com/news/lunacalcipol.html | https://adisinsight.springer.com/drugs/800022679

Lunacalcipol (CTA-018 or MT-2832) is a vitamin D analog having a dual mechanism of action. It inhibits CYP24A1 and induced VDR expression. It was being developed for the treatment of clinical consequences of vitamin D insufficiency and secondary hyperparathyroidism associated with chronic kidney disease. Lunacalcipol development has been discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial 1 Target ID: Q07973 Gene ID: 1591.0 Gene Symbol: CYP24A1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/30286109 \| https://www.ncbi.nlm.nih.gov/pubmed/20347976	Inhibitor 8297		27.0 nM [IC50]

PubMed

Title	Date	PubMed
Vitamin D analogues targeting CYP24 in chronic kidney disease.	2010 Jul	20347976
E-pharmacophore filtering and molecular dynamics simulation studies in the discovery of potent drug-like molecules for chronic kidney disease.	2016 Oct	26513595
A theoretical insight to understand the molecular mechanism of dual target ligand CTA-018 in the chronic kidney disease pathogenesis.	2018	30286109

Patents

Sample Use Guides

In Vivo Use Guide

Phase II Four Week, Pharmacodynamic/Pharmacokinetic, Efficacy, and Safety Study of Lunacalcipol (CTA018). A total of 11 doses of lunacalcipol Injection (180 or 270 µg) given three times per week over 24 days (day 1 to day 24), administered not more often than every other day.

Route of Administration: Parenteral

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:53:33 GMT 2023` Edited by `admin` on `Sat Dec 16 17:53:33 GMT 2023`
Record UNII	XN4TL6M50Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LUNACALCIPOL

Official Name

English

LUNACALCIPOL [USAN]

Common Name

English

CTA018

Code

English

Lunacalcipol [WHO-DD]

Common Name

English

CTA-018

Code

English

lunacalcipol [INN]

Common Name

English

1,3-CYCLOHEXANEDIOL, 5-((2E)-2-((3AS,7AS)-1-((1R,3E)-4-((1,1-DIMETHYLETHYL)SULFONYL)-1- METHYL-3-BUTEN-1-YL)-3,3A,5,6,7,7A-HEXAHYDRO-7A-METHYL-4H-INDEN-4- YLIDENE)ETHYLIDENE)-4-METHYLENE-, (1R,3S,5Z)-

Common Name

English

(5Z,7E,16Z,23E)-(1S,3R)-25-NOR-25-T-BUTYLSULFONYL-9,10-SECO-5,7,10(19),16,23- CHOLESTAPENTAENE-1,3-DIOL

Common Name

English

Code System Code Type Description

NCI_THESAURUS

C170140