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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H40O3
Molecular Weight 412.6047
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 3
Charge 0

SHOW SMILES / InChI
Structure of CALCIPOTRIOL, 24R-

SMILES

[H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C3\C[C@@H](O)C[C@H](O)C3=C)[C@H](C)\C=C\[C@H](O)C4CC4

InChI

InChIKey=LWQQLNNNIPYSNX-CIJZWTHJSA-N
InChI=1S/C27H40O3/c1-17(6-13-25(29)20-8-9-20)23-11-12-24-19(5-4-14-27(23,24)3)7-10-21-15-22(28)16-26(30)18(21)2/h6-7,10,13,17,20,22-26,28-30H,2,4-5,8-9,11-12,14-16H2,1,3H3/b13-6+,19-7+,21-10-/t17-,22-,23-,24+,25+,26+,27-/m1/s1

HIDE SMILES / InChI
Molecular Formula C27H40O3
Molecular Weight 412.6047
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 3
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.medchemexpress.com/24R-Calcipotriol.html

24R-Calcipotriol (PRI 2202) is an impurity of Calcipotriol. 24R-Calcipotriol shows the strong antiproliferative activity on the human breast cancer cell line MCF-7

Originator

Approval Year

Unknown
139594
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
The antitumor effect of lowered doses of cytostatics combined with new analogs of vitamin D in mice.
2007 Sep-Oct
Patents

Patents

JP2002541188A
5
WO0061123
1

Sample Use Guides

In Vivo Use Guide
Mammary gland cancer 4T1-bearing mice were treated by 24R-Calcipotriol alone and 24R-Calcipotriol with cytostatic (cyclophosphamide). Cytostatic was administered i.p., dose 20 mg/kg on days 2, 5, 7, 9, 12, 14, 16, 19 and 21; 3vitamin D analogs were administered s.c., dose 10 Мg/kg on the same days as Cytostatic
Route of Administration: Transdermal
In Vitro Use Guide
The cultured MCF-7 cells were exposed to the 24R-Calcipotriol at the concentration of 10 nM for 24 h.
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:39:54 UTC 2023
Edited
by admin
on Sat Dec 16 01:39:54 UTC 2023
Record UNII
TYF37XV46I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CALCIPOTRIOL, 24R-
Common Name English
24-EPI--CALCIPOTRIOL
Common Name English
9,10-SECOCHOLA-5,7,10(19),22-TETRAENE-1,3,24-TRIOL, 24-CYCLOPROPYL-, (1.ALPHA.,3.BETA.,5Z,7E,22E,24R)-
Common Name English
PRI 2202
Code English
24R-CALCIPOTRIENE
Common Name English
24R-CALCIPOTRIOL
Common Name English
CALCIPOTRIENE IMPURITY D [USP IMPURITY]
Common Name English
1,3-CYCLOHEXANEDIOL, 5-((2E)-2-((1R,3AS,7AR)-1-((1R,2E,4R)-4-CYCLOPROPYL-4-HYDROXY-1-METHYL-2-BUTEN-1-YL)OCTAHYDRO-7A-METHYL-4H-INDEN-4-YLIDENE)ETHYLIDENE)-4-METHYLENE-, (1S,3S,5Z)-
Common Name English
(5Z,7E,22E,24R)-24-CYCLOPROPYL-9,10-SECOCHOLA-5,7,10(19),22-TETRAENE-1.ALPHA.,3.BETA.,24-TRIOL
Common Name English
CALCIPOTRIOL MONOHYDRATE IMPURITY D [EP IMPURITY]
Common Name English
PRI-2202
Code English
CALCIPOTRIOL IMPURITY D [EP IMPURITY]
Common Name English
Code System Code Type Description
FDA UNII
TYF37XV46I
Created by admin on Sat Dec 16 01:39:54 UTC 2023 , Edited by admin on Sat Dec 16 01:39:54 UTC 2023
PRIMARY
PUBCHEM
9547353
Created by admin on Sat Dec 16 01:39:54 UTC 2023 , Edited by admin on Sat Dec 16 01:39:54 UTC 2023
PRIMARY
CAS
112827-99-3
Created by admin on Sat Dec 16 01:39:54 UTC 2023 , Edited by admin on Sat Dec 16 01:39:54 UTC 2023
PRIMARY
Related Record Type Details
Structure of CALCIPOTRIENE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of CALCIPOTRIENE MONOHYDRATE
PARENT -> IMPURITY
NIH
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