U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 GMT 2023
Edited
by admin
on Sat Dec 16 01:39:54 GMT 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 GMT 2023 , Edited by admin on Sat Dec 16 01:39:54 GMT 2023
PRIMARY
PUBCHEM
9547353
Created by admin on Sat Dec 16 01:39:54 GMT 2023 , Edited by admin on Sat Dec 16 01:39:54 GMT 2023
PRIMARY
CAS
112827-99-3
Created by admin on Sat Dec 16 01:39:54 GMT 2023 , Edited by admin on Sat Dec 16 01:39:54 GMT 2023
PRIMARY
Related Record Type Details
Structure of CALCIPOTRIENE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of CALCIPOTRIENE MONOHYDRATE
PARENT -> IMPURITY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966