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Details

Stereochemistry ABSOLUTE
Molecular Formula C30H46O3
Molecular Weight 454.6844
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 4
Charge 0

SHOW SMILES / InChI
Structure of SEOCALCITOL

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=C\C(O)(CC)CC

InChI

InChIKey=LVLLALCJVJNGQQ-SEODYNFXSA-N
InChI=1S/C30H46O3/c1-6-30(33,7-2)18-9-8-11-21(3)26-15-16-27-23(12-10-17-29(26,27)5)13-14-24-19-25(31)20-28(32)22(24)4/h8-9,11,13-14,18,21,25-28,31-33H,4,6-7,10,12,15-17,19-20H2,1-3,5H3/b11-8+,18-9+,23-13+,24-14-/t21-,25-,26-,27+,28+,29-/m1/s1

HIDE SMILES / InChI
Molecular Formula C30H46O3
Molecular Weight 454.6844
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 4
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://books.google.ru/books?id=p9VRjKlCXmcC&pg=PA71&lpg=PA71&dq=seocalcitol+discontinued&source=bl&ots=8CIlJR1gJm&sig=wj6rotcTmghtfbonv8nhNOKzKeo&hl=ru&sa=X&ved=0ahUKEwjOzvL4wujSAhXJjiwKHYoODxYQ6AEIKzAC#v=onepage&q=seocalcitol%20discontinued&f=false

Seocalcitol (EB 1089) is a vitamin D analog, and agonist of the vitamin D receptor. Antineoplastic activity of seocalcitol was tested in clinical trials against hepatocellular carcinoma, pancreatic, breast and colorectal cancer. Due to inconsistent results of clinical trials, development of seocalcitol was discontinued by Leo Pharma.

Originator

Leo Pharma
20
Curator's Comment: In June 2005, seocalcitol was licensed to Coguar Pharma http://www.nasdaq.com/markets/ipos/filing.ashx?filingid=4848351

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 0.02 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
656
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase I
428
Unknown

Approved Use

Unknown
Primary
Phase I
428
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
146 pg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/11037113
2.4 μg/kg 1 times / day multiple, oral
dose: 2.4 μg/kg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
SEOCALCITOL plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
738 pg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/11037113
2.4 μg/kg 1 times / day multiple, oral
dose: 2.4 μg/kg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
SEOCALCITOL plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.8 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/11037113
2.4 μg/kg 1 times / day multiple, oral
dose: 2.4 μg/kg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
SEOCALCITOL plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P009CVE
https://www.1pchem.com/search?query=1P009CVE
AK Scientific
4036AH
https://aksci.com/item_detail.php?cat=4036AH
AlchemyPharm
AP00502
https://www.alchemypharm.com/pharm/search.do?q=AP00502
AstaTech
41539
http://astatechinc.com/CPSResult.php?CRNO=41539
BLD Pharm
BD151041
http://www.bldpharm.com/search/Search.html?keyword=BD151041
BOC Sciences
134404-52-7
http://www.bocsci.com/description.asp?cas=134404-52-7
Cayman Chemical
21579
http://www.caymanchem.com/app/template/Product.vm/catalog/21579
MedChem Express
HY-32341
https://www.medchemexpress.com/search.html?q=HY-32341&ft=&fa=&fp=
MolPort
MolPort-023-277-025
https://www.molport.com/shop/molecule-link/MolPort-023-277-025
Tocris
3993
https://www.tocris.com/search.php?Type=QuickSearch&Value=3993
eMolecules
45475475
https://orderbb.emolecules.com/search/#?query=45475475
mcule
MCULE-1400666187
https://mcule.com/MCULE-1400666187/
PubMed

PubMed

TitleDatePubMed
EB1089: a new vitamin D analogue that inhibits the growth of breast cancer cells in vivo and in vitro.
1992 Dec 15
Actions of vitamin D3, analogs on human prostate cancer cell lines: comparison with 1,25-dihydroxyvitamin D3.
1995 Jan
Studies on two new vitamin D analogs, EB 1089 and KH 1060: effects on bone resorption and osteoclast recruitment in vitro.
1995 Oct
Cytotoxic effects of 1 alpha,25-dihydroxyvitamin D3 and synthetic vitamin D3 analogues on a glioma cell line.
1996 Feb 27
Apoptotic regression of MCF-7 xenografts in nude mice treated with the vitamin D3 analog, EB1089.
1998 Apr
A phase I study of the vitamin D analogue EB 1089 in patients with advanced breast and colorectal cancer.
1998 Jul
Effects of Seocalcitol (EB1089) on nitrosomethyl urea-induced rat mammary tumors.
2003 Aug
MNU-induced mammary gland carcinogenesis: chemopreventive and therapeutic effects of vitamin D and Seocalcitol on selected regulatory vitamin D receptor pathways.
2011 Nov 10
Patents

Patents

07175854
29
20040058896
57
20070122474
47
9221753
2

Sample Use Guides

In Vivo Use Guide
In a phase II clinical study against hepatocellular carcinoma, Seocalcitol was administered orally at starting doses 10 ug/day.
Route of Administration: Oral
In Vitro Use Guide
U937 cells were seeded at 1 × 105 cells/ml in culture flasks at 5ml cells/flask. EB 1089 was added in the concentrations 10-9 - 10-12 M; control cultures received the diluent, 2-propanol. After 96 h, proliferation was assessed by counting of cells, and IC50 was calculated from the dose-response curves.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:53:17 GMT 2023
Edited
by admin
on Fri Dec 15 15:53:17 GMT 2023
Record UNII
Q0OZ0D9223
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SEOCALCITOL
INN   MART.   MI   WHO-DD  
INN  
Official Name English
seocalcitol [INN]
Common Name English
CB-1089
Code English
SEOCALCITOL [MI]
Common Name English
SEOCALCITOL [MART.]
Common Name English
Seocalcitol [WHO-DD]
Common Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/01/052
Created by admin on Fri Dec 15 15:53:18 GMT 2023 , Edited by admin on Fri Dec 15 15:53:18 GMT 2023
NCI_THESAURUS C39713
Created by admin on Fri Dec 15 15:53:18 GMT 2023 , Edited by admin on Fri Dec 15 15:53:18 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C26669
Created by admin on Fri Dec 15 15:53:18 GMT 2023 , Edited by admin on Fri Dec 15 15:53:18 GMT 2023
PRIMARY
MERCK INDEX
m9865
Created by admin on Fri Dec 15 15:53:18 GMT 2023 , Edited by admin on Fri Dec 15 15:53:18 GMT 2023
PRIMARY Merck Index
FDA UNII
Q0OZ0D9223
Created by admin on Fri Dec 15 15:53:18 GMT 2023 , Edited by admin on Fri Dec 15 15:53:18 GMT 2023
PRIMARY
PUBCHEM
5288149
Created by admin on Fri Dec 15 15:53:18 GMT 2023 , Edited by admin on Fri Dec 15 15:53:18 GMT 2023
PRIMARY
CAS
134404-52-7
Created by admin on Fri Dec 15 15:53:18 GMT 2023 , Edited by admin on Fri Dec 15 15:53:18 GMT 2023
PRIMARY
INN
7666
Created by admin on Fri Dec 15 15:53:18 GMT 2023 , Edited by admin on Fri Dec 15 15:53:18 GMT 2023
PRIMARY
MESH
C078903
Created by admin on Fri Dec 15 15:53:18 GMT 2023 , Edited by admin on Fri Dec 15 15:53:18 GMT 2023
PRIMARY
SMS_ID
100000084092
Created by admin on Fri Dec 15 15:53:18 GMT 2023 , Edited by admin on Fri Dec 15 15:53:18 GMT 2023
PRIMARY
ChEMBL
CHEMBL1908376
Created by admin on Fri Dec 15 15:53:18 GMT 2023 , Edited by admin on Fri Dec 15 15:53:18 GMT 2023
PRIMARY
DRUG BANK
DB04258
Created by admin on Fri Dec 15 15:53:18 GMT 2023 , Edited by admin on Fri Dec 15 15:53:18 GMT 2023
PRIMARY
EVMPD
SUB10483MIG
Created by admin on Fri Dec 15 15:53:18 GMT 2023 , Edited by admin on Fri Dec 15 15:53:18 GMT 2023
PRIMARY
EPA CompTox
DTXSID601025740
Created by admin on Fri Dec 15 15:53:18 GMT 2023 , Edited by admin on Fri Dec 15 15:53:18 GMT 2023
PRIMARY
Related Record Type Details
VITAMIN D3 RECEPTOR
TARGET -> AGONIST
Structure of Cholecalciferol
PARENT -> DERIVATIVE
Related Record Type Details
Structure of SEOCALCITOL
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