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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H42O4
Molecular Weight 418.6093
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of MAXACALCITOL

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)OCCC(C)(C)O

InChI

InChIKey=DTXXSJZBSTYZKE-ZDQKKZTESA-N
InChI=1S/C26H42O4/c1-17-20(15-21(27)16-24(17)28)9-8-19-7-6-12-26(5)22(10-11-23(19)26)18(2)30-14-13-25(3,4)29/h8-9,18,21-24,27-29H,1,6-7,10-16H2,2-5H3/b19-8+,20-9-/t18-,21+,22+,23-,24-,26+/m0/s1

HIDE SMILES / InChI
Molecular Formula C26H42O4
Molecular Weight 418.6093
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 2
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12617040 | https://www.chugai-pharm.co.jp/english/news/detail/20081128000000.html

Maxacalcitol (OXAROL®) is a derivative of vitamin D and is used to treat the secondary hyperparathyroidism of hemodialysis (HD) patients as an injection and psoriasis as an ointment. Secondary hyperparathyroidism is one of the complications in HD patients with hyperplasia of parathyroid glands and elevated serum parathyroid hormone (PTH) levels. Maxacalcitol (OXAROL®) suppresses synthesis and secretion of parathyroid hormone, and decreases a concentration of parathyroid hormone in blood. It also inhibits proliferation and induces differentiation of epidermal keratinocytes. Maxacalcitol (OXAROL®) used in patients with keratosis including psoriasis vulgaris, remarkably improving the symptoms.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 37.9 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
OXAROL

Approved Use

It is usually used to treat secondary hyperparathyroidism of the patient on dialysis.
Palliative
Approved
8429
OXAROL

Approved Use

Treatment drug for keratosis including psoriasis vulgaris.
Palliative
Approved
8429
OXAROL

Approved Use

Treatment of palmoplantar pustulosis.
PubMed

PubMed

TitleDatePubMed
Effects of two new vitamin D3 derivatives, 22-oxa-1 alpha-25-dihydroxyvitamin D3 (OCT) and 2 beta-(3-hydroxypropoxy)-1 alpha, 25-dihydroxyvitamin D3 (ED-71), on bone metabolism in organ culture.
1993
Differential effects of 1,25-(OH)2D3 and 22-oxacalcitriol on phosphate and calcium metabolism.
1993 Mar
Actions of vitamin D3, analogs on human prostate cancer cell lines: comparison with 1,25-dihydroxyvitamin D3.
1995 Jan
Comparison of the efficacy of an oral calcitriol pulse or intravenous 22-oxacalcitriol therapies in chronic hemodialysis patients.
2005 Sep
Active vitamin D and its analogue, 22-oxacalcitriol, ameliorate puromycin aminonucleoside-induced nephrosis in rats.
2009 Aug
Patents

Patents

07175854
29
07951398
20
JP2002542293A
14
JP2007224022A
1
JP2011157326A
1
JP4426729B2
8
JPH00892098A
1
JPH0892098A
1
US20140051875
1

Sample Use Guides

In Vivo Use Guide
Inject Oxarol® at a venous side of dialysis circuit just before the completion of dialysis three times a week. Appropriate amount of Oxarol® product (ointment, lotion) should be applied to the affected area twice daily.
Route of Administration: Other
In Vitro Use Guide
To investigate the activation of the vitamin D receptor (VDR) by 20S,24R(OH)2D3 and 20S,24S(OH)2D3 together with their 1a-OH derivatives, two cell lines (HaCaT and Caco-2) were transduced by a lentiviral VDRE luciferase reporter vector. 1,25-(OH)2D3 and 22-oxa-1,25(OH)2D3 (maxacalcitol) were used as positive controls. Both 1,25-(OH)2D3 and maxacalcitol showed the expected strong activations of VDRE in both cell lines, with the EC50 values showing that maxacalcitol (HaCaT EC50=37.9 ± 1.2 nM, Caco-2 EC50=40.8 ± 1.7 nM) is more potent than 1,25(OH)2D3 (HaCaT EC50=321.5 ± 14.2 nM, Caco-2 EC50=515.2 ± 22.4 nM).
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:51:55 GMT 2023
Edited
by admin
on Fri Dec 15 15:51:55 GMT 2023
Record UNII
N2UJM5NBF6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MAXACALCITOL
INN   JAN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
OXAROL
Brand Name English
OCT
Code English
22-OXACALCITRIOL
Common Name English
MAXACALCITOL [JAN]
Common Name English
(1S-(1.ALPHA.(R*),3A.BETA.,4E(1S*,3R*,5Z),7A.ALPHA.))-4-METHYLENE-5-(2-(OCTAHYDRO-1-(1-(3-HYDROXY-3-METHYLBUTOXY)ETHYL)-7A-METHYL-4H-INDEN-4-YLIDIENE)ETHYLIDENE-1,3-CYCLOHEXANEDIOL
Common Name English
SCH209579
Code English
MAXACALCITOL [USAN]
Common Name English
(+)-(5Z,7E,20S)-20-(3-HYDROXY-3-METHYLBUTOXY)-9,10-SECOPREGNA-5,7,10(19)-TRIENE-1.ALPHA.,3.BETA.-DIOL
Common Name English
maxacalcitol [INN]
Common Name English
Maxacalcitol [WHO-DD]
Common Name English
MAXACALCITOL [MI]
Common Name English
MAXACALCITOL [MART.]
Common Name English
SCH-209579
Code English
PREZIOS
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C39713
Created by admin on Fri Dec 15 15:51:55 GMT 2023 , Edited by admin on Fri Dec 15 15:51:55 GMT 2023
Code System Code Type Description
CAS
103909-75-7
Created by admin on Fri Dec 15 15:51:55 GMT 2023 , Edited by admin on Fri Dec 15 15:51:55 GMT 2023
PRIMARY
DRUG CENTRAL
1638
Created by admin on Fri Dec 15 15:51:55 GMT 2023 , Edited by admin on Fri Dec 15 15:51:55 GMT 2023
PRIMARY
ChEMBL
CHEMBL333950
Created by admin on Fri Dec 15 15:51:55 GMT 2023 , Edited by admin on Fri Dec 15 15:51:55 GMT 2023
PRIMARY
SMS_ID
100000081726
Created by admin on Fri Dec 15 15:51:55 GMT 2023 , Edited by admin on Fri Dec 15 15:51:55 GMT 2023
PRIMARY
MESH
C051883
Created by admin on Fri Dec 15 15:51:55 GMT 2023 , Edited by admin on Fri Dec 15 15:51:55 GMT 2023
PRIMARY
DRUG BANK
DB06272
Created by admin on Fri Dec 15 15:51:55 GMT 2023 , Edited by admin on Fri Dec 15 15:51:55 GMT 2023
PRIMARY
EVMPD
SUB08653MIG
Created by admin on Fri Dec 15 15:51:55 GMT 2023 , Edited by admin on Fri Dec 15 15:51:55 GMT 2023
PRIMARY
FDA UNII
N2UJM5NBF6
Created by admin on Fri Dec 15 15:51:55 GMT 2023 , Edited by admin on Fri Dec 15 15:51:55 GMT 2023
PRIMARY
USAN
KK-114
Created by admin on Fri Dec 15 15:51:55 GMT 2023 , Edited by admin on Fri Dec 15 15:51:55 GMT 2023
PRIMARY
NCI_THESAURUS
C143087
Created by admin on Fri Dec 15 15:51:55 GMT 2023 , Edited by admin on Fri Dec 15 15:51:55 GMT 2023
PRIMARY
PUBCHEM
6398761
Created by admin on Fri Dec 15 15:51:55 GMT 2023 , Edited by admin on Fri Dec 15 15:51:55 GMT 2023
PRIMARY
MERCK INDEX
m7098
Created by admin on Fri Dec 15 15:51:55 GMT 2023 , Edited by admin on Fri Dec 15 15:51:55 GMT 2023
PRIMARY Merck Index
INN
7438
Created by admin on Fri Dec 15 15:51:55 GMT 2023 , Edited by admin on Fri Dec 15 15:51:55 GMT 2023
PRIMARY
EPA CompTox
DTXSID4048648
Created by admin on Fri Dec 15 15:51:55 GMT 2023 , Edited by admin on Fri Dec 15 15:51:55 GMT 2023
PRIMARY
Related Record Type Details
Structure of Cholecalciferol
PARENT -> DERIVATIVE
PARATHYROID HORMONE
TARGET->INHIBITOR OF RELEASE
Related Record Type Details
Structure of MAXACALCITOL
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