MAXACALCITOL

Possibly Marketed Outside US

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 Search

SMILES

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

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
Sources: https://chugai-pharm.jp/hc/ss/pr/drug/oxa_amp0100/shiori/PDF/en/oxa_s_en.pdf
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

Targets

Primary Target	Pharmacology	Condition	Potency
Vitamin D receptor 25 Target ID: CHEMBL1977 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12617040	Agonist 2752		37.9 nM [EC50]

Conditions

Condition	Modality	Highest Phase	Product
Secondary hyperparathyroidism 9 Sources: https://chugai-pharm.jp/hc/ss/pr/drug/oxa_amp0100/shiori/PDF/en/oxa_s_en.pdf	Primary	Approved 8583	OXAROL Approved Use It is usually used to treat secondary hyperparathyroidism of the patient on dialysis.
Psoriasis vulgaris 5 Sources: https://www.chugai-pharm.co.jp/english/news/detail/20081128000000.html	Palliative	Approved 8583	OXAROL Approved Use Treatment drug for keratosis including psoriasis vulgaris.
Palmoplantar pustulosis 1 Sources: https://www.chugai-pharm.co.jp/english/news/detail/20081128000000.html	Palliative	Approved 8583	OXAROL Approved Use Treatment of palmoplantar pustulosis.

C_max

Value	Dose	Analyte	Population
74.7 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32181403/	1.25 μg single, intravenous dose: 1.25 μg route of administration: Intravenous experiment type: SINGLE co-administered:	MAXACALCITOL serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
159 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32181403/	2.5 μg single, intravenous dose: 2.5 μg route of administration: Intravenous experiment type: SINGLE co-administered:	MAXACALCITOL serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
321 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32181403/	5 μg single, intravenous dose: 5 μg route of administration: Intravenous experiment type: SINGLE co-administered:	MAXACALCITOL serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
591 pg/mL DRUG LABEL https://www.kegg.jp/medicus-bin/japic_med?japic_code=00052905	200 μg single, transdermal dose: 200 μg route of administration: Transdermal experiment type: SINGLE co-administered:	MAXACALCITOL blood	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
475 pg/mL DRUG LABEL https://www.kegg.jp/medicus-bin/japic_med?japic_code=00052905	200 μg 1 times / day multiple, transdermal dose: 200 μg route of administration: Transdermal experiment type: MULTIPLE co-administered:	MAXACALCITOL blood	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
473 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32181403/	1.25 μg single, intravenous dose: 1.25 μg route of administration: Intravenous experiment type: SINGLE co-administered:	MAXACALCITOL serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
763 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32181403/	2.5 μg single, intravenous dose: 2.5 μg route of administration: Intravenous experiment type: SINGLE co-administered:	MAXACALCITOL serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1460 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32181403/	5 μg single, intravenous dose: 5 μg route of administration: Intravenous experiment type: SINGLE co-administered:	MAXACALCITOL serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
4177 pg × h/mL DRUG LABEL https://www.kegg.jp/medicus-bin/japic_med?japic_code=00052905	200 μg single, transdermal dose: 200 μg route of administration: Transdermal experiment type: SINGLE co-administered:	MAXACALCITOL blood	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
2452 pg × h/mL DRUG LABEL https://www.kegg.jp/medicus-bin/japic_med?japic_code=00052905	200 μg 1 times / day multiple, transdermal dose: 200 μg route of administration: Transdermal experiment type: MULTIPLE co-administered:	MAXACALCITOL blood	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
431 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32181403/	1.25 μg single, intravenous dose: 1.25 μg route of administration: Intravenous experiment type: SINGLE co-administered:	MAXACALCITOL serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
828 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32181403/	2.5 μg single, intravenous dose: 2.5 μg route of administration: Intravenous experiment type: SINGLE co-administered:	MAXACALCITOL serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
316 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32181403/	5 μg single, intravenous dose: 5 μg route of administration: Intravenous experiment type: SINGLE co-administered:	MAXACALCITOL serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
3.9 h DRUG LABEL https://www.kegg.jp/medicus-bin/japic_med?japic_code=00052905	200 μg single, transdermal dose: 200 μg route of administration: Transdermal experiment type: SINGLE co-administered:	MAXACALCITOL blood	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
2.2 h DRUG LABEL https://www.kegg.jp/medicus-bin/japic_med?japic_code=00052905	200 μg 1 times / day multiple, transdermal dose: 200 μg route of administration: Transdermal experiment type: MULTIPLE co-administered:	MAXACALCITOL blood	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
12 ug 3 times / week multiple, intravenous Studied dose Dose: 12 ug, 3 times / week Route: intravenous Route: multiple Dose: 12 ug, 3 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/33685864/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/33685864/	Sources: https://pubmed.ncbi.nlm.nih.gov/33685864/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 substrate 1946	inhibitor 2438 substrate 1193	inhibitor 2507 substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2A6 879 CYP2C19 2057 CYP2E1 1060	CYP2C8 810 CYP1A1 389 CYP2E1 729 CYP1A2 1197 CYP2B6 776 CYP2C19 1119 CYP2A6 626

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2000/g000713/29ctdp_1-302.pdf Page: 183.0	no
CYP2A6 911	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2000/g000713/29ctdp_1-302.pdf Page: 183.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2000/g000713/29ctdp_1-302.pdf Page: 183.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2000/g000713/29ctdp_1-302.pdf Page: 183.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2000/g000713/29ctdp_1-302.pdf Page: 183.0	no
CYP2E1 1146	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2000/g000713/29ctdp_1-302.pdf Page: 183.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2000/g000713/29ctdp_1-302.pdf Page: 183.0	no

Drug as victim

Target	Modality	Activity
CYP3A4 1946	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2001/P200100025/45004500_21300AMZ00485_264_1.pdf Page: 7.0	major
CYP2A6 626	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2001/P200100025/45004500_21300AMZ00485_264_1.pdf Page: 7.0	no
CYP2C19 1119	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2001/P200100025/45004500_21300AMZ00485_264_1.pdf Page: 7.0	no
CYP2C8 810	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2001/P200100025/45004500_21300AMZ00485_264_1.pdf Page: 7.0	no
CYP2C9 1193	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2001/P200100025/45004500_21300AMZ00485_264_1.pdf Page: 7.0	no
CYP2D6 1388	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2001/P200100025/45004500_21300AMZ00485_264_1.pdf Page: 7.0	no
CYP2E1 729	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2001/P200100025/45004500_21300AMZ00485_264_1.pdf Page: 7.0	no
CYP1A1 389	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2001/P200100025/45004500_21300AMZ00485_264_1.pdf Page: 7.0	weak
CYP1A2 1197	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2001/P200100025/45004500_21300AMZ00485_264_1.pdf Page: 7.0	weak
CYP2B6 776	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2001/P200100025/45004500_21300AMZ00485_264_1.pdf Page: 7.0	weak

PubMed

Title	Date	PubMed
Active vitamin D and its analogue, 22-oxacalcitriol, ameliorate puromycin aminonucleoside-induced nephrosis in rats.	2009-08	19297354
Hypercalcemia caused by vitamin D3 analogs in psoriasis treatment.	2007-12	18173537
Inhibitory effect of 22-oxa-1,25-dihydroxyvitamin D3, maxacalcitol, on the proliferation of pancreatic cancer cell lines.	2005-10	16039115
Comparison of the efficacy of an oral calcitriol pulse or intravenous 22-oxacalcitriol therapies in chronic hemodialysis patients.	2005-09	16189633
Topical treatment with 22-oxacalcitriol (OCT), a new vitamin D analogue, caused severe hypercalcemia with exacerbation of chronic renal failure in a psoriatic patient with diabetic nephropathy; a case report and analysis of the potential for hypercalcemia.	2003-12	14714959
Clinical effects of maxacalcitol on secondary hyperparathyroidism of uremic patients.	2001-10	11576942
22-oxacalcitriol suppresses secondary hyperparathyroidism without inducing low bone turnover in dogs with renal failure.	1999-03	10027919
Effect of 22-oxacalcitriol on hyperparathyroidism of dialysis patients: results of a preliminary study.	1996	8840326
Actions of vitamin D3, analogs on human prostate cancer cell lines: comparison with 1,25-dihydroxyvitamin D3.	1995-01	7530193
Differential effects of 1,25-(OH)2D3 and 22-oxacalcitriol on phosphate and calcium metabolism.	1993-03	8455354
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	8443002
A novel vitamin D3 analog, 22-oxa-1,25-dihydroxyvitamin D3, inhibits the growth of human breast cancer in vitro and in vivo without causing hypercalcemia.	1991-08	1855478

Patents

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 `Mon Mar 31 18:11:19 GMT 2025` Edited by `admin` on `Mon Mar 31 18:11:19 GMT 2025`
Record UNII	N2UJM5NBF6
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

OXAROL

Preferred Name

English

MAXACALCITOL

Official 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