Maxacalcitol
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MedKoo CAT#: 329666

CAS#: 103909-75-7

Description: Maxacalcitol, also known as 22-Oxacalcitriol, is an analog of calcitriol that, like calcitriol, is a receptor-active form of vitamin D3 which effectively blocks PTH synthesis. Maxacalcitol (OCT) induces hCAP-18/LL-37 production in human oral epithelial cells. Maxacalcitol Provides Cardioprotective Effects in Diabetes Mellitus. Maxacalcitol ameliorates tubulointerstitial fibrosis in obstructed kidneys by recruiting PPM1A/VDR complex to pSmad3.


Chemical Structure

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Maxacalcitol
CAS# 103909-75-7

Theoretical Analysis

MedKoo Cat#: 329666
Name: Maxacalcitol
CAS#: 103909-75-7
Chemical Formula: C26H42O4
Exact Mass: 418.3083
Molecular Weight: 418.618
Elemental Analysis: C, 74.60; H, 10.11; O, 15.29

Price and Availability

Size Price Availability Quantity
1.0mg USD 290.0 2 Weeks
5.0mg USD 790.0 2 Weeks
10.0mg USD 1290.0 2 Weeks
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Synonym: Maxacalcitol; Maxacalcitriol; 22-Oxacalcitriol; MC 1275; OCT; Prezios; Sch 209579; alpha,25-Dihydroxy-22-oxavitamin D3; 22-Oxa-1,25-dihydroxyvitamin D3.

IUPAC/Chemical Name: (1R,3S,Z)-5-(2-((1S,3aS,7aS,E)-1-((S)-1-(3-hydroxy-3-methylbutoxy)ethyl)-7a-methyloctahydro-4H-inden-4-ylidene)ethylidene)-4-methylenecyclohexane-1,3-diol

InChi Key: DTXXSJZBSTYZKE-ZDQKKZTESA-N

InChi Code: 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

SMILES Code: C[C@H](OCCC(C)(O)C)[C@H]1CC[C@@H]2[C@]1(C)CCC/C2=C\C=C3C[C@@H](O)C[C@H](O)C\3=C

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 418.618 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Karakawa M, Komine M, Kishimoto M, Maki N, Matsumoto A, Sugai J, Ohtsuki M. Effects of maxacalcitol ointment on skin lesions in patients with psoriasis receiving treatment with adalimumab. J Dermatol. 2016 Nov;43(11):1354-1357. doi: 10.1111/1346-8138.13515. Epub 2016 Jul 23. PubMed PMID: 27450634.

2: Tada H, Shimizu T, Nagaoka I, Takada H. Vitamin D3 analog maxacalcitol (OCT) induces hCAP-18/LL-37 production in human oral epithelial cells. Biomed Res. 2016;37(3):199-205. doi: 10.2220/biomedres.37.199. PubMed PMID: 27356607.

3: Nakamura K, Tohyama N, Yamasaki M, Ohta H, Morishita K, Takiguchi M. Hypercalcemia in a Dog with Chronic Ingestion of Maxacalcitol Ointment. J Am Anim Hosp Assoc. 2016 Jul-Aug;52(4):256-8. doi: 10.5326/JAAHA-MS-6286. Epub 2016 Jun 3. PubMed PMID: 27259026.

4: Wróbel A, Rechberger T. The Influence of Maxacalcitol, Vitamin D3 Analog, on Detrusor Overactivity in Conscious Rats. Urology. 2016 Jul;93:224.e7-224.e15. doi: 10.1016/j.urology.2016.03.008. Epub 2016 Mar 23. PubMed PMID: 27018369.

5: Fujii H, Nakai K, Yonekura Y, Kono K, Goto S, Hirata M, Shinohara M, Nishi S, Fukagawa M. The Vitamin D Receptor Activator Maxacalcitol Provides Cardioprotective Effects in Diabetes Mellitus. Cardiovasc Drugs Ther. 2015 Dec;29(6):499-507. PubMed PMID: 26602563.

6: Umezawa Y, Nakagawa H, Tamaki K. Phase III clinical study of maxacalcitol ointment in patients with palmoplantar pustulosis: A randomized, double-blind, placebo-controlled trial. J Dermatol. 2016 Mar;43(3):288-93. doi: 10.1111/1346-8138.13064. Epub 2015 Aug 18. PubMed PMID: 26282062.

7: Hoshina D, Tsujiwaki M, Furuya K. Successful treatment of subcorneal pustular dermatosis with maxacalcitol. Clin Exp Dermatol. 2016 Jan;41(1):102-3. doi: 10.1111/ced.12680. Epub 2015 May 19. PubMed PMID: 25991581.

8: Akizawa T, Akiba T, Hirakata H, Kinugasa E, Tominaga Y, Fukagawa M, Yokoyama K, Zhang W, Linde PG, Suzuki M. Comparison of paricalcitol with maxacalcitol injection in Japanese hemodialysis patients with secondary hyperparathyroidism. Ther Apher Dial. 2015 Jun;19(3):225-34. doi: 10.1111/1744-9987.12242. Epub 2014 Nov 3. PubMed PMID: 25363733.

9: Zhao GD, Liu ZP. Stereoselective reduction of C-20 ketone of vitamin D CD-ring and a new synthetic approach to maxacalcitol. Steroids. 2014 Oct;88:72-6. doi: 10.1016/j.steroids.2014.07.005. Epub 2014 Jul 17. PubMed PMID: 25042469.

10: Honda H, Koiwa F, Ogata H, Shishido K, Sekiguchi T, Michihata T, Ogawa H, Mukai M, Takahashi K, Suzuki R, Kino K, Kato K, Yamamoto K, Kinugasa E, Akizawa T. Active vitamin D analogs, maxacalcitol and alfacalcidol, as maintenance therapy for mild secondary hyperparathyroidism in hemodialysis patients - a randomized study. Int J Clin Pharmacol Ther. 2014 May;52(5):360-8. doi: 10.5414/CP202020. PubMed PMID: 24569127.

11: Yoshiya H, Okuyama R, Uhara H. Effectiveness of topical maxacalcitol for acquired perforating disorder. J Am Acad Dermatol. 2013 Jun;68(6):e181-2. doi: 10.1016/j.jaad.2012.10.044. PubMed PMID: 23680211.

12: Inoue K, Matsui I, Hamano T, Fujii N, Shimomura A, Nakano C, Kusunoki Y, Takabatake Y, Hirata M, Nishiyama A, Tsubakihara Y, Isaka Y, Rakugi H. Maxacalcitol ameliorates tubulointerstitial fibrosis in obstructed kidneys by recruiting PPM1A/VDR complex to pSmad3. Lab Invest. 2012 Dec;92(12):1686-97. doi: 10.1038/labinvest.2012.107. Epub 2012 Aug 27. PubMed PMID: 22926646.

13: Okubo Y, Natsume S, Usui K, Muro M, Tsuboi R. Combination therapy using maxacalcitol and corticosteroid lotions preliminary to monotherapy with maxacalcitol lotion for scalp psoriasis. J Dermatolog Treat. 2014 Feb;25(1):34-7. doi: 10.3109/09546634.2012.687087. Epub 2012 Jun 12. PubMed PMID: 22515652.

14: Karashima T, Hashikawa K, Ono F, Eguchi H, Hamada T, Ishii N, Dainichi T, Yasumoto S, Tsuruta D, Hashimoto T. Successful treatment of Bowen's disease with topical maxacalcitol. Acta Derm Venereol. 2012 Nov;92(6):660-1. doi: 10.2340/00015555-1294. PubMed PMID: 22281814.

15: Murao K, Oshima M, Miyajima O, Kubo Y. Verrucous skin lesions on the feet in diabetic neuropathy successfully treated with topical maxacalcitol. Eur J Dermatol. 2012 Mar-Apr;22(2):274-5. doi: 10.1684/ejd.2012.1640. PubMed PMID: 22236391.

16: Adachi M, Miyoshi T, Shiraishi N, Shimada H, Sakaguchi S, Tomita K, Kitamura K. A study of maintenance therapy after intravenous maxacalcitol for secondary hyperparathyroidism. Clin Nephrol. 2011 Oct;76(4):266-72. PubMed PMID: 21955861.

17: Kimura M, Higuchi T, Yoshida M. Infantile acropustulosis treated successfully with topical maxacalcitol. Acta Derm Venereol. 2011 May;91(3):363-4. doi: 10.2340/00015555-1060. PubMed PMID: 21336473.

18: Saito A, Matsumoto Y, Oyama Y, Asaka M, Yokoyama H. Effectiveness of weekly percutaneous maxacalcitol injection therapy in patients with secondary hyperparathyroidism. Ther Apher Dial. 2010 Feb;14(1):98-103. doi: 10.1111/j.1744-9987.2009.00706.x. PubMed PMID: 20438525.

19: Shiizaki K, Hatamura I, Imazeki I, Moriguchi Y, Sakaguchi T, Saji F, Nakazawa E, Kato S, Akizawa T, Kusano E. Improvement of impaired calcium and skeletal homeostasis in vitamin D receptor knockout mice by a high dose of calcitriol and maxacalcitol. Bone. 2009 Nov;45(5):964-71. doi: 10.1016/j.bone.2009.07.013. Epub 2009 Jul 23. PubMed PMID: 19631778.

20: Abe M, Syuto T, Hasegawa M, Yokoyama Y, Ishikawa O. Clinical usefulness of a supplementary cyclosporin administration with a topical application of maxacalcitol ointment for patients with moderate psoriasis vulgaris. J Dermatol. 2009 Apr;36(4):197-201. doi: 10.1111/j.1346-8138.2009.00623.x. PubMed PMID: 19348657.