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MedKoo Cat#: 329666 | Name: Maxacalcitol
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Maxacalcitol
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: 418.62

Elemental Analysis: C, 74.60; H, 10.11; O, 15.29

Price and Availability

Size Price Availability Quantity
1mg USD 350.00 2 weeks
5mg USD 850.00 2 weeks
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Related CAS #
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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
>95% (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
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Maxacalcitol (22-Oxacalcitriol) is non-calcemic vitamin D3 analog and ligand of VDR-like receptors.
In vitro activity:
Maxacalcitol (22-oxacalcitriol: OCT) is a biologically active metabolite of vitamin D3 analog, and OCT increases hCAP-18/LL-37 production by human gingival epithelial cells. The increasing expression of LL-37 mRNA by OCT was down-regulated by infection of the cells with P. gingivalis ATCC 33277 in Ca9-22 cells. Reference: Biomed Res. 2017;38(3):167-173. https://pubmed.ncbi.nlm.nih.gov/28637951/
In vivo activity:
In Nx (nephrectomized) dogs, OCT (22-oxacalcitriol) significantly decreased serum PTH levels soon after the induction of renal insufficiency. In animals with normal renal function, OCT induced a transient decrease in serum PTH levels at a dose of 0.1 microg/kg, which was not sustained with lowering of the doses. In Nx dogs, OCT reversed abnormal bone formation, such as woven osteoid and fibrosis, but did not significantly alter the level of bone turnover. In addition, OCT improved mineralization lag time, (that is, the rate at which osteoid mineralizes) in both Nx and Sham dogs. Reference: Kidney Int. 1999 Mar;55(3):821-32. https://pubmed.ncbi.nlm.nih.gov/10027919/
Solvent mg/mL mM
Solubility
DMSO 50.0 119.44
Ethanol 1.0 2.39
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 418.62 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
Formulation protocol:
1. Tada H, Shimizu T, Matsushita K, Takada H. Porphyromonas gingivalis-induced IL-33 down-regulates hCAP-18/LL-37 production in human gingival epithelial cells. Biomed Res. 2017;38(3):167-173. doi: 10.2220/biomedres.38.167. PMID: 28637951. 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. PMID: 27356607. 3. 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. PMID: 22926646. 4. Monier-Faugere MC, Geng Z, Friedler RM, Qi Q, Kubodera N, Slatopolsky E, Malluche HH. 22-oxacalcitriol suppresses secondary hyperparathyroidism without inducing low bone turnover in dogs with renal failure. Kidney Int. 1999 Mar;55(3):821-32. doi: 10.1046/j.1523-1755.1999.055003821.x. PMID: 10027919.
In vitro protocol:
1. Tada H, Shimizu T, Matsushita K, Takada H. Porphyromonas gingivalis-induced IL-33 down-regulates hCAP-18/LL-37 production in human gingival epithelial cells. Biomed Res. 2017;38(3):167-173. doi: 10.2220/biomedres.38.167. PMID: 28637951. 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. PMID: 27356607.
In vivo protocol:
1. 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. PMID: 22926646. 2. Monier-Faugere MC, Geng Z, Friedler RM, Qi Q, Kubodera N, Slatopolsky E, Malluche HH. 22-oxacalcitriol suppresses secondary hyperparathyroidism without inducing low bone turnover in dogs with renal failure. Kidney Int. 1999 Mar;55(3):821-32. doi: 10.1046/j.1523-1755.1999.055003821.x. PMID: 10027919.
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.

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