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Maxacalcitol

CAS No.:
103909-75-7
Catalog Number:
AG00857B
Molecular Formula:
C21H31O2
Molecular Weight:
315.4696
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥95%
1 week
United States
$221
- +
5mg
99%
1 week
United States
$741
- +
10mg
99%
1 week
United States
$1085
- +
25mg
99%
1 week
United States
$2307
- +
Product Description
Catalog Number:
AG00857B
Chemical Name:
Maxacalcitol
CAS Number:
103909-75-7
Molecular Formula:
C21H31O2
Molecular Weight:
315.4696
MDL Number:
MFCD00871502
IUPAC Name:
(1R,3S,5Z)-5-[(2E)-2-[(1S,3aS,7aS)-1-[(1S)-1-(3-hydroxy-3-methylbutoxy)ethyl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
InChI:
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
InChI Key:
DTXXSJZBSTYZKE-ZDQKKZTESA-N
SMILES:
C[CH][C@H]1CC[C@@H]2[C@]1(C)CCCC2=CC=C1C[C@@H](O)C[C@@H](C1=C)O
UNII:
N2UJM5NBF6
Properties
Complexity:
691  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
6  
Defined Bond Stereocenter Count:
2  
Exact Mass:
418.308g/mol
Formal Charge:
0
Heavy Atom Count:
30  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
418.618g/mol
Monoisotopic Mass:
418.308g/mol
Rotatable Bond Count:
6  
Topological Polar Surface Area:
69.9A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3.5  
Literature
Title Journal
Topical vitamin D₃ analogues induce thymic stromal lymphopoietin and cathelicidin in psoriatic skin lesions. The British journal of dermatology 20120701
Effects of rotation of topical vitamin D3 in chronic plaque-type psoriasis. The Journal of dermatology 20120301
Effects of 22-oxa-calcitriol on podocyte injury in adriamycin-induced nephrosis. American journal of nephrology 20120101
Verrucous skin lesions on the feet in diabetic neuropathy successfully treated with topical maxacalcitol. European journal of dermatology : EJD 20120101
A study of maintenance therapy after intravenous maxacalcitol for secondary hyperparathyroidism. Clinical nephrology 20111001
Formulation study of topically applied O/W lotion containing vitamin D3 derivative, focusing on skin permeability of the drug. Drug development and industrial pharmacy 20110801
Duration of remission period of narrowband ultraviolet B therapy on psoriasis vulgaris. The Journal of dermatology 20110701
Infantile acropustulosis treated successfully with topical maxacalcitol. Acta dermato-venereologica 20110501
22-oxa-1,25-dihydroxyvitamin D3 efficiently inhibits tumor growth in inoculated mice and primary histoculture of cholangiocarcinoma. Cancer 20101201
Striate palmoplantar keratoderma. The Journal of dermatology 20100901
Clinical effectiveness and safety evaluation of long-term pioglitazone treatment for erythropoietin responsiveness and insulin resistance in type 2 diabetic patients on hemodialysis. Expert opinion on pharmacotherapy 20100701
Effectiveness of weekly percutaneous maxacalcitol injection therapy in patients with secondary hyperparathyroidism. Therapeutic apheresis and dialysis : official peer-reviewed journal of the International Society for Apheresis, the Japanese Society for Apheresis, the Japanese Society for Dialysis Therapy 20100201
Contact immunotherapy-induced Renbök phenomenon in a patient with alopecia areata and psoriasis vulgaris. European journal of dermatology : EJD 20100101
Improvement of impaired calcium and skeletal homeostasis in vitamin D receptor knockout mice by a high dose of calcitriol and maxacalcitol. Bone 20091101
Active vitamin D and its analogue, 22-oxacalcitriol, ameliorate puromycin aminonucleoside-induced nephrosis in rats. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20090801
Drug-induced acute pancreatitis associated with 22-oxacalcitriol ointment for treatment of psoriasis. JOP : Journal of the pancreas 20090518
Clinical usefulness of a supplementary cyclosporin administration with a topical application of maxacalcitol ointment for patients with moderate psoriasis vulgaris. The Journal of dermatology 20090401
Type 2 segmental manifestation of disseminated superficial actinic porokeratosis in a 7-year-old girl. European journal of dermatology : EJD 20090101
A bivariate autoregressive linear mixed effects model for the analysis of longitudinal data. Statistics in medicine 20081230
Aza- and oxadithiolates are probable proton relays in functional models for the [FeFe]-hydrogenases. Journal of the American Chemical Society 20081217
A case of mosaic-type bullous congenital ichthyosiform erythroderma successfully treated with topical maxacalcitol, a vitamin D3 analogue. Clinical and experimental dermatology 20080701
Cutaneous pharmacokinetics of topically applied maxacalcitol ointment and lotion. International journal of clinical pharmacology and therapeutics 20080601
Molecular and morphological approach of uremia-induced hyperplastic parathyroid gland following direct maxacalcitol injection. Medical molecular morphology 20080601
Efficacy of high-concentration tacalcitol ointment in psoriasis vulgaris after changing from other high-concentration vitamin D3 ointments. Dermatology online journal 20080227
Clinical effect of vitamin D3 analogues is not inactivated by subsequent UV exposure. Photodermatology, photoimmunology & photomedicine 20080201
Direct injection of calcitriol or its analog improves abnormal gene expression in the hyperplastic parathyroid gland in uremia. American journal of nephrology 20080101
Vitamin D and the digestive system. European journal of drug metabolism and pharmacokinetics 20080101
Hypercalcemia caused by vitamin D3 analogs in psoriasis treatment. International journal of dermatology 20071201
Clinical features and hyperplastic patterns of parathyroid glands in hemodialysis patients with advanced secondary hyperparathyroidism refractory to maxacalcitol treatment and required parathyroidectomy. Therapeutic apheresis and dialysis : official peer-reviewed journal of the International Society for Apheresis, the Japanese Society for Apheresis, the Japanese Society for Dialysis Therapy 20070801
Analysis of in vitro skin permeation of 22-oxacalcitriol from ointments based on a two- or three-layer diffusion model considering diffusivity in a vehicle. International journal of pharmaceutics 20070524
An autoregressive linear mixed effects model for the analysis of longitudinal data which show profiles approaching asymptotes. Statistics in medicine 20070430
Binding of highly concentrated maxacalcitol to the nuclear vitamin D receptors of parathyroid cells. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20070401
Successful treatment of refractory warts with topical vitamin D3 derivative (maxacalcitol, 1alpha, 25-dihydroxy-22-oxacalcitriol) in 17 patients. The Journal of dermatology 20070401
Prospective comparison of the effects of maxacalcitol and calcitriol in chronic hemodialysis patients with secondary hyperparathyroidism: a multicenter, randomized crossover study. Clinical nephrology 20070101
Nonclassical aspects of differential vitamin D receptor activation: implications for survival in patients with chronic kidney disease. Drugs 20070101
Comedolytic effect of topically applied active vitamin D3 analogue on pseudocomedones in the rhino mouse. The British journal of dermatology 20061101
Successful treatment of stucco keratosis with maxacalcitol. The British journal of dermatology 20061101
Comparison of the efficacy of calcipotriol and maxacalcitol in combination with narrow-band ultraviolet B therapy for the treatment of psoriasis vulgaris. Photodermatology, photoimmunology & photomedicine 20061001
Direct maxacalcitol injection into hyperplastic parathyroids improves skeletal changes in secondary hyperparathyroidism. Kidney international 20060801
Direct injection of calcitriol or its analog into hyperplastic parathyroid glands induces apoptosis of parathyroid cells. Kidney international. Supplement 20060701
[Progress in research on vitamin D analogs]. Clinical calcium 20060701
Design and evaluation of new antipsoriatic antedrug candidates having 16-en-22-oxa-vitamin D3 structures. Bioorganic & medicinal chemistry letters 20060615
Epidermodysplasia verruciformis and generalized verrucosis: the same disease? Clinical and experimental dermatology 20060501
Successful treatment of warts with a combination of maxacalcitol ointment and salicylic acid sticking plaster. The Journal of dermatology 20060501
Analysis of in vitro skin permeation of 22-oxacalcitriol having a complicated metabolic pathway. Pharmaceutical research 20060401
Is the volume of the parathyroid gland a predictor of Maxacalcitol response in advanced secondary hyperparathyroidism? Therapeutic apheresis and dialysis : official peer-reviewed journal of the International Society for Apheresis, the Japanese Society for Apheresis, the Japanese Society for Dialysis Therapy 20060401
A case of maxacalcitol-resistant confluent and reticulated papillomatosis successfully treated with minocycline. The Journal of dermatology 20060301
No change in circulating osteoprotegerin levels by intravenous calcitriol therapy among dialysis patients with secondary hyperparathyroidism. Clinical nephrology 20060201
Combination therapy of intravenous maxacalcitol and percutaneous ethanol injection therapy lowers serum parathyroid hormone level and calcium x phosphorus product in secondary hyperparathyroidism. Nephron. Clinical practice 20060101
Treatment of psoriasis vulgaris with narrow-band UVB and topical Maxacalcitol. Acta dermato-venereologica 20060101
Inhibitory effect of 22-oxa-1,25-dihydroxyvitamin D3, maxacalcitol, on the proliferation of pancreatic cancer cell lines. The Journal of steroid biochemistry and molecular biology 20051001
Comparison of the efficacy of an oral calcitriol pulse or intravenous 22-oxacalcitriol therapies in chronic hemodialysis patients. Clinical and experimental nephrology 20050901
[Influence of serum phosphate level for effects of OCT pulse therapy in hyper-PTH HD patients]. Clinical calcium 20050901
[Suitable examination intervals for hemodialysis patients with secondary hyperparathyroidism treated with maxacalcitol]. Clinical calcium 20050901
[Acute response of serum PTH and bone markers after injection of 1alpha,25 (OH)2D3 and 22-oxacalcitrol in hemodialysis patient]. Clinical calcium 20050901
Maxacalcitol is a possible less phosphatemic vitamin D analog. Therapeutic apheresis and dialysis : official peer-reviewed journal of the International Society for Apheresis, the Japanese Society for Apheresis, the Japanese Society for Dialysis Therapy 20050801
Maxacalcitol therapy decreases circulating osteoprotegerin levels in dialysis patients with secondary hyperparathyroidism. Clinical nephrology 20050701
Assessment of therapeutic effect in patients with secondary hyperparathyroidism using bone scintigraphy. Annals of nuclear medicine 20050701
22-Oxa-1alpha,25-dihydroxyvitamin D3 inhibits metastasis and angiogenesis in lung cancer. Carcinogenesis 20050601
Pretreatment plasma intact parathyroid hormone and serum calcium levels, but not serum phosphate levels, predict the response to maxacalcitol therapy in dialysis patients with secondary hyperparathyroidism. Clinical and experimental nephrology 20050601
In vivo assessment of the cutaneous bioavailability of topically applied maxacalcitol. Methods and findings in experimental and clinical pharmacology 20050601
Measurement and characterization of C-3 epimerization activity toward vitamin D3. Archives of biochemistry and biophysics 20050401
The influence of dialysate calcium on the therapeutic effects of sevelamer hydrochloride in hemodialysis patients with secondary hyperparathyroidism under treatment of intravenous vitamin d metabolites. Therapeutic apheresis and dialysis : official peer-reviewed journal of the International Society for Apheresis, the Japanese Society for Apheresis, the Japanese Society for Dialysis Therapy 20050201
Biochemical and cellular effects of direct maxacalcitol injection into parathyroid gland in uremic rats. Journal of the American Society of Nephrology : JASN 20050101
Pharmacokinetics of calcitriol and maxacalcitol administered into peritoneal dialysate bags in peritoneal dialysis patients. Peritoneal dialysis international : journal of the International Society for Peritoneal Dialysis 20050101
[Therapy for ROD and measurement of the bone mass]. Clinical calcium 20041201
Dose-response study of 22-oxacalcitriol in patients with secondary hyperparathyroidism. Therapeutic apheresis and dialysis : official peer-reviewed journal of the International Society for Apheresis, the Japanese Society for Apheresis, the Japanese Society for Dialysis Therapy 20041201
Adsorption of oxacalcitriol by polysulphone haemodialyser in patients with secondary hyperparathyroidism. British journal of clinical pharmacology 20041101
[Advantage of intravenous pulse therapy with calcitriol or maxacalcitol in dialysis patients with renal hyperparathyroidism]. Clinical calcium 20040901
[Serum calcium concentration and the safety of vitamin D therapy]. Clinical calcium 20040901
Comparison of the effects of calcitriol and maxacalcitol on secondary hyperparathyroidism in patients on chronic haemodialysis: a randomized prospective multicentre trial. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20040801
Chronopharmacology of oxacalcitriol in 5/6 nephrectomized rats. Life sciences 20040702
Avoidance of direct injury to the peripheral nerve with maxacalcitol (22oxa-1,25(OH)2D3) in rats. Nephrology (Carlton, Vic.) 20040601
Suppression of parathyroid hormone secretion in CAPD patients by intraperitoneal administration of Maxacalcitol. Clinical and experimental nephrology 20040601
[Parathyroid intervention and surgical treatment in renal hyperparathyroidism]. Nihon rinsho. Japanese journal of clinical medicine 20040601
[The trend in the development of the active vitamin D3 and its analogues]. Nihon rinsho. Japanese journal of clinical medicine 20040501
Intact PTH assay overestimates true 1-84 PTH levels after maxacalcitol therapy in dialysis patients with secondary hyperparathyroidism. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20040401
Chronopharmacology of oxacalcitriol in rat model of osteoporosis. European journal of pharmacology 20040319
Calcimimetics versus vitamin D: what are their relative roles? Blood purification 20040101
Receptor microscopic autoradiography for the study of percutaneous absorption, in vivo skin penetration, and cellular-intercellular deposition. Journal of pharmacological and toxicological methods 20040101
Intravenous vitamin D therapy reduces PTH-(1-84)/large C fragments ratio in chronic hemodialysis patients. Nephron. Clinical practice 20040101
Relationship between parathyroid gland size and responsiveness to maxacalcitol therapy in patients with secondary hyperparathyroidism. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20031201
Anti-tumor effect of vitamin A and D on head and neck squamous cell carcinoma. Auris, nasus, larynx 20031201
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. Internal medicine (Tokyo, Japan) 20031201
Development of hungry bone syndrome after rapid lowering of PTH with intravenous maxacalcitol therapy in a patient with non-uremic secondary hyperparathyroidism. Clinical nephrology 20031101
Effect of 22-oxacalcitriol on secondary hyperparathyroidism in hemodialysis patients. Internal medicine (Tokyo, Japan) 20031001
Percutaneous maxacalcitol injection therapy regresses hyperplasia of parathyroid and induces apoptosis in uremia. Kidney international 20030901
In subtotally nephrectomized rats 22-oxacalcitriol suppresses parathyroid hormone with less risk of cardiovascular calcification or deterioration of residual renal function than 1,25(OH)2 vitamin D3. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20030901
Surgical verification of percutaneous maxacalcitol injection therapy on enlarged parathyroid glands in chronic dialysis patients. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20030601
Time course of change in calcium x phosphorus product after percutaneous ethanol injection therapy. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20030601
Combined radioguided parathyroidectomy and intravenous vitamin D therapy for the treatment of uraemic hyperparathyroidism. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20030601
Multicenter clinical trial of 22-oxa-1,25-dihydroxyvitamin D3 for chronic dialysis patients. American journal of kidney diseases : the official journal of the National Kidney Foundation 20030301
Similarly potent action of 1,25-dihydroxyvitamin D3 and its analogues, tacalcitol, calcipotriol, and maxacalcitol on normal human keratinocyte proliferation and differentiation. Journal of dermatological science 20030201
Two novel metabolic pathways of 22-oxacalcitriol (OCT). C-25 dehydration and C-3 epimerization and biological activities of novel OCT metabolites. The Journal of biological chemistry 20030117
[Maxacalcitol, a medicine for secondary hyperparathyroidism (2 degrees HPT)]. Nihon yakurigaku zasshi. Folia pharmacologica Japonica 20030101
[Mechanism of uremic osteodystrophy and prevention of hyperparathyroidism in the uremic patient]. Giornale italiano di nefrologia : organo ufficiale della Societa italiana di nefrologia 20030101
Effects of 'non-calcaemic' vitamin D analogues on 24-hydroxylase expression in MG-63 osteoblast-like cells. Nephron. Physiology 20030101
The effect of intraperitoneal 22-oxacalcitriol on secondary hyperparathyroidism in continuous ambulatory peritoneal dialysis patients (IPOX study). Advances in peritoneal dialysis. Conference on Peritoneal Dialysis 20030101
Different effects of 22-oxacalcitriol and calcitriol on the course of experimental chronic renal failure. The Journal of laboratory and clinical medicine 20021001
Combination of 22-oxa-1,25-dihydroxyvitamin D(3), a vitamin D(3) derivative, with vitamin K(2) (VK2) synergistically enhances cell differentiation but suppresses VK2-inducing apoptosis in HL-60 cells. Leukemia 20020801
1Alpha25(OH)2D3 interferes with retinoic acid-induced inhibition of c-fos gene expression for AP-1 formation in osteoblastic cells. Journal of oral science 20020301
Effects of vitamin D analog, 22-oxa-1,25-dihydroxyvitamin D(3), on bone reconstruction by vascularized bone allograft. Bone 20020201
[The clinical evaluation of maxacalcitol on therapy for secondary hyperparathyroidism of chronic hemodialysis patients]. Nihon Jinzo Gakkai shi 20020101
[A case with secondary hyperparathyroidism suggesting the direct suppressive effect of maxacalcitol on osteoblasts]. Nihon Jinzo Gakkai shi 20020101
Vitamin D analogues for secondary hyperparathyroidism. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20020101
Effects of 1,25-dihydroxy-22-oxavitamin D(3) on parathyroid gland function in haemodialysis patients with secondary hyperparathyroidism. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20020101
Long-term effect of 1,25-dihydroxy-22-oxavitamin D(3) on secondary hyperparathyroidism in haemodialysis patients. One-year administration study. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20020101
A comparison between daily and thrice-weekly i.v. administration of 1,25-dihydroxy-22-oxavitamin D(3) regarding suppression of parathyroid hormone secretion and calcaemic action in uraemic rats. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20020101
A comparison between 1,25-dihydroxy-22-oxavitamin D(3) and 1,25-dihydroxyvitamin D(3) regarding suppression of parathyroid hormone secretion and calcaemic action. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20020101
Effects of i.v. and oral 1,25-dihydroxy-22-oxavitamin D(3) on secondary hyperparathyroidism in dogs with chronic renal failure. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20020101
In vivo time-course of receptor binding in the parathyroid gland of the vitamin D analogue [(3)H]1,25-dihydroxy-22-oxavitamin D(3) compared with [(3)H]1,25-dihydroxyvitamin D(3), determined by micro-autoradiography. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20020101
Clinical effects of maxacalcitol on secondary hyperparathyroidism of uremic patients. American journal of kidney diseases : the official journal of the National Kidney Foundation 20011001
Vitamin D and cancer: effects of 1,25(OH)2D3 and its analogs on growth control and tumorigenesis. Frontiers in bioscience : a journal and virtual library 20010701
A vitamin D analog ameliorates glomerular injury on rat glomerulonephritis. The American journal of pathology 20010501
Synthesis and evaluation of A-ring diastereomers of 1alpha,25-dihydroxy-22-oxavitamin D3 (OCT). Bioorganic & medicinal chemistry 20010201
History of the development of new vitamin D analogs: studies on 22-oxacalcitriol (OCT) and 2beta-(3-hydroxypropoxy)calcitriol (ED-71). Steroids 20010101
22-oxacalcitriol suppresses secondary hyperparathyroidism without inducing low bone turnover in dogs with renal failure. Kidney international 19990301
Effect of 22-oxacalcitriol on hyperparathyroidism of dialysis patients: results of a preliminary study. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 19960101
Actions of vitamin D3, analogs on human prostate cancer cell lines: comparison with 1,25-dihydroxyvitamin D3. Endocrinology 19950101
Hypocalcemia, regardless of the vitamin D status, decreases epidermal growth factor receptor density and autophosphorylation in rat livers. Endocrinology 19930801
Differential effects of 1,25-(OH)2D3 and 22-oxacalcitriol on phosphate and calcium metabolism. Kidney international 19930301
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. Bone 19930101
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. Endocrinology 19910801
Properties