CALCITRIOL MONOHYDRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H44O3.H2O
Molecular Weight	434.6517
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.[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)CCCC(C)(C)O

InChI

InChIKey=VMBWEMQRTFKRSU-RFHBVEJWSA-N

InChI=1S/C27H44O3.H2O/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2;/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3;1H2/b20-10+,21-11-;/t18-,22-,23-,24+,25+,27-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C27H44O3
Molecular Weight	416.6365
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	2
Optical Activity	UNSPECIFIED

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/1998/21068lbl.pdfhttps://www.ncbi.nlm.nih.gov/mesh/68002117 | https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/021068a_phrmr_P1.pdf
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/cdi/calcitriol.html http://www.wikidoc.org/index.php/Calcitriol_(oral)

Trans-calcitriol or Calcitriol Impurity A, is the impurity of Calcitriol. Calcitriol is the hormonally active form of vitamin D, Calcitriol is the active metabolite of vitamin D3 that activates the vitamin D receptor (VDR). Calcitriol Impurity A is the physiologically active form of vitamin D. It is formed primarily in the kidney by enzymatic hydroxylation of 25-hydroxycholecalciferol (CALCIFEDIOL). Its production is stimulated by low blood calcium levels and parathyroid hormone. Calcitriol increases intestinal absorption of calcium and phosphorus, and in concert with parathyroid hormone increases bone resorption.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Vitamin D3 receptor 9 Target ID: P11473 Gene ID: 7421.0 Gene Symbol: VDR Target Organism: Homo sapiens (Human) Sources: http://www.drugbank.ca/drugs/DB00136 \| https://www.ncbi.nlm.nih.gov/pubmed/10517670	Binding Agent 1064	0.22 nM [Kd]
Cytochrome P450 24A1 6 Target ID: CHEMBL4521 Sources: http://www.drugbank.ca/drugs/DB00136 \| https://www.ncbi.nlm.nih.gov/pubmed/16207822 Ahn, J. et al. (2016) 'Vitamin D Hormone', p.327 Retrieved from \| https://books.google.ru/books?id=-OSECgAAQBAJ	Substrate 661
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: http://www.drugbank.ca/drugs/DB00136 \| https://www.ncbi.nlm.nih.gov/pubmed/16207822	Substrate 661

Conditions

Condition	Modality	Highest Phase	Product
Unknown 2578
Secondary hyperparathyroidism 9 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/1998/21068lbl.pdf	Primary	Approved 8429	ROCALTROL Approved Use Predialysis Patients Calcitriol Capsules are indicated in the management of secondary hyperparathyroidism and resultant metabolic bone disease in patients with moderate to severe chronic renal failure (Ccr 15 to 55 mL/min) not yet on dialysis. In children, the creatinine clearance value must be corrected for a surface area of 1.73 square meters. A serum iPTH level of ≥100 pg/mL is strongly suggestive of secondary hyperparathyroidism. Dialysis Patients Calcitriol Capsules are indicated in the management of hypocalcemia and the resultant metabolic bone disease in patients undergoing chronic renal dialysis. In these patients, calcitriol administration enhances calcium absorption, reduces serum alkaline phosphatase levels, and may reduce elevated parathyroid hormone levels and the histological manifestations of osteitis fibrosa cystica and defective mineralization. Hypoparathyroidism Patients Calcitriol Capsules are also indicated in the management of hypocalcemia and its clinical manifestations in patients with postsurgical hypoparathyroidism, idiopathic hypoparathyroidism, and pseudohypoparathyroidism. Launch Date 2.72159998E11
Hypocalcemia 75 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/1998/21068lbl.pdf	Preventing	Approved 8429	ROCALTROL Approved Use Predialysis Patients Calcitriol Capsules are indicated in the management of secondary hyperparathyroidism and resultant metabolic bone disease in patients with moderate to severe chronic renal failure (Ccr 15 to 55 mL/min) not yet on dialysis. In children, the creatinine clearance value must be corrected for a surface area of 1.73 square meters. A serum iPTH level of ≥100 pg/mL is strongly suggestive of secondary hyperparathyroidism. Dialysis Patients Calcitriol Capsules are indicated in the management of hypocalcemia and the resultant metabolic bone disease in patients undergoing chronic renal dialysis. In these patients, calcitriol administration enhances calcium absorption, reduces serum alkaline phosphatase levels, and may reduce elevated parathyroid hormone levels and the histological manifestations of osteitis fibrosa cystica and defective mineralization. Hypoparathyroidism Patients Calcitriol Capsules are also indicated in the management of hypocalcemia and its clinical manifestations in patients with postsurgical hypoparathyroidism, idiopathic hypoparathyroidism, and pseudohypoparathyroidism. Launch Date 2.72159998E11
Mild to moderate plaque psoriasis 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022087lbl.pdf	Primary	Approved 8429	VECTICAL Approved Use VECTICAL Ointment is indicated for the topical treatment of mild to moderate plaque psoriasis in adults 18 years and older. Launch Date 2.72159998E11

C_max

Value	Dose	Co-administered	Analyte	Population
1100 pg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12496746	38 μg 3 times / week multiple, oral dose: 38 μg route of administration: Oral experiment type: MULTIPLE co-administered: PACLITAXEL	PACLITAXEL	CALCITRIOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
73.1799999999999 pg/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00419666	3 ug/g 2 times / day multiple, topical dose: 3 ug/g route of administration: topical experiment type: multiple co-administered:		CALCITRIOL plasma	Homo sapiens population: unhealthy age: Adolescents sex: F+M food status:
75.74 pg/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00419666	3 ug/g single, topical dose: 3 ug/g route of administration: topical experiment type: single co-administered:		CALCITRIOL plasma	Homo sapiens population: unhealthy age: Adolescents sex: F+M food status:

AUC

Value	Dose	Co-administered	Analyte	Population
8100 pg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12496746	38 μg 3 times / week multiple, oral dose: 38 μg route of administration: Oral experiment type: MULTIPLE co-administered: PACLITAXEL	PACLITAXEL	CALCITRIOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
737.74 pg*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00419666	3 ug/g 2 times / day multiple, topical dose: 3 ug/g route of administration: topical experiment type: multiple co-administered:		CALCITRIOL plasma	Homo sapiens population: unhealthy age: Adolescents sex: F+M food status:
764.74 pg*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00419666	3 ug/g single, topical dose: 3 ug/g route of administration: topical experiment type: single co-administered:		CALCITRIOL plasma	Homo sapiens population: unhealthy age: Adolescents sex: F+M food status:
549.29 pg*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00419666	3 ug/g 2 times / day multiple, topical dose: 3 ug/g route of administration: topical experiment type: multiple co-administered:		CALCITRIOL plasma	Homo sapiens population: unhealthy age: Adolescents sex: F+M food status:
575.12 pg*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00419666	3 ug/g single, topical dose: 3 ug/g route of administration: topical experiment type: single co-administered:		CALCITRIOL plasma	Homo sapiens population: unhealthy age: Adolescents sex: F+M food status:

T_1/2

Value	Dose	Co-administered	Analyte	Population
25 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12496746	38 μg 3 times / week multiple, oral dose: 38 μg route of administration: Oral experiment type: MULTIPLE co-administered: PACLITAXEL	PACLITAXEL	CALCITRIOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
AHH Chemical co.,ltd	NP-1040	http://www.ahhchemical.com/product/NP-1040.html
AbMole Bioscience	M2174	http://www.abmole.com/products/calcitriol.html
Achemo Scientific Limited	AC-16679	http://www.achemo.com/search/?Keyword= 32222-06-3
Achemtek	0101-001973	http://www.achemtek.com/32222-06-3
Alfa Chemistry	AP32222063-C	https://reagents.alfa-chemistry.com/product/1-25-dihydroxyvitamin-d3-cas-32222-06-3-9957.html
Alfa Chemistry	AP32222063-A	https://reagents.alfa-chemistry.com/product/1-25-dihydroxyvitamin-d3-solution-cas-32222-06-3-9955.html
Alfa Chemistry	AP32222063-B	https://reagents.alfa-chemistry.com/product/calcitriol-solution-cas-32222-06-3-9956.html
Alfa Chemistry	32222-06-3	https://www.alfa-chemistry.com/calcitriol-cas-32222-06-3-item-291485.htm
Alsachim	1921	http://www.alsachim.com/product-C2847-glo.bal-view.html
ApexBio Technology	B2141	http://www.apexbt.com/calcitriol.html
Aurora Fine Chemicals LLC	A17.877.497	http://online.aurorafinechemicals.com/info?ID=A17.877.497
Aurora Fine Chemicals LLC	K02.111.135	http://online.aurorafinechemicals.com/info?ID=K02.111.135
Aurum Pharmatech LLC	W-5161	http://www.Aurumpharmatech.com/Product/ProductDetails/W_5161
AvaChem Scientific	2191	http://www.avachem.com/productSearch.asp?2191
BLD Pharm	BD01358017	http://www.bldpharm.com/products/1000873-74-4.html
BioCrick	BCC4950	http://www.biocrick.com/Calcitriol-BCC4950.html
Boerchem	BC208534	http://www.boerchem.com/?product_35283.html
Calbiochem	679101	http://www.emdbiosciences.com/product/679101
Capot Chemical	18818	http://www.capotchem.com/en/18818.htm
Capot Chemical	PubChem18818	http://www.capotchem.com/en/18818.htm
Capot Chemical	19327	http://www.capotchem.com/en/19327.htm
Capot Chemical	PubChem19327	http://www.capotchem.com/en/19327.htm
Chem Scene	CS-0388	http://www.chemscene.com/32222-06-3.html
ChemMol	30104349	http://www.chemmol.com/chemmol/30104349.html
ChemMol	44003293	http://www.chemmol.com/chemmol/44003293.html
ChemMol	49408407	http://www.chemmol.com/chemmol/49408407.html
ChemMol	99070257	http://www.chemmol.com/chemmol/99070257.html
Chemspace	CSSB00020610488	https://chem-space.com/CSSB00020610488
Chiralblock Biosciences	CB11406	http://www.chiralblock.com/products/32222-06-3.html
Clearsynth	CS-O-06153	https://www.clearsynth.com/en/CSO06153.html
EMD Millipore	679101	http://www.emdbiosciences.com/product/679101
Excenen	EX-A4435	https://www.excenen.com/searchresultlist.php?id=EX-A4435
Glentham Life Sciences	GP9482	http://www.glentham.com/products/product/GP9482/
Hello Bio	HB3962	http://www.hellobio.com/luteolin-5897.html
LGC Standards	DRE-A10934950AL-100	https://www.lgcstandards.com/US/en/p/DRE-A10934950AL-100
LGC Standards	DRE-C10934950	https://www.lgcstandards.com/US/en/p/DRE-C10934950
LGC Standards	MM0205.00	https://www.lgcstandards.com/US/en/p/MM0205.00
Lab Network	LN01276594	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01276594
Matrix Scientific	144307	https://www.matrixscientific.com/144307.html
MedChem Express	HY-10002	https://www.medchemexpress.com/Calcitriol.html
MuseChem	A000862	https://www.musechem.com/product/A000862.html
OChem	1562	http://www.ocheminc.com/index.php?act=psearch&pid=222C063
Parchem	28433	http://www.parchem.com/chemical-supplier-distributor/Calcitriol-018433.aspx
Selleck Chemicals	S1466	http://www.selleckchem.com/products/Calcitriol-(Rocaltrol).html
Sigma-Aldrich	C0225000_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/c0225000?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	17936_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/17936?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	D1530_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/d1530?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S800501	https://www.smolecule.com/products/s800501
Sun-shine Chemical	Calcitriol	http://sun-shinechem.com/
TCI (Tokyo Chemical Industry)	C3078	http://www.tcichemicals.com/eshop/en/us/commodity/C3078/index.html
Tocris	2551	https://www.tocris.com/products/calcitriol_2551
VladaChem	VL266434-2.5mg	https://www.vladachem.com/product.php?products=32222-06-3
Yuhao Chemical	LT7054	http://www.chemyuhao.com/32222-06-3.html
abcr GmbH	AB465093	http://www.abcr.com/shop/en/AB465093
eNovation Chemicals	D371145	http://www.enovationchem.com/productDetails.asp?productID=D371145
eNovation Chemicals	Y0974280	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y0974280
iChemical	EBD646297	http://www.ichemical.com/products/32222-06-3.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Calcitriol-mediated hypercalcaemia and increased interleukins in a patient with sarcoid myopathy.	1999	10638776
Hypercalcemia-induced renal insufficiency during therapy with dihydrotachysterol.	1999	10515239
Hypercalcaemia and hypercalciuria after topical treatment of psoriasis with excessive amounts of calcipotriol.	1999 Jan	10086871
Physician-induced hypocalcaemia, nephrocalcinosis, and incomplete distal renal tubular acidosis.	2000 Aug	10910456
Calcitriol-induced apoptosis in LNCaP cells is blocked by overexpression of Bcl-2.	2000 Jan	10614618
Association of transforming growth factor beta1 genotype with therapeutic response to active vitamin D for postmenopausal osteoporosis.	2000 Mar	10750555
1 Alpha,25-dihydroxyvitamin D3 inhibits differentiation, maturation, activation, and survival of dendritic cells leading to impaired alloreactive T cell activation.	2000 Mar 1	10679076
The anti-proliferative effect of calcitriol on HL-60 cells is neutralized by uraemic biological fluids.	2001 Feb	11158396
Failure of high doses of calcitriol and hypercalcaemia to induce apoptosis in hyperplastic parathyroid glands of azotaemic rats.	2001 Mar	11239023
Amphiregulin is a vitamin D3 target gene in squamous cell and breast carcinoma.	2001 Mar 9	11237771
1,25-dihydroxyvitamin D3 and retonic acid analogues induce differentiation in breast cancer cells with function- and cell-specific additive effects.	2001 May	11519864
Stabilization of hypoxia-inducible factor-1alpha is involved in the hypoxic stimuli-induced expression of vascular endothelial growth factor in osteoblastic cells.	2002 Jan 7	11886167
Deletion of deoxyribonucleic acid binding domain of the vitamin D receptor abrogates genomic and nongenomic functions of vitamin D.	2002 Jul	12089348
HL60 cells halted in G1 or S phase differentiate normally.	2002 Nov 15	12441127
Differentiation of murine melanocyte precursors induced by 1,25-dihydroxyvitamin D3 is associated with the stimulation of endothelin B receptor expression.	2002 Sep	12230499
Vitamin D inhibits G1 to S progression in LNCaP prostate cancer cells through p27Kip1 stabilization and Cdk2 mislocalization to the cytoplasm.	2003 Nov 21	12954644
DNA microarray analysis of vitamin D-induced gene expression in a human colon carcinoma cell line.	2004 Apr 13	14996990
Unique regulation of SOST, the sclerosteosis gene, by BMPs and steroid hormones in human osteoblasts.	2004 Aug	15268896
Calcitriol-induced prostate-derived factor: autocrine control of prostate cancer cell growth.	2004 Dec 20	15386353
Structural determinants for vitamin D receptor response to endocrine and xenobiotic signals.	2004 Jan	14525957
FGF-23 is a potent regulator of vitamin D metabolism and phosphate homeostasis.	2004 Mar	15040831
1,25(OH)2D3 inhibits bone marrow adipogenesis in senescence accelerated mice (SAM-P/6) by decreasing the expression of peroxisome proliferator-activated receptor gamma 2 (PPARgamma2).	2004 Mar	15036392
Leptin corrects increased gene expression of renal 25-hydroxyvitamin D3-1 alpha-hydroxylase and -24-hydroxylase in leptin-deficient, ob/ob mice.	2004 Mar	14657008
Modulation of CYP27B1 and CYP24 mRNA expression in bone is independent of circulating 1,25(OH)2D3 levels.	2005 Apr	15781002
Daily or intermittent calcitriol administration during growth hormone therapy in rats with renal failure and advanced secondary hyperparathyroidism.	2005 Apr	15728789
Amphiregulin is a novel growth factor involved in normal bone development and in the cellular response to parathyroid hormone stimulation.	2005 Feb 4	15509566
Selective activation of vitamin D receptor by lithocholic acid acetate, a bile acid derivative.	2005 Jan	15489543
Type 2 iodothyronine selenodeiodinase is expressed throughout the mouse skeleton and in the MC3T3-E1 mouse osteoblastic cell line during differentiation.	2005 Jan	15471965
Regulation of renal calcium receptor gene expression by 1,25-dihydroxyvitamin D3 in genetic hypercalciuric stone-forming rats.	2005 May	15788476
Androgen receptor signaling and vitamin D receptor action in prostate cancer cells.	2005 Sep 1	15754350

Patents

Sample Use Guides

In Vivo Use Guide

Calcitriol can be administered orally either as a capsule (0.25 mcg or 0.50 mcg) or as an oral solution (1 mcg/mL).

Route of Administration: Other

In Vitro Use Guide

CYP3A4 mRNA expression in LS180 cells treated with 100 nM of Calcitriol for 6 and 24 h was approximately 80- and 500-fold higher than the control.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:54:30 UTC 2023` Edited by `admin` on `Fri Dec 15 18:54:30 UTC 2023`
Record UNII	97SK7L66LH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CALCITRIOL MONOHYDRATE

Common Name

English

(5Z,7E)-9,10-SECOCHOLESTA-5,7,10(19)-TRIENE-1.ALPHA.,3.BETA.,25-TRIOL MONOHYDRATE

Common Name

English

Code System Code Type Description

PUBCHEM

71587284

Created by admin on Fri Dec 15 18:54:30 UTC 2023 , Edited by admin on Fri Dec 15 18:54:30 UTC 2023

PRIMARY

CAS

77326-95-5

Created by admin on Fri Dec 15 18:54:30 UTC 2023 , Edited by admin on Fri Dec 15 18:54:30 UTC 2023

PRIMARY

FDA UNII

97SK7L66LH

Created by admin on Fri Dec 15 18:54:30 UTC 2023 , Edited by admin on Fri Dec 15 18:54:30 UTC 2023

PRIMARY

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Details

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Approved Use

Launch Date

Approved Use

Launch Date

Cmax

AUC

T1/2

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2