Identification
- Summary
Dihydrotachysterol is a synthetic analog of vitamin D that does not require renal activation like vitamin D2 or Vitamin D3.
- Generic Name
- Dihydrotachysterol
- DrugBank Accession Number
- DB01070
- Background
A vitamin D that can be regarded as a reduction product of vitamin D2.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Dihydrotachysterol (DB01070)
- Weight
- Average: 398.6642
Monoisotopic: 398.354866094 - Chemical Formula
- C28H46O
- Synonyms
- Anti-tetany substance 10
- Dihidrotaquisterol
- Dihydrotachysterol
- Dihydrotachysterolum
Pharmacology
- Indication
Used for the prevention and treatment of rickets or osteomalacia, and to manage hypocalcemia associated with hypoparathyroidism or pseudohypoparathyroidism. Also used for the treatment of vitamin D dependent rickets, rickets or osteomalacia secondary to long-term high dose anticonvulsant therapy, early renal osteodystrophy, osteoporosis (in conjunction with calcium), and hypophosphatemia associated with Fanconi syndrome (with treatment of acidosis).
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Pseudohypoparathyroidism •••••••••••• Treatment of Parathyroid deficiency •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Dihydrotachysterol is hydroxylated in the liver to 25-hydroxydihydrotachysterol, which is the major circulating active form of the drug. It does not undergo further hydroxylation by the kidney and therefore is the analogue of 1, 25-dihydroxyvitamin D. Dihydrotachysterol is effective in the elevation of serum calcium by stimulating intestinal calcium absorption and mobilizing bone calcium in the absence of parathyroid hormone and of functioning renal tissue. Dihydrotachysterol also increases renal phosphate excretion.
- Mechanism of action
Once hydroxylated to 25-hydroxydihydrotachysterol, the modified drug binds to the vitamin D receptor. The bound form of the vitamin D receptor serves as a transcriptional regulator of bone matrix proteins, inducing the expression of osteocalcin and suppressing synthesis of type I collagen. Vitamin D (when bound to the vitamin D receptor)stimulates the expression of a number of proteins involved in transporting calcium from the lumen of the intestine, across the epithelial cells and into blood. This stimulates intestinal calcium absorption and increases renal phosphate excretion. These are functions that are normally carried out by the parathyroid hormone.
Target Actions Organism AVitamin D3 receptor agonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
>99%
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Toxicity associated with dihydrotachysterol is similar to that seen with large doses of vitamin D.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcetyldigitoxin The risk or severity of ventricular arrhythmias and Cardiac Arrhythmia can be increased when Dihydrotachysterol is combined with Acetyldigitoxin. Alfacalcidol The risk or severity of adverse effects can be increased when Dihydrotachysterol is combined with Alfacalcidol. Aluminum hydroxide The serum concentration of Aluminum hydroxide can be increased when it is combined with Dihydrotachysterol. Beclomethasone dipropionate The therapeutic efficacy of Dihydrotachysterol can be decreased when used in combination with Beclomethasone dipropionate. Bendroflumethiazide The risk or severity of hypercalcemia can be increased when Bendroflumethiazide is combined with Dihydrotachysterol. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- AT 10 / Atiten (Bayer) / Dihydral (Solvay) / Dygratyl (Dishman) / Tachystin (Chauvin)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Hytakerol Capsule .125 mg Oral Sanofi Synthelabo 1952-12-31 2003-07-30 Canada 
Categories
- ATC Codes
- A11CC02 — Dihydrotachysterol
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as vitamin d and derivatives. These are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Vitamin D and derivatives
- Direct Parent
- Vitamin D and derivatives
- Alternative Parents
- Triterpenoids / Secondary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
- Substituents
- Alcohol / Aliphatic homopolycyclic compound / Cyclic alcohol / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Secondary alcohol / Triterpenoid
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- hydroxy seco-steroid, seco-ergostane, vitamin D (CHEBI:4591) / Vitamin D2 and derivatives (LMST03010056)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- R5LM3H112R
- CAS number
- 67-96-9
- InChI Key
- ILYCWAKSDCYMBB-OPCMSESCSA-N
- InChI
- InChI=1S/C28H46O/c1-19(2)20(3)9-10-22(5)26-15-16-27-23(8-7-17-28(26,27)6)12-13-24-18-25(29)14-11-21(24)4/h9-10,12-13,19-22,25-27,29H,7-8,11,14-18H2,1-6H3/b10-9+,23-12+,24-13+/t20-,21-,22+,25-,26+,27-,28+/m0/s1
- IUPAC Name
- (1S,3E,4S)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylcyclohexan-1-ol
- SMILES
- CC(C)[C@@H](C)\C=C\[C@@H](C)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1/C[C@@H](O)CC[C@@H]1C
References
- Synthesis Reference
von Werder, F.; U.S. Patent 2,228,491; January 14,1941; assigned to Winthrop Chemical Company, Inc.
- General References
- DeLuca HF: Overview of general physiologic features and functions of vitamin D. Am J Clin Nutr. 2004 Dec;80(6 Suppl):1689S-96S. [Article]
- Bosch R, Thijssen JH, Duursma SA: Action and metabolism of dihydrotachysterol2. J Steroid Biochem. 1987;27(4-6):829-36. [Article]
- Pierides AM: Pharmacology and therapeutic use of vitamin D and its analogues. Drugs. 1981 Apr;21(4):241-56. [Article]
- Gagnon R, Ogden GW, Just G, Kaye M: Comparison of dihydrotachysterol and 5,6-trans vitamin D3 on intestinal calcium absorption in patients with chronic renal failure. Can J Physiol Pharmacol. 1974 Apr;52(2):272-4. [Article]
- Codifa: Atiten (dihydrotachisterol) oral drops [Link]
- External Links
- Human Metabolome Database
- HMDB0015203
- KEGG Drug
- D00299
- KEGG Compound
- C06957
- PubChem Compound
- 5311071
- PubChem Substance
- 46507699
- ChemSpider
- 4470607
- 3429
- ChEBI
- 4591
- ChEMBL
- CHEMBL2356023
- ZINC
- ZINC000004212953
- Therapeutic Targets Database
- DAP000365
- PharmGKB
- PA164744345
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Dihydrotachysterol
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 2 Completed Treatment Advanced Malignant Glioma 1 2 Completed Treatment Advanced Renal Cell Carcinoma 1 2 Recruiting Treatment Facial Cutaneous Squamous Cell Carcinoma in Situ 1 2 Withdrawn Treatment Parkinson's Disease (PD) 1 1 Completed Not Available Healthy Subjects (HS) 2
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Murfreesboro Pharmaceutical Nursing Supply
- Professional Co.
- Sanofi-Aventis Inc.
- Dosage Forms
Form Route Strength Capsule Oral 0.5 mg Solution Oral 1 mg/mL Solution / drops Oral 1 MG/ML Capsule Oral .125 mg - Prices
Unit description Cost Unit Dihydrotachysterol powder 15.56USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 7.5 Not Available - Predicted Properties
Property Value Source Water Solubility 0.000125 mg/mL ALOGPS logP 7.86 ALOGPS logP 7.4 Chemaxon logS -6.5 ALOGPS pKa (Strongest Acidic) 18.3 Chemaxon pKa (Strongest Basic) -1.4 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 20.23 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 129.11 m3·mol-1 Chemaxon Polarizability 51.77 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9443 Caco-2 permeable + 0.822 P-glycoprotein substrate Substrate 0.6576 P-glycoprotein inhibitor I Inhibitor 0.6558 P-glycoprotein inhibitor II Non-inhibitor 0.8328 Renal organic cation transporter Non-inhibitor 0.8051 CYP450 2C9 substrate Non-substrate 0.817 CYP450 2D6 substrate Non-substrate 0.8853 CYP450 3A4 substrate Substrate 0.7432 CYP450 1A2 substrate Non-inhibitor 0.908 CYP450 2C9 inhibitor Non-inhibitor 0.9053 CYP450 2D6 inhibitor Non-inhibitor 0.9546 CYP450 2C19 inhibitor Non-inhibitor 0.9027 CYP450 3A4 inhibitor Non-inhibitor 0.8342 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7962 Ames test Non AMES toxic 0.9236 Carcinogenicity Non-carcinogens 0.9223 Biodegradation Not ready biodegradable 0.9623 Rat acute toxicity 3.1244 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8502 hERG inhibition (predictor II) Non-inhibitor 0.708
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-001i-2019000000-a25426597248c698f736 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0aps-0059000000-df5eaa80703ccc598495 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0009000000-1497cd748f8b9690ef03 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0219000000-ccc8503afaacf515cfde Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-05o1-7679000000-60503adf49a36243fc46 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-002k-1329000000-a0f577130588a9679c29 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-01x0-5934000000-49be97513840653ad942 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 221.031725 predictedDarkChem Lite v0.1.0 [M-H]- 223.035225 predictedDarkChem Lite v0.1.0 [M-H]- 225.022825 predictedDarkChem Lite v0.1.0 [M-H]- 221.234525 predictedDarkChem Lite v0.1.0 [M-H]- 205.45628 predictedDeepCCS 1.0 (2019) [M+H]+ 221.139125 predictedDarkChem Lite v0.1.0 [M+H]+ 206.3925031 predictedDarkChem Standard v0.1.0 [M+H]+ 224.676225 predictedDarkChem Lite v0.1.0 [M+H]+ 221.551725 predictedDarkChem Lite v0.1.0 [M+H]+ 207.28117 predictedDeepCCS 1.0 (2019) [M+Na]+ 220.966625 predictedDarkChem Lite v0.1.0 [M+Na]+ 222.620525 predictedDarkChem Lite v0.1.0 [M+Na]+ 224.626425 predictedDarkChem Lite v0.1.0 [M+Na]+ 221.460225 predictedDarkChem Lite v0.1.0 [M+Na]+ 212.88698 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific Function
- Nuclear hormone receptor. Transcription factor that mediates the action of vitamin D3 by controlling the expression of hormone sensitive genes. Recruited to promoters via its interaction with BAZ1B...
- Gene Name
- VDR
- Uniprot ID
- P11473
- Uniprot Name
- Vitamin D3 receptor
- Molecular Weight
- 48288.64 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Qaw F, Calverley MJ, Schroeder NJ, Trafford DJ, Makin HL, Jones G: In vivo metabolism of the vitamin D analog, dihydrotachysterol. Evidence for formation of 1 alpha,25- and 1 beta,25-dihydroxy-dihydrotachysterol metabolites and studies of their biological activity. J Biol Chem. 1993 Jan 5;268(1):282-92. [Article]
- Qaw FS, Makin HL, Jones G: Metabolism of 25-hydroxydihydrotachysterol3 in bone cells in vitro. Steroids. 1992 May;57(5):236-43. [Article]
- Gallagher JC, Sai AJ: Vitamin D insufficiency, deficiency, and bone health. J Clin Endocrinol Metab. 2010 Jun;95(6):2630-3. doi: 10.1210/jc.2010-0918. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2021 10:52