Tacalcitol

HCID 5283734
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Basic information

CAS
57333-96-7
Standard SMILES
C=C1/C(=C\C=C2/CCC[C@]3(C)[C@@H]([C@H](C)CC[C@@H](O)C(C)C)CC[C@@H]23)C[C@@H](O)C[C@@H]1O
InChIKey
BJYLYJCXYAMOFT-RSFVBTMBSA-N
Molecular formula
C27H44O3
Average molar mass
416.6 g/mol
Monoisotopic mass
416.32904527

Overview

Tacalcitol is a hydroxy seco-steroid that is calciol which carries hydroxy groups at positions 1S and 24R. It is a vitamin D3 analog which is used for the treatment of psoriasis vulgaris in adults, especially on the scalp. It has a role as a vitamin D receptor agonist, an antineoplastic agent and an antipsoriatic. It is a secondary alcohol, a seco-cholestane, a hydroxy seco-steroid and a member of D3 vitamins. It is functionally related to a calciol.

Names & identifiers

Preferred name
Tacalcitol
IUPAC
trans-(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R,5R)-5-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
English name
Tacalcitol
Molecular formula
C27H44O3
Molecular weight
416.64

Names & synonyms

tacalcitol57333-96-7BonalfaTacalcitolumTV-02PRI 21911-alpha,24(R)-Dihydroxyvitamin D3TV 02(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R,5R)-5-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diolC2W72OJ5ZUCHEBI:32176DTXSID90905111
Show more names
trans-CalcitriolC12919TacalcitalCuratodermTacalcitol RSTacalcitol (Standard)
(1S,3R,5Z,7E,24R)-9,10-secocholesta-5,7,10-triene-1,3,24-triol(+)-(5Z,7E,24R)-9,10-Secocholesta-5,7,10(19)-triene-1alpha,3beta,24-triol(1R,3S,5Z)-5-((2E)-2-((1R,3aS,7aR)-1-((2R,5R)-5-hydroxy-6-methylheptan-2-yl)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene)ethylidene)-4-methylidenecyclohexane-1,3-diolRefChem:890199D05AX04DTXCID6013342141 alpha,24-dihydroxyvitamin D3, (1alpha,3beta,5Z,7E,24R)-1alpha,24-Dihydroxycholecalciferol

Database identifiers

CAS
57333-96-7
PubChem CID
5283734
DTXSID
DTXSID90905111
ChEMBL
CHEMBL2105611
ChEBI
CHEBI:32176
UNII
C2W72OJ5ZU
EC Number
692-683-2
Nikkaji
J240.190H

Properties

Computed structural properties

XLogP
5.3
Topological polar surface area
60.7 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
3
Rotatable bonds
6
Heavy atoms
30

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
LipidsLipids -> Sterol Lipids [ST] -> Secosteroids [ST03] -> Vitamin D3 and derivatives [ST0302]
Human DrugsDermatological medicines > Medicines affecting skin differentiation and proliferation
Endocrine DisruptorsPotential endocrine disrupting compound

Physicochemical properties

Boiling point
565 · 565.0±50.0 °C(Predicted)
Density
1.06 · 1.06
storage temp.
-20 °C · Sealed in dry,Store in freezer, under -20°C
solubility
20 mg/mL · 20mg/mL in DMSO, 20mg/mL in DMF, 20mg/mL in Ethanol
pka
14.43 · 14.43±0.40(Predicted)
form
Powder

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 1 (100%)

Safety data

wgk
WGK 3
Signal word
Danger
Symbol(GHS)
GHS06
Storage Class
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard statements
H300
Hazard Classifications
Acute Tox. 1 Oral

Chemistry & industry

Pharmacology

ATC Code · 3 items

D05AX04

D - Dermatologicals

QD - Dermatologicals

MeSH Pharmacological Classification · 2 items

Substances that reduce or suppress INFLAMMATION.

Drugs used to treat or prevent skin disorders or for the routine care of skin.

Applications · 2 items

DescriptionTacalcitol, the second vitamin D analog developed as a topical antipsoriatic, was introduced for keratosis, psoriasis, ichthyosis, pityriasis rubra pilaris and palmoplantar pustulosis and keratoderma. It shows improvement in appearance of skin lesions for psoriasis patients without significant side effects. In patients with psoriasis vulgaris, it effectively inhibits keratinocyte growth. Some in vitro studies have shown that tacalcitol inhibits interleukin-1-α-induced granulocyte macrophage colony-stimulating-factor mRNA expression of the human dermal microvascular endothelial cells, which may be involved in mediation of angioproliferation in skin inflammation.

UsesTacalcitol is a synthetic vitamin D3 analog.

Upstream & downstream products

Suppliers100 total

陕西凯尔凯医药科技有限公司029-2148545164 17392779578 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
上海策嵘生物科技有限公司[email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
江苏智芯廷科技有限公司18221391031 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Tacalcitol is a hydroxy seco-steroid that is calciol which carries hydroxy groups at positions 1S and 24R. It is a vitamin D3 analog which is used for the treatment of psoriasis vulgaris in adults, especially on the scalp. It has a role as an antipsoriatic, a vitamin D receptor agonist and an antineoplastic agent. It is a member of D3 vitamins, a hydroxy seco-steroid, a secondary alcohol and a seco-cholestane. It is functionally related to a calciol.

Related reactions

2 records
New reaction record

Compound notes

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