タカルシトール

Tacalcitol

HCID 5283734CAS 57333-96-7

基本情報

標準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
分子式: C27H44O3
平均分子量: 416.6 g/mol
単同位体質量: 416.32904527

概要

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.

名称と識別子

優先名称: 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
現地名: タカルシトール
英語名: Tacalcitol
分子式: C27H44O3
分子量: 416.64

名称と別名

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

名称をさらに表示

ボンアルファ-ハイ[5Z,7E,24R,(+)]-9,10-セココレスタ-5,7,10(19)-トリエン-1α,3β,24-トリオール(5Z,7E,24R)-9,10-セココレスタ-5,7,10(19)-トリエン-1α,3β,24-トリオール1α,24R-ジヒドロキシビタミンD3タカルシトール(24R)-1α,24-ジヒドロキシコレカルシフェロールアルファタカシルボンアルファ1α,24(R)-ジヒドロキシビタミンD31-アルファ,24R-ジヒドロキシビタミンD3(1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R,5R)-5-ヒドロキシ-6-メチルヘプタン-2-イル]-7a-メチル-オクタヒドロ-1H-インデン-4-イリデン]エチリデン}-4-メチリデンシクロヘキサン-1,3-ジオール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

データベース識別子

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

物性

構造計算による物性

XLogP: 5.3
極性表面積: 60.7 Å²
水素結合供与体数: 3
水素結合受容体数: 3
回転可能結合数: 6
重原子数: 30
形式電荷: 0
複雑度: 676

実験および物理化学的性質

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

物理化学的性質

沸点: 565 · 565.0±50.0 °C(Predicted)
比重(密度): 1.06 · 1.06
貯蔵温度: -20 °C · Sealed in dry,Store in freezer, under -20°C
溶解性: 20 mg/mL · 20mg/mL in DMSO, 20mg/mL in DMF, 20mg/mL in Ethanol
酸解離定数(Pka): 14.43 · 14.43±0.40(Predicted)
外見: Powder
色: White to off-white
由来生物: synthetic (organic)
InChIKey: BJYLYJCXYAMOFT-RSFVBTMBSA-N
SMILES: [C@@H]1(O)C/C(=C/C=C2\CCC[C@@]3(C)[C@@]\2([H])CC[C@@H]3[C@H](C)CC[C@@H](O)C(C)C)/C(=C)[C@@H](O)C1
CAS データベース: 57333 · 57333-96-7(CAS DataBase Reference)

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 1 (100%)

安全データ

wgk: WGK 3
Hazard Classifications: Acute Tox. 1 Oral
ストレージクラス: 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials

化学と産業

薬理情報

ATC Code · 3 件

D05AX04

D - Dermatologicals

QD - Dermatologicals

MeSH Pharmacological Classification · 2 件

Substances that reduce or suppress INFLAMMATION.

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

応用分野 · 1 件

説明Tacalcitol, 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.

上流・下流製品情報

上流原料

水素化カルシウムアルゴンシリカゲルカリウム tert-ブトキシド 3-クロロ過安息香酸テトラヒドロフラン水素化リチウムアルミニウム

サプライヤー50 社

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]