Tacalcitol

HCID 5283734CAS 57333-96-7
TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

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
Summenformel
C27H44O3
Durchschnittliche Molmasse
416,6 g/mol
Monoisotopische Masse
416,32904527

Überblick

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.

Namen und Bezeichner

Bevorzugter 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
Englischer Name
Tacalcitol
Summenformel
C27H44O3
Molmasse
416.64

Namen und Synonyme

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
Weitere Namen anzeigen
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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP
5,3
Polarare Oberfläche (TPSA)
60,7 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
6
Schwere Atome
30

Experimentelle und physikochemische Eigenschaften

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

Physikochemische Eigenschaften

Siedepunkt
565 · 565.0±50.0 °C(Predicted)
Dichte
1.06 · 1.06
storage temp.
-20 °C · Sealed in dry,Store in freezer, under -20°C
Löslichkeit
20 mg/mL · 20mg/mL in DMSO, 20mg/mL in DMF, 20mg/mL in Ethanol
pka
14.43 · 14.43±0.40(Predicted)
Aggregatzustand
Powder

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 1 (100%)

Sicherheitsdaten

wgk
WGK 3
Speicherklasse
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications
Acute Tox. 1 Oral

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

D05AX04

D - Dermatologicals

QD - Dermatologicals

MeSH Pharmacological Classification · 2 Einträge

Substances that reduce or suppress INFLAMMATION.

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

Anwendungen · 1 Eintrag

BeschreibungTacalcitol, 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.

Vor- und nachgelagerte Produkte

Anbieter50 Anbieter

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]

Zugehörige Reaktionen

2
Reaktionsaufzeichnung erstellen

Verknüpfte Notizen

Wird geladen…