Becocalcidiol
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Basic information
- CAS
524067-21-8- Standard SMILES
C=C1[C@H](O)CC(=C/C=C2\CCC[C@]3(C)[C@@H]([C@@H](C)CC)CC[C@@H]23)C[C@H]1O- InChIKey
QSLUXQQUPXBIHH-YHSKWIAJSA-N- Molecular formula
- C23H36O2
- Average molar mass
- 344.5 g/mol
- Monoisotopic mass
- 344.27153039
Overview
Becocalcidiol is an organic molecular entity.
Names & identifiers
- Preferred name
- Becocalcidiol
- IUPAC
- trans-(1R,3R)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2S)-butan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-2-methylidenecyclohexane-1,3-diol
- English name
- Becocalcidiol
- Molecular formula
- C23H36O2
- Molecular weight
- 344.53
Names & synonyms
Becocalcidiol2MBISP524067-21-8Becocalcidiol [INN]Becocalcidiol [USAN:INN]N75R59YD0FQRX 101QRX-101DP-006BECOCALCIDIOL [USAN]DTXSID50415362DP006
Show more names
COL121COL-1211,3-Cyclohexanediol, 2-methylene-5-[(2E)-2-[(1R,3aS,7aR)-octahydro-7a-methyl-1-[(1S)-1-methylpropyl]-4H-inden-4-ylidene]ethylidene]-, (1R,3R)-
1,3-CYCLOHEXANEDIOL, 2-METHYLENE-5-((2E)-((1R,3AS,7AR)-OCTAHYDRO-7A-METHYL-1-((1S)-1-METHYLPROPYL)-4H-INDEN-4-YLIDENE)ETHYLIDENE)-, (1R,3R)-becocalcidiolum(1R,3R)-2-METHYLENE-5-((2E)-2-((1R,3AS,7AR)-7A-METHYL-1-((1S)-1-METHYLPROPYL)OCTAHYDRO-4H-INDEN-4-YLIDENE)ETHYLIDENE)CYCLOHEXANE-1,3-DIOL(1R,3R)-2-Methylene-5-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(1S)-1-methylpropyl]octahydro-4H-inden-4-ylidene]ethylidene]cyclohexane-1,3-diolRefChem:561164DTXCID80366212(1R,3R)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2S)-butan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-2-methylidenecyclohexane-1,3-diolQRX101
Database identifiers
- CAS
524067-21-8- PubChem CID
- 5289547
- DTXSID
DTXSID50415362
Properties
Computed structural propertiesFilling in
- XLogP
- 4.7
- Topological polar surface area
- 40.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 3
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 557
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LipidsLipids -> Sterol Lipids [ST] -> Secosteroids [ST03] -> Vitamin D3 and derivatives [ST0302]
Physicochemical properties
- FDA UNII
- 75 R59YD0F · N75R59YD0F
Chemistry & industry
Pharmacology
Pharmacodynamics
Becocalcidiol (formerly QRX-101) is a novel vitamin D analogue for the treatment of mild to moderate psoriasis. In clinical and preclinical studies, becocalcidiol has been well tolerated with a low incidence of skin irritation. Based on the completed Phase IIb study, becocalcidiol was statistically superior to placebo in reducing plaque and did not result in excessive blood calcium levels, a side effect of existing calcitriol topical treatments for psoriasis.
Mechanism of ActionThe mechanism of action of becocalcidiol in the treatment of psoriasis is accounted for by an antiproliferative activity for keratinocytes and the stimulation of epidermal cell differentiation.
Applications
UsesTreatment of psoriasis (vitamin D analog).
Related reactions
2 records
Compound notes
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