Deacylketoconazole

CAT: 0804-HY-129315-01Size: 5 mgDry Ice: NoHazardous: No

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CAT#:0804-HY-129315-01Size:5 mg

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Description

Deacylketoconazole (N-Deacetylketoconazole; R-39519) is an orally active metabolite of Ketoconazole. Deacylketoconazole exhibits antifungal and antibacterial activity. Deacylketoconazole is cytotoxic in rats hepatocyte[1][2][3].

CAS Number

67914-61-8

Product Name Alternative

N-Deacetylketoconazole; R-39519

UNSPSC

12352005

Hazard Statement

H302, H315, H319, H335

Target

Bacterial; Fungal

Type

Reference compound

Related Pathways

Anti-infection

Applications

COVID-19-immunoregulation

Field of Research

Infection

Assay Protocol

https://www.medchemexpress.com/deacylketoconazole.html

Purity

99.60

Solubility

DMSO : 2.5 mg/mL (ultrasonic; warming; heat to 60°C)

Smiles

ClC1=CC=C(C(Cl)=C1)[C@@]2(OC[C@H](O2)COC3=CC=C(C=C3)N4CCNCC4)CN5C=CN=C5

Molecular Formula

C24H26Cl2N4O3

Molecular Weight

489.39

Precautions

H302, H315, H319, H335

References & Citations

[1]Pfaller MA, et al., Activity of ketoconazole and its deacyl derivative against Plasmodium falciparum and Candida isolates. Antimicrob Agents Chemother. 1982 Nov;22 (5) :917-9.|[2]Bossche H V, et al., Molecular basis for the antimycotic and antibacterial activity of N‐substituted imidazoles and triazoles: The inhibition of isoprenoid biosynthesis[J]. Pesticide science, 1984, 15 (2) : 188-198.|[3]Fukami T, et al., Human arylacetamide deacetylase hydrolyzes ketoconazole to trigger hepatocellular toxicity. Biochem Pharmacol. 2016 Sep 15;116:153-61.

Shipping Conditions

Room Temperature

Storage Conditions

-20°C, 3 years; 4°C, 2 years (Powder)

Scientific Category

Reference compound1

Clinical Information

No Development Reported

Chemical Information

Deacetylketoconazole

RN given refers to cis-isomer

CAS Number	67914-61-8
PubChem CID	12854716
IUPAC Name	1-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine
Molecular Formula	C24H26Cl2N4O3
Molecular Weight	489.4
XLogP	4.4
Topological Polar Surface Area	60.8
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	7
Heavy Atom Count	33
Formal Charge	0
Complexity	621

SMILES

C1CN(CCN1)C2=CC=C(C=C2)OC[C@H]3CO[C@](O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl

InChI

InChI=1S/C24H26Cl2N4O3/c25-18-1-6-22(23(26)13-18)24(16-29-10-7-28-17-29)32-15-21(33-24)14-31-20-4-2-19(3-5-20)30-11-8-27-9-12-30/h1-7,10,13,17,21,27H,8-9,11-12,14-16H2/t21-,24-/m0/s1

InChIKey

LOUXSEJZCPKWAX-URXFXBBRSA-N

Chemical Structure

2D Structure

CAS: 67914-61-8

CID: 12854716

Formula: C24H26Cl2N4O3

MW: 489.4

Interactive 3D Structure

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View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	489.4
XLogP3	4.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	7
Exact Mass	488.1381961
Monoisotopic Mass	488.1381961
Topological Polar Surface Area	60.8 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	621
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

Alternative Products

Catalog	Name
MBS5756617	Deacylketoconazole

Deacylketoconazole

Chemical Information

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