KLN

1-ACETYL-4-(4-{[(2S,4R)-2-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL]METHOXY}PHENYL)PIPERAZINE

Created: 2007-05-15
Last modified:  2011-06-04

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Chemical Details

Formal Charge0
Atom Count64
Chiral Atom Count2
Bond Count68
Aromatic Bond Count17
2D diagram of KLN
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Chemical Component Summary

Name1-ACETYL-4-(4-{[(2S,4R)-2-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL]METHOXY}PHENYL)PIPERAZINE
Systematic Name (OpenEye OEToolkits)1-[4-[4-[[(2S,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone
FormulaC26 H28 Cl2 N4 O4
Molecular Weight531.431
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C(N5CCN(c4ccc(OCC1OC(OC1)(c2ccc(Cl)cc2Cl)Cn3cncc3)cc4)CC5)C
SMILESCACTVS3.341CC(=O)N1CCN(CC1)c2ccc(OC[CH]3CO[C](Cn4ccnc4)(O3)c5ccc(Cl)cc5Cl)cc2
SMILESOpenEye OEToolkits1.5.0CC(=O)N1CCN(CC1)c2ccc(cc2)OCC3COC(O3)(Cn4ccnc4)c5ccc(cc5Cl)Cl
Canonical SMILESCACTVS3.341 CC(=O)N1CCN(CC1)c2ccc(OC[C@@H]3CO[C@](Cn4ccnc4)(O3)c5ccc(Cl)cc5Cl)cc2
Canonical SMILESOpenEye OEToolkits1.5.0 CC(=O)N1CCN(CC1)c2ccc(cc2)OC[C@@H]3CO[C@@](O3)(Cn4ccnc4)c5ccc(cc5Cl)Cl
InChIInChI1.03 InChI=1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3/t23-,26-/m1/s1
InChIKeyInChI1.03 XMAYWYJOQHXEEK-ZEQKJWHPSA-N

Drug Info: DrugBank

DrugBank IDDB05667 
NameLevoketoconazole
Groups
  • approved
  • investigational
DescriptionCushing's syndrome (CS) is underpinned by chronic hypercortisolism leading to multisystem morbidity, including effects on the cardiovascular and endocrine systems, metabolic syndrome with accompanying changes in body composition, neuropsychiatric effects, changes in blood pressure and chemistry, and opportunistic infections.[A244078, A244083] [Ketoconazole] has been used both on- and off-label to treat CS due to its ability to inhibit cortisol production. Still, toxicity has limited its use, notably hepatic toxicity and a tendency to prolong the QT interval.[A244083] Levoketoconazole is one of two enantiomers present in racemic [ketoconazole]. It possesses most of the inhibitory effect towards steroidogenic enzymes, making it an attractive candidate for CS treatment with a potentially lower toxicity profile than its racemate.[A244083, A29319, L39573] Levoketoconazole was approved by the FDA on December 30, 2021, and is currently marketed under the registered trademark RECORLEV by Xeris Pharmaceuticals, Inc.[L39563]
SynonymsLevoketoconazole
Brand NamesRecorlev
IndicationLevoketoconazole is indicated for the treatment of endogenous hypercortisolemia in adult patients with Cushing’s syndrome for whom surgery is not an option or has not been curative. Levoketoconazole is not indicated for the treatment of fungal infections.[L39563]
Categories
  • Adrenal Cortex Hormones
  • Antiadrenal Preparations
  • Anticorticosteroids
  • Antifungal Agents
  • Azole Antifungals
ATC-CodeH02CA04
CAS number142128-57-2

Drug Targets

NameTarget SequencePharmacological ActionActions
Steroid 17-alpha-hydroxylase/17,20 lyaseMWELVALLLLTLAYLFWPKRRCPGAKYPKSLLSLPLVGSLPFLPRHGHMH...unknowninhibitor
Cytochrome P450 11B1, mitochondrialMALRAKAEVCMAVPWLSLQRAQALGTRAARVPRTVLPFEAMPRRPGNRWL...unknowninhibitor
Cytochrome P450 11B2, mitochondrialMALRAKAEVCVAAPWLSLQRARALGTRAARAPRTVLPFEAMPQHPGNRWL...unknowninhibitor
Cholesterol side-chain cleavage enzyme, mitochondrialMLAKGLPPRSVLVKGCQTFLSAPREGLGRLRVPTGEGAGISTRSPRPFNE...unknowninhibitor
Lanosterol 14-alpha demethylaseMLLLGLLQAGGSVLGQAMEKVTGGNLLSMLLIACAFTLSLVYLIRLAAGH...unknowninhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL295698
PubChem 47576
ChEMBL CHEMBL295698
ChEBI CHEBI:47518
CCDC/CSD YINWID, YINWAV, RADXIH
COD 4508146, 4508144