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B8686

(+)-N-3-Benzylnirvanol

≥98% (HPLC), powder, CYP2C19 inhibitor

Synonym(s):

(5S)-5-Ethyl-5-phenyl-3-(phenylmethyl)-2,4-imidazolidinedione, 5-Ethyl-5-phenyl-3-(phenylmethyl)hydantoin

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$491.00

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$928.00

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About This Item

Empirical Formula (Hill Notation):
C18H18N2O2
CAS Number:
790676-40-3
Molecular Weight:
294.35
UNSPSC Code:
12161501
PubChem Substance ID:
329773138
NACRES:
NA.77
MDL number:
MFCD09840024
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100

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Product Name

(+)-N-3-Benzylnirvanol, ≥98% (HPLC), powder

SMILES string

CC[C@]1(NC(=O)N(Cc2ccccc2)C1=O)c3ccccc3

InChI key

ZMZDHUHMXXALFX-SFHVURJKSA-N

InChI

1S/C18H18N2O2/c1-2-18(15-11-7-4-8-12-15)16(21)20(17(22)19-18)13-14-9-5-3-6-10-14/h3-12H,2,13H2,1H3,(H,19,22)/t18-/m0/s1

assay

≥98% (HPLC)

form

powder

solubility

DMSO: >20 mg/mL, H2O: insoluble

storage temp.

2-8°C

Quality Level

100

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1 of 4

This Item
UC180UC179T7580
(+)-N-3-Benzylnirvanol ≥98% (HPLC), powder

Sigma-Aldrich

B8686

(+)-N-3-Benzylnirvanol

(S)-(+)-Nirvanol

Sigma-Aldrich

UC180

(S)-(+)-Nirvanol

(R)-(−)-Nirvanol

Sigma-Aldrich

UC179

(R)-(−)-Nirvanol

TN-16 ≥98% (HPLC)

Sigma-Aldrich

T7580

TN-16

form

powder

form

solid

form

solid

form

powder

assay

≥98% (HPLC)

assay

-

assay

-

assay

≥98% (HPLC)

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

100

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

solubility

DMSO: >20 mg/mL, H2O: insoluble

solubility

DMF: soluble

solubility

DMF: soluble

solubility

DMSO: ≥17 mg/mL

Application

(+)-N-3-Benzylnirvanol may be used as a cytochrome P450 2C19 (CYP2C19) inhibitor in a comparison study to treat cocktail and individual substrates for the screening for potent cytochrome P450 (CYP) inhibition.[1] It may also be used in comparative studies to investigate its potential as CYP and non-CYP selective inhibitors of CYP2C19 in suspended human hepatocytes.[2]

Biochem/physiol Actions

(+)-N-3-Benzyl-nirvanol is a potent selective CYP2C19 inhibitor.
(+)-N-3-Benzyl-nirvanol is a potent selective CYP2C19 inhibitor. CYP2C19 has a high frequency of drug resistance; highly polymorphic.
(+)-N-3-Benzylnirvanol serves as an inhibitor of cytochrome P450 2B6 (CYP2B6).[3]

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000219890
0000219890
0000403966
0000403967
0000403967

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James P Driscoll et al.
Chemical research in toxicology, 20(10), 1488-1497 (2007-09-26)
The hypothesis that the psychological side effects associated with the anesthetic phencyclidine (PCP) may be caused by irreversible binding of PCP or its reactive metabolite(s) to critical macromolecules in the brain has resulted in numerous in vitro studies aimed at
Guru R Valicherla et al.
Xenobiotica; the fate of foreign compounds in biological systems, 49(12), 1396-1402 (2019-02-13)
1. A protocol has been developed and validated for the high-throughput screening of eight major human cytochrome P450 (CYP) isozymes inhibition (CYP 1A2, 2C9, 2C19, 2D6, 3A4, 2B6, 2C8 and 2E1) using an in vitro probe cocktail containing eight substrates
Dustyn A Barnette et al.
Biochemical pharmacology, 170, 113661-113661 (2019-10-13)
Terbinafine N-dealkylation pathways result in formation of 6,6-dimethyl-2-hepten-4-ynal (TBF-A), a reactive allylic aldehyde, that may initiate idiosyncratic drug-induced liver toxicity. Previously, we reported on the importance of CYP2C19 and 3A4 as major contributors to TBF-A formation. In this study, we
Marie-Lynn Cuypers et al.
Drug metabolism and disposition: the biological fate of chemicals, 48(11), 1121-1128 (2020-08-26)
Early assessment of metabolism pathways of new chemical entities guides the understanding of drug-drug interactions. Selective enzyme inhibitors are indispensable in CYP reaction phenotyping. The most commonly applied CYP2C19 inhibitor, omeprazole, lacks selectivity. Two promising alternatives, (+)-N-3-benzylnirvanol and (-)-N-3-benzylphenobarbital, are

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