Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C24H28N2O3 |
Molecular Weight | 392.4907 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C(C=CC=C1)N2CCN(C[C@@H](O)COC3=CC=CC4=C3C=CC=C4)CC2
InChI
InChIKey=HRRBJVNMSRJFHQ-HXUWFJFHSA-N
InChI=1S/C24H28N2O3/c1-28-24-11-5-4-10-22(24)26-15-13-25(14-16-26)17-20(27)18-29-23-12-6-8-19-7-2-3-9-21(19)23/h2-12,20,27H,13-18H2,1H3/t20-/m1/s1
Molecular Formula | C24H28N2O3 |
Molecular Weight | 392.4907 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Naftopidil,(R)- is an enantiomer of Naftopidil (NAF), a specific subtype selective α1-adrenoceptor blocker. Racemic Naftopidil is frequently used for the treatment of lower urinary tract symptoms/benign prostatic hyperplasia. No significant differences in pharmacokinetic parameters were observed between R(+)- and S(−)-NAF after intravenous administration. However, mean plasma concentrations of R(+)-NAF were lower than those of S(-)-NAF after intragastric administration. R(+)-NAF bioavailability in rats was consistently about two-fold lower than that of S(-)-NAF. The fractions of R(+)- NAF reaching the prostate and metabolized in the liver were higher than those of S(−)-NAF. The major pathways of R(+)- NAF metabolism in vitro were demethylation and hydroxylation. CYP2C9 played the most important role in the demethylation and hydroxylation of both NAF enantiomers. CYP2C19 was another CYP isoform that played a major role in R(+)-NAF metabolism.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3397 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24944083 |
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Target ID: CHEMBL3622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24944083 |
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Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24944083 |
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Target ID: CHEMBL3721 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24944083 |
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Target ID: CHEMBL289 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24944083 |
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Target ID: CHEMBL2111472 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24944083 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
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Asymmetric aminolytic kinetic resolution of racemic epoxides using recyclable chiral polymeric Co(III)-salen complexes: a protocol for total utilization of racemic epoxide in the synthesis of (R)-Naftopidil and (S)-Propranolol. | 2013 Sep 20 |
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Identification of human cytochrome P450 isozymes involved in the metabolism of naftopidil enantiomers in vitro. | 2014 Nov |
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Enantiospecific determination of naftopidil by RRLC-MS/MS reveals stereoselective pharmacokinetics and tissue distributions in rats. | 2015 Aug 10 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25985066
Rat: 5 and 20 mg/kg
Route of Administration:
Other
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 07:53:57 GMT 2023
by
admin
on
Sat Dec 16 07:53:57 GMT 2023
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Record UNII |
PG1LF4426M
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Record Status |
Validated (UNII)
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Record Version |
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