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136817-59-9 molecular structure
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N-[2-(4-{3-[(propan-2-yl)amino]pyridin-2-yl}piperazine-1-carbonyl)-1H-indol-5-yl]methanesulfonamide

ChemBase ID: 586
Molecular Formular: C22H28N6O3S
Molecular Mass: 456.56112
Monoisotopic Mass: 456.19435979
SMILES and InChIs

SMILES:
S(=O)(=O)(Nc1cc2cc([nH]c2cc1)C(=O)N1CCN(CC1)c1ncccc1NC(C)C)C
Canonical SMILES:
CC(Nc1cccnc1N1CCN(CC1)C(=O)c1cc2c([nH]1)ccc(c2)NS(=O)(=O)C)C
InChI:
InChI=1S/C22H28N6O3S/c1-15(2)24-19-5-4-8-23-21(19)27-9-11-28(12-10-27)22(29)20-14-16-13-17(26-32(3,30)31)6-7-18(16)25-20/h4-8,13-15,24-26H,9-12H2,1-3H3
InChIKey:
WHBIGIKBNXZKFE-UHFFFAOYSA-N

Cite this record

CBID:586 http://www.chembase.cn/molecule-586.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
N-[2-(4-{3-[(propan-2-yl)amino]pyridin-2-yl}piperazine-1-carbonyl)-1H-indol-5-yl]methanesulfonamide
IUPAC Traditional name
N-(2-{4-[3-(isopropylamino)pyridin-2-yl]piperazine-1-carbonyl}-1H-indol-5-yl)methanesulfonamide
delavirdine
Brand Name
Bhap Der
Rescriptor
Synonyms
DLV
SPP
Delavirdine
(1-(5-METHANSULPHONAMIDO-1H-INDOL-2-YL-CARBONYL)4-[METHYLAMINO)PYRIDINYL]PIPERAZINE
N-[2-[[4-[3-[(1-Methylethyl)amino]-2-pyridinyl]-1-piperazinyl]carbonyl]-1H-indol-5-yl]methanesulfonamide
BHAP-U 90152
U-90152
1-[3-(Isopropylamino)-2-pyridyl]-4-[(5-methanesulfonamidoindol-2-yl)carbonyl]piperazine
N-(2-(4-(3-(IsopropylaMino)pyridin-2-yl)piperazine-1-carbonyl)-1H-indol-5-yl)MethanesulfonaMide
CAS Number
136817-59-9
PubChem SID
160964049
46508878
PubChem CID
5625

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 9.392162  H Acceptors
H Donor LogD (pH = 5.5) -0.08998388 
LogD (pH = 7.4) 0.9233841  Log P 1.0243266 
Molar Refractivity 126.6434 cm3 Polarizability 48.65747 Å3
Polar Surface Area 110.43 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.77  LOG S -3.73 
Solubility (Water) 8.60e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Ethyl Acetate expand Show data source
Apperance
Pale Yellow Solid expand Show data source
Melting Point
226-228°C expand Show data source
Hydrophobicity(logP)
2.8 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Purity
97% expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank TRC TRC
DrugBank - DB08563 external link
Drug information: experimental
DrugBank - DB00705 external link
Item Information
Drug Groups approved
Description A potent, non-nucleoside reverse transcriptase inhibitor with activity specific for HIV-1. [PubChem]
Indication For the treatment of HIV-1 infection in combination with appropriate antiretroviral agents when therapy is warranted
Pharmacology Delavirdine is a non-nucleoside reverse transcriptase inhibitor (nNRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Delavirdine binds directly to reverse transcriptase (RT) and blocks the RNA-dependent and DNA-dependent DNA polymerase activities by causing a disruption of the enzyme's catalytic site. The activity of Delavirdine does not compete with template or nucleoside triphosphates. HIV-2 RT and eukaryotic DNA polymerases (such as human DNA polymerases alpha, beta, or sigma) are not inhibited by Delavirdine.
Toxicity Major toxicity of delavirdine is rash and should be advised to promptly notify their physician should rash occur. The majority of rashes associated with delavirdine occur within 1 to 3 weeks after initiating treatment with delavirdine. The rash normally resolves in 3 to 14 days and may be treated symptomatically while therapy with delavirdine is continued. Any patient experiencing severe rash or rash accompanied by symptoms such as fever, blistering, oral lesions, conjunctivitis, swelling, muscle or joint aches should discontinue medication and consult a physician.
Affected Organisms
Human Immunodeficiency Virus
Biotransformation Hepatic
Absorption Rapidly absorbed
Half Life 5.8 hours
Protein Binding 98%
Elimination Delavirdine is extensively converted to several inactive metabolites by cytochrome P450 3A (CYP3A). Delavirdine was excreted in the milk of lactating rats at a concentration three to five times that of rat plasma.
External Links
Wikipedia
Drugs.com
Toronto Research Chemicals - D230625 external link
A bisheteroarylpiperazine (BHAP) reverse transcriptase inhibitor.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Dueweke, T.J., et al.: Antimicrob. Ag. Chemother., 37, 1127 (1993)
  • • Althaus, I.W., et al.: Biochem. Pharmacol., 47, 2017 (1994)
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PATENTS

PATENTS

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INTERNET

INTERNET

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