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159989-64-7 molecular structure
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(3S,4aS,8aS)-N-tert-butyl-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methylphenyl)formamido]-4-(phenylsulfanyl)butyl]-decahydroisoquinoline-3-carboxamide

ChemBase ID: 105
Molecular Formular: C32H45N3O4S
Molecular Mass: 567.7824
Monoisotopic Mass: 567.31307794
SMILES and InChIs

SMILES:
S(C[C@H](NC(=O)c1c(c(O)ccc1)C)[C@H](O)CN1C[C@@H]2[C@H](C[C@H]1C(=O)NC(C)(C)C)CCCC2)c1ccccc1
Canonical SMILES:
O[C@@H]([C@@H](NC(=O)c1cccc(c1C)O)CSc1ccccc1)CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C
InChI:
InChI=1S/C32H45N3O4S/c1-21-25(15-10-16-28(21)36)30(38)33-26(20-40-24-13-6-5-7-14-24)29(37)19-35-18-23-12-9-8-11-22(23)17-27(35)31(39)34-32(2,3)4/h5-7,10,13-16,22-23,26-27,29,36-37H,8-9,11-12,17-20H2,1-4H3,(H,33,38)(H,34,39)/t22-,23+,26-,27-,29+/m0/s1
InChIKey:
QAGYKUNXZHXKMR-HKWSIXNMSA-N

Cite this record

CBID:105 http://www.chembase.cn/molecule-105.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(3S,4aS,8aS)-N-tert-butyl-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methylphenyl)formamido]-4-(phenylsulfanyl)butyl]-decahydroisoquinoline-3-carboxamide
IUPAC Traditional name
nelfinavir
Brand Name
Viracept
Synonyms
1UN
Nelfinavir mesylate
NFV
NLF
AG1343
Nelfinavir
CAS Number
159989-64-7
PubChem SID
46507719
160963568
PubChem CID
64143

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 64143 external link
DrugBank DB00220 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 9.317774  H Acceptors
H Donor LogD (pH = 5.5) 2.3172343 
LogD (pH = 7.4) 4.085969  Log P 4.718828 
Molar Refractivity 162.6745 cm3 Polarizability 63.215218 Å3
Polar Surface Area 101.9 Å2 Rotatable Bonds 10 
Lipinski's Rule of Five false 
Log P 4.61  LOG S -5.47 
Solubility (Water) 1.91e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
Slightly soluble expand Show data source
Hydrophobicity(logP)
6 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00220 external link
Item Information
Drug Groups approved
Description A potent HIV-1 protease inhibitor. It is used in combination with other antiviral drugs in the treatment of HIV in both adults and children. [PubChem]
Indication Used in combination with other antiviral drugs in the treatment of HIV in both adults and children.
Pharmacology Nelfinavir is a protease inhibitor with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Protease inhibitors block the part of HIV called protease. HIV-1 protease is an enzyme required for the proteolytic cleavage of the viral polyprotein precursors into the individual functional proteins found in infectious HIV-1. Nelfinavir binds to the protease active site and inhibits the activity of the enzyme. This inhibition prevents cleavage of the viral polyproteins resulting in the formation of immature non-infectious viral particles. Protease inhibitors are almost always used in combination with at least two other anti-HIV drugs.
Toxicity Oral LD50 is over 5g/kg in rats. Side effects include thirst and hunger, unexplained weight loss, increased urination, fatigue, and dry, itchy skin.
Affected Organisms
Human Immunodeficiency Virus
Biotransformation Primarily hepatic via cytochrome P450 (CYP450) enzymes. CYP3A and CYP2C19 appear to be the predominant enzymes that metabolize nelfinavir in humans. One major and several minor metabolites are found in plasma; the major oxidative metabolite has in vitro antiviral activity comparable to that of the parent drug.
Absorption Well absorbed following oral administration.
Half Life 3.5 - 5 hours
Protein Binding >98%
Elimination The terminal half-life in plasma was typically 3.5 to 5 hours. The majority (87%) of an oral 750 mg dose containing 14C-nelfinavir was recovered in the feces; fecal radioactivity consisted of numerous oxidative metabolites (78%) and unchanged nelfinavir (22%). Only 1–2% of the dose was recovered in urine, of which unchanged nelfinavir was the major component.
Distribution * 2 to 7 L/kg
References
Kaldor SW, Kalish VJ, Davies JF 2nd, Shetty BV, Fritz JE, Appelt K, Burgess JA, Campanale KM, Chirgadze NY, Clawson DK, Dressman BA, Hatch SD, Khalil DA, Kosa MB, Lubbehusen PP, Muesing MA, Patick AK, Reich SH, Su KS, Tatlock JH: Viracept (nelfinavir mesylate, AG1343): a potent, orally bioavailable inhibitor of HIV-1 protease. J Med Chem. 1997 Nov 21;40(24):3979-85. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Kaldor SW, Kalish VJ, Davies JF 2nd, Shetty BV, Fritz JE, Appelt K, Burgess JA, Campanale KM, Chirgadze NY, Clawson DK, Dressman BA, Hatch SD, Khalil DA, Kosa MB, Lubbehusen PP, Muesing MA, Patick AK, Reich SH, Su KS, Tatlock JH: Viracept (nelfinavir mesylate, AG1343): a potent, orally bioavailable inhibitor of HIV-1 protease. J Med Chem. 1997 Nov 21;40(24):3979-85. Pubmed
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PATENTS

PATENTS

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INTERNET

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