Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:45 UTC
HMDB IDHMDB0014839
Secondary Accession Numbers
  • HMDB14839
Metabolite Identification
Common NameAmprenavir
DescriptionAmprenavir, also known as agenerase or vertex VX478, belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring. Amprenavir is a drug which is used for the treatment of hiv-1 infection in combination with other antiretroviral agents. It was patented in 1992 and approved for medical use in 1999. Incorporation of an amino alcohol moiety proved crucial to inhibitory activity for many of these agents. Research aimed at development of renin inhibitors as potential antihypertensive agents had led to the discovery of compounds that blocked the action of this peptide cleaving enzyme. Amprenavir is a moderately basic compound (based on its pKa). Amprenavir is a potentially toxic compound. Structure–activity studies on renin inhibitors proved to be of great value for developing HIV protease inhibitors. Amprenavir (original brand name Agenerase, GlaxoSmithKline) is a protease inhibitor used to treat HIV infection. The convenient dosing came at a price, as the dose required is 1,200 mg, delivered in 8 (eight) very large 150 mg gel capsules or 24 (twenty-four) 50 mg gel capsules twice daily. This unit is closely related to the one found in the statine, an unusual amino acid that forms part of the pepstatin, a fermentation product that inhibits protease enzymes. The amino acid sequence cleaved by renin was found to be fortuitously the same as that required to produce the HIV peptide coat. Production of amprenavir was discontinued by the manufacturer on December 31, 2004; a prodrug version (fosamprenavir), is available. It was approved by the Food and Drug Administration on April 15, 1999, for twice-a-day dosing instead of needing to be taken every eight hours.
Structure
Data?1582753226
Synonyms
ValueSource
(3S)-Tetrahydro-3-furanyl ((1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)carbamateChEBI
AgeneraseChEBI
(3S)-Tetrahydro-3-furanyl ((1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)carbamic acidGenerator
(3S)-Tetrahydro-3-furanyl ((1S,2R)-3-(((4-aminophenyl)sulphonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)carbamateGenerator
(3S)-Tetrahydro-3-furanyl ((1S,2R)-3-(((4-aminophenyl)sulphonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)carbamic acidGenerator
AMPHMDB
AMVHMDB
VX-478HMDB
GlaxoSmithKline brand OF amprenavirHMDB
Vertex VX478HMDB
Glaxo wellcome brand OF amprenavirHMDB
Tetrahydro-3-furyl N-(3-(4-amino-N-isobutylbenzenesulfonamido)-1-benzyl-2-hydroxypropyl)carbamateHMDB
Chemical FormulaC25H35N3O6S
Average Molecular Weight505.627
Monoisotopic Molecular Weight505.224656557
IUPAC Name(3S)-oxolan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-1-phenylbutan-2-yl]carbamate
Traditional Nameamprenavir
CAS Registry Number161814-49-9
SMILES
CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N)C=C1
InChI Identifier
InChI=1S/C25H35N3O6S/c1-18(2)15-28(35(31,32)22-10-8-20(26)9-11-22)16-24(29)23(14-19-6-4-3-5-7-19)27-25(30)34-21-12-13-33-17-21/h3-11,18,21,23-24,29H,12-17,26H2,1-2H3,(H,27,30)/t21-,23-,24+/m0/s1
InChI KeyYMARZQAQMVYCKC-OEMFJLHTSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentAminobenzenesulfonamides
Alternative Parents
Substituents
  • Aminobenzenesulfonamide
  • Phenylbutylamine
  • Amphetamine or derivatives
  • Benzenesulfonyl group
  • Aniline or substituted anilines
  • Organosulfonic acid amide
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Aminosulfonyl compound
  • Carbamic acid ester
  • Tetrahydrofuran
  • Sulfonyl
  • Carbonic acid derivative
  • Secondary alcohol
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Amine
  • Alcohol
  • Carbonyl group
  • Primary amine
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.049 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.049 g/LALOGPS
logP1.85ALOGPS
logP2.43ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)13.61ChemAxon
pKa (Strongest Basic)2.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area131.19 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity134.08 m³·mol⁻¹ChemAxon
Polarizability53.6 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+215.82731661259
DarkChem[M-H]-208.98431661259
DeepCCS[M+H]+220.90430932474
DeepCCS[M-H]-218.90130932474
DeepCCS[M-2H]-252.14330932474
DeepCCS[M+Na]+226.81730932474
AllCCS[M+H]+219.632859911
AllCCS[M+H-H2O]+217.832859911
AllCCS[M+NH4]+221.332859911
AllCCS[M+Na]+221.832859911
AllCCS[M-H]-209.432859911
AllCCS[M+Na-2H]-211.132859911
AllCCS[M+HCOO]-213.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AmprenavirCC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N)C=C16596.2Standard polar33892256
AmprenavirCC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N)C=C14061.3Standard non polar33892256
AmprenavirCC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N)C=C14087.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Amprenavir,1TMS,isomer #1CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N)C=C14047.3Semi standard non polar33892256
Amprenavir,1TMS,isomer #2CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C14181.4Semi standard non polar33892256
Amprenavir,1TMS,isomer #3CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N)C=C13908.6Semi standard non polar33892256
Amprenavir,2TMS,isomer #1CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C14111.0Semi standard non polar33892256
Amprenavir,2TMS,isomer #1CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C13651.9Standard non polar33892256
Amprenavir,2TMS,isomer #1CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C15089.5Standard polar33892256
Amprenavir,2TMS,isomer #2CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N)C=C13894.0Semi standard non polar33892256
Amprenavir,2TMS,isomer #2CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N)C=C13656.5Standard non polar33892256
Amprenavir,2TMS,isomer #2CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N)C=C15503.0Standard polar33892256
Amprenavir,2TMS,isomer #3CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C14017.1Semi standard non polar33892256
Amprenavir,2TMS,isomer #3CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C13757.4Standard non polar33892256
Amprenavir,2TMS,isomer #3CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C15178.3Standard polar33892256
Amprenavir,2TMS,isomer #4CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C14060.9Semi standard non polar33892256
Amprenavir,2TMS,isomer #4CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C13751.0Standard non polar33892256
Amprenavir,2TMS,isomer #4CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C15195.6Standard polar33892256
Amprenavir,3TMS,isomer #1CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C14017.5Semi standard non polar33892256
Amprenavir,3TMS,isomer #1CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C13749.3Standard non polar33892256
Amprenavir,3TMS,isomer #1CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C14820.2Standard polar33892256
Amprenavir,3TMS,isomer #2CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C14036.8Semi standard non polar33892256
Amprenavir,3TMS,isomer #2CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C13750.6Standard non polar33892256
Amprenavir,3TMS,isomer #2CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C14811.0Standard polar33892256
Amprenavir,3TMS,isomer #3CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C13979.9Semi standard non polar33892256
Amprenavir,3TMS,isomer #3CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C13847.8Standard non polar33892256
Amprenavir,3TMS,isomer #3CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C14898.6Standard polar33892256
Amprenavir,4TMS,isomer #1CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C14005.7Semi standard non polar33892256
Amprenavir,4TMS,isomer #1CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C13857.5Standard non polar33892256
Amprenavir,4TMS,isomer #1CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C14556.8Standard polar33892256
Amprenavir,1TBDMS,isomer #1CC(C)CN(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N)C=C14272.9Semi standard non polar33892256
Amprenavir,1TBDMS,isomer #2CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C14402.6Semi standard non polar33892256
Amprenavir,1TBDMS,isomer #3CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N)C=C14172.2Semi standard non polar33892256
Amprenavir,2TBDMS,isomer #1CC(C)CN(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C14555.0Semi standard non polar33892256
Amprenavir,2TBDMS,isomer #1CC(C)CN(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C14109.5Standard non polar33892256
Amprenavir,2TBDMS,isomer #1CC(C)CN(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C15130.2Standard polar33892256
Amprenavir,2TBDMS,isomer #2CC(C)CN(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N)C=C14369.0Semi standard non polar33892256
Amprenavir,2TBDMS,isomer #2CC(C)CN(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N)C=C14123.9Standard non polar33892256
Amprenavir,2TBDMS,isomer #2CC(C)CN(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N)C=C15462.0Standard polar33892256
Amprenavir,2TBDMS,isomer #3CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C14479.4Semi standard non polar33892256
Amprenavir,2TBDMS,isomer #3CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C14211.1Standard non polar33892256
Amprenavir,2TBDMS,isomer #3CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C15191.4Standard polar33892256
Amprenavir,2TBDMS,isomer #4CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C14494.1Semi standard non polar33892256
Amprenavir,2TBDMS,isomer #4CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C14199.2Standard non polar33892256
Amprenavir,2TBDMS,isomer #4CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C15175.1Standard polar33892256
Amprenavir,3TBDMS,isomer #1CC(C)CN(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C14684.9Semi standard non polar33892256
Amprenavir,3TBDMS,isomer #1CC(C)CN(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C14411.7Standard non polar33892256
Amprenavir,3TBDMS,isomer #1CC(C)CN(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C14897.5Standard polar33892256
Amprenavir,3TBDMS,isomer #2CC(C)CN(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C14660.1Semi standard non polar33892256
Amprenavir,3TBDMS,isomer #2CC(C)CN(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C14393.6Standard non polar33892256
Amprenavir,3TBDMS,isomer #2CC(C)CN(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C14851.2Standard polar33892256
Amprenavir,3TBDMS,isomer #3CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C14614.3Semi standard non polar33892256
Amprenavir,3TBDMS,isomer #3CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C14497.6Standard non polar33892256
Amprenavir,3TBDMS,isomer #3CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C14925.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Amprenavir GC-MS (Non-derivatized) - 70eV, Positivesplash10-022d-8491400000-418cbb7f08471fa846192017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Amprenavir GC-MS (1 TMS) - 70eV, Positivesplash10-03kc-7192320000-fa264cdbd41779709c302017-10-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Amprenavir LC-ESI-qTof , Positive-QTOFsplash10-05mk-2692510000-696582f37a165753c2f52017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amprenavir 10V, Positive-QTOFsplash10-0a4r-9000500000-e60fa95c31e43c49b0312016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amprenavir 20V, Positive-QTOFsplash10-0a4i-9001100000-2c5d3283dd48ceae82dd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amprenavir 40V, Positive-QTOFsplash10-0a4i-9010000000-cd15933ef1ecd45d9b1c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amprenavir 10V, Negative-QTOFsplash10-0gbi-4304930000-6cf1884fae8acb8332ab2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amprenavir 20V, Negative-QTOFsplash10-0173-9432500000-a4d70ca4c7ac6bd2930d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amprenavir 40V, Negative-QTOFsplash10-052f-9825100000-b5b4efee0204074368f42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amprenavir 10V, Positive-QTOFsplash10-000i-0046920000-a443e441b8dc951bec992021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amprenavir 20V, Positive-QTOFsplash10-0a4i-2922000000-15960e61915142ff5b1e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amprenavir 40V, Positive-QTOFsplash10-0006-9200000000-78c87a49bf59b5f6c0142021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amprenavir 10V, Negative-QTOFsplash10-0uxr-2302980000-1c2dbf56f0de2b3df5972021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amprenavir 20V, Negative-QTOFsplash10-0a4i-3911710000-48ad17f577dc556faafc2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amprenavir 40V, Negative-QTOFsplash10-0a4i-7900200000-41ad730c9ba505f337932021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00701 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00701 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Metastatic melanoma
details
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease References
Metastatic melanoma
  1. Frankel AE, Coughlin LA, Kim J, Froehlich TW, Xie Y, Frenkel EP, Koh AY: Metagenomic Shotgun Sequencing and Unbiased Metabolomic Profiling Identify Specific Human Gut Microbiota and Metabolites Associated with Immune Checkpoint Therapy Efficacy in Melanoma Patients. Neoplasia. 2017 Oct;19(10):848-855. doi: 10.1016/j.neo.2017.08.004. Epub 2017 Sep 15. [PubMed:28923537 ]
Associated OMIM IDsNone
DrugBank IDDB00701
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID58532
KEGG Compound IDC08086
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAmprenavir
METLIN IDNot Available
PubChem Compound65016
PDB ID478
ChEBI ID40050
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular weight:
57108.065
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular weight:
55824.275
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o- glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency
Gene Name:
ABCC1
Uniprot ID:
P33527
Molecular weight:
171589.5
References
  1. Olson DP, Scadden DT, D'Aquila RT, De Pasquale MP: The protease inhibitor ritonavir inhibits the functional activity of the multidrug resistance related-protein 1 (MRP-1). AIDS. 2002 Sep 6;16(13):1743-7. [PubMed:12218384 ]
General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Perloff MD, von Moltke LL, Fahey JM, Daily JP, Greenblatt DJ: Induction of P-glycoprotein expression by HIV protease inhibitors in cell culture. AIDS. 2000 Jun 16;14(9):1287-9. [PubMed:10894301 ]
  2. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [PubMed:11602674 ]