Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1462)
Drug Name
Saquinavir mesylate
Synonyms
Saquinavir mesilate; Saquinavir mesylate; Saquinavir mesylate (AIDS Initiative); Saquinavir monomethanesulfonate salt; Saquinavir, Mesylate; UHB9Z3841A; UNII-UHB9Z3841A; (S)-N-((alphaS)-alpha-((1R)-2-((3S,4aS,8aS)-3-(tert-Butylcarbamoyl)octahydro-2(1H)-isoquinolyl)-1-hydroxyethyl)phenethyl)-2-quinaldamidosuccinamide monomethanesulfonate (salt); 149845-06-7; CHEBI:32121; DSSTox_CID_3835; DSSTox_GSID_23835; DSSTox_RID_77202; NCGC00091469-01; Ro 31-8959/003; (2s)-N-[(2s,3r)-4-[(2s,3s,4as,8as)-3-(Tert-Butylcarbamoyl)-3,4,4a,5,6,7,8,8a-Octahydro-1h-Isoquinolin-2-Yl]-3-Hydroxy-1-Phenyl-Butan-2-Yl]-2-(Quinolin-2-Ylcarbonylamino)butanediamide; 127779-20-8; CHEBI:63621; Fortovase (TN); Fortovase(TM); HSDB 7161; L3JE09KZ2F; ROC; Ro 318959; Ro-31-8959; Ro-318959000; SAQUINAVIR; UNII-L3JE09KZ2F; saguinavir
Indication Human immunodeficiency virus infection [ICD11: 1C60] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 766.9 Topological Polar Surface Area 230
Heavy Atom Count 54 Rotatable Bond Count 13
Hydrogen Bond Donor Count 6 Hydrogen Bond Acceptor Count 10
Cross-matching ID
PubChem CID
60934
ChEBI ID
CHEBI:32121
CAS Number
149845-06-7
TTD Drug ID
D0WI3T
Formula
C39H54N6O8S
Canonical SMILES
CC(C)(C)NC(=O)C1CC2CCCCC2CN1CC(C(CC3=CC=CC=C3)NC(=O)C(CC(=O)N)NC(=O)C4=NC5=CC=CC=C5C=C4)O.CS(=O)(=O)O
InChI
1S/C38H50N6O5.CH4O3S/c1-38(2,3)43-37(49)32-20-26-14-7-8-15-27(26)22-44(32)23-33(45)30(19-24-11-5-4-6-12-24)41-36(48)31(21-34(39)46)42-35(47)29-18-17-25-13-9-10-16-28(25)40-29;1-5(2,3)4/h4-6,9-13,16-18,26-27,30-33,45H,7-8,14-15,19-23H2,1-3H3,(H2,39,46)(H,41,48)(H,42,47)(H,43,49);1H3,(H,2,3,4)/t26-,27+,30-,31-,32-,33+;/m0./s1
InChIKey
IRHXGOXEBNJUSN-YOXDLBRISA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
(2S)-N-[(2S,3R)-4-[(3S,4aR,8aS)-3-(tert-butylcarbamoyl)-6-hydroxy-decahydroisoquinolin-2-yl]-3-hydroxy-1-phenylbutan-2-yl]-2-[(quinolin-2-yl)formamido]butanediamide DM001283 N. A. Oxidation - Hydroxylation 1 [4]
(2S)-N-[(2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)-7-hydroxy-decahydroisoquinolin-2-yl]-3-hydroxy-1-phenylbutan-2-yl]-2-[(quinolin-2-yl)formamido]butanediamide DM001284 N. A. Oxidation - Hydroxylation 1 [4]
(2S)-N-[(2S,3R)-4-[(3S,4aS,8aS)-3-[(1-hydroxy-2-methylpropan-2-yl)carbamoyl]-decahydroisoquinolin-2-yl]-3-hydroxy-1-phenylbutan-2-yl]-2-[(quinolin-2-yl)formamido]butanediamide DM001282 N. A. Oxidation - Hydroxylation 1 [4]
M2 di-hydroxylated metabolite DM001281
131770012
Oxidation - Hydroxylation 1 [2] , [3] , [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002885 Saquinavir mesylate M2 di-hydroxylated metabolite Oxidation - Hydroxylation CYP3A4 ... [2], [3], [5]
MR002886 Saquinavir mesylate (2S)-N-[(2S,3R)-4-[(3S,4aS,8aS)-3-[(1-hydroxy-2-methylpropan-2-yl)carbamoyl]-decahydroisoquinolin-2-yl]-3-hydroxy-1-phenylbutan-2-yl]-2-[(quinolin-2-yl)formamido]butanediamide Oxidation - Hydroxylation CYP3A4 [4]
MR002887 Saquinavir mesylate (2S)-N-[(2S,3R)-4-[(3S,4aR,8aS)-3-(tert-butylcarbamoyl)-6-hydroxy-decahydroisoquinolin-2-yl]-3-hydroxy-1-phenylbutan-2-yl]-2-[(quinolin-2-yl)formamido]butanediamide Oxidation - Hydroxylation CYP3A4 [4]
MR002888 Saquinavir mesylate (2S)-N-[(2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)-7-hydroxy-decahydroisoquinolin-2-yl]-3-hydroxy-1-phenylbutan-2-yl]-2-[(quinolin-2-yl)formamido]butanediamide Oxidation - Hydroxylation CYP3A4 [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[3]
References
1 Saquinavir Mesylate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Effect of saquinavir-ritonavir on cytochrome P450 3A4 activity in healthy volunteers using midazolam as a probe. Pharmacotherapy. 2009 Oct;29(10):1175-81.
3 Differential inhibition of cytochrome P450 3A4, 3A5 and 3A7 by five human immunodeficiency virus (HIV) protease inhibitors in vitro. Basic Clin Pharmacol Toxicol. 2006 Jan;98(1):79-85.
4 DrugBank(Pharmacology-Metabolism)Saquinavir mesylate
5 Inhibition of desipramine hydroxylation (Cytochrome P450-2D6) in vitro by quinidine and by viral protease inhibitors: relation to drug interactions in vivo. J Pharm Sci. 1998 Oct;87(10):1184-9.

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