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Compound Detail

CHEMBL114

SAQUINAVIR
💊 Approved Drug
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💊 Approved Drug
CC(C)(C)NC(=O)[C@@H]1C[C@@H]2CCCC[C@@H]2CN1C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(N)=O)NC(=O)c1ccc2ccccc2n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL114
Name SAQUINAVIR
Phase Approved
Structure Type MOL
InChI Key QWAXKHKRTORLEM-UGJKXSETSA-N
Therapeutic ✓ Yes

Known Names

Fortovase RO 31-8959/000 RO-31-8959/000 Saquinavir Saquinavirum SCH-52852
40
Targets
311
Activities
4
Assay Types
30
PK Parameters
20
Publications
6
Known Names
6
Indications
1
Mechanisms

Molecular Properties

670.9
MW (Da)
3.09
ALogP
7
HBA
5
HBD
166.8
PSA (Ų)
0.20
QED
1
Ro5 Violations
12
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1995
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -vir
USAN Year 1994

Extended Properties

Molecular Formula C38H50N6O5
MW 670.86
Aromatic Rings 3
Heavy Atoms 49
NP-Likeness -0.04

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Human immunodeficiency virus type 1 protease inhibitor INHIBITOR Human immunodeficiency virus type 1 protease ✓ ✓

Indications

HIV Infections HIV Infections Virus Diseases Acquired Immunodeficiency Syndrome AIDS-Associated Nephropathy Hypertension, Pulmonary

ATC Classification

J05AE01
saquinavir
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Drug Warnings

Black Box Warning
General Warning
Country: United States

Activity Summary

IC50 124 meas. best 10.3
EC50 122 meas. best 9.7
Ki 59 meas. best 10.4
Kd 6 meas. best 9.51

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus type 1 protease
CHEMBL243
 Ki 10.4 9.0404 0.0 28
Protease
CHEMBL2366517
 Ki 10.4 9.6425 0.0 8
HIV-1 protease
CHEMBL4296312
 IC50 10.3 10.3 0.1 1
Human immunodeficiency virus 2
CHEMBL380
 EC50 9.7 8.5511 0.2 9
Human immunodeficiency virus type 1 protease
CHEMBL243
 IC50 9.7 8.87 0.2 21
Human immunodeficiency virus type 1 protease
CHEMBL243
 Kd 9.51 8.7267 0.3 3
Protease
CHEMBL2366517
 IC50 9.4 9.4 0.4 1
Human rhinovirus A protease
CHEMBL2857
 IC50 9.3 9.3 0.5 1
Human immunodeficiency virus type 2 pol protein
CHEMBL5074
 IC50 9.3 9.3 0.5 1
Unchecked
CHEMBL612545
 IC50 9.3 5.515 0.5 8
Protease
CHEMBL2366517
 Kd 9.24 8.94 0.6 3
Human immunodeficiency virus 1
CHEMBL378
 EC50 9.22 7.4951 0.6 99
Unchecked
CHEMBL612545
 Ki 8.99 6.7723 1.0 13
Human immunodeficiency virus 2
CHEMBL380
 IC50 8.72 6.86 1.9 16
CCRF-CEM
CHEMBL382
 IC50 8.7 8.7 2.0 1
Human immunodeficiency virus
CHEMBL613758
 IC50 8.7 8.21 2.0 2
MT4
CHEMBL388
 EC50 8.7 8.55 2.0 2
C8166
CHEMBL614533
 EC50 8.7 8.7 2.0 1
MT2
CHEMBL614184
 IC50 8.52 8.1275 3.0 4
MT2
CHEMBL614184
 EC50 8.3 8.3 5.0 1
CEM-SS
CHEMBL614548
 IC50 8.18 8.18 6.6 1
Human immunodeficiency virus 1
CHEMBL378
 IC50 8.1 7.3421 8.0 29
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.0 8.0 10.0 1
Human immunodeficiency virus
CHEMBL613758
 EC50 7.85 7.85 14.0 1
Human T-cell leukemia virus type I
CHEMBL613551
 IC50 7.75 7.75 18.0 1
MT4
CHEMBL388
 IC50 7.7 7.06 20.0 4
H9
CHEMBL614806
 IC50 7.7 7.7 20.0 1
SUP-T1
CHEMBL614940
 IC50 7.7 7.7 20.0 1
Unchecked
CHEMBL612545
 EC50 7.52 7.52 30.0 1
Plasmodium yoelii yoelii
CHEMBL612328
 IC50 7.45 7.45 35.2 1
Cytochrome P450 3A4
CHEMBL340
 Ki 6.77 6.48 170.0 2
Plasmodium falciparum
CHEMBL364
 EC50 6.02 5.524 960.0 5
Cytochrome P450 3A4
CHEMBL340
 IC50 5.82 5.82 1500.0 1
ATP-dependent translocase ABCB1
CHEMBL4302
 IC50 5.8 4.966 1600.0 5
Voltage-gated L-type calcium channel
CHEMBL2095229
 IC50 5.72 5.72 1900.0 1
Substance-K receptor
CHEMBL2327
 Ki 5.68 5.68 2071.0 1
Thromboxane-A synthase
CHEMBL1835
 IC50 5.66 5.66 2182.0 1
5-hydroxytryptamine receptor 1A
CHEMBL273
 Ki 5.61 5.61 2442.0 1
Kappa-type opioid receptor
CHEMBL237
 Ki 5.56 5.56 2780.0 1
Bile salt export pump
CHEMBL6020
 IC50 5.54 5.425 2900.0 4
Mu-type opioid receptor
CHEMBL233
 Ki 5.41 5.41 3907.0 1
5-hydroxytryptamine receptor 1A
CHEMBL273
 IC50 5.37 5.37 4273.0 1
Plasmodium vivax
CHEMBL613013
 IC50 5.37 5.37 4230.0 1
D(3) dopamine receptor
CHEMBL234
 Ki 5.28 5.28 5219.0 1
Substance-K receptor
CHEMBL2327
 IC50 5.21 5.21 6214.0 1
Kappa-type opioid receptor
CHEMBL237
 IC50 5.16 5.16 6951.0 1
Vasopressin V1a receptor
CHEMBL1889
 Ki 5.15 5.15 7030.0 1
Solute carrier family 22 member 1
CHEMBL2073670
 IC50 5.08 5.08 8260.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.08 5.08 8305.0 1
Mu-type opioid receptor
CHEMBL233
 IC50 5.02 5.02 9625.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 34283.0 ng.hr.mL-1 Homo sapiens
AUC 99535.0 ng.hr.mL-1 Homo sapiens
AUC 35308.0 ng.hr.mL-1 Homo sapiens
AUC 132158.0 ng.hr.mL-1 Homo sapiens
AUC 17546.5 ng.hr.mL-1 Homo sapiens
AUC 33700.0 ng.hr.mL-1 Homo sapiens
AUC 1192.0 ng.hr.mL-1 Homo sapiens
AUC 1062.0 ng.hr.mL-1 Homo sapiens
AUC 1514.0 ng.hr.mL-1 Homo sapiens
AUC 1235.0 ng.hr.mL-1 Homo sapiens
AUC 1086.0 ng.hr.mL-1 Homo sapiens
AUC 1485.0 ng.hr.mL-1 Homo sapiens
AUC 1039.0 ng.hr.mL-1 Homo sapiens
AUC 1028.0 ng.hr.mL-1 Homo sapiens
AUC 6499.29 ng.hr.mL-1 Homo sapiens
CL 12.6 mL.min-1.kg-1 Homo sapiens
CL 13.0 mL.min-1.kg-1 Homo sapiens
CL 13.0 mL.min-1.kg-1 Homo sapiens
CL 23.1 L/hr Homo sapiens
CL 25.7 uL.min-1.(10^6cells)-1 Homo sapiens
CL 150.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 150.0 mL.min-1.g-1 Homo sapiens
CL 1469.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 1675.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL/F 1080.0 ml.min-1 Homo sapiens
CL/F 941.0 ml.min-1 Homo sapiens
CL/F 1059.0 ml.min-1 Homo sapiens
CL/F 809.0 ml.min-1 Homo sapiens
Cmax 5473.57 nM Homo sapiens
Cmax 15070.21 nM Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus type 1 protease Ki = 0.04 nM 10.4 Inhibition of HIV protease 10866371
Protease Ki = 0.04 nM 10.4 Inhibition of wild-type HIV1 BH10 protease expressed in Escherichia coli by spec... 18598016
HIV-1 protease IC50 = 0.05 nM 10.3 Enzyme Inhibition of Purified HIV-1 Protease: Protease inhibitors (PI) are used ... -
Human immunodeficiency virus type 1 protease Ki = 0.062 nM 10.21 Dissociation constant obtained by inhibition of Wild-type protease 10978186
Protease Ki = 0.08 nM 10.1 Inhibition of HIV1 protease 17638694
Human immunodeficiency virus type 1 protease Ki = 0.12 nM 9.92 Compound was tested for its inhibitory potency against human immunodeficiency vi... 12113826
Human immunodeficiency virus type 1 protease Ki = 0.12 nM 9.92 Binding activity against HIV-1 Protease 1956054
Human immunodeficiency virus type 1 protease Ki = 0.12 nM 9.92 The compound was tested for binding activity against HIV-1 protease 1956054
Human immunodeficiency virus type 1 protease Ki = 0.1202 nM 9.92 Binding affinity to HIV-1 protease 8021917
Human immunodeficiency virus type 1 protease Ki = 0.12 nM 9.92 Binding affinity to HIV1 protease assessed as inhibition constant 26799988
Protease Ki = 0.138 nM 9.86 Inhibition of HIV1 protease 17981045
Human immunodeficiency virus type 1 protease Ki = 0.19 nM 9.72 Inhibitory activity against HIV-1 protease 12699395
Human immunodeficiency virus 2 EC50 = 0.2 nM 9.7 Antiviral activity against HIV2 ROD with protease G17N/V47A mutation infected in... 17576848
Human immunodeficiency virus type 1 protease IC50 = 0.2 nM 9.7 In vitro inhibition HIV-1 IIIB protease. -
Human immunodeficiency virus 2 EC50 = 0.2 nM 9.7 Antiviral activity against HIV2 ROD with protease V47A mutation infected in huma... 17576848
Protease Ki = 0.2 nM 9.7 Inhibition of HIV1 protease expressed in Escherichia coli by fluorometric assay 19961222
Protease Ki = 0.221 nM 9.66 Inhibition of HIV1 protease using fluorogenic hexapeptide substrate (2-aminobenz... -
Human immunodeficiency virus type 1 protease Ki = 0.22 nM 9.66 Inhibition of HIV1 recombinant protease V32I/I47A mutant expressed in Escherichi... 18598016
Human immunodeficiency virus type 1 protease Ki = 0.23 nM 9.64 Inhibitory concentration against HIV-1 protease 11543677
Human immunodeficiency virus type 1 protease IC50 = 0.23 nM 9.64 Inhibition of HIV1 protease using H-Val-Ser-Gln-Am-(L-b-naphthyl-alanine)-Pro-Il... 32686940

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 278
17638694 10.1128/aac.00149-07 Human immunodeficiency virus 1 53
18227188 10.1128/aac.01284-07 Human immunodeficiency virus 2 36
18955518 10.1128/aac.00689-08 Human immunodeficiency virus 1 33
17101675 10.1128/aac.00690-06 Human immunodeficiency virus 1 33
17371813 10.1128/aac.01136-06 Homo sapiens 24
17371811 10.1128/aac.01413-06 Human immunodeficiency virus 1 24
21051535 10.1124/dmd.110.034629 ADMET 21
16472241 10.2174/1570163043334794 Hepatotoxicity 18
17981045 10.1016/j.bmc.2007.10.062 Human immunodeficiency virus 1 17
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
26799988 10.1021/acs.jmedchem.5b01697 Human immunodeficiency virus 1 13
12699389 10.1021/jm021012t ATP-dependent translocase ABCB1 13
20439612 10.1128/aac.01766-09 Human immunodeficiency virus 1 13
19746963 10.1021/jm900695w Human immunodeficiency virus 1 13
16913714 10.1021/jm060561m Human immunodeficiency virus 1 11
24805780 10.1021/jm500139a Human immunodeficiency virus 1 11
20028821 10.1128/aac.01512-09 Plasmodium falciparum 11
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
17576848 10.1128/aac.00146-07 Human immunodeficiency virus 2 10

Data from ChEMBL 36 via Core Engine