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Compound Detail

CHEMBL1380

ABACAVIR
💊 Approved Drug
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💊 Approved Drug
Nc1nc(NC2CC2)c2ncn([C@H]3C=C[C@@H](CO)C3)c2n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1380
Name ABACAVIR
Phase Approved
Structure Type MOL
InChI Key MCGSCOLBFJQGHM-SCZZXKLOSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL1201395

Known Names

Abacavir Avacavir Epzicom NSC-742406 Ziagen
8
Targets
67
Activities
3
Assay Types
30
PK Parameters
20
Publications
5
Known Names
10
Indications

Molecular Properties

286.3
MW (Da)
1.09
ALogP
7
HBA
3
HBD
101.9
PSA (Ų)
0.73
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1998
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Natural Product Prodrug
USAN Stem -vir
USAN Year 1996

Extended Properties

Molecular Formula C14H18N6O
MW 286.34
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness 0.03

Indications

Acquired Immunodeficiency Syndrome HIV Infections HIV Infections Tuberculosis Virus Diseases Acidosis, Lactic Lipodystrophy Sarcoma, Kaposi Glioma Hepatitis C

ATC Classification

J05AF06
abacavir
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Activity Summary

EC50 61 meas. best 6.7
IC50 5 meas. best 6.89
Kd 1 meas. best 4.36

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 IC50 6.89 6.89 130.0 1
Unchecked
CHEMBL612545
 IC50 6.89 6.89 130.0 1
Human immunodeficiency virus 1
CHEMBL378
 EC50 6.7 5.2683 200.0 41
Human immunodeficiency virus
CHEMBL613758
 EC50 6.5 6.5 320.0 1
Human immunodeficiency virus 1
CHEMBL378
 IC50 6.1 6.1 800.0 1
Human immunodeficiency virus 2
CHEMBL380
 EC50 5.52 5.214 3000.0 5
Hepatitis B virus
CHEMBL613497
 EC50 5.47 5.3757 3400.0 7
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 EC50 5.28 5.045 5300.0 2
Moloney murine sarcoma virus
CHEMBL613501
 EC50 5.06 5.06 8800.0 1
Albumin
CHEMBL3253
 Kd 4.36 4.36 44000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1718.04 ng.hr.mL-1 Cercopithecidae
AUC 1718.04 ng.hr.mL-1 Cercopithecidae
AUC 10700.0 ng.hr.mL-1 Homo sapiens
AUC 9880.0 ng.hr.mL-1 Homo sapiens
AUC 11700.0 ng.hr.mL-1 Homo sapiens
AUC 10900.0 ng.hr.mL-1 Homo sapiens
AUC 7580.0 ng.hr.mL-1 Homo sapiens
AUC 7040.0 ng.hr.mL-1 Homo sapiens
AUC 7260.0 ng.hr.mL-1 Homo sapiens
AUC 6740.0 ng.hr.mL-1 Homo sapiens
AUC 1080.0 ng.hr.mL-1 Homo sapiens
AUC 1080.0 ng.hr.mL-1 Homo sapiens
AUC 8500.0 ng.hr.mL-1 Homo sapiens
AUC 7880.0 ng.hr.mL-1 Homo sapiens
AUC 8520.0 ng.hr.mL-1 Homo sapiens
AUC 7900.0 ng.hr.mL-1 Homo sapiens
AUC 11700.0 ng.hr.mL-1 Homo sapiens
CL - mL.min-1.kg-1 Cercopithecidae
CL 13.0 mL.min-1.kg-1 Homo sapiens
CL 13.0 mL.min-1.kg-1 Homo sapiens
Cmax 1.0 hr Cercopithecidae
Cmax 11978.77 nM Homo sapiens
Cmax 5552.84 nM Homo sapiens
Cmax 7299.02 nM Homo sapiens
Cmax 7299.02 nM Homo sapiens
Cmax 13375.71 nM Homo sapiens
Cmax 6425.93 nM Homo sapiens
Cmax 13445.55 nM Homo sapiens
Cmax 6425.93 nM Homo sapiens
Cmax 5797.3 nM Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 130.0 nM 6.89 Inhibition of wild type HIV reverse transcriptase 18029175
Human immunodeficiency virus type 1 reverse transcriptase IC50 = 130.0 nM 6.89 Inhibition on HIV1 reverse transcriptase p66/p51 19179082
Human immunodeficiency virus 1 EC50 = 200.0 nM 6.7 Effective concentration against human immunodeficiency virus type 1 in PBL cells 15887959
Human immunodeficiency virus EC50 = 320.0 nM 6.5 Antiviral activity against wild type HIV 18029175
Human immunodeficiency virus 1 EC50 = 320.0 nM 6.5 Antiviral activity against HIV1 3a infected human MT2 cells assessed as inhibiti... 19179082
Human immunodeficiency virus 1 IC50 = 800.0 nM 6.1 Antiviral activity against HIV-1 SF162 infected in TZM-bl cells after 2 days by ... 26711143
Human immunodeficiency virus 1 EC50 = 1500.0 nM 5.82 Antiviral activity against HIV1 isolate 056 expressing wild type reverse transcr... 20439609
Human immunodeficiency virus 1 EC50 = 1600.0 nM 5.8 Antiviral activity against HIV1 replication in CEM cell line 16458506
Human immunodeficiency virus 1 EC50 = 1700.0 nM 5.77 Antiviral activity against HIV1 isolate 057 expressing wild type reverse transcr... 20439609
Human immunodeficiency virus 1 EC50 = 1900.0 nM 5.72 Effective concentration against human immunodeficiency virus type 1 in CEM cells 15887959
Human immunodeficiency virus 1 EC50 = 1900.0 nM 5.72 Effective concentration against human immunodeficiency virus type 1 in CEM cells 15887959
Human immunodeficiency virus 1 EC50 = 2150.0 nM 5.67 Effective concentration against human immunodeficiency virus type 1 in MT-4 cell... 15887959
Human immunodeficiency virus 1 EC50 = 2400.0 nM 5.62 Antiviral activity against HIV1 isolate 215 harboring reverse transcriptase D67N... 20439609
Human immunodeficiency virus 1 EC50 = 2500.0 nM 5.6 Antiviral activity against HIV1 isolate 206 harboring reverse transcriptase D67N... 20439609
Human immunodeficiency virus 2 EC50 = 3000.0 nM 5.52 Effective concentration against human immunodeficiency virus type 2 (ROD) in CEM... 15887959
Human immunodeficiency virus 2 EC50 = 3000.0 nM 5.52 Effective concentration against human immunodeficiency virus type 2 in CEM cells 15887959
Human immunodeficiency virus 1 EC50 = 3300.0 nM 5.48 Antiviral activity against HIV1 isolate 166 harboring reverse transcriptase L74V... 20439609
Human immunodeficiency virus 1 EC50 = 3400.0 nM 5.47 Antiviral activity against HIV1 isolate 192 harboring reverse transcriptase M41L... 20439609
Human immunodeficiency virus 1 EC50 = 3400.0 nM 5.47 Antiviral activity against HIV1 isolate 153 harboring reverse transcriptase L74V... 20439609
Hepatitis B virus EC50 = 3400.0 nM 5.47 Inhibition of HBV L180M/ M204V mutant transfected in D88 cell line 16539393

Literature References

PubMed DOI Target Context # Activities
20439609 10.1128/aac.00068-10 Human immunodeficiency virus 1 62
19188387 10.1128/aac.01000-08 Homo sapiens 48
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
24273637 10.1039/c3md00196b ATP-dependent translocase ABCB1 7
15887959 10.1021/jm0491400 CCRF-CEM 7
15887959 10.1021/jm0491400 ADMET 7
15887959 10.1021/jm0491400 Human immunodeficiency virus 1 6
17876005 10.1128/aac.00687-07 Human immunodeficiency virus 1 5
19223644 10.1128/aac.01593-08 Human immunodeficiency virus 1 4
18029175 10.1016/j.bmcl.2007.10.038 Human immunodeficiency virus 4
16759112 10.1021/jm060102l Hepatitis B virus 4
16539393 10.1021/jm058271d Hepatitis B virus 4
15887959 10.1021/jm0491400 Human immunodeficiency virus 2 4
18426954 10.1124/dmd.108.020479 ADMET 4
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
19179082 10.1016/j.bmc.2008.12.028 Human immunodeficiency virus 1 3
37468498 10.1038/s41467-023-40064-9 Histamine H1 receptor 3
15887959 10.1021/jm0491400 Hepatitis B virus 3
15887959 10.1021/jm0491400 HepG2 3
17967913 10.1128/aac.01004-07 Human immunodeficiency virus 1 3

Data from ChEMBL 36 via Core Engine