Abacavir

Summary

Abacavir (CHEMBL1380) is an approved small-molecule HIV-1 reverse transcriptase inhibitor (ATC J05AF06); indicated across 10 conditions including hiv infectious disease and aids.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: J05AF06
• Indications: 10 conditions
• Clinical trials: 77
• Chemistry: 286.33 Da · C14H18N6O

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1380
Name	Abacavir
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	441300
ChEBI	CHEBI:421707
ATC	J05AF06
Molecular formula	C14H18N6O
Molecular weight	286.33
InChIKey	MCGSCOLBFJQGHM-SCZZXKLOSA-N

SMILES: C1CC1NC2=C3C(=NC(=N2)N)N(C=N3)[C@@H]4C[C@@H](C=C4)CO

IUPAC name: [(1S,4R)-4-[2-amino-6-(cyclopropylamino)purin-9-yl]cyclopent-2-en-1-yl]methanol

ChEBI definition: A 2,6-diaminopurine that is (1S)-cyclopent-2-en-1-ylmethanol in which the pro-R hydrogen at the 4-position is substituted by a 2-amino-6-(cyclopropylamino)-9H-purin-9-yl group. A nucleoside analogue reverse transcriptase inhibitor (NRTI) with antiretroviral activity against HIV, it is used (particularly as the sulfate) with other antiretrovirals in combination therapy of HIV infection.

Pharmacological roles (ChEBI): HIV-1 reverse transcriptase inhibitor, antiviral drug, drug allergen.

Also known as: Abacavir, Avacavir, Epzicom, NSC-742406, Ziagen, Abacavir (ABC), abacavir, SID26757979, ABACAVIR

Parent form; salt/anhydrous children: CHEMBL2106686, CHEMBL4303288

Patent coverage: 7,643 distinct patent families (30,419 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 30,418 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 3 (assay-derived). Sample: 3’,5’-cyclic-AMP phosphodiesterase 4D, Albumin, Nuclear receptor subfamily 1 group I member 2.

Bioactivity

ChEMBL activities: 2 potent at pChembl ≥ 5 of 3 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
NR1I2	5.01	AC50	9700	nM	CHEMBL_ACT_25188131
PDE4D	5	AC50	10000	nM	CHEMBL_ACT_25185257

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

10 indications (0 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
HIV infectious disease	3	MONDO:0005109	EFO:0000764
AIDS	3	MONDO:0012268	EFO:0000765
viral infectious disease	3	MONDO:0005108	EFO:0000763
tuberculosis	3	MONDO:0018076	MONDO:0018076
lipodystrophy	2	MONDO:0006573	EFO:1000727
Kaposi’s sarcoma	2	MONDO:0005055	EFO:0000558
lactic acidosis	2	MONDO:0006040	EFO:1000036
hepatitis C virus infection	1	MONDO:0005231	EFO:0003047
glioma	1	MONDO:0021042	MONDO:0100342

1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 77.

Phase distribution

Phase	Trials
PHASE3	22
PHASE4	21
PHASE2	13
PHASE1	11
Not specified	6
PHASE2/PHASE3	3
PHASE1/PHASE2	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00004585	PHASE4	COMPLETED	A Study of the Safety and Effectiveness of Combination Anti-HIV Therapy in HIV-Infected Adults
NCT00011895	PHASE4	UNKNOWN	Safety and Effectiveness of TRIZIVIR (Abacavir/Lamivudine/Zidovudine) With Efavirenz in HIV-Infected Patients Who Have Never Taken Anti-HIV Drugs
NCT00038506	PHASE4	COMPLETED	Study Of Investigational Regimen Combining FDA Approved HIV Drugs In HIV Subjects Experiencing Early Virologic Failure
NCT00192660	PHASE4	COMPLETED	HIV Infection And Metabolic Abnormalities Protocol 1 (HAMA001)
NCT00244712	PHASE4	COMPLETED	Abacavir/Lamivudine Versus Emtricitabine/Tenofovir Both In Combination With Lopinavir/Ritonavir For The Treatment Of HIV
NCT00335270	PHASE4	COMPLETED	A Randomized, Prospective Study of the Efficacy, Safety and Tolerability of Two Doses of GW433908Ritonavir Given With Abacavir/Lamivudine Fixed Dose Combination
NCT00335322	PHASE4	COMPLETED	ALTAIR - Alternative Antiretroviral Strategies : a Comparison of Three Initial Regimens
NCT00340080	PHASE4	COMPLETED	Clinical Utility Of Genetic Screening For HLA-B*5701, On Susceptibility To Abacavir Hypersensitivity
NCT00386659	PHASE4	TERMINATED	Immune Reconstitution in naïve HIV Patients With CD4 <100 Cells/mL When Treated With Lopinavir or Efavirenz.
NCT00544128	PHASE4	COMPLETED	Comparison of Epzicom and Truvada for the Initial Once Daily HIV Treatment
NCT00549198	PHASE4	COMPLETED	KIVEXA Vs TRUVADA, Both Administered With Efavirenz, In ART-Naive Subjects
NCT00647244	PHASE4	COMPLETED	Efficacy and Safety of Switching From Retrovir to Tenofovir or Abacavir in HIV-infected Patients
NCT00724711	PHASE4	COMPLETED	Safety and Efficacy Study of Switching From Epzicom to Truvada
NCT00851630	PHASE4	COMPLETED	Tuberculosis and Human Immunodeficiency Virus (HIV) Immune Reconstitution Syndrome Trial (THIRST)
NCT01102972	PHASE4	COMPLETED	A Simplification Study of Unboosted Reyataz With Epzicom (ASSURE)
NCT01608269	PHASE4	COMPLETED	Nucleoside Switch Pilot for Virologically Controlled HIV Subjects With Decreasing CD4 Cells Who Have Received TDF-based ARV Therapy
NCT01886638	PHASE4	COMPLETED	Determining the Effect of Abacavir on Platelet Activation
NCT02470650	PHASE4	WITHDRAWN	Cost-effectiveness of Different Antiretroviral Treatment in Patients HIV Naive
NCT02659761	PHASE4	TERMINATED	Triumeq As an Integrase Single Tablet Regimen in People With HIV Who Inject Drugs
NCT02957864	PHASE4	UNKNOWN	Switching From Tenofovir Disoproxil Fumarate to Abacavir or Tenofovir Alafenamide
NCT03360682	PHASE4	COMPLETED	Clinical Trial to Evaluate the Efficacy, Pharmacokinetics (PK) Interactions and Safety of Dolutegravir Plus 2 Nucleoside Reverse Transcriptase Inhibitors (NRTIs) in HIV-1-Infected Solid Organ Transplant Patients
NCT00004981	PHASE3	UNKNOWN	Safety and Effectiveness of Three Anti-HIV Drugs Combined in One Pill (Trizivir)
NCT00013520	PHASE3	COMPLETED	Comparison of Three Different Initial Treatments Without Protease Inhibitors for HIV Infection
NCT00044577	PHASE3	COMPLETED	New Tablet Containing Two FDA Approved Anti-HIV Drugs For Antiretroviral Therapy Experienced HIV-1 Infected Subjects
NCT00046176	PHASE3	COMPLETED	A HIV Study Of A Fixed-Dose Combination Tablet In Antiretroviral Experienced Patients
NCT00053638	PHASE3	COMPLETED	A New Tablet Containing Two FDA-Approved Drugs In HIV-Infected Patients Who Have Not Received Prior Therapy
NCT00078247	PHASE3	COMPLETED	Anti-HIV Drugs for Ugandan Patients With HIV and Tuberculosis
NCT00085943	PHASE3	COMPLETED	KALETRA Or LEXIVA With Ritonavir Combined With EPIVIR And Abacavir In Naive Subjects Over 48 Weeks
NCT00086359	PHASE3	COMPLETED	Comparison of Anti-HIV Drug Combinations to Prevent Mother-to-Child Transmission of HIV
NCT00094367	PHASE3	COMPLETED	A Study Comparing Safety Of Abacavir And Lamivudine Administered Once-Daily As A Single Tablet Versus The Same Drugs Administered Twice-Daily As Separate Tablets (ALOHA Study)
NCT00118898	PHASE3	COMPLETED	Efavirenz or Atazanavir/Ritonavir Given With Emtricitabine/Tenofovir Disoproxil Fumarate or Abacavir/Lamivudine in HIV Infected Treatment-Naive Adults
NCT00143702	PHASE2/PHASE3	COMPLETED	D4T or Abacavir Plus Vitamin Enhancement in HIV-Infected Patients (DAVE)
NCT00234091	PHASE3	COMPLETED	When to Start Anti-HIV Drugs in Children Infected With HIV (The PREDICT Study)
NCT00314626	PHASE3	COMPLETED	Antiretroviral Treatment Simplification Study With Efavirenz + Abacavir + 3TC Once Daily
NCT00338390	PHASE3	COMPLETED	Study to Evaluate Changes in CD4 on Replacing TDF With ABC or DDI+TDF With ABC+3TC
NCT00405925	PHASE3	COMPLETED	FREE Study: Efficacy and Toxicity of Trizivir
NCT00427297	PHASE3	TERMINATED	Optimizing Pediatric HIV-1 Treatment in Infants With Prophylactic Exposure to Nevirapine, Nairobi, Kenya
NCT00440947	PHASE3	COMPLETED	Induction/Simplification With Atazanavir + Ritonavir + Abacavir/Lamivudine Fixed-Dose Combination In HIV-1 Infection
NCT00834457	PHASE2/PHASE3	COMPLETED	A Pilot Study Of the Effects of Highly Active Antiretroviral Therapy on Kaposi’s Sarcoma in Zimbabwe
NCT01146873	PHASE3	COMPLETED	Treatment Options for Protease Inhibitor-exposed Children

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

PharmGKB dosing guidelines (3) — CPIC / DPWG genotype-guided dosing for this drug (drug × pharmacogene):

Guideline	Source	Gene(s)	Dosing	Recommendation
Annotation of DPWG Guideline for abacavir and HLA-B	DPWG	HLA-B		yes
Annotation of CPIC Guideline for abacavir and HLA-B	CPIC	HLA-B		yes
Annotation of RNPGx Guideline for abacavir and HLA-B	RNPGx	HLA-B		yes

PharmGKB also curates 2 clinical and 19 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).