ABACAVIR HYDROXYACETATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H20N6O3
Molecular Weight	344.3684
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

NC1=NC2=C(N=CN2[C@@H]3C[C@H](COC(=O)CO)C=C3)C(NC4CC4)=N1

InChI

InChIKey=ZBBZROWQLKCFQK-KOLCDFICSA-N

InChI=1S/C16H20N6O3/c17-16-20-14(19-10-2-3-10)13-15(21-16)22(8-18-13)11-4-1-9(5-11)7-25-12(24)6-23/h1,4,8-11,23H,2-3,5-7H2,(H3,17,19,20,21)/t9-,11+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C16H20N6O3
Molecular Weight	344.3684
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Abacavir is a nucleoside reverse transcriptase inhibitor used for treatment of HIV infection (either alone or in combination with other antiviral drugs). It was shown that abacavir exerts its antiviral activity through its active metabolite, carbovir triphosphate. Carbovir triphosphate is a guanine analogue and a potent and selective inhibitor of viral reverse transcriptases. Upon administration, abacavir is first converted to abacavir monophosphate by ADK, then the monophosphate is deaminated to carbovir monophosphate, which is then anabolized by cellular kinases to carbovir diphosphate and then finally to carbovir triphosphate. Abacavir causes hypersensitivity reaction in patients with HLA-B*57:01 allele.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Human immunodeficiency virus type 1 reverse transcriptase 67	Inhibitor 8,297		21.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
HIV-1 infection 151	Primary		Approved 8,429	ZIAGEN

C_max

Value	Dose	Co-administered	Analyte	Population
3 μg/mL	300 mg 2 times / day steady-state, oral		ABACAVIR SULFATE plasma	Homo sapiens
4.26 μg/mL	600 mg single, oral		ABACAVIR SULFATE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
6.02 μg × h/mL	300 mg 2 times / day steady-state, oral		ABACAVIR SULFATE plasma	Homo sapiens
11.95 μg × h/mL	600 mg single, oral		ABACAVIR SULFATE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.54 h	600 mg single, oral		ABACAVIR SULFATE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
50%	300 mg 2 times / day steady-state, oral		ABACAVIR SULFATE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
150 mg single, intravenous	unhealthy, 27–39 years n = 6
1200 mg single, oral Highest studied dose	unhealthy, 38 years (range: 24–48 years) n = 12	Other AEs: Asthenia, Abdominal pain...
600 mg 3 times / day steady, oral Highest studied dose	unhealthy, > 13 years n = 20
600 mg 1 times / day steady, oral Recommended	unhealthy n = 2670	Other AEs: Hypersensitivity reaction...

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AEs

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AE	Significance	Dose	Population
Diarrhea	17%	1200 mg single, oral Highest studied dose	unhealthy, 38 years (range: 24–48 years) n = 12
Dyspepsia	17%	1200 mg single, oral Highest studied dose	unhealthy, 38 years (range: 24–48 years) n = 12
Headache	25%	1200 mg single, oral Highest studied dose	unhealthy, 38 years (range: 24–48 years) n = 12
Abdominal pain	33%	1200 mg single, oral Highest studied dose	unhealthy, 38 years (range: 24–48 years) n = 12
Asthenia	33%	1200 mg single, oral Highest studied dose	unhealthy, 38 years (range: 24–48 years) n = 12

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:421707	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:421707
ChemicalBook	CB5698138	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5698138
MolPort	MolPort-006-069-118	https://www.molport.com/shop/molecule-link/MolPort-006-069-118
ZINC	ZINC000002015928	http://zinc15.docking.org/substances/ZINC000002015928
eMolecules	30512521	https://www.emolecules.com/cgi-bin/more?vid=30512521

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PubMed

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Title	Date	PubMed
Prevalence and characteristics of multinucleoside-resistant human immunodeficiency virus type 1 among European patients receiving combinations of nucleoside analogues.	2000 Aug	10898683
Mutational patterns in the HIV genome and cross-resistance following nucleoside and nucleotide analogue drug exposure.	2001	11678471
A comparison of the steady-state pharmacokinetics and safety of abacavir, lamivudine, and zidovudine taken as a triple combination tablet and as abacavir plus a lamivudine-zidovudine double combination tablet by HIV-1-infected adults.	2001 Apr	11310515
Amino acid deletion at codon 67 and Thr-to-Gly change at codon 69 of human immunodeficiency virus type 1 reverse transcriptase confer novel drug resistance profiles.	2001 Apr	11264389
Antiviral activity of tenofovir (PMPA) against nucleoside-resistant clinical HIV samples.	2001 Apr-Jul	11562951

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Sample Use Guides

In Vivo Use Guide

Adults: 600 mg daily, administered as either 300 mg twice daily or 600 mg once daily. Pediatric Patients Aged 3 Months and Older: Administered either once or twice daily. Dose should be calculated on body weight (kg) and should not exceed 600 mg daily.

Route of Administration: Oral

In Vitro Use Guide

In order to study the inhibitory effect of abacavir on HIV strains, MT-2 cell line was infected with HIV-1 strain IIIB and was treated with increasing concentrations of the drug (up to 100 uM).

Substance Class	Chemical
Record UNII	B3C7MG354B
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ABACAVIR HYDROXYACETATE

Common Name

English

ACETIC ACID, 2-HYDROXY-, ((1S,4R)-4-(2-AMINO-6-(CYCLOPROPYLAMINO)-9H-PURIN-9-YL)-2-CYCLOPENTEN-1-YL)METHYL ESTER

Systematic Name

English

PRURISOL

Common Name

English

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Code System

Code

Type

Description

CAS

1446418-48-9

PRIMARY

DRUG BANK

DB12187

PRIMARY

FDA UNII

B3C7MG354B

PRIMARY

PUBCHEM

71605071

PRIMARY

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Related Record

Type

Details


					WR2TIP26VS

ABACAVIR

ACTIVE MOIETY

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound