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Also known as: 136470-78-5, Ziagen, Abacavir sulfate, Abacavir [inn], 1592u89, (1s,4r)-4-[2-amino-6-(cyclopropylamino)-9h-purin-9-yl]-2-cyclopentene-1-methanol
Molecular Formula
C14H18N6O
Molecular Weight
286.33  g/mol
InChI Key
MCGSCOLBFJQGHM-SCZZXKLOSA-N
FDA UNII
WR2TIP26VS

Abacavir
Abacavir is a nucleoside reverse transcriptase inhibitor analog of guanosine. This agent decreases HIV viral loads, retards or prevents the damage to the immune system, and reduces the risk of developing AIDS.
Abacavir is a Human Immunodeficiency Virus Nucleoside Analog Reverse Transcriptase Inhibitor. The mechanism of action of abacavir is as a Nucleoside Reverse Transcriptase Inhibitor, and Cytochrome P450 1A1 Inhibitor.
1 2D Structure

Abacavir

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(1S,4R)-4-[2-amino-6-(cyclopropylamino)purin-9-yl]cyclopent-2-en-1-yl]methanol
2.1.2 InChI
InChI=1S/C14H18N6O/c15-14-18-12(17-9-2-3-9)11-13(19-14)20(7-16-11)10-4-1-8(5-10)6-21/h1,4,7-10,21H,2-3,5-6H2,(H3,15,17,18,19)/t8-,10+/m1/s1
2.1.3 InChI Key
MCGSCOLBFJQGHM-SCZZXKLOSA-N
2.1.4 Canonical SMILES
C1CC1NC2=C3C(=NC(=N2)N)N(C=N3)C4CC(C=C4)CO
2.1.5 Isomeric SMILES
C1CC1NC2=C3C(=NC(=N2)N)N(C=N3)[C@@H]4C[C@@H](C=C4)CO
2.2 Other Identifiers
2.2.1 UNII
WR2TIP26VS
2.3 Synonyms
2.3.1 MeSH Synonyms

1. ((1r,4r)-4-(2-amino-6-(cyclopropylamino)-9h-purin-9-yl)-cyclopent-2-enyl)methanol

2. ((1r,4s)-4-(2-amino-6-(cyclopropylamino)-9h-purin-9-yl)cyclopent-2-enyl)methanol

3. (+)-abacavir

4. (+)-abacavir Sulfate

5. (+-)-abacavir Sulfate

6. (-)-cis-4-(2-amino-6-(cyclopropylamino)-9h-purin-9-yl)-2-cyclopentene-1-methanol

7. (1r,4r)-abacavir

8. (1r,4s)-abacavir Sulfate

9. (1s,4r)-4-(2-amino-6-(cyclopropylamino)-9h-purin-9-yl)-2-cyclopentene-1-methanol

10. (1s,4r)-4-(2-amino-6-(cyclopropylamino)-9h-purin-9-yl)-2-cyclopentene-1-methanol Succinate (1:1) (salt)

11. 1592u89

12. 2-cyclopentene-1-methanol, 4-(2-amino-6-(cyclopropylamino)-9h-purin-9-yl)-, (1r,4s)-, Sulfate (2:1)

13. 2-cyclopentene-1-methanol, 4-(2-amino-6-(cyclopropylamino)-9h-purin-9-yl)-, (1s,4r)-, Rel-, Sulfate (2:1)

14. 2-cyclopentene-1-methanol, 4-(2-amino-6-(cyclopropylamino)-9h-purin-9-yl)-, Hydrochloride, Hydrate (1:1:1), (1s,4r)-

15. Abacavir Enantiomer

16. Abacavir Hydrochloride Monohydrate

17. Abacavir Succinate

18. Abacavir Sulfate

19. Abacavir Sulfate Racemic

20. Abacavir Sulfate, (+)-

21. Abacavir Sulfate, (+-)-

22. Abacavir Sulfate, (1r,4s)-

23. Abacavir Sulphate

24. Abacavir, (+)-

25. Abacavir, (1r,4s)-

26. Abacavir, Trans-

27. Abacavir, Trans-, (+-)-

28. Abamune

29. Avacavir

30. Drg 0257

31. Drg-0257

32. Drg0257

33. Trans-abacavir

34. Trans-abacavir R,r-

35. Ziagen

2.3.2 Depositor-Supplied Synonyms

1. 136470-78-5

2. Ziagen

3. Abacavir Sulfate

4. Abacavir [inn]

5. 1592u89

6. (1s,4r)-4-[2-amino-6-(cyclopropylamino)-9h-purin-9-yl]-2-cyclopentene-1-methanol

7. Abacavir (inn)

8. Chebi:421707

9. Wr2tip26vs

10. ((1s,4r)-4-(2-amino-6-(cyclopropylamino)-9h-purin-9-yl)cyclopent-2-en-1-yl)methanol

11. Abc

12. [(1s,4r)-4-[2-amino-6-(cyclopropylamino)purin-9-yl]cyclopent-2-en-1-yl]methanol

13. {(1s-cis)-4-[2-amino-6-(cyclopropylamino)-9h-purin-9-yl]cyclopent-2-en-1-yl}methanol

14. Nsc-742406

15. [(1s,4r)-4-[2-amino-6-(cyclopropylamino)purin-9-yl]-1-cyclopent-2-enyl]methanol

16. 2-cyclopentene-1-methanol, 4-[2-amino-6-(cyclopropylamino)-9h-purin-9-yl]-, (1s,4r)-

17. Avacavir

18. 136777-48-5

19. (1s,4r)-4-(2-amino-6-(cyclopropylamino)-9h-purin-9-yl)-2-cyclopentene-1-methanol

20. [(1s,4r)-4-[2-amino-6-(cyclopropylamino)-9h-purin-9-yl]cyclopent-2-en-1-yl]methanol

21. 2-cyclopentene-1-methanol, 4-(2-amino-6-(cyclopropylamino)-9h-purin-9-yl)-, (1s-cis)-

22. (+/-)-abacavir

23. Abacavir [inn:ban]

24. Unii-wr2tip26vs

25. Nsc742406

26. Ziagen (tm)(*succinate Salt*)

27. {(1s,4r)-4-[2-amino-6-(cyclopropylamino)-9h-purin-9-yl]cyclopent-2-en-1-yl}methanol

28. 2-cyclopentene-1-methanol, 4-(2-amino-6-(cyclopropylamino)-9h-purin-9-yl)-, (1s,4r)-

29. Ncgc00164560-01

30. Mfcd00903850

31. Abacavir [mi]

32. Abacavir [vandf]

33. Avacavir [vandf]

34. Abacavir [mart.]

35. Abacavir [who-dd]

36. Epitope Id:137341

37. Abacavir [ema Epar]

38. Chembl1380

39. Schembl38632

40. Mls006010117

41. Dtxsid4046444

42. Gtpl11152

43. Srca-00004

44. Act03218

45. Bcp07728

46. Zinc2015928

47. Bdbm50366816

48. S5215

49. Akos024464970

50. Ac-1299

51. Ccg-267342

52. Cs-1354

53. Db01048

54. Dt-0030

55. Nsc 742406

56. (+/-)-4-[2-amino-6-(cyclopropylamino)-9h-purin-9-yl]-2-cyclopentene-1-methanol

57. (-)-cis-4-(2-amino-6-(cyclopropylamino)-9h-purin-9-yl)-2-cyclopentene-1-methanol

58. Ncgc00164560-02

59. Ncgc00164560-05

60. Ncgc00164560-17

61. Ba166801

62. Hy-17423

63. Smr004701251

64. C07624

65. D07057

66. Ab01566826_01

67. 470a785

68. A807079

69. A905952

70. Q304330

71. J-700136

72. ((1s,4r)-4-(2-amino-6-(cyclopropylamino)-9h-purin-9-yl)cyclopent-2-enyl)methanol

73. (+/-)-cis-4-[2-amino-6-(cyclopropylamino)-9h-purin-9-yl]-2-cyclopentene-1-methanol

74. [(1s,4r)-4-[2-amino-6-(cyclopropylamino)purin-9-yl]cyclopent-2-en-1-yl]methanol;abacavir

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 286.33 g/mol
Molecular Formula C14H18N6O
XLogP30.9
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Exact Mass286.15420922 g/mol
Monoisotopic Mass286.15420922 g/mol
Topological Polar Surface Area102 Ų
Heavy Atom Count21
Formal Charge0
Complexity414
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 6  
Drug NameAbacavir
PubMed HealthAbacavir (By mouth)
Drug ClassesAntiretroviral Agent
Drug LabelAbacavir sulfate is a synthetic carbocyclic nucleoside analogue with inhibitory activity against HIV-1. The chemical name of abacavir sulfate is (1S,cis)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol sulfate (salt) (2:1). A...
Active IngredientAbacavir; Abacavir sulfate
Dosage FormSolution
Routeoral
Strength20mg/ml
Market StatusTentative Approval
CompanyAurobindo Pharma; Hetero Labs Unit Iii

2 of 6  
Drug NameEpzicom
PubMed HealthAbacavir/Lamivudine (By mouth)
Drug ClassesAntiretroviral Agent
Active IngredientAbacavir sulfate; lamivudine
Dosage FormTablet
RouteOral
Strength300mg; eq 600mg base
Market StatusPrescription
CompanyViiv Hlthcare

3 of 6  
Drug NameZiagen
PubMed HealthAbacavir (By mouth)
Drug ClassesAntiretroviral Agent
Drug LabelZIAGEN is the brand name for abacavir sulfate, a synthetic carbocyclic nucleoside analogue with inhibitory activity against HIV-1. The chemical name of abacavir sulfate is (1S,cis)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-metha...
Active IngredientAbacavir sulfate
Dosage FormTablet; Solution
RouteOral
Strengtheq 20mg base/ml; eq 300mg base
Market StatusPrescription
CompanyViiv Hlthcare

4 of 6  
Drug NameAbacavir
PubMed HealthAbacavir (By mouth)
Drug ClassesAntiretroviral Agent
Drug LabelAbacavir sulfate is a synthetic carbocyclic nucleoside analogue with inhibitory activity against HIV-1. The chemical name of abacavir sulfate is (1S,cis)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol sulfate (salt) (2:1). A...
Active IngredientAbacavir; Abacavir sulfate
Dosage FormSolution
Routeoral
Strength20mg/ml
Market StatusTentative Approval
CompanyAurobindo Pharma; Hetero Labs Unit Iii

5 of 6  
Drug NameEpzicom
PubMed HealthAbacavir/Lamivudine (By mouth)
Drug ClassesAntiretroviral Agent
Active IngredientAbacavir sulfate; lamivudine
Dosage FormTablet
RouteOral
Strength300mg; eq 600mg base
Market StatusPrescription
CompanyViiv Hlthcare

6 of 6  
Drug NameZiagen
PubMed HealthAbacavir (By mouth)
Drug ClassesAntiretroviral Agent
Drug LabelZIAGEN is the brand name for abacavir sulfate, a synthetic carbocyclic nucleoside analogue with inhibitory activity against HIV-1. The chemical name of abacavir sulfate is (1S,cis)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-metha...
Active IngredientAbacavir sulfate
Dosage FormTablet; Solution
RouteOral
Strengtheq 20mg base/ml; eq 300mg base
Market StatusPrescription
CompanyViiv Hlthcare

4.2 Therapeutic Uses

Abacavir is indicated, in combination with other agents, for treatment of HIV-1 infection. /Included in US product labeling/

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 23rd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2003. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 1


4.3 Drug Warning

A unique and potentially fatal hypersensitivity reaction occurs in 2% to 5% of patients receiving abacavir. Symptoms typically occur within the first six weeks of therapy and include fever, rash, nausea, malaise, and respiratory complaints, in various combinations. Symptoms initially may be mild but increase in severity with continued administration. Discontinuation of the medication usually resolves all signs and symptoms, but rechallenge may cause rapid onset of severe reactions, hypotension, and death. Once an abacavir hypersensitivity reaction is suspected or confirmed, it is recommended that the patient never by rechallenged with abacavir.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1359


The major toxicity associated with abacavir therapy is potentially life-threatening hypersensitivity reactions. In clinical studies, hypersensitivity reactions have been reported in approximately 5% of adult and pediatric patients receiving abacavir in conjunction with lamivudine and zidovudine. Fatalities related to hypersensitivity reactions to abacavir have been reported. Manifestations of hypersensitivity usually are apparent within the first 6 weeks of abacavir therapy, but may occur at any time during therapy. Severe hypersensitivity reactions are likely to recur within hours following rechallenge in patients with a prior history of hypersensitivity to the drug, and these reactions may include life-threatening hypotension and death. The most severe hypersensitivity reactions reported to date have been in individuals who were rechallenged with abacavir after a previous hypersensitivity reaction to the drug. There also have been reports of severe or fatal hypersensitivity reactions occurring after abacavir was reintroduced in patients with no identified history of abacavir hypersensitivity or with unrecognized manifestations of hypersensitivity to the drug. Although these patients had discontinued abacavir for reasons unrelated to hypersensitivity (e.g., interruption in drug supply, discontinuance of abacavir during treatment for other medical conditions), some may have had symptoms present before discontinuance of the drug that were consistent with hypersensitivity but were attributed to other medical conditions (e.g., acute onset respiratory disease, gastroenteritis, adverse reactions to other drugs). Most of the hypersensitivity reactions reported following reintroduction of abacavir in these patients were indistinguishable from hypersensitivity reactions associated with abacavir rechallenge (i.e., short time to onset, increased severity of symptoms, poor outcome including death).Hypersensitivity reactions can occur within hours after abacavir is reintroduced; however, in some cases, these reactions occurred days to weeks following reintroduction of the drug.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 619


Lactic acidosis and severe hepatomegaly with steatosis (sometimes fatal) have been reported rarely in patients receiving abacavir and also have been reported in patients receiving dideoxynucleoside reverse transcriptase inhibitors. Most reported cases have involved women; obesity and long-term therapy with a nucleoside reverse transcriptase inhibitor also may be risk factors. Increased serum concentrations of Gamma-glutamyltransferase (GGT, GGPT) have been reported in patients receiving abacavir.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 620


Hypersensitivity reactions reported in patients receiving abacavir are characterized by the appearance of manifestations indicating involvement of multiple organ and body systems; these reactions have occurred in association with anaphylaxis, liver failure, renal failure, hypotension, and death. The most frequent manifestations of hypersensitivity reactions to abacavir include fever, rash, fatigue, GI symptoms such as nausea, vomiting, diarrhea, and abdominal pain, and respiratory symptoms such as pharyngitis, dyspnea, and cough. Other signs and symptoms include malaise, lethargy, myalgia, myolysis, headache, arthralgia, edema, paresthesia, lymphadenopathy, and mucous membrane lesions (e.g., conjunctivitis, mouth ulceration). Respiratory symptoms, including cough, dyspnea, and pharyngitis, have been reported in approximately 20% of patients with hypersensitivity reactions to abacavir. Fatalities have occurred in patients who developed hypersensitivity reactions in which the initial presentation included respiratory symptoms; some patients who experienced fatal hypersensitivity reactions were initially diagnosed as having an acute respiratory disease (pneumonia, bronchitis, flu-like illness). Hypersensitivity reactions can occur without rash; if rash occurs, it usually is maculopapular or urticarial, but may be variable in appearance. Laboratory abnormalities reported in patients experiencing a hypersensitivity reaction to abacavir include lymphopenia and increases in serum concentrations of liver enzymes, creatine kinase (CK, creatine phosphokinase, CPK), or creatinine.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 619


For more Drug Warnings (Complete) data for ABACAVIR SULFATE (17 total), please visit the HSDB record page.


4.4 Drug Indication

For the treatment of HIV-1 infection, in combination with other antiretroviral agents.


FDA Label


Ziagen is indicated in antiretroviral combination therapy for the treatment of Human Immunodeficiency Virus (HIV) infection in adults, adolescents and children.

The demonstration of the benefit of Ziagen is mainly based on results of studies performed with a twice daily regimen, in treatment-nave adult patients on combination therapy.

Before initiating treatment with abacavir, screening for carriage of the HLA-B*5701 allele should be performed in any HIV-infected patient, irrespective of racial origin. Abacavir should not be used in patients known to carry the HLA-B*5701 allele.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Abacavir is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Abacavir is phosphorylated to active metabolites that compete for incorporation into viral DNA. They inhibit the HIV reverse transcriptase enzyme competitively and act as a chain terminator of DNA synthesis. The concentration of drug necessary to effect viral replication by 50 percent (EC50) ranged from 3.7 to 5.8 M (1 M = 0.28 mcg/mL) and 0.07 to 1.0 M against HIV-1IIIB and HIV-1BaL, respectively, and was 0.26 0.18 M against 8 clinical isolates. Abacavir had synergistic activity in cell culture in combination with the nucleoside reverse transcriptase inhibitor (NRTI) zidovudine, the non-nucleoside reverse transcriptase inhibitor (NNRTI) nevirapine, and the protease inhibitor (PI) amprenavir; and additive activity in combination with the NRTIs didanosine, emtricitabine, lamivudine, stavudine, tenofovir, and zalcitabine.


5.2 MeSH Pharmacological Classification

Reverse Transcriptase Inhibitors

Inhibitors of reverse transcriptase (RNA-DIRECTED DNA POLYMERASE), an enzyme that synthesizes DNA on an RNA template. (See all compounds classified as Reverse Transcriptase Inhibitors.)


Anti-HIV Agents

Agents used to treat AIDS and/or stop the spread of the HIV infection. These do not include drugs used to treat symptoms or opportunistic infections associated with AIDS. (See all compounds classified as Anti-HIV Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
ABACAVIR
5.3.2 FDA UNII
WR2TIP26VS
5.3.3 Pharmacological Classes
Human Immunodeficiency Virus Nucleoside Analog Reverse Transcriptase Inhibitor [EPC]; Nucleoside Analog [EXT]; Nucleoside Reverse Transcriptase Inhibitors [MoA]; Cytochrome P450 1A1 Inhibitors [MoA]; Human Immunodeficiency Virus Nucleoside Analog Reverse Transcriptase Inhibitor [EPC]
5.4 ATC Code

J05AF06


J - Antiinfectives for systemic use

J05 - Antivirals for systemic use

J05A - Direct acting antivirals

J05AF - Nucleoside and nucleotide reverse transcriptase inhibitors

J05AF06 - Abacavir


5.5 Absorption, Distribution and Excretion

Absorption

Rapid and extensive after oral administration (83% bioavailability, tablet). When a 300 mg tablet is given twice daily to subjects, the peak plasma concentration (Cmax) was 3.0 0.89 mcg/mL and the area under the curve (AUC 0-12 hours) was 6.02 1.73 mcghr/mL.


Route of Elimination

Elimination of abacavir was quantified in a mass balance study following administration of a 600-mg dose of 14C-abacavir: 99% of the radioactivity was recovered, 1.2% was excreted in the urine as abacavir, 30% as the 5-carboxylic acid metabolite, 36% as the 5-glucuronide metabolite, and 15% as unidentified minor metabolites in the urine. Fecal elimination accounted for 16% of the dose. Renal excretion of unchanged abacavir is a minor route of elimination in humans.


Volume of Distribution

0.86 0.15 L/kg [IV administration]


Clearance

0.80 0.24 L/hr/kg [asymptomatic, HIV-1-infected adult patients receiving single (IV dose of 150mg]


Following oral administration of a 600-mg dose of radiolabeled abacavir, 82.2% of the dose is excreted in urine and 16% of the dose is excreted in feces. The 5-carboxylic acid metabolite, 5-glucuronide metabolite, and unchanged abacavir accounted for 30, 36, and 1.2%, respectively, of recovered radioactivity in urine; unidentified minor metabolites accounted for 15% of recovered radioactivity in urine.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 623


It is not known whether abacavir is distributed into human milk; the drug is distributed into milk in rats.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 621


Abacavir crosses the placenta in rats.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 621


The oral bioavailability of abacavir is high with or without food; the CSF-to-plasma AUC ratio is approximately 0.3.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1359


For more Absorption, Distribution and Excretion (Complete) data for ABACAVIR SULFATE (7 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Hepatic, by alcohol dehydrogenase and glucuronosyltransferase to a 5′-carboxylic acid metabolite and 5′-glucuronide metabolite, respectively. These metabolites have no antiviral activity. Abacavir is not significantly metabolized by cytochrome P450 enzymes.


Abacavir is partially metabolized by alcohol dehydrogenase (to form the 5'-carboxylic acid) and glucuronidation (to form the 5'-glucuronide).

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1359


The metabolic fate of abacavir has not been fully determined, but the drug is metabolized in the liver. Abacavir is metabolized by alcohol dehydrogenase to form the 5-carboxylic acid and by glucuronyltransferase to form the 5-glucuronide; these metabolites do not appear to have any antiviral activity. Any involvement of cytochrome p450 isoenzymes in the metabolism of abacavir is limited.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 623


Intracellularly, abacavir is phosphorylated to abacavir monophosphate by adenosine phosphotransferase; abacavir monophosphate is then converted to carbovir monophosphate in a reaction catalyzed by cytosolic enzymes and then to carbovir triphosphate by cellular kinases. Intracellular (host cell) conversion of abacavir to carbovir triphosphate is necessary for the antiviral activity of the drug. The in vitro intracellular half-life of carbovir triphosphate in CD4+ CEM cells is 3.3 hours.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 623


5.7 Biological Half-Life

1.54 0.63 hours


The in vitro intracellular half-life of carbovir triphosphate /SRP: a metabolite of abacavir sulfate,/ in CD4+ CEM cells is 3.3 hours.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 623


The plasma elimination half-life of abacavir following a single oral dose (given as abacavir sulfate) is about 1.5 hours. In HIV-infected children 3 months to 13 years of age who received 8 mg/kg of abacavir every 12 hours (given as an oral solution containing abacavir sulfate), steady-state plasma elimination half-life averaged 1.3 hours and was essentially the same as that reported after a single dose. Following oral administration of a single 300-mg dose of abacavir to an individual with renal failure (glomerular filtration rate less than 10 mL/minute) undergoing peritoneal dialysis, the plasma elimination half-life of the drug was 1.33 hours.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 623


5.8 Mechanism of Action

Abacavir is a carbocyclic synthetic nucleoside analogue and an antiviral agent. Intracellularly, abacavir is converted by cellular enzymes to the active metabolite carbovir triphosphate, an analogue of deoxyguanosine-5'-triphosphate (dGTP). Carbovir triphosphate inhibits the activity of HIV-1 reverse transcriptase (RT) both by competing with the natural substrate dGTP and by its incorporation into viral DNA. Viral DNA growth is terminated because the incorporated nucleotide lacks a 3'-OH group, which is needed to form the 5 to 3 phosphodiester linkage essential for DNA chain elongation.


Like dideoxynucleoside reverse transcriptase inhibitors (e.g., didanosine, lamivudine, stavudine, zalcitabine, zidovudine), the antiviral activity of abacavir appears to depend on intracellular conversion of the drug to a 5-triphosphate metabolite; thus, carbovir triphosphate (carbocyclic guanosine triphosphate) and not unchanged abacavir appears to be the pharmacologically active form of the drug. Substantial differences exist in the rates at which human cells phosphorylate various nucleoside antiviral agents and in the enzymatic pathways involved.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 621


Enzymatic conversion of abacavir to carbovir triphosphate appears to be complex and involves certain steps and enzymes that differ from those involved in the enzymatic conversion of dideoxynucleoside reverse transcriptase inhibitors. Abacavir is phosphorylated by adenosine phosphotransferase to abacavir monophosphate, which is converted to carbovir monophosphate by a cytosolic enzyme. Subsequently, carbovir monophosphate is phosphorylated by cellular kinases to carbovir triphosphate. Abacavir is not a substrate for enzymes (i.e., thymidine kinase, deoxycytidine kinase, adenosine kinase, mitochondrial deoxyguanosine kinase) known to phosphorylate other nucleoside analogs. Because phosphorylation of abacavir depends on cellular rather than viral enzymes, conversion of the drug to the active triphosphate derivative occurs in both virus-infected and uninfected cells. Carbovir triphosphate is a structural analog of deoxyguanosine-5-triphosphate (dGTP), the usual substrate for viral RNA-directed DNA polymerase. Although other mechanisms may be involved in the antiretroviral activity of the drug, carbovir triphosphate appears to compete with deoxyguanosine-5-triphosphate for viral RNA-directed DNA polymerase and incorporation into viral DNA. Following incorporation of carbovir triphosphate into the viral DNA chain instead of deoxyguanosine-5-triphosphate, DNA synthesis is prematurely terminated because the absence of the 3-hydroxy group on the drug prevents further 5 to 3 phosphodiester linkages.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 621


The complete mechanism(s) of antiviral activity of abacavir has not been fully elucidated. Following conversion to a pharmacologically active metabolite, abacavir apparently inhibits replication of retroviruses, including human immunodeficiency virus type 1 (HIV-1) and type 2 (HIV-2), by interfering with viral RNA-directed DNA polymerase (reverse transcriptase). The drug, therefore, exerts a virustatic effect against retroviruses by acting as a reverse transcriptase inhibitor.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 621


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13-Jan-2021
17-Aug-2024
KGS
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Average Price (USD/KGS)

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Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

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