Identification

Name
Zidovudine
Accession Number
DB00495  (APRD00449)
Type
Small Molecule
Groups
Approved
Description

A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia. [PubChem]

Structure
Thumb
Synonyms
  • Azidothymidine
  • AZT
  • ZDV
  • Zidovudina
  • Zidovudine
  • Zidovudinum
External IDs
BW-A-509U / BW-A509U / NSC-602670
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
RetrovirSyrup10 mg/1mLOralViiV Healthcare Company2010-10-28Not applicableUs
RetrovirSyrup50 mg/5mLOralGlaxosmithkline Inc1989-10-102013-09-30Us
RetrovirCapsule100 mg/1OralPhysicians Total Care, Inc.1987-06-222013-06-30Us
RetrovirTablet, film coated300 mg/1OralViiV Healthcare Company2010-10-282010-11-01Us
RetrovirCapsule100 mg/1OralGlaxosmithkline Inc1987-06-222013-06-30Us
RetrovirInjection, solution10 mg/1mLIntravenousGlaxosmithkline Inc2000-03-192013-05-31Us
RetrovirInjection, solution10 mg/1mLIntravenousViiV Healthcare Company2010-11-04Not applicableUs
RetrovirCapsule100 mg/1OralViiV Healthcare Company2010-10-28Not applicableUs
RetrovirTablet, film coated300 mg/1OralGlaxosmithkline Inc1996-10-142013-03-14Us
Retrovir (azt)Capsule100 mgOralViiV Healthcare ULC1990-12-31Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-zidovudineCapsule100 mgOralApotex Corporation1992-12-31Not applicableCanada
Novo-azt Cap 100mgCapsule100 mgOralNovopharm Limited1992-12-312015-10-26Canada
ZidovudineSyrup50 mg/5mLOralEdenbridge Pharmaceuticals Llc2012-04-012017-03-31Us
ZidovudineCapsule100 mg/1OralAurobindo Pharma Limited2006-03-27Not applicableUs
ZidovudineTablet300 mg/1OralAvera McKennan Hospital2016-01-272018-07-10Us
ZidovudineTablet, film coated300 mg/1OralProdigy Health Supplier2013-03-012013-12-31Us
ZidovudineTablet300 mg/1OralWest-Ward Pharmaceuticals Corp.2005-09-192011-09-07Us
ZidovudineTablet, film coated300 mg/1OralLannett Company, Inc.2014-03-25Not applicableUs
ZidovudineTablet, film coated300 mg/1OralRemedy Repack2015-05-142016-07-10Us
ZidovudineCapsule100 mg/1OralAcetris Health, Llc2006-03-27Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Abacavir Sulfate, Lamivudine and ZidovudineZidovudine (300 mg/1) + Abacavir Sulfate (300 mg/1) + Lamivudine (150 mg/1)TabletOralLupin Pharmaceuticals2013-12-17Not applicableUs
Abacavir, Lamivudine and ZidovudineZidovudine (300 mg/1) + Abacavir Sulfate (300 mg/1) + Lamivudine (150 mg/1)TabletOralLupin Pharmaceuticals, Inc.2013-12-17Not applicableUs
Apo-abacavir-lamivudine-zidovudineZidovudine (300 mg) + Abacavir (300 mg) + Lamivudine (150 mg)TabletOralApotex Corporation2015-12-28Not applicableCanada
Apo-lamivudine-zidovudineZidovudine (300 mg) + Lamivudine (150 mg)TabletOralApotex Corporation2012-06-04Not applicableCanada
Apo-zidovudine-lamivudine-nevirapineZidovudine (300 mg) + Lamivudine (150 mg) + Nevirapine (200 mg)TabletOralApotex CorporationNot applicableNot applicableCanada
Auro-lamivudine/zidovudineZidovudine (300 mg) + Lamivudine (150 mg)TabletOralAuro Pharma Inc2014-03-03Not applicableCanada
CombivirZidovudine (300 mg/1) + Lamivudine (150 mg/1)Tablet, film coatedOralGlaxosmithkline Inc1997-09-302014-07-31Us0173 059520180907 15195 ehvd0k
CombivirZidovudine (300 mg/1) + Lamivudine (150 mg/1)Tablet, film coatedOralViiV Healthcare Company2010-10-19Not applicableUs
CombivirZidovudine (300 mg) + Lamivudine (150 mg)TabletOralViiV Healthcare ULC1998-12-08Not applicableCanada
CombivirZidovudine (300 mg/1) + Lamivudine (150 mg/1)Tablet, film coatedOralRemedy Repack2013-04-232017-02-01Us49702 0202 18 nlmimage10 34191a68
Categories
UNII
4B9XT59T7S
CAS number
30516-87-1
Weight
Average: 267.2413
Monoisotopic: 267.096753929
Chemical Formula
C10H13N5O4
InChI Key
HBOMLICNUCNMMY-XLPZGREQSA-N
InChI
InChI=1S/C10H13N5O4/c1-5-3-15(10(18)12-9(5)17)8-2-6(13-14-11)7(4-16)19-8/h3,6-8,16H,2,4H2,1H3,(H,12,17,18)/t6-,7+,8+/m0/s1
IUPAC Name
1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
SMILES
CC1=CN([C@H]2C[C@H](N=[N+]=[N-])[C@@H](CO)O2)C(=O)NC1=O

Pharmacology

Indication

Used in combination with other antiretroviral agents for the treatment of human immunovirus (HIV) infections.

Associated Conditions
Pharmacodynamics

Zidovudine is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Zidovudine 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 lack of a 3'-OH group in the incorporated nucleoside analogue prevents the formation of the 5' to 3' phosphodiester linkage essential for DNA chain elongation, and therefore, the viral DNA growth is terminated.

Mechanism of action

Zidovudine, a structural analog of thymidine, is a prodrug that must be phosphorylated to its active 5′-triphosphate metabolite, zidovudine triphosphate (ZDV-TP). It inhibits the activity of HIV-1 reverse transcriptase (RT) via DNA chain termination after incorporation of the nucleotide analogue. It competes with the natural substrate dGTP and incorporates itself into viral DNA. It is also a weak inhibitor of cellular DNA polymerase α and γ.

TargetActionsOrganism
AReverse transcriptase/RNaseH
inhibitor
Human immunodeficiency virus 1
UTelomerase reverse transcriptase
inhibitor
Human
Absorption

Rapid and nearly complete absorption from the gastrointestinal tract following oral administration; however, because of first-pass metabolism, systemic bioavailability of zidovudine capsules and solution is approximately 65% (range, 52 to 75%). Bioavailability in neonates up to 14 days of age is approximately 89%, and it decreases to approximately 61% and 65% in neonates over 14 days of age and children 3 months to 12 years, respectively. Administration with a high-fat meal may decrease the rate and extent of absorption.

Volume of distribution

Apparent volume of distribution, HIV-infected patients, IV administration = 1.6 ± 0.6 L/kg

Protein binding

30-38%

Metabolism

Hepatic. Metabolized by glucuronide conjugation to major, inactive metabolite, 3′-azido-3′-deoxy-5′- O-beta-D-glucopyranuronosylthymidine (GZDV). UGT2B7 is the primary UGT isoform that is responsible for glucuronidation. Compared to zidovudine, GZDV's area under the curve is approximately 3-fold greater. The cytochrome P450 isozymes are responsible for the reduction of the azido moiety to form 3'-amino-3'- deoxythymidine (AMT).

Route of elimination

As in adult patients, the major route of elimination was by metabolism to GZDV. After intravenous dosing, about 29% of the dose was excreted in the urine unchanged and about 45% of the dose was excreted as GZDV.

Half life

Elimination half life, HIV-infected patients, IV administration = 1.1 hours (range of 0.5 - 2.9 hours)

Clearance
  • 0.65 +/- 0.29 L/hr/kg [HIV-infected, Birth to 14 Days of Age]
  • 1.14 +/- 0.24 L/hr/kg [HIV-infected, 14 Days to 3 Months of Age]
  • 1.85 +/- 0.47 L/hr/kg [HIV-infected, 3 Months to 12 Years of Age]. The transporters, ABCB1, ABCC4, ABCC5, and ABCG2 are involved with the clearance of zidovudine.
Toxicity

Symptoms of overdose include fatigue, headache, nausea, and vomiting. LD50 is 3084 mg/kg (orally in mice).

Affected organisms
  • Human Immunodeficiency Virus
Pathways
PathwayCategory
Zidovudine Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Zidovudine.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Zidovudine.
2-MethoxyethanolThe risk or severity of adverse effects can be increased when Zidovudine is combined with 2-Methoxyethanol.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Zidovudine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Zidovudine.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Zidovudine.
6-Deoxyerythronolide BThe metabolism of Zidovudine can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Zidovudine.
7-ethyl-10-hydroxycamptothecinThe metabolism of Zidovudine can be decreased when combined with 7-ethyl-10-hydroxycamptothecin.
9-(N-methyl-L-isoleucine)-cyclosporin AThe risk or severity of adverse effects can be increased when Zidovudine is combined with 9-(N-methyl-L-isoleucine)-cyclosporin A.
Food Interactions
Not Available

References

General References
  1. De Clercq E: HIV resistance to reverse transcriptase inhibitors. Biochem Pharmacol. 1994 Jan 20;47(2):155-69. [PubMed:7508227]
  2. Yarchoan R, Mitsuya H, Broder S: AIDS therapies. Sci Am. 1988 Oct;259(4):110-9. [PubMed:3072667]
  3. Connor EM, Sperling RS, Gelber R, Kiselev P, Scott G, O'Sullivan MJ, VanDyke R, Bey M, Shearer W, Jacobson RL, et al.: Reduction of maternal-infant transmission of human immunodeficiency virus type 1 with zidovudine treatment. Pediatric AIDS Clinical Trials Group Protocol 076 Study Group. N Engl J Med. 1994 Nov 3;331(18):1173-80. [PubMed:7935654]
  4. Mitsuya H, Yarchoan R, Broder S: Molecular targets for AIDS therapy. Science. 1990 Sep 28;249(4976):1533-44. [PubMed:1699273]
  5. Mitsuya H, Weinhold KJ, Furman PA, St Clair MH, Lehrman SN, Gallo RC, Bolognesi D, Barry DW, Broder S: 3'-Azido-3'-deoxythymidine (BW A509U): an antiviral agent that inhibits the infectivity and cytopathic effect of human T-lymphotropic virus type III/lymphadenopathy-associated virus in vitro. Proc Natl Acad Sci U S A. 1985 Oct;82(20):7096-100. [PubMed:2413459]
  6. Court MH, Krishnaswamy S, Hao Q, Duan SX, Patten CJ, Von Moltke LL, Greenblatt DJ: Evaluation of 3'-azido-3'-deoxythymidine, morphine, and codeine as probe substrates for UDP-glucuronosyltransferase 2B7 (UGT2B7) in human liver microsomes: specificity and influence of the UGT2B7*2 polymorphism. Drug Metab Dispos. 2003 Sep;31(9):1125-33. [PubMed:12920168]
External Links
Human Metabolome Database
HMDB0014638
KEGG Drug
D00413
KEGG Compound
C07210
PubChem Compound
35370
PubChem Substance
46508240
ChemSpider
32555
BindingDB
50002692
ChEBI
10110
ChEMBL
CHEMBL129
Therapeutic Targets Database
DAP000701
PharmGKB
PA451954
HET
AZZ
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Zidovudine
ATC Codes
J05AR01 — Zidovudine and lamivudineJ05AR05 — Zidovudine, lamivudine and nevirapineJ05AF01 — ZidovudineJ05AR04 — Zidovudine, lamivudine and abacavir
AHFS Codes
  • 08:18.08.20 — Nucleoside and Nucleotide Reverse Transcriptase Inhibitors
PDB Entries
2jj8 / 3b9l / 3b9m / 3bcr / 4lhm
FDA label
Download (217 KB)
MSDS
Download (57.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Plasmodium Infections1
1CompletedNot AvailableInfection, Human Immunodeficiency Virus I1
1CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
1CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections / Pregnancy1
1CompletedTreatmentAIDS-Related Dementia Complex / Human Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentCytopenias / Human Immunodeficiency Virus (HIV) Infections2
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentHemophilia A / Human Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV)2
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections43
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infections, Cytomegalovirus1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Kaposi s Sarcoma (KS)6
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Pregnancy6
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Toxoplasmosis, Cerebral1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
1Enrolling by InvitationTreatmentAmyotrophic Lateral Sclerosis (ALS)1
1RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
1Unknown StatusTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV)1
1WithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections / Kidney Diseases1
1, 2CompletedTreatmentHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV)1
1, 2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
2Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2CompletedPreventionHIV Prevention / HIV Transmission / Human Immunodeficiency Virus (HIV) Infections1
2CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections2
2CompletedTreatmentAIDS-Related Dementia Complex / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentEncephalopathies / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentEpstein Barr Virus Associated Hodgkin's Lymphoma / Epstein Barr Virus Associated Non Hodgkin's Lymphoma / Post-transplant Lymphoproliferative Disease (PTLD)1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections63
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Kaposi s Sarcoma (KS)1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Lipodystrophies1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Progressive Multifocal Leukoencephalopathy1
2CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)1
2CompletedTreatmentInfection, Human Immunodeficiency Virus I2
2CompletedTreatmentMalignant Lymphomas4
2RecruitingTreatmentAdult T-cell lymphomas/leukaemias1
2RecruitingTreatmentCastleman's Disease / Giant Lymph Node Hyperplasia1
2RecruitingTreatmentHHV-8 / Human Immunodeficiency Virus (HIV) / Lymphoproliferative Disorders / Malignancies1
2RecruitingTreatmentHHV-8 / KSHV / KSHV Inflammatory Cytokine Syndrome (KICS)1
2RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2RecruitingTreatmentMetastatic Colorectal Cancers1
2SuspendedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
2TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
2TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Human Immunodeficiency Virus I1
2Unknown StatusPreventionHuman Immunodeficiency Virus (HIV) Infections1
2Unknown StatusPreventionHuman Immunodeficiency Virus (HIV) / Viral Hepatitis B1
2Unknown StatusTreatmentMalignant Lymphomas2
2WithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2, 3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
2, 3CompletedTreatmentKaposi's Sarcoma AIDS Related1
2, 3CompletedTreatmentPrimary Biliary Cholangitis1
2, 3CompletedTreatmentTropical Spastic Paraparesis1
2, 3RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Pediatric AIDS1
2, 3Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) / Zidovudine Adverse Reaction1
3Active Not RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
3Active Not RecruitingTreatmentAcute HIV Infection1
3CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
3CompletedPreventionAcquired Immune Deficiency Syndrome (AIDS)1
3CompletedPreventionDisease Transmission, Vertical / Human Immunodeficiency Virus (HIV) Infections / Vertical Human Immunodeficiency Virus Transmission1
3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections6
3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections / Plasmodium Infections1
3CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / AIDS-Related Complex1
3CompletedTreatmentAIDS-Related Dementia Complex / Human Immunodeficiency Virus (HIV) Infections2
3CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections45
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Pneumonia, Pneumocystis Carinii2
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Pregnancy3
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
3CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)1
3CompletedTreatmentInfection, Human Immunodeficiency Virus I1
3TerminatedPreventionHuman Immunodeficiency Virus (HIV) Infections / Pregnancy1
3TerminatedPreventionSevere or persistent diarrhea1
3TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections2
4Active Not RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
4Active Not RecruitingPreventionInfection, Human Immunodeficiency Virus I1
4CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
4CompletedNot AvailableHuman Immunodeficiency Virus (HIV) / Proteinuria1
4CompletedBasic ScienceCardiovascular Disease (CVD) / Dyslipidemias / Glucose Metabolism Disorders / Human Immunodeficiency Virus (HIV) Infections / Lipodystrophies / Metabolic Diseases1
4CompletedDiagnosticCardiovascular Disease (CVD) / HIV-Associated Lipodystrophy Syndrome1
4CompletedOtherHuman Immunodeficiency Virus (HIV)1
4CompletedPreventionCentral Nervous System Diseases / Dementias / Human Immunodeficiency Virus (HIV) Infections1
4CompletedPreventionHuman Immunodeficiency Virus (HIV)1
4CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections2
4CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS)1
4CompletedTreatmentHIV test positive / Malnourished1
4CompletedTreatmentHemophilia A / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV)3
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections8
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Human Immunodeficiency Virus I1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Lipodystrophies1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Viral Hepatitis B1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Mitochondrial Toxicity1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Tuberculosis Infection1
4CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)1
4CompletedTreatmentInfection, Human Immunodeficiency Virus I1
4RecruitingPreventionDiabetes Mellitus (DM) / Human Immunodeficiency Virus (HIV) / Insulin Sensitivity1
4RecruitingPreventionHIV/AIDS and Infections1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
4TerminatedTreatmentMalignant Lymphomas / Precancerous/Nonmalignant Condition1
4Unknown StatusPreventionHIV-Associated Lipodystrophy Syndrome / Human Immunodeficiency Virus (HIV) Infections1
4Unknown StatusTreatmentAcquired Immune Deficiency Syndrome (AIDS)1
4Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV)1
4Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections2
Not AvailableCompletedNot AvailableHealthy Volunteers2
Not AvailableCompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedNot AvailableHuman Immunodeficiency Virus (HIV) / Kwashiorkor / Marasmus / Severe Acute Malnutrition1
Not AvailableCompletedNot AvailableInfection, Human Immunodeficiency Virus I1
Not AvailableCompletedPreventionHuman Immunodeficiency Virus (HIV)1
Not AvailableCompletedPreventionHuman Immunodeficiency Virus (HIV) Infections3
Not AvailableCompletedTreatmentAIDS-Related Dementia Complex / Human Immunodeficiency Virus (HIV) Infections / Neuromuscular Diseases1
Not AvailableCompletedTreatmentChronic Renal Failure (CRF) / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentCytomegalovirus Retinitis / Human Immunodeficiency Virus (HIV) Infections3
Not AvailableCompletedTreatmentCytopenias / Human Immunodeficiency Virus (HIV) Infections3
Not AvailableCompletedTreatmentHemophilia A / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections62
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infections, Cytomegalovirus1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Liver Diseases1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Lymphatic Diseases1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Non-Hodgkin's Lymphoma (NHL)2
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Pneumonia, Pneumocystis Carinii1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Progressive Multifocal Leukoencephalopathy1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Psoriasis1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
Not AvailableRecruitingNot AvailableAutoimmune Diseases / Neurological Disorders1
Not AvailableRecruitingNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableTerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableTerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Non-Hodgkin's Lymphoma (NHL)1
Not AvailableUnknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculous Meningitis1

Pharmacoeconomics

Manufacturers
  • Viiv healthcare co
  • Aurobindo pharma ltd inc
  • Cipla ltd
  • Pharmaforce inc
  • Aurobindo pharma ltd
  • Hetero drugs ltd unit iii
  • Matrix laboratories ltd
  • Ranbaxy laboratories ltd
  • Roxane laboratories inc
Packagers
  • Amerisource Health Services Corp.
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Aurobindo Pharma Ltd.
  • Aurolife Pharma LLC
  • Camber Pharmaceuticals Inc.
  • Cardinal Health
  • Cipla Ltd.
  • DAVA Pharmaceuticals
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • GlaxoSmithKline Inc.
  • Greenstone LLC
  • H.J. Harkins Co. Inc.
  • Hetero Drugs Ltd.
  • Lake Erie Medical and Surgical Supply
  • Matrix Laboratories Ltd.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Neuman Distributors Inc.
  • Nucare Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Physicians Total Care Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Ranbaxy Laboratories
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Remedy Repack
  • Roxane Labs
  • Sandhills Packaging Inc.
  • Southwood Pharmaceuticals
  • St Mary's Medical Park Pharmacy
  • Stat Rx Usa
  • Tya Pharmaceuticals
  • ViiV Healthcare ULC
Dosage forms
FormRouteStrength
TabletOral
Tablet, coatedOral
Tablet, film coatedOral
CapsuleOral100 mg/1
Injection, solutionIntravenous10 mg/1mL
SyrupOral10 mg/1mL
SyrupOral50 mg/5mL
Tablet, film coatedOral300 mg/1
CapsuleOral100 mg
LiquidIntravenous10 mg
SyrupOral50 mg
TabletOral300 mg
SolutionOral50 mg/5mL
TabletOral300 mg/1
Prices
Unit descriptionCostUnit
Retrovir 50 mg/5ml Syrup 240ml Bottle74.11USD bottle
Retrovir 300 mg tablet9.1USD tablet
Zidovudine 300 mg tablet6.17USD tablet
Retrovir 100 mg capsule3.09USD capsule
Retrovir iv infusion vial1.61USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2216634No2004-07-202016-03-28Canada
CA2105487No2002-09-242012-03-05Canada
US5905082Yes1999-05-182016-11-18Us
US6294540Yes2001-09-252018-11-14Us
US6417191Yes2002-07-092016-09-28Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)113-115 °CPhysProp
water solubility2.01E+004 mg/L (at 25 °C)PHYSICIANS DESK REFERENCE (2003)
logP0.05HANSCH,C ET AL. (1995)
Caco2 permeability-5.16ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility16.3 mg/mLALOGPS
logP-0.1ALOGPS
logP-0.3ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)9.96ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area108.3 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity61.7 m3·mol-1ChemAxon
Polarizability24.93 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9343
Blood Brain Barrier+0.6224
Caco-2 permeable-0.8728
P-glycoprotein substrateNon-substrate0.6959
P-glycoprotein inhibitor INon-inhibitor0.9118
P-glycoprotein inhibitor IINon-inhibitor0.8981
Renal organic cation transporterNon-inhibitor0.8798
CYP450 2C9 substrateNon-substrate0.663
CYP450 2D6 substrateNon-substrate0.8987
CYP450 3A4 substrateSubstrate0.5329
CYP450 1A2 substrateNon-inhibitor0.9355
CYP450 2C9 inhibitorNon-inhibitor0.9143
CYP450 2D6 inhibitorNon-inhibitor0.9315
CYP450 2C19 inhibitorNon-inhibitor0.9175
CYP450 3A4 inhibitorNon-inhibitor0.848
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9585
Ames testAMES toxic0.9107
CarcinogenicityNon-carcinogens0.7484
BiodegradationReady biodegradable0.5673
Rat acute toxicity2.0464 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7124
hERG inhibition (predictor II)Non-inhibitor0.8821
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00di-0190000000-46ee7eb3034a9b20706d
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00di-0790000000-19916045eff2f2277d60
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0fk9-0900000000-836aff54cb90ce573db4
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00di-0900000000-cb1ef888d872056bce56
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00di-0900000000-97660ea43493fa2fa991
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-05fr-0900000000-407e81a32dbf5eb07134
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004i-0900000000-743290b40f399a527da5
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004i-0900000000-667b9ae1f4c499b8cef6
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004i-0900000000-c6bf89700e58ad9aff83
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004i-1900000000-b644d0eec4449bae7675
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-01t9-2900000000-d794028d708aa5c5d04f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03gi-5900000000-b2b0a6ddec7e2e91e8c4
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as pyrimidine 2',3'-dideoxyribonucleosides. These are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at positions 2 and 3.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Pyrimidine nucleosides
Sub Class
Pyrimidine 2',3'-dideoxyribonucleosides
Direct Parent
Pyrimidine 2',3'-dideoxyribonucleosides
Alternative Parents
Pyrimidones / Hydroxypyrimidines / Hydropyrimidines / Tetrahydrofurans / Heteroaromatic compounds / Azo imides / Azo compounds / Oxacyclic compounds / Azacyclic compounds / Primary alcohols
show 4 more
Substituents
Pyrimidine 2',3'-dideoxyribonucleoside / Pyrimidone / Hydroxypyrimidine / Hydropyrimidine / Pyrimidine / Tetrahydrofuran / Heteroaromatic compound / Azo imide / Azo compound / Oxacycle
show 13 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
azide, pyrimidine 2',3'-dideoxyribonucleoside (CHEBI:10110)

Targets

Kind
Protein
Organism
Human immunodeficiency virus 1
Pharmacological action
Yes
Actions
Inhibitor
General Function
Rna-dna hybrid ribonuclease activity
Specific Function
Not Available
Gene Name
pol
Uniprot ID
Q72547
Uniprot Name
Reverse transcriptase/RNaseH
Molecular Weight
65223.615 Da
References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  2. Barry M, Gibbons S, Back D, Mulcahy F: Protease inhibitors in patients with HIV disease. Clinically important pharmacokinetic considerations. Clin Pharmacokinet. 1997 Mar;32(3):194-209. [PubMed:9084959]
  3. De Clercq E: Antiretroviral drugs. Curr Opin Pharmacol. 2010 Oct;10(5):507-15. doi: 10.1016/j.coph.2010.04.011. Epub 2010 May 12. [PubMed:20471318]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Trna binding
Specific Function
Telomerase is a ribonucleoprotein enzyme essential for the replication of chromosome termini in most eukaryotes. Active in progenitor and cancer cells. Inactive, or very low activity, in normal som...
Gene Name
TERT
Uniprot ID
O14746
Uniprot Name
Telomerase reverse transcriptase
Molecular Weight
126995.435 Da
References
  1. Leeansyah E, Cameron PU, Solomon A, Tennakoon S, Velayudham P, Gouillou M, Spelman T, Hearps A, Fairley C, Smit de V, Pierce AB, Armishaw J, Crowe SM, Cooper DA, Koelsch KK, Liu JP, Chuah J, Lewin SR: Inhibition of telomerase activity by human immunodeficiency virus (HIV) nucleos(t)ide reverse transcriptase inhibitors: a potential factor contributing to HIV-associated accelerated aging. J Infect Dis. 2013 Apr;207(7):1157-65. doi: 10.1093/infdis/jit006. Epub 2013 Jan 9. [PubMed:23303810]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Veal GJ, Back DJ: Metabolism of Zidovudine. Gen Pharmacol. 1995 Nov;26(7):1469-75. [PubMed:8690233]
  3. PharmGKB: Zidovudine Pathway, Pharmacokinetics/Pharmacodynamics Overview [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Zinc ion binding
Specific Function
Not Available
Gene Name
TK1
Uniprot ID
P04183
Uniprot Name
Thymidine kinase, cytosolic
Molecular Weight
25468.455 Da
References
  1. Furman PA, Fyfe JA, St Clair MH, Weinhold K, Rideout JL, Freeman GA, Lehrman SN, Bolognesi DP, Broder S, Mitsuya H, et al.: Phosphorylation of 3'-azido-3'-deoxythymidine and selective interaction of the 5'-triphosphate with human immunodeficiency virus reverse transcriptase. Proc Natl Acad Sci U S A. 1986 Nov;83(21):8333-7. [PubMed:2430286]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Glucuronosyltransferase activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
Gene Name
UGT2B7
Uniprot ID
P16662
Uniprot Name
UDP-glucuronosyltransferase 2B7
Molecular Weight
60694.12 Da
References
  1. Court MH, Krishnaswamy S, Hao Q, Duan SX, Patten CJ, Von Moltke LL, Greenblatt DJ: Evaluation of 3'-azido-3'-deoxythymidine, morphine, and codeine as probe substrates for UDP-glucuronosyltransferase 2B7 (UGT2B7) in human liver microsomes: specificity and influence of the UGT2B7*2 polymorphism. Drug Metab Dispos. 2003 Sep;31(9):1125-33. [PubMed:12920168]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
Inducer
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
References
  1. Williams JA, Hyland R, Jones BC, Smith DA, Hurst S, Goosen TC, Peterkin V, Koup JR, Ball SE: Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8. doi: 10.1124/dmd.104.000794. Epub 2004 Aug 10. [PubMed:15304429]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
No
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Quevedo MA, Moroni GN, Brinon MC: Human serum albumin binding of novel antiretroviral nucleoside derivatives of AZT. Biochem Biophys Res Commun. 2001 Nov 9;288(4):954-60. [PubMed:11689002]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. Urakami Y, Akazawa M, Saito H, Okuda M, Inui K: cDNA cloning, functional characterization, and tissue distribution of an alternatively spliced variant of organic cation transporter hOCT2 predominantly expressed in the human kidney. J Am Soc Nephrol. 2002 Jul;13(7):1703-10. [PubMed:12089365]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Worner P, Brossmer R: Platelet aggregation and the release induced by inophores for divalent cations. Thromb Res. 1975 Apr;6(4):295-305. [PubMed:1094583]
  2. Takeda M, Khamdang S, Narikawa S, Kimura H, Kobayashi Y, Yamamoto T, Cha SH, Sekine T, Endou H: Human organic anion transporters and human organic cation transporters mediate renal antiviral transport. J Pharmacol Exp Ther. 2002 Mar;300(3):918-24. [PubMed:11861798]
  3. VanWert AL, Gionfriddo MR, Sweet DH: Organic anion transporters: discovery, pharmacology, regulation and roles in pathophysiology. Biopharm Drug Dispos. 2010 Jan;31(1):1-71. doi: 10.1002/bdd.693. [PubMed:19953504]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulf...
Gene Name
SLC22A7
Uniprot ID
Q9Y694
Uniprot Name
Solute carrier family 22 member 7
Molecular Weight
60025.025 Da
References
  1. Takeda M, Khamdang S, Narikawa S, Kimura H, Kobayashi Y, Yamamoto T, Cha SH, Sekine T, Endou H: Human organic anion transporters and human organic cation transporters mediate renal antiviral transport. J Pharmacol Exp Ther. 2002 Mar;300(3):918-24. [PubMed:11861798]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Takeda M, Khamdang S, Narikawa S, Kimura H, Kobayashi Y, Yamamoto T, Cha SH, Sekine T, Endou H: Human organic anion transporters and human organic cation transporters mediate renal antiviral transport. J Pharmacol Exp Ther. 2002 Mar;300(3):918-24. [PubMed:11861798]
  2. VanWert AL, Gionfriddo MR, Sweet DH: Organic anion transporters: discovery, pharmacology, regulation and roles in pathophysiology. Biopharm Drug Dispos. 2010 Jan;31(1):1-71. doi: 10.1002/bdd.693. [PubMed:19953504]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
Gene Name
SLC22A11
Uniprot ID
Q9NSA0
Uniprot Name
Solute carrier family 22 member 11
Molecular Weight
59970.945 Da
References
  1. Takeda M, Khamdang S, Narikawa S, Kimura H, Kobayashi Y, Yamamoto T, Cha SH, Sekine T, Endou H: Human organic anion transporters and human organic cation transporters mediate renal antiviral transport. J Pharmacol Exp Ther. 2002 Mar;300(3):918-24. [PubMed:11861798]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Pyrimidine- and adenine-specific:sodium symporter activity
Specific Function
Sodium-dependent and pyrimidine-selective. Exhibits the transport characteristics of the nucleoside transport system cit or N2 subtype (N2/cit) (selective for pyrimidine nucleosides and adenosine)....
Gene Name
SLC28A1
Uniprot ID
O00337
Uniprot Name
Sodium/nucleoside cotransporter 1
Molecular Weight
71583.18 Da
References
  1. Cano-Soldado P, Lorrayoz IM, Molina-Arcas M, Casado FJ, Martinez-Picado J, Lostao MP, Pastor-Anglada M: Interaction of nucleoside inhibitors of HIV-1 reverse transcriptase with the concentrative nucleoside transporter-1 (SLC28A1). Antivir Ther. 2004 Dec;9(6):993-1002. [PubMed:15651758]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Nucleoside transmembrane transporter activity
Specific Function
Mediates equilibrative transport of purine, pyrimidine nucleosides and the purine base hypoxanthine. Very less sensitive than SLC29A1 to inhibition by nitrobenzylthioinosine (NBMPR), dipyridamole, ...
Gene Name
SLC29A2
Uniprot ID
Q14542
Uniprot Name
Equilibrative nucleoside transporter 2
Molecular Weight
50112.335 Da
References
  1. Yao SY, Ng AM, Sundaram M, Cass CE, Baldwin SA, Young JD: Transport of antiviral 3'-deoxy-nucleoside drugs by recombinant human and rat equilibrative, nitrobenzylthioinosine (NBMPR)-insensitive (ENT2) nucleoside transporter proteins produced in Xenopus oocytes. Mol Membr Biol. 2001 Apr-Jun;18(2):161-7. [PubMed:11463208]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Anderson PL, Lamba J, Aquilante CL, Schuetz E, Fletcher CV: Pharmacogenetic characteristics of indinavir, zidovudine, and lamivudine therapy in HIV-infected adults: a pilot study. J Acquir Immune Defic Syndr. 2006 Aug 1;42(4):441-9. [PubMed:16791115]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Atpase activity, coupled to transmembrane movement of substances
Specific Function
May be an organic anion pump relevant to cellular detoxification.
Gene Name
ABCC4
Uniprot ID
O15439
Uniprot Name
Multidrug resistance-associated protein 4
Molecular Weight
149525.33 Da
References
  1. Abla N, Chinn LW, Nakamura T, Liu L, Huang CC, Johns SJ, Kawamoto M, Stryke D, Taylor TR, Ferrin TE, Giacomini KM, Kroetz DL: The human multidrug resistance protein 4 (MRP4, ABCC4): functional analysis of a highly polymorphic gene. J Pharmacol Exp Ther. 2008 Jun;325(3):859-68. doi: 10.1124/jpet.108.136523. Epub 2008 Mar 25. [PubMed:18364470]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Organic anion transmembrane transporter activity
Specific Function
Acts as a multispecific organic anion pump which can transport nucleotide analogs.
Gene Name
ABCC5
Uniprot ID
O15440
Uniprot Name
Multidrug resistance-associated protein 5
Molecular Weight
160658.8 Da
References
  1. Jorajuria S, Dereuddre-Bosquet N, Becher F, Martin S, Porcheray F, Garrigues A, Mabondzo A, Benech H, Grassi J, Orlowski S, Dormont D, Clayette P: ATP binding cassette multidrug transporters limit the anti-HIV activity of zidovudine and indinavir in infected human macrophages. Antivir Ther. 2004 Aug;9(4):519-28. [PubMed:15456083]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Pan G, Giri N, Elmquist WF: Abcg2/Bcrp1 mediates the polarized transport of antiretroviral nucleosides abacavir and zidovudine. Drug Metab Dispos. 2007 Jul;35(7):1165-73. Epub 2007 Apr 16. [PubMed:17437964]

Drug created on June 13, 2005 07:24 / Updated on December 18, 2018 09:08