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Identification
NameZidovudine
Accession NumberDB00495  (APRD00449)
TypeSmall Molecule
GroupsApproved
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A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group.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
Zidovudin
Zidovudinum
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Novo-azt Cap 100mgcapsule100 mgoralNovopharm Limited1992-12-312015-10-26Canada
Retrovircapsule100 mg/1oralVii V Healthcare Company2010-10-282016-04-05Us
Retrovirinjection, solution10 mg/mLintravenousVii V Healthcare Company2010-11-042016-04-05Us
Retrovirsyrup10 mg/mLoralVii V Healthcare Company2010-10-282016-04-05Us
Retrovir (azt)syrup50 mgoralViiv Healthcare Ulc1991-12-31Not applicableCanada
Retrovir (azt)liquid10 mgintravenousViiv Healthcare Ulc1991-12-31Not applicableCanada
Retrovir (azt)capsule100 mgoralViiv Healthcare Ulc1990-12-31Not applicableCanada
Retrovir (azt) 300mgtablet300 mgoralGlaxo Wellcome Inc.1998-09-232000-11-30Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-zidovudinecapsule100 mgoralApotex Inc1992-12-31Not applicableCanada
Lamivudine and Zidovudinetablet, film coated150 mg/1oralREMEDYREPACK INC.2013-04-112016-04-05Us
Zidovudinesolution50 mg/5mLoralBoca Pharmacal, LLC2012-08-172016-04-05Us
Zidovudinecapsule100 mg/1oralBoca Pharmacal, LLC2012-08-172016-04-05Us
Zidovudinetablet, film coated300 mg/1oralREMEDYREPACK INC.2013-04-152016-04-05Us
Zidovudinetablet300 mg/1oralRoxane Laboratories, Inc2005-09-192016-04-23Us
Zidovudinetablet, film coated300 mg/1oralbryant ranch prepack2005-09-192016-04-05Us
Zidovudinetablet300 mg/1oralREMEDYREPACK INC.2013-05-092016-04-05Us
Zidovudinetablet, film coated300 mg/1oralLucid Pharma Llc2005-09-192016-04-05Us
Zidovudinetablet, film coated300 mg/1oralREMEDYREPACK INC.2015-05-192016-04-05Us
Zidovudinesyrup50 mg/5mLoralEdenbridge Pharmaceuticals, LLC2012-04-012016-04-05Us
Zidovudinetablet, film coated300 mg/1oralState of Florida DOH Central Pharmacy2013-01-012016-04-05Us
Zidovudinecapsule100 mg/1oralEdenbridge Pharmaceuticals, LLC2012-04-012016-04-05Us
Zidovudinetablet, film coated300 mg/1oralAmerican Health Packaging2011-01-032016-04-05Us
Zidovudinesyrup50 mg/5mLoralCipla Ltd.2008-06-262016-04-05Us
Zidovudinetablet300 mg/1oralCamber Pharmaceuticals2011-01-012016-04-05Us
Zidovudinecapsule100 mg/1oralAmerican Health Packaging2013-07-052016-04-05Us
Zidovudinetablet, film coated300 mg/1oralCipla Limited2010-10-272016-04-05Us
Zidovudinetablet, film coated300 mg/1oralRebel Distributors Corp2009-07-012016-04-05Us
Zidovudinecapsule100 mg/1oralAurobindo Pharma Limited2006-03-272016-04-05Us
Zidovudinesyrup10 mg/mLoralAurobindo Pharma Limited2005-09-192016-04-05Us
Zidovudinecapsule100 mg/1oralCipla Ltd.2007-05-232016-04-05Us
Zidovudinetablet, film coated300 mg/1oralLannett Company, Inc.2014-03-252016-04-23Us
Zidovudinetablet, film coated300 mg/1oralAurobindo Pharma Limited2005-09-192016-04-05Us
Zidovudinecapsule100 mg/1oralGen Source Rx2006-03-272016-04-05Us
Zidovudinetablet, film coated300 mg/1oralMylan Pharmaceuticals Inc.2008-12-192016-04-23Us
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
Abacavir Sulfate, Lamivudine and ZidovudineLupin Pharmaceuticals, Inc.
Apo-abacavir-lamivudine-zidovudineApotex Inc
Apo-lamivudine-zidovudineApotex Inc
Auro-lamivudine/zidovudineAuro Pharma Inc
CombivirStat Rx USA
Direct RxDIRECT RX
Lamivudine and ZidovudineTeva Pharmaceuticals USA Inc
Teva-lamivudine/zidovudineTeva Canada Limited
TrizivirVii V Healthcare Company
SaltsNot Available
Categories
UNII4B9XT59T7S
CAS number30516-87-1
WeightAverage: 267.2413
Monoisotopic: 267.096753929
Chemical FormulaC10H13N5O4
InChI KeyInChIKey=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([[email protected]]2C[[email protected]](N=[N+]=[N-])[C@@H](CO)O2)C(=O)NC1=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyrimidine nucleosides. These are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleosides
Sub ClassNot Available
Direct ParentPyrimidine nucleosides
Alternative Parents
Substituents
  • Pyrimidine nucleoside
  • Pyrimidone
  • Pyrimidine
  • Hydropyrimidine
  • Saccharide
  • Heteroaromatic compound
  • Vinylogous amide
  • Oxolane
  • Urea
  • Lactam
  • Azo imide
  • Azo compound
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic salt
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic zwitterion
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationUsed in combination with other antiretroviral agents for the treatment of human immunovirus (HIV) infections.
PharmacodynamicsZidovudine 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 actionZidovudine, 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.
Related Articles
AbsorptionRapid 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 binding30-38%
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).

SubstrateEnzymesProduct
Zidovudine
Not Available
3'-azido-3'-deoxy-5'- O-beta-D-glucopyranuronosylthymidineDetails
Zidovudine
Not Available
3’-amino-3’-deoxythimidineDetails
Zidovudine
Not Available
3’-amino-3’-deoxythimidine glucuronideDetails
Zidovudine
Not Available
5’glucuronyl zidovudineDetails
Route of eliminationAs 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 lifeElimination 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.
ToxicitySymptoms of overdose include fatigue, headache, nausea, and vomiting. LD50 is 3084 mg/kg (orally in mice).
Affected organisms
  • Human Immunodeficiency Virus
Pathways
PathwayCategorySMPDB ID
Zidovudine Action PathwayDrug actionSMP00747
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
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
Dosage forms
FormRouteStrength
Tabletoral
Tablet, film coatedoral
Tablet, film coatedoral150 mg/1
Injection, solutionintravenous10 mg/mL
Syruporal10 mg/mL
Capsuleoral100 mg
Liquidintravenous10 mg
Syruporal50 mg
Tabletoral300 mg
Capsuleoral100 mg/1
Solutionoral50 mg/5mL
Syruporal50 mg/5mL
Tabletoral300 mg/1
Tablet, film coatedoral300 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)
CA2105487 No2002-09-242012-03-05Canada
CA2216634 No2004-07-202016-03-28Canada
US5905082 Yes1996-11-182016-11-18Us
US6294540 Yes1998-11-142018-11-14Us
US6417191 Yes1996-09-282016-09-28Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point113-115 °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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
References
Synthesis ReferenceNot Available
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
ATC CodesJ05AF01J05AR01J05AR04J05AR05
AHFS Codes
  • 08:18.08.20
PDB EntriesNot Available
FDA labelDownload (217 KB)
MSDSDownload (57.2 KB)
Interactions
Drug Interactions
Drug
AciclovirAciclovir may increase the central nervous system depressant (CNS depressant) activities of Zidovudine.
AmodiaquineZidovudine may increase the neutropenic activities of Amodiaquine.
AtazanavirThe serum concentration of Zidovudine can be decreased when it is combined with Atazanavir.
BatimastatThe serum concentration of Zidovudine can be decreased when it is combined with Batimastat.
ClarithromycinClarithromycin may increase the myelosuppressive activities of Zidovudine.
ClozapineThe risk or severity of adverse effects can be increased when Zidovudine is combined with Clozapine.
DarunavirThe serum concentration of Zidovudine can be decreased when it is combined with Darunavir.
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Zidovudine.
DoxorubicinThe risk or severity of adverse effects can be increased when Doxorubicin is combined with Zidovudine.
FluconazoleThe metabolism of Zidovudine can be decreased when combined with Fluconazole.
FosamprenavirThe serum concentration of Zidovudine can be decreased when it is combined with Fosamprenavir.
GanciclovirThe risk or severity of adverse effects can be increased when Ganciclovir is combined with Zidovudine.
IndinavirThe serum concentration of Zidovudine can be decreased when it is combined with Indinavir.
Interferon alfa-n3The risk or severity of adverse effects can be increased when Interferon alfa-n3 is combined with Zidovudine.
Interferon alfacon-1The risk or severity of adverse effects can be increased when Interferon alfacon-1 is combined with Zidovudine.
Interferon beta-1aThe risk or severity of adverse effects can be increased when Interferon beta-1a is combined with Zidovudine.
Interferon beta-1bThe risk or severity of adverse effects can be increased when Interferon beta-1b is combined with Zidovudine.
Interferon gamma-1bThe risk or severity of adverse effects can be increased when Interferon gamma-1b is combined with Zidovudine.
IsoflurophateThe serum concentration of Zidovudine can be decreased when it is combined with Isoflurophate.
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Zidovudine.
MethadoneThe serum concentration of Zidovudine can be increased when it is combined with Methadone.
NelfinavirThe serum concentration of Zidovudine can be decreased when it is combined with Nelfinavir.
Peginterferon alfa-2aThe risk or severity of adverse effects can be increased when Peginterferon alfa-2a is combined with Zidovudine.
Peginterferon alfa-2bThe risk or severity of adverse effects can be increased when Peginterferon alfa-2b is combined with Zidovudine.
Peginterferon beta-1aThe risk or severity of adverse effects can be increased when Peginterferon beta-1a is combined with Zidovudine.
ProbenecidThe metabolism of Zidovudine can be decreased when combined with Probenecid.
RaltegravirRaltegravir may increase the myopathic rhabdomyolysis activities of Zidovudine.
RibavirinThe risk or severity of adverse effects can be increased when Zidovudine is combined with Ribavirin.
RifampicinThe serum concentration of Zidovudine can be decreased when it is combined with Rifampicin.
RifapentineThe serum concentration of Zidovudine can be decreased when it is combined with Rifapentine.
RitonavirThe serum concentration of Zidovudine can be decreased when it is combined with Ritonavir.
SaquinavirThe serum concentration of Zidovudine can be decreased when it is combined with Saquinavir.
SimeprevirThe serum concentration of Zidovudine can be decreased when it is combined with Simeprevir.
StavudineThe therapeutic efficacy of Stavudine can be decreased when used in combination with Zidovudine.
TeriflunomideThe serum concentration of Zidovudine can be increased when it is combined with Teriflunomide.
TipranavirThe serum concentration of Zidovudine can be decreased when it is combined with Tipranavir.
ValaciclovirValaciclovir may increase the central nervous system depressant (CNS depressant) activities of Zidovudine.
Valproic AcidThe serum concentration of Zidovudine can be increased when it is combined with Valproic Acid.
Food InteractionsNot Available

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
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 somatic cells. Catalytic component of the teleromerase holoenzyme complex whose main activity is the elongation of telomeres by acting as a reverse transcriptase that adds simple sequence repeats to chro...
Gene Name:
TERT
Uniprot ID:
O14746
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. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
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:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 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. 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. Authors unspecified: Letter: Exercise testing and coronary heart disease. N Engl J Med. 1975 Dec 4;293(23):1208-10. [PubMed:1186798 ]
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
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 ]
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Zinc ion binding
Specific Function:
Not Available
Gene Name:
TK1
Uniprot ID:
P04183
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 suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol...
Gene Name:
UGT2B7
Uniprot ID:
P16662
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 ]

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 colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
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, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridiniu...
Gene Name:
SLC22A2
Uniprot ID:
O15244
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
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 molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
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 ]
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 sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha-ketoglutarate.
Gene Name:
SLC22A7
Uniprot ID:
Q9Y694
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
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, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
Gene Name:
SLC22A8
Uniprot ID:
Q8TCC7
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 ]
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
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). It also transports the antiviral pyrimidine nucleoside analogs 3'-azido-3'-deoxythymidine (AZT) and 2',3'-dideoxycytidine (ddC). It may be involved in the intestinal absorption and renal handling of ...
Gene Name:
SLC28A1
Uniprot ID:
O00337
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, dilazep and draflazine.
Gene Name:
SLC29A2
Uniprot ID:
Q14542
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
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
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
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 from mitochondria to cytosol and from cytosol to extracellular space, and cellular export of hemin, and heme. Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from t...
Gene Name:
ABCG2
Uniprot ID:
Q9UNQ0
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 ]
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Drug created on June 13, 2005 07:24 / Updated on April 29, 2016 03:10