zidovudine indications/contra

Stem definitionDrug idCAS RN
uridine derivatives used as antiviral agents and as antineoplastics 2861 30516-87-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • zidovudine
  • azidothymidine
  • azitidin
  • AZT
A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group.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.
  • Molecular weight: 267.25
  • Formula: C10H13N5O4
  • CLOGP: 0.04
  • LIPINSKI: 0
  • HAC: 9
  • HDO: 2
  • TPSA: 108.30
  • ALOGS: -1.21
  • ROTB: 3

Drug dosage:

DoseUnitRoute
0.60 g O
0.60 g P

Approvals:

DateAgencyCompanyOrphan
March 19, 1987 FDA VIIV HLTHCARE

FDA Adverse Event Reporting System

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MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Exposure during pregnancy 6476.35 49.54 1526 5925 26037 3352371
Foetal exposure during pregnancy 4587.73 49.54 1043 6408 14508 3363900
Premature baby 1967.96 49.54 458 6993 6795 3371613
Virologic failure 1440.46 49.54 266 7185 1088 3377320
Anaemia 1317.99 49.54 534 6917 53799 3324609
Stillbirth 1281.70 49.54 247 7204 1328 3377080
Immune reconstitution inflammatory syndrome 1280.65 49.54 263 7188 2050 3376358
Drug resistance 1169.95 49.54 277 7174 4386 3374022
Abortion spontaneous 1113.89 49.54 316 7135 10469 3367939
Maternal drugs affecting foetus 704.95 49.54 177 7274 3594 3374814
Lipodystrophy acquired 700.18 49.54 125 7326 398 3378010
HIV infection 667.97 49.54 118 7333 347 3378061
Caesarean section 620.39 49.54 166 7285 4360 3374048
Pregnancy 618.61 49.54 187 7264 7693 3370715
Maternal exposure during pregnancy 549.68 49.54 182 7269 10089 3368319
Premature delivery 545.60 49.54 133 7318 2372 3376036
Abortion induced 513.36 49.54 137 7314 3554 3374854
Live birth 489.41 49.54 102 7349 851 3377557
Maternal exposure during breast feeding 459.43 49.54 102 7349 1178 3377230
Foetal death 439.25 49.54 107 7344 1899 3376509
Hypertriglyceridaemia 435.61 49.54 103 7348 1601 3376807
Treatment failure 432.06 49.54 136 7315 6388 3372020
Pyrexia 417.29 49.54 283 7168 80832 3297576
Congenital anomaly 414.73 49.54 100 7351 1696 3376712
Blood lactic acid increased 406.52 49.54 93 7358 1240 3377168
Viral mutation identified 399.56 49.54 80 7371 533 3377875
Neutropenia 397.37 49.54 201 7250 33185 3345223
Atrial septal defect 382.18 49.54 103 7348 2770 3375638
Mitochondrial toxicity 374.99 49.54 64 7387 142 3378266
Polydactyly 370.76 49.54 70 7381 326 3378082

Pharmacologic Action:

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SourceCodeDescription
ATC J05AF01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Nucleoside and nucleotide reverse transcriptase inhibitors
ATC J05AR01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Antivirals for treatment of HIV infections, combinations
ATC J05AR04 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Antivirals for treatment of HIV infections, combinations
ATC J05AR05 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Antivirals for treatment of HIV infections, combinations
FDA EPC N0000175462 Human Immunodeficiency Virus Nucleoside Analog Reverse Transcriptase Inhibitor
FDA Chemical/Ingredient N0000175459 Nucleoside Analog
FDA MoA N0000009947 Nucleoside Reverse Transcriptase Inhibitors
CHEBI has role CHEBI:36044 antiviral drug
MeSH PA D019380 Anti-HIV Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D044966 Anti-Retroviral Agents
MeSH PA D000963 Antimetabolites
MeSH PA D000998 Antiviral Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D009676 Noxae
MeSH PA D019384 Nucleic Acid Synthesis Inhibitors
MeSH PA D018894 Reverse Transcriptase Inhibitors

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Human immunodeficiency virus infection indication 86406008 DOID:526
Prevention of Maternal-Fetal Transmission of HIV indication
Toxic amblyopia contraindication 965003
Myositis contraindication 26889001 DOID:633
Hepatic failure contraindication 59927004
Pancreatitis contraindication 75694006 DOID:4989
Large liver contraindication 80515008
Kidney disease contraindication 90708001 DOID:2527
Lactic acidosis contraindication 91273001 DOID:3650
Disorder of muscle contraindication 129565002 DOID:423
Steatosis of liver contraindication 197321007 DOID:9452
Acute pancreatitis contraindication 197456007 DOID:2913
Chronic pancreatitis contraindication 235494005
Disease of liver contraindication 235856003 DOID:409
Anemia contraindication 271737000 DOID:2355
Hypertriglyceridemia contraindication 302870006
Neutropenic disorder contraindication 303011007 DOID:1227
Bone marrow depression contraindication 307762000
Breastfeeding (mother) contraindication 413712001
Obesity contraindication 414916001 DOID:9970
HLA-B 5701 Positive Status contraindication
Drug Resistance to Anti-retroviral Therapy contraindication
Prevention of HIV Infection after Exposure off-label use

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.17 acidic
pKa2 13.72 acidic

Orange Book patent data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
300MG TRIZIVIR VIIV HLTHCARE N021205 Nov. 14, 2000 RX TABLET ORAL 6294540 May 14, 2018 METHOD OF TREATMENT OF A PATIENT INFECTED WITH HIV

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Thymidine kinase, cytosolic Kinase Ki 5.54 CHEMBL
Thymidylate kinase Kinase Ki 4.55 WOMBAT-PK
5-hydroxytryptamine receptor 2A GPCR IC50 5.51 WOMBAT-PK
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 4 WOMBAT-PK
Reverse transcriptase/RNaseH Enzyme INHIBITOR IC50 8.52 CHEMBL CHEMBL
Thymidylate kinase Kinase Ki 4.55 CHEMBL
Pol polyprotein Enzyme IC50 8.22 CHEMBL
Gag-Pro-Pol polyprotein Polyprotein EC50 8.31 WOMBAT-PK
Reverse transcriptase/RNaseH Enzyme IC50 6.11 WOMBAT-PK
Thymidine kinase Unclassified IC50 4.90 CHEMBL
Reverse transcriptase Enzyme IC50 4.74 CHEMBL

External reference:

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IDSource
DB00495 DRUGBANK_ID
4825 IUPHAR_LIGAND_ID
4019502 VUID
N0000147622 NUI
C0043474 UMLSCUI
D00413 KEGG_DRUG
CHEMBL129 ChEMBL_ID
4B9XT59T7S UNII
6118 INN_ID
35370 PUBCHEM_CID
4019502 VANDF
71929 MMSL
N0000006933 NDFRT
N0000147622 NDFRT
11413 RXNORM
27479000 SNOMEDCT_US
387151007 SNOMEDCT_US
5703 MMSL
d00034 MMSL
003019 NDDF
CHEBI:10110 CHEBI
D015215 MESH_DESCRIPTOR_UI
AZZ PDB_CHEM_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Lamivudine and Zidovudine HUMAN PRESCRIPTION DRUG LABEL 2 0093-5385 TABLET, FILM COATED 300 mg ORAL ANDA 18 sections
Lamivudine and Zidovudine HUMAN PRESCRIPTION DRUG LABEL 2 0378-5180 TABLET, FILM COATED 300 mg ORAL ANDA 18 sections
Zidovudine HUMAN PRESCRIPTION DRUG LABEL 1 0378-6106 TABLET, FILM COATED 300 mg ORAL ANDA 17 sections
Zidovudine HUMAN PRESCRIPTION DRUG LABEL 1 0527-1905 TABLET, FILM COATED 300 mg ORAL ANDA 17 sections
Combivir HUMAN PRESCRIPTION DRUG LABEL 2 16590-061 TABLET, FILM COATED 300 mg ORAL NDA 16 sections
Zidovudine HUMAN PRESCRIPTION DRUG LABEL 1 21695-369 TABLET, FILM COATED 300 mg ORAL ANDA 18 sections
COMBIVIR HUMAN PRESCRIPTION DRUG LABEL 2 21695-846 TABLET, FILM COATED 300 mg ORAL NDA 18 sections
Lamivudine and Zidovudine HUMAN PRESCRIPTION DRUG LABEL 2 21695-996 TABLET, FILM COATED 300 mg ORAL ANDA 17 sections
LAMIVUDINE and ZIDOVUDINE HUMAN PRESCRIPTION DRUG LABEL 2 31722-506 TABLET, FILM COATED 300 mg ORAL ANDA 18 sections
Zidovudine HUMAN PRESCRIPTION DRUG LABEL 1 31722-509 TABLET 300 mg ORAL ANDA 18 sections
Lamivudine and Zidovudine HUMAN PRESCRIPTION DRUG LABEL 2 31722-739 TABLET, FILM COATED 300 mg ORAL ANDA 18 sections
Lamivudine and Zidovudine HUMAN PRESCRIPTION DRUG LABEL 2 42291-363 TABLET, FILM COATED 300 mg ORAL ANDA 18 sections
Lamivudine and Zidovudine HUMAN PRESCRIPTION DRUG LABEL 2 43063-346 TABLET, FILM COATED 300 mg ORAL ANDA 17 sections
COMBIVIR HUMAN PRESCRIPTION DRUG LABEL 2 49702-202 TABLET, FILM COATED 300 mg ORAL NDA 18 sections
RETROVIR HUMAN PRESCRIPTION DRUG LABEL 1 49702-211 CAPSULE 100 mg ORAL NDA 18 sections
RETROVIR HUMAN PRESCRIPTION DRUG LABEL 1 49702-212 SYRUP 10 mg ORAL NDA 18 sections
RETROVIR HUMAN PRESCRIPTION DRUG LABEL 1 49702-213 INJECTION, SOLUTION 10 mg INTRAVENOUS NDA 18 sections
TRIZIVIR HUMAN PRESCRIPTION DRUG LABEL 3 49702-217 TABLET, FILM COATED 300 mg ORAL NDA 19 sections
Lamivudine and Zidovudine HUMAN PRESCRIPTION DRUG LABEL 2 50436-0597 TABLET, FILM COATED 300 mg ORAL ANDA 18 sections
Zidovudine HUMAN PRESCRIPTION DRUG LABEL 1 52343-044 CAPSULE 100 mg ORAL ANDA 17 sections
Zidovudine HUMAN PRESCRIPTION DRUG LABEL 1 52343-045 TABLET, FILM COATED 300 mg ORAL ANDA 17 sections
COMBIVIR HUMAN PRESCRIPTION DRUG LABEL 2 52959-546 TABLET, FILM COATED 300 mg ORAL NDA 18 sections
Zidovudine HUMAN PRESCRIPTION DRUG LABEL 1 53104-0100 CAPSULE 100 mg ORAL ANDA 18 sections
Zidovudine HUMAN PRESCRIPTION DRUG LABEL 1 53104-0101 TABLET, FILM COATED 300 mg ORAL ANDA 18 sections
zidovudine HUMAN PRESCRIPTION DRUG LABEL 1 53104-0105 SYRUP 50 mg ORAL ANDA 18 sections
Zidovudine HUMAN PRESCRIPTION DRUG LABEL 1 53808-0812 TABLET, FILM COATED 300 mg ORAL ANDA 18 sections
Zidovudine HUMAN PRESCRIPTION DRUG LABEL 1 53808-0878 TABLET, FILM COATED 300 mg ORAL ANDA 18 sections
COMBIVIR HUMAN PRESCRIPTION DRUG LABEL 2 53808-0895 TABLET, FILM COATED 300 mg ORAL NDA 17 sections
TRIZIVIR HUMAN PRESCRIPTION DRUG LABEL 3 53808-0990 TABLET, FILM COATED 300 mg ORAL NDA 19 sections
Lamivudine and Zidovudine HUMAN PRESCRIPTION DRUG LABEL 2 55700-096 TABLET, FILM COATED 300 mg ORAL ANDA 17 sections