zidovudine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

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A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group.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

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.60 g O
0.60 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 25 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 2.80 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 37.42 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 63 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 1.80 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 25 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.80 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1.30 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
March 19, 1987 FDA VIIV HLTHCARE

FDA Adverse Event Reporting System (Female)

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 2444.17 21.62 1043 15947 107169 46561903
Foetal exposure during pregnancy 1364.71 21.62 486 16504 30261 46638811
Stillbirth 961.89 21.62 259 16731 6232 46662840
Abortion spontaneous 862.29 21.62 385 16605 43261 46625811
Premature baby 793.62 21.62 284 16706 17828 46651244
Viral mutation identified 626.16 21.62 144 16846 1755 46667317
Virologic failure 599.07 21.62 141 16849 1914 46667158
Maternal exposure during pregnancy 540.31 21.62 379 16611 102170 46566902
Pregnancy 527.58 21.62 237 16753 26900 46642172
Caesarean section 503.56 21.62 199 16791 16404 46652668
Abortion induced 472.22 21.62 167 16823 10093 46658979
Drug resistance 450.32 21.62 186 16804 17182 46651890
Live birth 407.35 21.62 150 16840 10180 46658892
Pathogen resistance 378.29 21.62 124 16866 5936 46663136
Immune reconstitution inflammatory syndrome 344.70 21.62 114 16876 5611 46663461
Premature rupture of membranes 331.43 21.62 104 16886 4319 46664753
Foetal death 315.56 21.62 119 16871 8624 46660448
Lipodystrophy acquired 299.61 21.62 76 16914 1429 46667643
Maternal drugs affecting foetus 281.39 21.62 97 16893 5421 46663651
Premature labour 265.89 21.62 113 16877 11186 46657886
Premature delivery 248.82 21.62 133 16857 21936 46647136
Foetal growth restriction 189.47 21.62 76 16914 6491 46662581
Pre-eclampsia 158.88 21.62 71 16919 7923 46661149
Anaemia 150.20 21.62 304 16686 255475 46413597
HIV infection 148.46 21.62 36 16954 557 46668515
Normal newborn 131.20 21.62 57 16933 5944 46663128
Congenital anomaly 130.51 21.62 40 16950 1532 46667540
Patent ductus arteriosus 126.49 21.62 49 16941 3813 46665259
Amniotic cavity infection 123.97 21.62 36 16954 1142 46667930
Treatment noncompliance 122.42 21.62 95 16895 29636 46639436
Blood HIV RNULL increased 118.71 21.62 31 16959 656 46668416
Sudden infant death syndrome 117.16 21.62 25 16965 209 46668863
Atrial septal defect 115.56 21.62 53 16937 6279 46662793
Trisomy 21 113.85 21.62 27 16963 378 46668694
Hypertriglyceridaemia 111.23 21.62 50 16940 5654 46663418
Polydactyly 110.65 21.62 26 16964 349 46668723
Ventricular septal defect 110.55 21.62 45 16945 3989 46665083
Foetal distress syndrome 104.52 21.62 32 16958 1221 46667851
Human immunodeficiency virus transmission 101.32 21.62 19 16971 74 46668998
CD4 lymphocytes decreased 96.63 21.62 32 16958 1578 46667494
Drug ineffective 92.01 21.62 68 16922 677770 45991302
Neonatal disorder 91.50 21.62 25 16965 632 46668440
Gestational diabetes 91.25 21.62 47 16943 7172 46661900
Low birth weight baby 88.37 21.62 42 16948 5392 46663680
Alpha 1 foetoprotein abnormal 86.23 21.62 16 16974 58 46669014
Fall 85.29 21.62 10 16980 329087 46339985
Pain 84.72 21.62 34 16956 476914 46192158
Blood lactic acid increased 83.76 21.62 41 16949 5616 46663456
Acquired gene mutation 83.75 21.62 23 16967 593 46668479
Hydrops foetalis 81.04 21.62 20 16970 334 46668738
Mitochondrial cytopathy 78.77 21.62 19 16971 287 46668785
Small for dates baby 77.72 21.62 34 16956 3603 46665469
Mitochondrial toxicity 76.40 21.62 19 16971 328 46668744
Neural tube defect 75.79 21.62 17 16973 183 46668889
Umbilical cord abnormality 75.05 21.62 21 16969 581 46668491
Rheumatoid arthritis 74.51 21.62 3 16987 240212 46428860
Twin pregnancy 72.99 21.62 24 16966 1157 46667915
Placental disorder 72.70 21.62 25 16965 1384 46667688
Premature separation of placenta 71.42 21.62 26 16964 1702 46667370
Anaemia macrocytic 70.66 21.62 29 16961 2624 46666448
Meningomyelocele 69.66 21.62 19 16971 477 46668595
Congenital heart valve disorder 69.38 21.62 14 16976 86 46668986
Congenital pulmonary valve disorder 68.65 21.62 13 16977 54 46669018
Fatigue 68.14 21.62 73 16917 608624 46060448
Malaria 67.33 21.62 16 16974 226 46668846
Lipoatrophy 66.48 21.62 17 16973 330 46668742
Genitalia external ambiguous 64.39 21.62 14 16976 129 46668943
Cardiac murmur 64.08 21.62 44 16946 11360 46657712
Anaemia neonatal 61.86 21.62 15 16975 232 46668840
Off label use 61.23 21.62 31 16959 379810 46289262
Viral load increased 57.99 21.62 21 16969 1354 46667718
Portal hypertension 56.87 21.62 27 16963 3456 46665616
Hepatomegaly 55.30 21.62 40 16950 11213 46657859
Hyperlactacidaemia 54.90 21.62 23 16967 2192 46666880
Necrotising colitis 53.91 21.62 16 16974 548 46668524
Ultrasound antenatal screen abnormal 53.18 21.62 12 16978 133 46668939
Arthralgia 52.68 21.62 34 16956 364569 46304503
Neutropenia neonatal 52.20 21.62 11 16979 86 46668986
Meconium stain 51.07 21.62 12 16978 161 46668911
Neonatal respiratory arrest 50.04 21.62 10 16980 58 46669014
Pain in extremity 48.22 21.62 17 16973 258663 46410409
Spina bifida 47.17 21.62 15 16975 649 46668423
Polyhydramnios 47.02 21.62 20 16970 1979 46667093
Exomphalos 45.95 21.62 14 16976 525 46668547
Developmental delay 45.94 21.62 17 16973 1165 46667907
Meningitis cryptococcal 45.76 21.62 17 16973 1178 46667894
Oligohydramnios 45.43 21.62 27 16963 5438 46663634
Anencephaly 44.50 21.62 11 16979 185 46668887
Pneumonia 44.40 21.62 43 16947 376277 46292795
Hepatotoxicity 44.33 21.62 50 16940 24959 46644113
Bladder agenesis 43.66 21.62 10 16980 119 46668953
Dyspnoea 43.31 21.62 76 16914 515472 46153600
Cloacal exstrophy 43.07 21.62 10 16980 127 46668945
Skull malformation 42.64 21.62 12 16978 339 46668733
Neonatal respiratory distress syndrome 42.48 21.62 20 16970 2513 46666559
Enlarged clitoris 41.77 21.62 10 16980 146 46668926
Anal atresia 41.73 21.62 12 16978 367 46668705
Pulmonary valve sclerosis 41.20 21.62 8 16982 39 46669033
Astrocytoma malignant 41.03 21.62 8 16982 40 46669032
Urinary tract infection 40.15 21.62 15 16975 220251 46448821
Large for dates baby 39.36 21.62 12 16978 451 46668621
Anxiety 39.35 21.62 9 16981 181948 46487124
Congenital genital malformation 38.71 21.62 9 16981 115 46668957
Microcephaly 38.60 21.62 13 16977 675 46668397
Tethered cord syndrome 38.50 21.62 10 16980 207 46668865
Abdominal discomfort 38.10 21.62 5 16985 151160 46517912
Hyperbilirubinaemia 37.90 21.62 31 16959 10407 46658665
HIV antibody positive 37.88 21.62 6 16984 5 46669067
Single umbilical artery 37.49 21.62 9 16981 133 46668939
Coarctation of the aorta 37.31 21.62 12 16978 539 46668533
Neonatal aspiration 37.18 21.62 9 16981 138 46668934
Spine malformation 37.01 21.62 10 16980 242 46668830
Gastrointestinal malformation 36.83 21.62 9 16981 144 46668928
Complication of delivery 36.65 21.62 9 16981 147 46668925
Sepsis neonatal 36.48 21.62 11 16979 398 46668674
Congenital skin dimples 36.15 21.62 9 16981 156 46668916
Ultrasound scan abnormal 35.79 21.62 10 16980 275 46668797
Congenital genital malformation female 35.27 21.62 7 16983 39 46669033
Product dose omission issue 35.14 21.62 9 16981 168511 46500561
Placenta praevia 35.03 21.62 13 16977 898 46668174
Cleft palate 34.95 21.62 13 16977 904 46668168
Adrenogenital syndrome 34.41 21.62 7 16983 45 46669027
Completed suicide 34.09 21.62 6 16984 145914 46523158
Pulmonary valve stenosis 34.02 21.62 10 16980 331 46668741
AIDS cholangiopathy 34.00 21.62 6 16984 15 46669057
Placental insufficiency 33.59 21.62 14 16976 1317 46667755
Dizziness 33.50 21.62 45 16945 340369 46328703
Sinusitis 33.41 21.62 4 16986 129764 46539308
Multiple-drug resistance 33.28 21.62 17 16973 2548 46666524
Ergot poisoning 33.22 21.62 9 16981 220 46668852
Gestational hypertension 33.04 21.62 16 16974 2139 46666933
Micrognathia 32.96 21.62 9 16981 227 46668845
Caudal regression syndrome 32.73 21.62 8 16982 128 46668944
Rash maculo-papular 32.22 21.62 45 16945 27829 46641243
Ventricular hypertrophy 32.11 21.62 19 16971 3795 46665277
Alpha 1 foetoprotein increased 31.30 21.62 8 16982 155 46668917
Condition aggravated 31.25 21.62 26 16964 245026 46424046
Congenital anomaly in offspring 31.15 21.62 8 16982 158 46668914
Drug hypersensitivity 30.93 21.62 26 16964 243799 46425273
Haemorrhage in pregnancy 30.87 21.62 14 16976 1614 46667458
Fanconi syndrome acquired 30.68 21.62 12 16978 957 46668115
Ectopic pregnancy 30.30 21.62 16 16974 2566 46666506
Hydrocephalus 30.23 21.62 20 16970 4857 46664215
Fallot's tetralogy 30.14 21.62 7 16983 89 46668983
Constipation 29.84 21.62 13 16977 174084 46494988
Feeling abnormal 29.52 21.62 5 16985 125055 46544017
Gastrointestinal disorder congenital 29.45 21.62 7 16983 99 46668973
HIV test positive 29.31 21.62 6 16984 40 46669032
Foetal heart rate abnormal 29.26 21.62 10 16980 543 46668529
Acute lymphocytic leukaemia 29.23 21.62 16 16974 2757 46666315
Proteinuria 29.17 21.62 33 16957 16520 46652552
Cleft lip and palate 29.10 21.62 9 16981 355 46668717
Neutropenia 29.05 21.62 116 16874 143088 46525984
Hyperandrogenism 29.00 21.62 7 16983 106 46668966
Congenital hydrocephalus 28.88 21.62 7 16983 108 46668964
Pruritus 28.18 21.62 28 16962 242324 46426748
Foetal cardiac disorder 28.13 21.62 6 16984 50 46669022
Neonatal hepatomegaly 27.67 21.62 5 16985 15 46669057
Death 27.62 21.62 50 16940 335498 46333574
Cardiac malposition 27.52 21.62 6 16984 56 46669016
Hepatitis 27.28 21.62 45 16945 32170 46636902
Arnold-Chiari malformation 26.94 21.62 9 16981 456 46668616
Cerebral toxoplasmosis 26.60 21.62 10 16980 716 46668356
Hepatitis B surface antibody positive 25.85 21.62 6 16984 76 46668996
Chlamydial infection 25.69 21.62 8 16982 323 46668749
Cholestasis of pregnancy 25.62 21.62 11 16979 1113 46667959
Weight increased 25.58 21.62 14 16976 164459 46504613
Necrotising enterocolitis neonatal 25.36 21.62 7 16983 184 46668888
Musculoskeletal stiffness 25.27 21.62 3 16987 97990 46571082
Hepatic displacement 25.17 21.62 5 16985 28 46669044
Infection 24.48 21.62 9 16981 133583 46535489
Spinocerebellar disorder 24.21 21.62 5 16985 35 46669037
Induced labour 24.16 21.62 10 16980 924 46668148
Febrile neutropenia 24.14 21.62 3 16987 94624 46574448
Toxicity to various agents 24.00 21.62 25 16965 211741 46457331
Aspartate aminotransferase increased 24 21.62 73 16917 78627 46590445
Delivery 23.63 21.62 9 16981 668 46668404
Respiratory distress 23.63 21.62 42 16948 31874 46637198
Back pain 23.58 21.62 25 16965 210014 46459058
Swelling 23.48 21.62 8 16982 124503 46544569
Amniotic fluid volume decreased 23.45 21.62 8 16982 432 46668640
Stevens-Johnson syndrome 23.12 21.62 35 16955 23262 46645810
Diastasis recti abdominis 23.10 21.62 5 16985 45 46669027
Dysmorphism 22.90 21.62 12 16978 1895 46667177
Glycosuria 22.78 21.62 10 16980 1068 46668004
Hypotension 22.59 21.62 31 16959 232558 46436514
Disseminated Bacillus Calmette-Guerin infection 22.14 21.62 4 16986 12 46669060
Lactate pyruvate ratio increased 22.11 21.62 5 16985 56 46669016
Abortion missed 22.10 21.62 11 16979 1561 46667511
Bovine tuberculosis 21.79 21.62 5 16985 60 46669012
Nausea 21.73 21.62 154 16836 687300 45981772
Genotype drug resistance test positive 21.71 21.62 8 16982 542 46668530
High arched palate 21.64 21.62 5 16985 62 46669010

FDA Adverse Event Reporting System (Male)

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
Foetal exposure during pregnancy 1427.55 14.93 623 19247 36248 29896360
Exposure during pregnancy 867.04 14.93 298 19572 8963 29923645
Lipodystrophy acquired 835.97 14.93 232 19638 3328 29929280
Viral mutation identified 561.07 14.93 159 19711 2467 29930141
Mitochondrial toxicity 518.10 14.93 148 19722 2366 29930242
Virologic failure 516.16 14.93 156 19714 3063 29929545
Premature baby 470.90 14.93 227 19643 16464 29916144
Immune reconstitution inflammatory syndrome 461.86 14.93 187 19683 8914 29923694
Pathogen resistance 458.63 14.93 182 19688 8228 29924380
Eyelid ptosis 349.59 14.93 131 19739 5057 29927551
Pinealoblastoma 240.54 14.93 48 19822 130 29932478
Drug resistance 238.84 14.93 155 19715 19978 29912630
Progressive external ophthalmoplegia 236.15 14.93 69 19801 1197 29931411
Diplopia 230.03 14.93 132 19738 13640 29918968
Maternal drugs affecting foetus 193.54 14.93 81 19789 4192 29928416
Lipoatrophy 192.37 14.93 50 19820 547 29932061
Hypertriglyceridaemia 138.88 14.93 79 19791 8019 29924589
Dandy-Walker syndrome 133.18 14.93 28 19842 106 29932502
Blood lactic acid increased 128.06 14.93 67 19803 5763 29926845
HIV infection 126.62 14.93 46 19824 1622 29930986
Anaemia 113.97 14.93 349 19521 207643 29724965
Caesarean section 112.06 14.93 45 19825 2092 29930516
Hyperlactacidaemia 110.01 14.93 47 19823 2559 29930049
Neonatal disorder 107.14 14.93 35 19835 891 29931717
Small for dates baby 106.88 14.93 49 19821 3159 29929449
Hepatic fibrosis 101.75 14.93 49 19821 3531 29929077
Anaemia macrocytic 97.70 14.93 43 19827 2517 29930091
Low birth weight baby 95.46 14.93 56 19814 6020 29926588
Congenital anomaly 94.94 14.93 35 19835 1287 29931321
Volvulus 92.57 14.93 34 19836 1237 29931371
Trisomy 21 85.09 14.93 25 19845 442 29932166
Pregnancy 82.76 14.93 21 19849 207 29932401
Ventricular septal defect 75.91 14.93 40 19830 3489 29929119
Polydactyly 75.27 14.93 29 19841 1206 29931402
Ophthalmoplegia 73.74 14.93 29 19841 1275 29931333
Congenital central nervous system anomaly 70.66 14.93 21 19849 387 29932221
Speech disorder developmental 69.42 14.93 27 19843 1152 29931456
Anaemia neonatal 68.08 14.93 19 19851 277 29932331
CD4 lymphocytes decreased 67.02 14.93 31 19839 2039 29930569
Osteonecrosis 66.67 14.93 67 19803 16068 29916540
HIV-associated neurocognitive disorder 65.42 14.93 19 19851 322 29932286
Hypospadias 65.21 14.93 33 19837 2646 29929962
Hyperlipidaemia 63.52 14.93 61 19809 13846 29918762
Off label use 63.49 14.93 44 19826 249246 29683362
Atrial septal defect 61.35 14.93 44 19826 6657 29925951
Cryptorchism 60.24 14.93 27 19843 1650 29930958
Fall 59.77 14.93 23 19847 181849 29750759
CSF HIV escape syndrome 58.35 14.93 14 19856 107 29932501
Blood HIV RNULL increased 57.99 14.93 25 19845 1391 29931217
Congenital hydronephrosis 56.38 14.93 20 19850 657 29931951
Drug-induced liver injury 56.29 14.93 70 19800 21204 29911404
Foetal distress syndrome 55.90 14.93 22 19848 969 29931639
Extraocular muscle paresis 55.59 14.93 18 19852 445 29932163
Hydrocele 55.14 14.93 27 19843 2017 29930591
Cardiac murmur 53.85 14.93 41 19829 6793 29925815
Pneumonia 53.82 14.93 87 19783 334219 29598389
Human immunodeficiency virus transmission 53.27 14.93 10 19860 17 29932591
Viral load increased 52.05 14.93 29 19841 2825 29929783
Patent ductus arteriosus 51.87 14.93 30 19840 3139 29929469
Meningomyelocele 51.81 14.93 13 19857 122 29932486
Kaposi's sarcoma 51.67 14.93 21 19849 1007 29931601
Foetal growth restriction 51.00 14.93 31 19839 3554 29929054
Drug ineffective 50.76 14.93 93 19777 340294 29592314
Death 47.80 14.93 104 19766 357179 29575429
Chordee 46.32 14.93 11 19859 80 29932528
Portal hypertension 46.32 14.93 30 19840 3843 29928765
Splenomegaly 45.05 14.93 50 19820 13430 29919178
Pain 44.52 14.93 30 19840 172611 29759997
Optic nerve neoplasm 44.41 14.93 9 19861 27 29932581
Nodular regenerative hyperplasia 43.45 14.93 17 19853 737 29931871
Developmental delay 42.48 14.93 23 19847 2118 29930490
Blood antidiuretic hormone increased 42.20 14.93 10 19860 72 29932536
Acquired immunodeficiency syndrome 42.11 14.93 15 19855 499 29932109
Osteoporotic fracture 41.36 14.93 18 19852 1025 29931583
Aspartate aminotransferase increased 40.84 14.93 113 19757 63309 29869299
Hypotension 40.56 14.93 44 19826 200521 29732087
Lipohypertrophy 40.47 14.93 13 19857 313 29932295
Malaria 39.98 14.93 12 19858 229 29932379
Neurodevelopmental disorder 39.89 14.93 11 19859 153 29932455
Macrocephaly 39.67 14.93 13 19857 334 29932274
Congenital neoplasm 39.48 14.93 8 19862 24 29932584
Death neonatal 38.96 14.93 13 19857 354 29932254
Product dose omission issue 38.73 14.93 7 19863 91624 29840984
Atrial fibrillation 38.36 14.93 12 19858 108112 29824496
Multiple-drug resistance 38.20 14.93 24 19846 2917 29929691
Congenital naevus 37.70 14.93 8 19862 32 29932576
Product use in unapproved indication 37.57 14.93 3 19867 73690 29858918
Completed suicide 37.21 14.93 10 19860 99482 29833126
Adrenogenital syndrome 36.93 14.93 9 19861 74 29932534
Acquired gene mutation 36.38 14.93 17 19853 1144 29931464
Lymphadenopathy 36.21 14.93 61 19809 24315 29908293
Hypertonia 36.08 14.93 27 19843 4358 29928250
Treatment noncompliance 35.94 14.93 62 19808 25191 29907417
Limb deformity 35.36 14.93 13 19857 474 29932134
Cardiac arrest 35.36 14.93 9 19861 92841 29839767
Blood pyruvic acid increased 35.33 14.93 7 19863 18 29932590
Alanine aminotransferase increased 35.32 14.93 119 19751 74157 29858451
Blood creatine phosphokinase increased 35.31 14.93 85 19785 43763 29888845
Astrocytoma, low grade 35.02 14.93 8 19862 48 29932560
Hepatomegaly 34.84 14.93 38 19832 10009 29922599
Oesophageal candidiasis 34.81 14.93 26 19844 4184 29928424
Mitochondrial myopathy 34.74 14.93 10 19860 164 29932444
Febrile neutropenia 34.17 14.93 14 19856 106679 29825929
Malignant neoplasm progression 34.07 14.93 4 19866 72283 29860325
Dyspnoea 33.92 14.93 111 19759 333184 29599424
Diaphragmatic hernia 33.89 14.93 11 19859 274 29932334
Blood pressure increased 33.85 14.93 4 19866 71924 29860684
Congenital cytomegalovirus infection 33.83 14.93 7 19863 24 29932584
Normal newborn 33.81 14.93 10 19860 181 29932427
Pulmonary tuberculosis 33.63 14.93 27 19843 4830 29927778
Rhabdomyosarcoma 33.36 14.93 8 19862 61 29932547
Constipation 32.78 14.93 17 19853 112889 29819719
Mycobacterium avium complex infection 32.42 14.93 21 19849 2690 29929918
Cerebral ventricle dilatation 32.32 14.93 14 19856 788 29931820
Heart disease congenital 32.10 14.93 16 19854 1242 29931366
Congenital mitral valve incompetence 31.51 14.93 8 19862 79 29932529
Post streptococcal glomerulonephritis 30.93 14.93 7 19863 40 29932568
Neonatal hyponatraemia 30.81 14.93 8 19862 87 29932521
Macrocytosis 30.81 14.93 14 19856 883 29931725
Exomphalos 30.53 14.93 9 19861 161 29932447
Neutropenia neonatal 30.48 14.93 12 19858 529 29932079
Cerebrovascular accident 30.08 14.93 9 19861 83468 29849140
Congenital hydrocephalus 29.72 14.93 8 19862 101 29932507
Blood triglycerides increased 29.16 14.93 41 19829 13976 29918632
Prenatal screening test abnormal 28.90 14.93 6 19864 21 29932587
Cytomegalovirus chorioretinitis 28.86 14.93 21 19849 3247 29929361
Talipes 27.79 14.93 16 19854 1659 29930949
Drug abuse 27.55 14.93 10 19860 82062 29850546
Meningitis cryptococcal 27.50 14.93 17 19853 2007 29930601
Congenital anaemia 26.82 14.93 5 19865 8 29932600
Ear malformation 26.77 14.93 9 19861 251 29932357
Lactic acidosis 26.75 14.93 62 19808 31151 29901457
Sudden infant death syndrome 26.69 14.93 8 19862 152 29932456
Retinal toxicity 26.59 14.93 10 19860 389 29932219
Nephropathy toxic 26.53 14.93 34 19836 10605 29922003
Facial wasting 26.44 14.93 8 19862 157 29932451
Jaundice 26.18 14.93 63 19807 32423 29900185
Gamma-glutamyltransferase increased 25.92 14.93 59 19811 29291 29903317
Dyslipidaemia 25.91 14.93 25 19845 5702 29926906
Congenital syphilis 25.48 14.93 5 19865 12 29932596
Neonatal asphyxia 24.69 14.93 9 19861 320 29932288
Cachexia 24.67 14.93 26 19844 6585 29926023
Hemivertebra 24.65 14.93 7 19863 109 29932499
Strabismus 24.61 14.93 13 19857 1139 29931469
Torsade de pointes 24.59 14.93 27 19843 7163 29925445
Tuberculoid leprosy 24.44 14.93 6 19864 51 29932557
Mitochondrial cytopathy 24.43 14.93 8 19862 205 29932403
Sickle cell disease 24.25 14.93 7 19863 116 29932492
Gastroschisis 24.08 14.93 7 19863 119 29932489
Sickle cell anaemia 24.00 14.93 8 19862 217 29932391
Cerebellar hypoplasia 23.76 14.93 5 19865 19 29932589
Maternal exposure during pregnancy 23.63 14.93 20 19850 3851 29928757
Ultrasound antenatal screen abnormal 23.13 14.93 6 19864 65 29932543
Fatigue 23.11 14.93 122 19748 320551 29612057
Hydronephrosis 22.86 14.93 29 19841 8954 29923654
Drug interaction 22.80 14.93 217 19653 199351 29733257
Hepatitis C virus test 22.57 14.93 6 19864 72 29932536
Maternal condition affecting foetus 22.51 14.93 4 19866 4 29932604
Late developer 22.51 14.93 4 19866 4 29932604
CD4 lymphocytes increased 22.29 14.93 8 19862 272 29932336
Tuberculosis 22.04 14.93 27 19843 8050 29924558
Encephalitis 21.72 14.93 24 19846 6412 29926196
Transaminases increased 21.66 14.93 48 19822 23409 29909199
Cryptococcosis 21.65 14.93 14 19856 1788 29930820
Oesophageal atresia 21.50 14.93 9 19861 465 29932143
Attention deficit hyperactivity disorder 21.49 14.93 14 19856 1810 29930798
Meconium ileus 21.48 14.93 5 19865 33 29932575
Stillbirth 21.25 14.93 7 19863 183 29932425
Birth trauma 21.23 14.93 4 19866 7 29932601
Congenital aortic anomaly 21.22 14.93 6 19864 92 29932516
Cleft lip 20.94 14.93 8 19862 325 29932283
Hepatitis 20.93 14.93 46 19824 22310 29910298
ADAMTS13 activity decreased 20.92 14.93 6 19864 97 29932511
Live birth 20.76 14.93 7 19863 197 29932411
Polyneuropathy chronic 20.53 14.93 5 19865 41 29932567
Hepatosplenomegaly 20.32 14.93 18 19852 3683 29928925
HIV wasting syndrome 20.22 14.93 6 19864 110 29932498
Skull malformation 20.18 14.93 8 19862 359 29932249
Leukopenia 20.00 14.93 82 19788 56077 29876531
Meningitis tuberculous 19.98 14.93 9 19861 556 29932052
Lactate pyruvate ratio increased 19.74 14.93 4 19866 12 29932596
Lymphocytic infiltration 19.58 14.93 9 19861 583 29932025
Oral candidiasis 19.58 14.93 30 19840 11041 29921567
Hyperbilirubinaemia 19.55 14.93 38 19832 16904 29915704
Hepatitis B 19.39 14.93 22 19848 6050 29926558
Enophthalmos 19.27 14.93 4 19866 14 29932594
Pancytopenia 19.27 14.93 109 19761 84943 29847665
Cardio-respiratory arrest 19.20 14.93 7 19863 57299 29875309
Meconium peritonitis 19.05 14.93 4 19866 15 29932593
Acute lymphocytic leukaemia 19.01 14.93 16 19854 3056 29929552
Central nervous system lymphoma 18.99 14.93 10 19860 870 29931738
Vision abnormal neonatal 18.96 14.93 3 19867 0 29932608
Congenital retinoblastoma 18.96 14.93 3 19867 0 29932608
Neonatal intestinal obstruction 18.96 14.93 3 19867 0 29932608
White matter lesion 18.87 14.93 9 19861 634 29931974
Aplasia cutis congenita 18.86 14.93 6 19864 140 29932468
Treatment failure 18.67 14.93 58 19812 34621 29897987
Hypercholesterolaemia 18.52 14.93 24 19846 7568 29925040
Spine malformation 18.50 14.93 6 19864 149 29932459
Nervous system disorder 18.47 14.93 32 19838 13037 29919571
Nasopharyngitis 18.38 14.93 8 19862 58841 29873767
Congenital skin dimples 18.35 14.93 6 19864 153 29932455
Heart transplant rejection 18.24 14.93 11 19859 1242 29931366
Gynaecomastia 18.22 14.93 25 19845 8326 29924282
Back pain 18.07 14.93 25 19845 102571 29830037
Hepatic function abnormal 18.01 14.93 65 19805 41880 29890728
Neck deformity 17.91 14.93 5 19865 73 29932535
Rheumatoid arthritis 17.72 14.93 3 19867 41194 29891414
Red blood cell schistocytes present 17.68 14.93 7 19863 313 29932295
Pyelocaliectasis 17.64 14.93 10 19860 1007 29931601
Hyperkalaemia 17.62 14.93 11 19859 65999 29866609
Congenital hepatomegaly 17.51 14.93 4 19866 24 29932584
International normalised ratio increased 17.46 14.93 5 19865 47734 29884874
Limb malformation 17.45 14.93 7 19863 324 29932284
Neutropenia 17.34 14.93 145 19725 128395 29804213
Feeling abnormal 17.28 14.93 8 19862 56748 29875860
Abnormal dreams 17.27 14.93 24 19846 8091 29924517
Congenital abdominal hernia 17.23 14.93 4 19866 26 29932582
Anaemia megaloblastic 17.00 14.93 6 19864 194 29932414
Hypotonia 17.00 14.93 22 19848 6926 29925682
Lagophthalmos 16.98 14.93 5 19865 89 29932519
Gonadal dysgenesis 16.88 14.93 3 19867 3 29932605
Epistaxis 16.87 14.93 7 19863 52974 29879634
Disease progression 16.69 14.93 17 19853 79857 29852751
Osteoma 16.62 14.93 4 19866 31 29932577
Subacute sclerosing panencephalitis 16.62 14.93 4 19866 31 29932577
Cerebral toxoplasmosis 16.62 14.93 11 19859 1461 29931147
Intellectual disability 16.62 14.93 9 19861 829 29931779
Blood insulin increased 16.52 14.93 7 19863 373 29932235
Kidney malformation 16.44 14.93 5 19865 100 29932508
Congenital hearing disorder 16.35 14.93 5 19865 102 29932506
Osteoporosis 16.25 14.93 27 19843 10636 29921972
Thrombosis 16.24 14.93 4 19866 42227 29890381
Abdominal hernia 16.22 14.93 14 19856 2767 29929841
Long QT syndrome 16.22 14.93 13 19857 2320 29930288
Thalassaemia alpha 16.09 14.93 4 19866 36 29932572
Lipase increased 16.03 14.93 24 19846 8652 29923956
Total lung capacity decreased 15.92 14.93 8 19862 632 29931976
Genitalia external ambiguous 15.89 14.93 6 19864 236 29932372
Trisomy 18 15.86 14.93 6 19864 237 29932371
Reversible ischaemic neurological deficit 15.80 14.93 4 19866 39 29932569
Dysmorphism 15.67 14.93 12 19858 2005 29930603
Vanishing bile duct syndrome 15.59 14.93 8 19862 660 29931948
Scleral discolouration 15.58 14.93 6 19864 249 29932359
CSF virus identified 15.37 14.93 4 19866 44 29932564
Papilloma 15.35 14.93 5 19865 126 29932482
Twin pregnancy 15.35 14.93 3 19867 7 29932601
Progressive multifocal leukoencephalopathy 15.34 14.93 24 19846 8989 29923619
Joint swelling 15.28 14.93 6 19864 46940 29885668
HIV associated nephropathy 15.23 14.93 6 19864 265 29932343
Oxygen saturation decreased 15.07 14.93 5 19865 43435 29889173
Blood bilirubin increased 15.07 14.93 56 19814 36580 29896028
Confusional state 15.01 14.93 43 19827 134791 29797817
Coarctation of the aorta 14.99 14.93 7 19863 470 29932138
Lymph node tuberculosis 14.98 14.93 7 19863 471 29932137

Pharmacologic Action:

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 MoA N0000009947 Nucleoside Reverse Transcriptase Inhibitors
FDA EXT N0000175459 Nucleoside Analog
FDA EPC N0000175462 Human Immunodeficiency Virus Nucleoside Analog Reverse Transcriptase Inhibitor
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
CHEBI has role CHEBI:35221 antimetabolite
CHEBI has role CHEBI:36044 anti-virus drug
CHEBI has role CHEBI:53756 reverse transcriptase inhibitor
CHEBI has role CHEBI:36047 antibacterial drugs
CHEBI has role CHEBI:50696 pbp3 inhibitor
CHEBI has role CHEBI:88188 allergenic drug

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Human immunodeficiency virus infection indication 86406008 DOID:526
Prevention of Maternal-Fetal Transmission of HIV indication
Prevention of HIV Infection after Exposure off-label use
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:557
Lactic acidosis contraindication 91273001 DOID:3650
Disorder of muscle contraindication 129565002 DOID:423
Steatosis of liver contraindication 197321007
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

Acid dissociation constants calculated using MoKa v3.0.0

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

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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:

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

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Zidovudine HUMAN PRESCRIPTION DRUG LABEL 1 0527-1905 TABLET, FILM COATED 300 mg ORAL ANDA 25 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 27 sections
COMBIVIR HUMAN PRESCRIPTION DRUG LABEL 2 21695-846 TABLET, FILM COATED 300 mg ORAL NDA 26 sections
Lamivudine and Zidovudine HUMAN PRESCRIPTION DRUG LABEL 2 21695-996 TABLET, FILM COATED 300 mg ORAL ANDA 26 sections
LAMIVUDINE and ZIDOVUDINE Human Prescription Drug Label 2 31722-506 TABLET, FILM COATED 300 mg ORAL ANDA 25 sections
Zidovudine Human Prescription Drug Label 1 31722-509 TABLET 300 mg ORAL ANDA 27 sections
Lamivudine and Zidovudine HUMAN PRESCRIPTION DRUG LABEL 2 31722-739 TABLET, FILM COATED 300 mg ORAL ANDA 24 sections
Lamivudine and Zidovudine Human Prescription Drug Label 2 33342-003 TABLET 300 mg ORAL ANDA 25 sections
LAMIVUDINE and ZIDOVUDINE HUMAN PRESCRIPTION DRUG LABEL 2 43063-900 TABLET, FILM COATED 300 mg ORAL ANDA 25 sections
COMBIVIR HUMAN PRESCRIPTION DRUG LABEL 2 49702-202 TABLET, FILM COATED 300 mg ORAL NDA 25 sections
RETROVIR HUMAN PRESCRIPTION DRUG LABEL 1 49702-211 CAPSULE 100 mg ORAL NDA 25 sections
RETROVIR HUMAN PRESCRIPTION DRUG LABEL 1 49702-212 SOLUTION 10 mg ORAL NDA 25 sections
RETROVIR HUMAN PRESCRIPTION DRUG LABEL 1 49702-213 INJECTION, SOLUTION 10 mg INTRAVENOUS NDA 25 sections
TRIZIVIR HUMAN PRESCRIPTION DRUG LABEL 3 49702-217 TABLET, FILM COATED 300 mg ORAL NDA 26 sections
LAMIVUDINE and ZIDOVUDINE HUMAN PRESCRIPTION DRUG LABEL 2 50268-456 TABLET, FILM COATED 300 mg ORAL ANDA 25 sections
Zidovudine Human Prescription Drug Label 1 52343-044 CAPSULE 100 mg ORAL ANDA 25 sections
Zidovudine Human Prescription Drug Label 1 52343-045 TABLET, FILM COATED 300 mg ORAL ANDA 25 sections
COMBIVIR HUMAN PRESCRIPTION DRUG LABEL 2 52959-546 TABLET, FILM COATED 300 mg ORAL NDA 26 sections
Zidovudine HUMAN PRESCRIPTION DRUG LABEL 1 53104-0100 CAPSULE 100 mg ORAL ANDA 25 sections
Zidovudine HUMAN PRESCRIPTION DRUG LABEL 1 53104-0101 TABLET, FILM COATED 300 mg ORAL ANDA 21 sections
zidovudine HUMAN PRESCRIPTION DRUG LABEL 1 53104-0105 SYRUP 50 mg ORAL ANDA 27 sections
Zidovudine HUMAN PRESCRIPTION DRUG LABEL 1 53808-0812 TABLET, FILM COATED 300 mg ORAL ANDA 27 sections
Zidovudine HUMAN PRESCRIPTION DRUG LABEL 1 53808-0878 TABLET, FILM COATED 300 mg ORAL ANDA 27 sections
COMBIVIR HUMAN PRESCRIPTION DRUG LABEL 2 53808-0895 TABLET, FILM COATED 300 mg ORAL NDA 25 sections
TRIZIVIR HUMAN PRESCRIPTION DRUG LABEL 3 53808-0990 TABLET, FILM COATED 300 mg ORAL NDA 28 sections
Lamivudine and Zidovudine HUMAN PRESCRIPTION DRUG LABEL 2 54741-102 TABLET, FILM COATED 300 mg ORAL ANDA 26 sections
LAMIVUDINE AND ZIDOVUDINE HUMAN PRESCRIPTION DRUG LABEL 2 57297-284 TABLET 300 mg ORAL ANDA 25 sections
ABACAVIR SULFATE, LAMIVUDINE AND ZIDOVUDINE HUMAN PRESCRIPTION DRUG LABEL 3 57297-286 TABLET 300 mg ORAL ANDA 29 sections
Lamivudine Zidovudine HUMAN PRESCRIPTION DRUG LABEL 2 61919-061 TABLET 300 mg ORAL ANDA 17 sections