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A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group.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 2466.95 23.19 1065 16595 123795 53207611
Foetal exposure during pregnancy 1469.72 23.19 517 17143 34198 53297208
Stillbirth 974.31 23.19 259 17401 6538 53324868
Abortion spontaneous 908.44 23.19 396 17264 46239 53285167
Premature baby 840.75 23.19 296 17364 19505 53311901
Virologic failure 721.19 23.19 164 17496 2100 53329306
Viral mutation identified 708.15 23.19 159 17501 1915 53329491
Caesarean section 517.21 23.19 200 17460 17120 53314286
Pregnancy 515.61 23.19 237 17423 31204 53300202
Abortion induced 490.47 23.19 170 17490 10656 53320750
Maternal exposure during pregnancy 470.65 23.19 398 17262 155241 53176165
Drug resistance 469.25 23.19 194 17466 19768 53311638
Pathogen resistance 450.16 23.19 141 17519 6419 53324987
Live birth 404.15 23.19 161 17499 14898 53316508
Immune reconstitution inflammatory syndrome 367.92 23.19 120 17540 6226 53325180
Premature rupture of membranes 333.96 23.19 105 17555 4835 53326571
Foetal death 318.78 23.19 119 17541 9228 53322178
Lipodystrophy acquired 314.69 23.19 79 17581 1571 53329835
Maternal drugs affecting foetus 289.91 23.19 97 17563 5449 53325957
Premature labour 266.40 23.19 113 17547 12249 53319157
Premature delivery 259.05 23.19 140 17520 25964 53305442
Foetal growth restriction 193.41 23.19 77 17583 7097 53324309
Treatment noncompliance 183.55 23.19 122 17538 32913 53298493
Anaemia 163.36 23.19 312 17348 276406 53055000
Pre-eclampsia 159.98 23.19 71 17589 8576 53322830
HIV infection 151.91 23.19 36 17624 556 53330850
Congenital anomaly 141.82 23.19 42 17618 1575 53329831
Patent ductus arteriosus 131.54 23.19 50 17610 4068 53327338
Normal newborn 129.77 23.19 58 17602 7121 53324285
Amniotic cavity infection 124.66 23.19 36 17624 1234 53330172
Blood HIV RNA increased 121.52 23.19 32 17628 773 53330633
Sudden infant death syndrome 119.09 23.19 25 17635 213 53331193
Atrial septal defect 119.06 23.19 54 17606 6860 53324546
Trisomy 21 116.33 23.19 27 17633 379 53331027
Ventricular septal defect 114.84 23.19 46 17614 4304 53327102
Polydactyly 111.05 23.19 26 17634 380 53331026
Hypertriglyceridaemia 110.97 23.19 50 17610 6254 53325152
Foetal distress syndrome 104.57 23.19 32 17628 1343 53330063
Low birth weight baby 104.41 23.19 48 17612 6289 53325117
Human immunodeficiency virus transmission 103.12 23.19 19 17641 74 53331332
Pain 102.17 23.19 34 17626 588364 52743042
CD4 lymphocytes decreased 97.87 23.19 32 17628 1669 53329737
Drug ineffective 97.85 23.19 77 17583 817168 52514238
Neonatal disorder 93.59 23.19 25 17635 639 53330767
Rheumatoid arthritis 90.77 23.19 3 17657 314528 53016878
Gestational diabetes 90.67 23.19 47 17613 7992 53323414
Alpha 1 foetoprotein abnormal 87.74 23.19 16 17644 58 53331348
Neural tube defect 85.96 23.19 19 17641 211 53331195
Blood lactic acid increased 85.30 23.19 41 17619 5937 53325469
Umbilical cord abnormality 84.61 23.19 23 17637 629 53330777
Fall 84.25 23.19 10 17650 358430 52972976
Hydrops foetalis 82.04 23.19 20 17640 350 53331056
Acquired gene mutation 80.62 23.19 23 17637 754 53330652
Fatigue 79.81 23.19 75 17585 730431 52600975
Small for dates baby 79.80 23.19 34 17626 3718 53327688
Mitochondrial cytopathy 78.51 23.19 19 17641 322 53331084
Meningomyelocele 78.01 23.19 21 17639 553 53330853
Mitochondrial toxicity 75.69 23.19 19 17641 377 53331029
Genitalia external ambiguous 74.19 23.19 16 17644 157 53331249
Off label use 74.00 23.19 32 17628 472180 52859226
Twin pregnancy 73.90 23.19 24 17636 1225 53330181
Placental disorder 72.99 23.19 25 17635 1506 53329900
Premature separation of placenta 71.86 23.19 26 17634 1841 53329565
Anaemia macrocytic 71.54 23.19 29 17631 2797 53328609
Congenital heart valve disorder 70.70 23.19 14 17646 86 53331320
Congenital pulmonary valve disorder 69.88 23.19 13 17647 54 53331352
Lipoatrophy 68.08 23.19 17 17643 330 53331076
Hepatomegaly 66.40 23.19 44 17616 11787 53319619
Cardiac murmur 66.12 23.19 44 17616 11869 53319537
Malaria 65.53 23.19 16 17644 282 53331124
Arthralgia 62.49 23.19 34 17626 439749 52891657
Meconium stain 60.82 23.19 14 17646 189 53331217
Anal atresia 60.15 23.19 16 17644 402 53331004
Viral load increased 58.49 23.19 21 17639 1454 53329952
Anaemia neonatal 58.03 23.19 15 17645 336 53331070
Portal hypertension 57.56 23.19 27 17633 3701 53327705
Exomphalos 55.27 23.19 16 17644 553 53330853
Abdominal discomfort 54.89 23.19 5 17655 221057 53110349
Necrotising colitis 54.64 23.19 16 17644 576 53330830
Spina bifida 54.45 23.19 17 17643 763 53330643
Ultrasound antenatal screen abnormal 54.31 23.19 12 17648 133 53331273
Bladder agenesis 53.21 23.19 12 17648 147 53331259
Anencephaly 53.14 23.19 13 17647 231 53331175
Cloacal exstrophy 52.62 23.19 12 17648 155 53331251
Neutropenia neonatal 52.47 23.19 11 17649 93 53331313
Hyperlactacidaemia 52.40 23.19 23 17637 2702 53328704
CSF HIV escape syndrome 51.37 23.19 11 17649 104 53331302
Neonatal respiratory arrest 50.99 23.19 10 17650 58 53331348
Pain in extremity 48.39 23.19 17 17643 285033 53046373
Congenital genital malformation 48.17 23.19 11 17649 143 53331263
Tethered cord syndrome 47.95 23.19 12 17648 235 53331171
Polyhydramnios 46.78 23.19 20 17640 2205 53329201
Gastrointestinal malformation 46.22 23.19 11 17649 173 53331233
Developmental delay 45.80 23.19 17 17643 1294 53330112
Meningitis cryptococcal 45.80 23.19 17 17643 1294 53330112
Hepatotoxicity 45.46 23.19 51 17609 27829 53303577
Oligohydramnios 45.15 23.19 27 17633 6049 53325357
Spine malformation 44.94 23.19 12 17648 306 53331100
Neonatal respiratory distress syndrome 44.58 23.19 21 17639 2906 53328500
Dyspnoea 44.44 23.19 79 17581 586153 52745253
Sepsis neonatal 44.24 23.19 13 17647 474 53330932
Skull malformation 43.57 23.19 12 17648 345 53331061
Hyperbilirubinaemia 43.22 23.19 33 17627 11036 53320370
Enlarged clitoris 42.97 23.19 10 17650 142 53331264
Pulmonary valve sclerosis 41.96 23.19 8 17652 39 53331367
Pneumonia 41.76 23.19 44 17616 407125 52924281
Caudal regression syndrome 41.52 23.19 10 17650 166 53331240
Astrocytoma malignant 41.46 23.19 8 17652 42 53331364
Sinusitis 41.33 23.19 4 17656 168560 53162846
Microcephaly 41.33 23.19 14 17646 815 53330591
Urinary tract infection 39.53 23.19 15 17645 239888 53091518
Rickets 39.49 23.19 8 17652 56 53331350
Large for dates baby 39.13 23.19 12 17648 507 53330899
Gastrointestinal disorder congenital 38.93 23.19 9 17651 124 53331282
HIV antibody positive 38.45 23.19 6 17654 5 53331401
Anxiety 38.39 23.19 9 17651 196695 53134711
Coarctation of the aorta 37.66 23.19 12 17648 576 53330830
Complication of delivery 37.11 23.19 9 17651 154 53331252
Product dose omission issue 36.94 23.19 9 17651 191611 53139795
Swelling 36.79 23.19 9 17651 191096 53140310
Ultrasound scan abnormal 36.73 23.19 10 17650 275 53331131
Neonatal aspiration 36.52 23.19 9 17651 165 53331241
Congenital skin dimples 36.42 23.19 9 17651 167 53331239
Congenital genital malformation female 35.93 23.19 7 17653 39 53331367
Condition aggravated 35.32 23.19 28 17632 297106 53034300
Congenital hydrocephalus 35.23 23.19 9 17651 192 53331214
Adrenogenital syndrome 35.07 23.19 7 17653 45 53331361
Alopecia 34.93 23.19 17 17643 234566 53096840
Placenta praevia 34.88 23.19 13 17647 1001 53330405
Rash maculo-papular 34.79 23.19 46 17614 29703 53301703
Cleft palate 34.63 23.19 13 17647 1021 53330385
AIDS cholangiopathy 34.57 23.19 6 17654 15 53331391
Placental insufficiency 34.42 23.19 14 17646 1362 53330044
Single umbilical artery 34.31 23.19 9 17651 214 53331192
Ventricular hypertrophy 34.02 23.19 19 17641 3746 53327660
Ergot poisoning 33.95 23.19 9 17651 223 53331183
Pruritus 33.30 23.19 29 17631 293803 53037603
Gestational hypertension 33.28 23.19 16 17644 2317 53329089
Dizziness 33.07 23.19 45 17615 372214 52959192
Micrognathia 32.90 23.19 9 17651 252 53331154
Weight increased 31.73 23.19 14 17646 204553 53126853
Constipation 31.70 23.19 13 17647 198399 53133007
Hepatitis 31.58 23.19 47 17613 33847 53297559
Congenital anomaly in offspring 31.30 23.19 8 17652 171 53331235
Multiple-drug resistance 31.08 23.19 17 17643 3218 53328188
Fallot's tetralogy 30.80 23.19 7 17653 89 53331317
Alpha 1 foetoprotein increased 30.79 23.19 8 17652 183 53331223
Haemorrhage in pregnancy 30.76 23.19 14 17646 1791 53329615
Congenital ectopic bladder 30.73 23.19 7 17653 90 53331316
Hydrocephalus 30.66 23.19 20 17640 5216 53326190
Ectopic pregnancy 30.58 23.19 16 17644 2771 53328635
Fanconi syndrome acquired 30.51 23.19 12 17648 1069 53330337
Pulmonary valve stenosis 30.32 23.19 9 17651 340 53331066
Acute lymphocytic leukaemia 30.16 23.19 16 17644 2849 53328557
Foetal heart rate abnormal 30.07 23.19 10 17650 550 53330856
Infection 29.66 23.19 10 17650 172195 53159211
Hyperandrogenism 29.66 23.19 7 17653 106 53331300
Cleft lip and palate 29.49 23.19 9 17651 374 53331032
Proteinuria 29.36 23.19 33 17627 18035 53313371
HIV test positive 29.14 23.19 6 17654 46 53331360
Drug hypersensitivity 29.07 23.19 27 17633 265215 53066191
Feeling abnormal 28.87 23.19 5 17655 135296 53196110
Foetal cardiac disorder 28.70 23.19 6 17654 50 53331356
Neutropenia 28.34 23.19 116 17544 159069 53172337
Neonatal hepatomegaly 28.14 23.19 5 17655 15 53331391
Cardiac malposition 28.09 23.19 6 17654 56 53331350
Completed suicide 27.61 23.19 6 17654 138195 53193211
Respiratory distress 27.44 23.19 44 17616 33783 53297623
Congenital musculoskeletal anomaly 27.29 23.19 9 17651 482 53330924
Aspartate aminotransferase increased 27.27 23.19 75 17585 83954 53247452
Alanine aminotransferase increased 27.10 23.19 81 17579 95014 53236392
Arnold-Chiari malformation 26.68 23.19 9 17651 517 53330889
Cerebral toxoplasmosis 26.40 23.19 10 17650 805 53330601
Necrotising enterocolitis neonatal 26.01 23.19 7 17653 184 53331222
Cholestasis of pregnancy 25.85 23.19 11 17649 1198 53330208
Chlamydial infection 25.80 23.19 8 17652 351 53331055
Genotype drug resistance test positive 25.76 23.19 9 17651 575 53330831
Stevens-Johnson syndrome 25.69 23.19 36 17624 24546 53306860
Hepatic displacement 25.64 23.19 5 17655 28 53331378
Acute HIV infection 25.64 23.19 5 17655 28 53331378
Musculoskeletal stiffness 25.37 23.19 5 17655 123363 53208043
Death 25.35 23.19 50 17610 357182 52974224
Heart disease congenital 25.23 23.19 11 17649 1272 53330134
Arthropathy 24.73 23.19 8 17652 141445 53189961
Spinocerebellar disorder 24.68 23.19 5 17655 35 53331371
Induced labour 24.48 23.19 10 17650 983 53330423
Febrile neutropenia 24.42 23.19 3 17657 104933 53226473
Back pain 24.32 23.19 25 17635 234222 53097184
Delivery 24.02 23.19 9 17651 703 53330703
Drug intolerance 23.61 23.19 20 17640 205473 53125933
Diastasis recti abdominis 23.57 23.19 5 17655 45 53331361
Pulmonary artery stenosis congenital 23.42 23.19 7 17653 271 53331135
Amniotic fluid volume decreased 23.21 23.19 8 17652 491 53330915

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 1461.11 14.92 645 19841 40656 32452384
Lipodystrophy acquired 886.40 14.92 242 20244 3440 32489600
Exposure during pregnancy 879.08 14.92 297 20189 8932 32484108
Virologic failure 610.03 14.92 182 20304 3605 32489435
Viral mutation identified 609.90 14.92 173 20313 2846 32490194
Mitochondrial toxicity 541.60 14.92 153 20333 2477 32490563
Pathogen resistance 508.49 14.92 200 20286 9310 32483730
Premature baby 501.70 14.92 241 20245 18277 32474763
Immune reconstitution inflammatory syndrome 476.09 14.92 191 20295 9368 32483672
Eyelid ptosis 369.66 14.92 137 20349 5405 32487635
Drug resistance 254.06 14.92 166 20320 22799 32470241
Progressive external ophthalmoplegia 250.25 14.92 72 20414 1246 32491794
Pinealoblastoma 247.99 14.92 49 20437 133 32492907
Diplopia 243.39 14.92 137 20349 14375 32478665
Maternal drugs affecting foetus 197.50 14.92 81 20405 4196 32488844
Lipoatrophy 194.67 14.92 51 20435 610 32492430
Hypertriglyceridaemia 142.59 14.92 81 20405 8638 32484402
Blood lactic acid increased 140.95 14.92 72 20414 6209 32486831
HIV infection 133.49 14.92 49 20437 1877 32491163
Dandy-Walker syndrome 133.20 14.92 28 20458 113 32492927
Anaemia 116.95 14.92 357 20129 223267 32269773
Caesarean section 114.27 14.92 45 20441 2094 32490946
Neonatal disorder 111.70 14.92 36 20450 925 32492115
Hyperlactacidaemia 111.30 14.92 49 20437 3025 32490015
Hepatic fibrosis 109.84 14.92 51 20435 3567 32489473
Low birth weight baby 109.07 14.92 63 20423 6931 32486109
Small for dates baby 106.66 14.92 49 20437 3344 32489696
Anaemia macrocytic 97.17 14.92 43 20443 2687 32490353
Volvulus 92.28 14.92 34 20452 1316 32491724
Congenital anomaly 90.83 14.92 34 20452 1376 32491664
Ophthalmoplegia 89.89 14.92 34 20452 1417 32491623
Trisomy 21 82.87 14.92 25 20461 513 32492527
Pregnancy 79.41 14.92 21 20465 261 32492779
Blood HIV RNA increased 79.35 14.92 32 20454 1585 32491455
CSF HIV escape syndrome 79.17 14.92 19 20467 154 32492886
Off label use 77.34 14.92 49 20437 306271 32186769
Polydactyly 76.50 14.92 29 20457 1216 32491824
Ventricular septal defect 75.49 14.92 40 20446 3717 32489323
Anaemia neonatal 71.91 14.92 20 20466 304 32492736
Congenital central nervous system anomaly 70.35 14.92 21 20465 415 32492625
CD4 lymphocytes decreased 70.00 14.92 32 20454 2158 32490882
Osteonecrosis 67.90 14.92 67 20419 16555 32476485
Extraocular muscle paresis 65.85 14.92 21 20465 521 32492519
Hyperlipidaemia 63.98 14.92 61 20425 14450 32478590
HIV-associated neurocognitive disorder 63.67 14.92 19 20467 375 32492665
Hypospadias 63.32 14.92 33 20453 2964 32490076
Fall 62.19 14.92 23 20463 196178 32296862
Atrial septal defect 61.52 14.92 44 20442 6981 32486059
Human immunodeficiency virus transmission 61.43 14.92 12 20474 30 32493010
Meningomyelocele 60.49 14.92 16 20470 199 32492841
Speech disorder developmental 60.41 14.92 27 20459 1727 32491313
Cryptorchism 57.89 14.92 27 20459 1907 32491133
Congenital hydronephrosis 56.60 14.92 20 20466 685 32492355
Drug-induced liver injury 55.41 14.92 72 20414 23991 32469049
Pneumonia 55.08 14.92 87 20399 355165 32137875
Foetal distress syndrome 54.99 14.92 22 20464 1067 32491973
Hydrocele 54.30 14.92 27 20459 2197 32490843
Cardiac murmur 53.87 14.92 41 20445 7150 32485890
Viral load increased 53.48 14.92 30 20456 3120 32489920
Kaposi's sarcoma 52.83 14.92 21 20465 1001 32492039
Patent ductus arteriosus 52.30 14.92 30 20456 3255 32489785
Drug ineffective 51.27 14.92 103 20383 383374 32109666
Death 50.07 14.92 104 20382 382413 32110627
Optic nerve neoplasm 49.86 14.92 10 20476 30 32493010
Foetal growth restriction 49.25 14.92 31 20455 3981 32489059
Treatment noncompliance 48.55 14.92 72 20414 27130 32465910
Pain 47.24 14.92 30 20456 187526 32305514
Chordee 46.76 14.92 11 20475 81 32492959
Portal hypertension 46.41 14.92 30 20456 4034 32489006
Mitochondrial myopathy 45.66 14.92 13 20473 216 32492824
Aspartate aminotransferase increased 45.26 14.92 117 20369 66312 32426728
Congenital neoplasm 44.88 14.92 9 20477 27 32493013
Nodular regenerative hyperplasia 43.93 14.92 17 20469 754 32492286
Multiple-drug resistance 43.44 14.92 28 20458 3747 32489293
Product use in unapproved indication 43.29 14.92 3 20483 87201 32405839
Acquired immunodeficiency syndrome 43.09 14.92 15 20471 491 32492549
Blood antidiuretic hormone increased 42.71 14.92 10 20476 72 32492968
Splenomegaly 42.54 14.92 49 20437 14428 32478612
Macrocephaly 42.50 14.92 14 20472 386 32492654
Dyslipidaemia 42.45 14.92 35 20451 6848 32486192
Product dose omission issue 42.15 14.92 7 20479 102568 32390472
Lipohypertrophy 41.05 14.92 13 20473 315 32492725
Hypotension 40.45 14.92 46 20440 216064 32276976
Osteoporotic fracture 40.00 14.92 18 20468 1170 32491870
Atrial fibrillation 39.87 14.92 12 20474 116692 32376348
Death neonatal 39.41 14.92 13 20473 360 32492680
Neurodevelopmental disorder 39.20 14.92 11 20475 173 32492867
Developmental delay 39.18 14.92 23 20463 2605 32490435
Alanine aminotransferase increased 38.67 14.92 123 20363 78356 32414684
Rhabdomyosarcoma 38.66 14.92 9 20477 63 32492977
Malaria 38.44 14.92 12 20474 277 32492763
Blood creatine phosphokinase increased 38.36 14.92 87 20399 45389 32447651
Malignant neoplasm progression 38.10 14.92 3 20483 78493 32414547
Febrile neutropenia 37.87 14.92 14 20472 119552 32373488
Adrenogenital syndrome 37.72 14.92 9 20477 71 32492969
Congenital naevus 37.53 14.92 8 20478 35 32493005
Constipation 36.47 14.92 17 20469 126356 32366684
Lymphadenopathy 36.41 14.92 63 20423 27019 32466021
Acquired gene mutation 36.06 14.92 17 20469 1230 32491810
Blood pressure increased 35.95 14.92 4 20482 79350 32413690
Blood pyruvic acid increased 35.69 14.92 7 20479 18 32493022
Dyspnoea 35.36 14.92 114 20372 361931 32131109
Limb deformity 35.35 14.92 13 20473 500 32492540
Hepatomegaly 35.20 14.92 38 20448 10419 32482621
Hypertonia 35.10 14.92 27 20459 4782 32488258
Oesophageal candidiasis 34.91 14.92 26 20460 4388 32488652
Normal newborn 34.32 14.92 10 20476 181 32492859
Pulmonary tuberculosis 34.22 14.92 27 20459 4962 32488078
Congenital cytomegalovirus infection 33.97 14.92 7 20479 25 32493015
Astrocytoma, low grade 33.88 14.92 8 20478 60 32492980
Peripheral swelling 32.11 14.92 3 20483 68342 32424698
Neutropenia neonatal 32.10 14.92 13 20473 651 32492389
Mycobacterium avium complex infection 32 14.92 21 20465 2896 32490144
Heart disease congenital 31.53 14.92 16 20470 1359 32491681
Post streptococcal glomerulonephritis 31.29 14.92 7 20479 40 32493000
Neonatal hyponatraemia 31.22 14.92 8 20478 87 32492953
Macrocytosis 31.15 14.92 14 20472 907 32492133
Exomphalos 30.94 14.92 9 20477 162 32492878
White matter lesion 30.85 14.92 13 20473 720 32492320
Cerebral ventricle dilatation 30.83 14.92 14 20472 929 32492111
Completed suicide 30.72 14.92 10 20476 92507 32400533
Congenital hydrocephalus 30.13 14.92 8 20478 101 32492939
Diaphragmatic hernia 30.11 14.92 10 20476 283 32492757
Cardiac arrest 29.53 14.92 12 20474 96764 32396276
Blood triglycerides increased 29.46 14.92 41 20445 14578 32478462
Cerebrovascular accident 29.25 14.92 9 20477 86311 32406729
Prenatal screening test abnormal 29.21 14.92 6 20480 21 32493019
Congenital mitral valve incompetence 28.50 14.92 8 20478 126 32492914
Live birth 28.38 14.92 9 20477 219 32492821
Gamma-glutamyltransferase increased 28.34 14.92 61 20425 30721 32462319
Cytomegalovirus chorioretinitis 27.95 14.92 21 20465 3591 32489449
Congenital anaemia 27.08 14.92 5 20481 8 32493032
Meningitis cryptococcal 26.94 14.92 17 20469 2192 32490848
Talipes 26.86 14.92 16 20470 1862 32491178
Sudden infant death syndrome 26.85 14.92 8 20478 157 32492883
Nephropathy toxic 26.34 14.92 35 20451 11911 32481129
Jaundice 26.23 14.92 63 20423 34095 32458945
Facial wasting 26.16 14.92 8 20478 172 32492868
Retinal toxicity 26.11 14.92 10 20476 431 32492609
Lactic acidosis 25.91 14.92 62 20424 33474 32459566
Congenital syphilis 25.74 14.92 5 20481 12 32493028
Fatigue 25.56 14.92 124 20362 350577 32142463
Strabismus 25.38 14.92 14 20472 1409 32491631
Ear malformation 25.23 14.92 9 20477 317 32492723
Neonatal asphyxia 25.09 14.92 9 20477 322 32492718
Torsade de pointes 25.05 14.92 27 20459 7388 32485652
Hemivertebra 25.01 14.92 7 20479 109 32492931
Enophthalmos 24.93 14.92 5 20481 15 32493025
Tuberculoid leprosy 24.75 14.92 6 20480 51 32492989
Mitochondrial cytopathy 24.58 14.92 8 20478 212 32492828
Sickle cell anaemia 24.41 14.92 8 20478 217 32492823
Gastroschisis 24.38 14.92 7 20479 120 32492920
Cachexia 24.22 14.92 26 20460 7083 32485957
Cerebellar hypoplasia 24.02 14.92 5 20481 19 32493021
Ultrasound antenatal screen abnormal 23.44 14.92 6 20480 65 32492975
Nervous system disorder 23.37 14.92 36 20450 14013 32479027
Hepatitis C virus test 22.88 14.92 6 20480 72 32492968
Drug abuse 22.82 14.92 11 20475 80232 32412808
Anogenital warts 22.74 14.92 10 20476 615 32492425
Maternal condition affecting foetus 22.71 14.92 4 20482 4 32493036
Late developer 22.71 14.92 4 20482 4 32493036
CD4 lymphocytes increased 22.69 14.92 8 20478 272 32492768
Maternal exposure during pregnancy 22.47 14.92 20 20466 4337 32488703
Pancytopenia 22.31 14.92 115 20371 91120 32401920
Hyperbilirubinaemia 22.21 14.92 40 20446 17690 32475350
Congenital aortic anomaly 21.52 14.92 6 20480 92 32492948
Tuberculosis 21.47 14.92 27 20459 8702 32484338
Lagophthalmos 21.46 14.92 6 20480 93 32492947
Birth trauma 21.44 14.92 4 20482 7 32493033
Meconium ileus 21.35 14.92 5 20481 36 32493004
Oesophageal atresia 21.30 14.92 9 20477 502 32492538
Transaminases increased 21.23 14.92 48 20438 24980 32468060
Cleft lip 21.18 14.92 8 20478 332 32492708
Stillbirth 21.15 14.92 7 20479 196 32492844
Hydronephrosis 21.14 14.92 28 20458 9495 32483545
Drug interaction 21.08 14.92 220 20266 217965 32275075
Encephalitis 20.96 14.92 24 20462 7020 32486020
Polyneuropathy chronic 20.78 14.92 5 20481 41 32492999
Hepatitis 20.72 14.92 46 20440 23647 32469393
HIV wasting syndrome 20.68 14.92 6 20480 107 32492933
ADAMTS13 activity decreased 20.57 14.92 6 20480 109 32492931
Perinatal HIV infection 20.48 14.92 4 20482 10 32493030
Cryptococcosis 20.48 14.92 14 20472 2066 32490974
Hepatosplenomegaly 20.30 14.92 18 20468 3885 32489155
Hypercholesterolaemia 20.15 14.92 25 20461 7949 32485091
Cerebral disorder 19.99 14.92 15 20471 2560 32490480
Lactate pyruvate ratio increased 19.94 14.92 4 20482 12 32493028
Attention deficit hyperactivity disorder 19.70 14.92 14 20472 2198 32490842
Hepatitis B 19.53 14.92 22 20464 6319 32486721
Skull malformation 19.32 14.92 8 20478 424 32492616
Nasopharyngitis 19.30 14.92 8 20478 63779 32429261
Meconium peritonitis 19.26 14.92 4 20482 15 32493025
Leukopenia 19.25 14.92 82 20404 60040 32433000
Aplasia cutis congenita 19.16 14.92 6 20480 140 32492900
Congenital retinoblastoma 19.11 14.92 3 20483 0 32493040
Vision abnormal neonatal 19.11 14.92 3 20483 0 32493040
Neonatal intestinal obstruction 19.11 14.92 3 20483 0 32493040
Oral candidiasis 18.87 14.92 30 20456 11997 32481043
Sickle cell disease 18.81 14.92 6 20480 149 32492891
Meningitis tuberculous 18.62 14.92 9 20477 688 32492352
Central nervous system lymphoma 18.45 14.92 10 20476 972 32492068
Rheumatoid arthritis 18.37 14.92 3 20483 44541 32448499
Lymphocytic infiltration 18.33 14.92 9 20477 712 32492328
Heart transplant rejection 18.31 14.92 11 20475 1300 32491740
Back pain 18.28 14.92 26 20460 111027 32382013
Vanishing bile duct syndrome 18.27 14.92 9 20477 717 32492323
Congenital skin dimples 18.26 14.92 6 20480 164 32492876
Gynaecomastia 18.16 14.92 25 20461 8794 32484246
Red blood cell schistocytes present 18.16 14.92 7 20479 307 32492733
Neck deformity 18.16 14.92 5 20481 73 32492967
Disease progression 17.89 14.92 17 20469 86845 32406195
Acute lymphocytic leukaemia 17.85 14.92 16 20470 3502 32489538
Feeling abnormal 17.61 14.92 8 20478 60415 32432625
Congenital hepatomegaly 17.57 14.92 4 20482 25 32493015
Hepatic function abnormal 17.44 14.92 65 20421 44775 32448265
Congenital abdominal hernia 17.44 14.92 4 20482 26 32493014
Abnormal dreams 17.22 14.92 24 20462 8540 32484500
Posterior cortical atrophy 17.18 14.92 4 20482 28 32493012
Anaemia megaloblastic 17.13 14.92 6 20480 200 32492840
Gonadal dysgenesis 17.03 14.92 3 20483 3 32493037
Cardio-respiratory arrest 16.98 14.92 7 20479 55982 32437058
Pneumocystis jirovecii pneumonia 16.91 14.92 37 20449 18833 32474207
Epistaxis 16.91 14.92 7 20479 55848 32437192
Osteoma 16.83 14.92 4 20482 31 32493009
International normalised ratio increased 16.81 14.92 5 20481 49030 32444010
Myelosuppression 16.79 14.92 28 20458 11648 32481392
Blood insulin increased 16.76 14.92 7 20479 379 32492661
Spine malformation 16.67 14.92 6 20480 217 32492823
Thalassaemia alpha 16.60 14.92 4 20482 33 32493007
Cerebral toxoplasmosis 16.48 14.92 11 20475 1561 32491479
Joint swelling 16.46 14.92 6 20480 51729 32441311
Hyperkalaemia 16.40 14.92 12 20474 69738 32423302
Congenital hearing disorder 16.37 14.92 5 20481 107 32492933
Abdominal hernia 16.37 14.92 14 20472 2879 32490161
Oxygen saturation decreased 16.31 14.92 5 20481 48094 32444946
Treatment failure 16.27 14.92 58 20428 39105 32453935
Genitalia external ambiguous 16.19 14.92 6 20480 236 32492804
Hypotonia 16.15 14.92 22 20464 7665 32485375
Trisomy 18 16.02 14.92 6 20480 243 32492797
Congenital diaphragmatic hernia 15.91 14.92 6 20480 248 32492792
Pyelocaliectasis 15.90 14.92 10 20476 1282 32491758
Lipase increased 15.79 14.92 24 20462 9233 32483807
Total lung capacity decreased 15.67 14.92 8 20478 688 32492352
Neonatal respiratory distress syndrome 15.61 14.92 16 20470 4131 32488909
CSF virus identified 15.57 14.92 4 20482 44 32492996
Papilloma 15.53 14.92 5 20481 128 32492912
Proteinuria 15.52 14.92 34 20452 17321 32475719
Twin pregnancy 15.50 14.92 3 20483 7 32493033
Scleral discolouration 15.44 14.92 6 20480 269 32492771
Long QT syndrome 15.43 14.92 13 20473 2618 32490422
Confusional state 15.39 14.92 43 20443 143072 32349968
Progressive multifocal leukoencephalopathy 15.26 14.92 24 20462 9507 32483533
Hepatotoxicity 15.20 14.92 36 20450 19301 32473739
Subacute sclerosing panencephalitis 15.18 14.92 4 20482 49 32492991
Coarctation of the aorta 14.98 14.92 7 20479 496 32492544
Neutropenia 14.98 14.92 146 20340 142029 32351011
Reversible ischaemic neurological deficit 14.96 14.92 4 20482 52 32492988
Congenital nystagmus 14.96 14.92 3 20483 9 32493031
Retinal telangiectasia 14.96 14.92 3 20483 9 32493031
Immune reconstitution inflammatory syndrome associated tuberculosis 14.96 14.92 7 20479 498 32492542

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 EPC N0000175462 Human Immunodeficiency Virus Nucleoside Analog Reverse Transcriptase Inhibitor
CHEBI has role CHEBI:35221 antimetabolite
CHEBI has role CHEBI:36044 anti-virus drug
CHEBI has role CHEBI:53756 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: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
5-hydroxytryptamine receptor 2A GPCR IC50 5.51 WOMBAT-PK
Thymidine kinase, cytosolic Kinase Ki 5.54 CHEMBL
Thymidylate kinase Kinase Ki 4.55 WOMBAT-PK
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 4 WOMBAT-PK
Reverse transcriptase/RNaseH Enzyme INHIBITOR IC50 8.52 CHEMBL 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
Reverse transcriptase Enzyme IC50 4.74 CHEMBL
Thymidylate kinase Kinase Ki 4.55 CHEMBL
Thymidine kinase Kinase IC50 4.90 CHEMBL
Reverse transcriptase protein Unclassified IC50 5.44 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
D015215 MESH_DESCRIPTOR_UI
35370 PUBCHEM_CID
4825 IUPHAR_LIGAND_ID
6118 INN_ID
4B9XT59T7S UNII
11413 RXNORM
5703 MMSL
71929 MMSL
d00034 MMSL
003019 NDDF
27479000 SNOMEDCT_US
387151007 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
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
Lamivudine and Zidovudine HUMAN PRESCRIPTION DRUG LABEL 2 63629-4872 TABLET, FILM COATED 300 mg ORAL ANDA 24 sections