stavudine ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
uridine derivatives used as antiviral agents and as antineoplastics 2478 3056-17-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • zerit
  • stavudine
  • sanilvudine
  • staduvine
A dideoxynucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV.
  • Molecular weight: 224.22
  • Formula: C10H12N2O4
  • CLOGP: -0.74
  • LIPINSKI: 0
  • HAC: 6
  • HDO: 2
  • TPSA: 78.87
  • ALOGS: -0.74
  • ROTB: 2

  • Status: OFM

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

Drug dosage:

DoseUnitRoute
80 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 83 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 39 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 5.95 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 82 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.67 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 8.20 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 1 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1.40 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
June 24, 1994 FDA BRISTOL MYERS SQUIBB

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
Pregnancy 387.99 37.45 123 3294 29454 50572253
Drug resistance 382.74 37.45 110 3307 18879 50582828
Viral mutation identified 369.81 37.45 68 3349 1561 50600146
Virologic failure 295.88 37.45 56 3361 1508 50600199
Lipodystrophy acquired 279.32 37.45 52 3365 1277 50600430
Lactic acidosis 271.57 37.45 97 3320 33258 50568449
Immune reconstitution inflammatory syndrome 215.53 37.45 54 3363 5462 50596245
Pathogen resistance 174.82 37.45 46 3371 5643 50596064
Foetal exposure during pregnancy 158.21 37.45 62 3355 27297 50574410
Caesarean section 144.29 37.45 50 3367 15589 50586118
Abortion induced 135.21 37.45 42 3375 9302 50592405
Mitochondrial toxicity 134.84 37.45 23 3394 335 50601372
Portal hypertension 116.61 37.45 30 3387 3362 50598345
Hypertriglyceridaemia 84.97 37.45 26 3391 5465 50596242
Hyperlactacidaemia 81.09 37.45 21 3396 2412 50599295
Acquired gene mutation 80.23 37.45 17 3400 814 50600893
Pregnancy on contraceptive 76.24 37.45 17 3400 1035 50600672
Stillbirth 74.63 37.45 24 3393 5928 50595779
Exposure during pregnancy 74.29 37.45 63 3354 120952 50480755
Normal newborn 71.88 37.45 24 3393 6667 50595040
Abortion spontaneous 71.78 37.45 41 3376 41731 50559976
Live birth 70.19 37.45 30 3387 16378 50585329
Premature delivery 65.64 37.45 32 3385 23631 50578076
Fat tissue increased 62.78 37.45 13 3404 556 50601151
Blood lactic acid increased 59.85 37.45 20 3397 5565 50596142
Lipoatrophy 57.84 37.45 11 3406 302 50601405
Premature rupture of membranes 55.51 37.45 18 3399 4562 50597145
Premature baby 54.48 37.45 26 3391 18311 50583396
Blood HIV RNA increased 40.48 37.45 9 3408 540 50601167

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
Lipodystrophy acquired 906.84 22.46 195 6479 2899 29564954
Mitochondrial toxicity 678.23 22.46 147 6527 2264 29565589
Eyelid ptosis 527.64 22.46 139 6535 5047 29562806
Immune reconstitution inflammatory syndrome 410.73 22.46 125 6549 7677 29560176
Diplopia 358.29 22.46 129 6545 13389 29554464
Progressive external ophthalmoplegia 323.96 22.46 72 6602 1245 29566608
Virologic failure 231.43 22.46 64 6610 2783 29565070
Foetal exposure during pregnancy 183.77 22.46 107 6567 33760 29534093
Drug resistance 181.02 22.46 91 6583 21449 29546404
Blood lactic acid increased 137.58 22.46 51 6623 5715 29562138
Ophthalmoplegia 132.93 22.46 37 6637 1645 29566208
Lipoatrophy 132.74 22.46 29 6645 460 29567393
Hypertriglyceridaemia 131.60 22.46 53 6621 7422 29560431
Viral mutation identified 127.06 22.46 39 6635 2449 29565404
Hepatic fibrosis 112.82 22.46 38 6636 3214 29564639
Osteonecrosis 110.22 22.46 56 6618 13463 29554390
Pathogen resistance 101.04 22.46 45 6629 8071 29559782
Lactic acidosis 88.57 22.46 65 6609 30182 29537671
Portal hypertension 80.09 22.46 30 6644 3456 29564397
Hyperlipidaemia 79.53 22.46 44 6630 12546 29555307
Kaposi's sarcoma 77.54 22.46 21 6653 841 29567012
Dyslipidaemia 70.32 22.46 32 6642 6029 29561824
Facial wasting 70.30 22.46 14 6660 137 29567716
Hyperlactacidaemia 68.71 22.46 25 6649 2653 29565200
Drug-induced liver injury 66.69 22.46 48 6626 21607 29546246
Blood triglycerides increased 60.24 22.46 37 6637 12797 29555056
Acquired gene mutation 52.88 22.46 17 6657 1241 29566612
CD4 lymphocytes decreased 52.77 22.46 18 6656 1580 29566273
Blood bilirubin unconjugated increased 52.07 22.46 14 6660 545 29567308
Premature baby 47.99 22.46 36 6638 17244 29550609
Off label use 47.61 22.46 6 6668 300794 29267059
Mitochondrial myopathy 43.86 22.46 10 6664 194 29567659
Dysphagia 40.99 22.46 56 6618 54870 29512983
Meningitis cryptococcal 40.80 22.46 16 6658 2084 29565769
Progressive multifocal leukoencephalopathy 40.56 22.46 25 6649 8694 29559159
Multiple-drug resistance 40.28 22.46 19 6655 3881 29563972
Trisomy 21 39.35 22.46 11 6663 496 29567357
Enophthalmos 37.47 22.46 6 6668 13 29567840
Basedow's disease 36.09 22.46 7 6667 59 29567794
Pinealoblastoma 34.18 22.46 8 6666 175 29567678
Hypotension 32.94 22.46 3 6671 194351 29373502
Nodular regenerative hyperplasia 31.89 22.46 10 6664 673 29567180
Treatment failure 31.14 22.46 40 6634 36899 29530954
Cytomegalovirus chorioretinitis 31.07 22.46 15 6659 3223 29564630
Heart transplant rejection 30.47 22.46 11 6663 1140 29566713
Pulmonary tuberculosis 29.78 22.46 16 6658 4299 29563554
Gynaecomastia 29.44 22.46 20 6654 8197 29559656
Fall 29.32 22.46 3 6671 177175 29390678
Hepatic cirrhosis 29.23 22.46 25 6649 14419 29553434
Fanconi syndrome acquired 28.78 22.46 12 6662 1830 29566023
Lipohypertrophy 27.76 22.46 7 6667 211 29567642
Lagophthalmos 27.52 22.46 6 6668 94 29567759
Low set ears 27.27 22.46 8 6666 429 29567424
Hepatomegaly 27.18 22.46 20 6654 9297 29558556
Neuropathy peripheral 26.52 22.46 53 6621 70974 29496879
Mycobacterium avium complex infection 26.37 22.46 12 6662 2257 29565596
Drug ineffective 26.34 22.46 26 6648 363144 29204709
Pneumocystis jirovecii pneumonia 26.01 22.46 25 6649 16754 29551099
Glucose tolerance impaired 23.99 22.46 12 6662 2782 29565071
Protrusion tongue 23.69 22.46 6 6668 184 29567669
Central pain syndrome 23.66 22.46 5 6669 67 29567786
Atypical mycobacterial infection 23.55 22.46 8 6666 693 29567160

FDA Adverse Event Reporting System (Geriatric)

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
Lipodystrophy acquired 1173.56 23.73 231 8367 3796 64486338
Mitochondrial toxicity 847.67 23.73 165 8433 2541 64487593
Immune reconstitution inflammatory syndrome 680.92 23.73 183 8415 12287 64477847
Eyelid ptosis 530.25 23.73 142 8456 9383 64480751
Drug resistance 439.82 23.73 168 8430 34934 64455200
Virologic failure 417.30 23.73 96 8502 3370 64486764
Progressive external ophthalmoplegia 367.14 23.73 73 8525 1254 64488880
Diplopia 338.32 23.73 129 8469 26636 64463498
Viral mutation identified 335.97 23.73 80 8518 3266 64486868
Pregnancy 290.62 23.73 108 8490 20757 64469377
Lactic acidosis 260.99 23.73 138 8460 61272 64428862
Lipoatrophy 181.50 23.73 36 8562 609 64489525
Portal hypertension 180.93 23.73 56 8542 6163 64483971
Pathogen resistance 149.55 23.73 58 8540 12485 64477649
Ophthalmoplegia 134.82 23.73 37 8561 2665 64487469
Acquired gene mutation 131.41 23.73 34 8564 1952 64488182
Hepatic fibrosis 124.43 23.73 41 8557 5511 64484623
Osteonecrosis 112.88 23.73 61 8537 28168 64461966
Abortion induced 107.27 23.73 38 8560 6350 64483784
Hyperlactacidaemia 105.46 23.73 35 8563 4809 64485325
Dyslipidaemia 104.03 23.73 41 8557 9201 64480933
Hypertriglyceridaemia 103.07 23.73 43 8555 11162 64478972
Caesarean section 99.47 23.73 42 8556 11232 64478902
CD4 lymphocytes decreased 88.33 23.73 26 8572 2409 64487725
Blood lactic acid increased 79.45 23.73 35 8563 10366 64479768
Facial wasting 77.72 23.73 13 8585 78 64490056
Pulmonary tuberculosis 74.10 23.73 30 8568 7214 64482920
Neuropathy peripheral 73.00 23.73 84 8514 117441 64372693
Drug-induced liver injury 72.39 23.73 56 8542 47587 64442547
Kaposi's sarcoma 70.45 23.73 17 8581 732 64489402
Multiple-drug resistance 70.22 23.73 28 8570 6474 64483660
Pregnancy on contraceptive 69.53 23.73 17 8581 774 64489360
Foetal exposure during pregnancy 69.01 23.73 25 8573 4451 64485683
Fat tissue increased 68.45 23.73 17 8581 826 64489308
Normal newborn 60.00 23.73 24 8574 5593 64484541
Meningitis cryptococcal 58.61 23.73 20 8578 2989 64487145
Nodular regenerative hyperplasia 58.07 23.73 15 8583 855 64489279
Abortion spontaneous 57.69 23.73 38 8560 25105 64465029
Blood bilirubin unconjugated increased 57.28 23.73 15 8583 902 64489232
Hyperlipidaemia 55.84 23.73 36 8562 22940 64467194
Stillbirth 54.92 23.73 20 8578 3613 64486521
Blood triglycerides increased 51.96 23.73 32 8566 18834 64471300
Progressive multifocal leukoencephalopathy 50.40 23.73 31 8567 18201 64471933
Live birth 49.81 23.73 26 8572 11178 64478956
Hepatomegaly 47.42 23.73 29 8569 16853 64473281
Off label use 47.34 23.73 13 8585 632793 63857341
Premature delivery 47.33 23.73 30 8568 18559 64471575
Pancreatitis 46.37 23.73 48 8550 59559 64430575
Mitochondrial myopathy 45.64 23.73 10 8588 279 64489855
Fall 43.97 23.73 3 8595 416823 64073311
Gynaecomastia 41.96 23.73 19 8579 5997 64484137
Basedow's disease 41.28 23.73 9 8589 245 64489889
Stevens-Johnson syndrome 40.91 23.73 35 8563 34214 64455920
Dysphagia 39.23 23.73 59 8539 106753 64383381
Tuberculoma of central nervous system 39.16 23.73 10 8588 544 64489590
Pinealoblastoma 39.06 23.73 7 8591 66 64490068
Pneumocystis jirovecii pneumonia 38.76 23.73 31 8567 27603 64462531
Pain 38.43 23.73 13 8585 553498 63936636
Treatment failure 37.98 23.73 61 8537 116755 64373379
Tuberculosis 35.60 23.73 22 8576 13016 64477118
Ascites 34.61 23.73 42 8556 61959 64428175
Gene mutation 33.49 23.73 12 8586 2070 64488064
Blood HIV RNA increased 33.41 23.73 11 8587 1473 64488661
Mycobacterium avium complex infection 32.50 23.73 14 8584 3926 64486208
Enophthalmos 32.48 23.73 6 8592 68 64490066
Lymphadenopathy 31.72 23.73 35 8563 46651 64443483
Hepatosplenomegaly 31.44 23.73 15 8583 5328 64484806
Oesophageal varices haemorrhage 30.28 23.73 13 8585 3616 64486518
Hyperbilirubinaemia 30.19 23.73 24 8574 21181 64468953
Hepatic cirrhosis 29.63 23.73 26 8572 26272 64463862
Cytomegalovirus chorioretinitis 29.54 23.73 14 8584 4898 64485236
Hepatitis B 28.90 23.73 16 8582 7729 64482405
Hepatic steatosis 27.84 23.73 27 8571 30980 64459154
Gamma-glutamyltransferase increased 27.29 23.73 33 8565 48477 64441657
Immune reconstitution inflammatory syndrome associated tuberculosis 26.92 23.73 8 8590 765 64489369
Hepatic failure 26.89 23.73 35 8563 55359 64434775
Premature rupture of membranes 26.67 23.73 12 8586 3732 64486402
Molluscum contagiosum 26.26 23.73 7 8591 451 64489683
Oligohydramnios 25.44 23.73 11 8587 3113 64487021
Treatment noncompliance 25.15 23.73 30 8568 43452 64446682
Liver disorder 24.80 23.73 33 8565 53318 64436816
Placental insufficiency 24.74 23.73 8 8590 1012 64489122
Fanconi syndrome acquired 24.66 23.73 10 8588 2411 64487723
Hypotension 24.63 23.73 10 8588 380964 64109170
Viral load increased 24.40 23.73 10 8588 2477 64487657
Fatigue 24.38 23.73 39 8559 748691 63741443
Meningitis tuberculous 24.07 23.73 8 8590 1103 64489031

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC J05AF04 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Nucleoside and nucleotide reverse transcriptase inhibitors
ATC J05AR07 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
CHEBI has role CHEBI:22587 antiviral agents
CHEBI has role CHEBI:35221 antimetabolite
CHEBI has role CHEBI:59897 reverse transcriptase inhibitors
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 | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Human immunodeficiency virus infection indication 86406008 DOID:526
Prevention of HIV Infection after Exposure off-label use
Alcoholism contraindication 7200002
Diabetes mellitus contraindication 73211009 DOID:9351
Hyperglycemia contraindication 80394007 DOID:4195
Kidney disease contraindication 90708001 DOID:557
Lactic acidosis contraindication 91273001 DOID:3650
Steatosis of liver contraindication 197321007
Acute pancreatitis contraindication 197456007 DOID:2913
Chronic pancreatitis contraindication 235494005
Disease of liver contraindication 235856003 DOID:409
Peripheral nerve disease contraindication 302226006
Breastfeeding (mother) contraindication 413712001
Obesity contraindication 414916001 DOID:9970




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.3 acidic
pKa2 13.25 acidic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
100MG ZERIT XR BRISTOL MYERS SQUIBB N021453 Dec. 31, 2002 DISCN CAPSULE, EXTENDED RELEASE ORAL 7135465 Feb. 18, 2023 METHOD FOR TREATING HIV-1 INFECTION
37.5MG ZERIT XR BRISTOL MYERS SQUIBB N021453 Dec. 31, 2002 DISCN CAPSULE, EXTENDED RELEASE ORAL 7135465 Feb. 18, 2023 METHOD FOR TREATING HIV-1 INFECTION
50MG ZERIT XR BRISTOL MYERS SQUIBB N021453 Dec. 31, 2002 DISCN CAPSULE, EXTENDED RELEASE ORAL 7135465 Feb. 18, 2023 METHOD FOR TREATING HIV-1 INFECTION
75MG ZERIT XR BRISTOL MYERS SQUIBB N021453 Dec. 31, 2002 DISCN CAPSULE, EXTENDED RELEASE ORAL 7135465 Feb. 18, 2023 METHOD FOR TREATING HIV-1 INFECTION

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Reverse transcriptase/RNaseH Enzyme INHIBITOR EC50 7.30 CHEMBL CHEMBL
Gag-Pol polyprotein Polyprotein WOMBAT-PK
Reverse transcriptase Enzyme IC50 7.22 CHEMBL

External reference:

IDSource
D00445 KEGG_DRUG
4020865 VANDF
C0164662 UMLSCUI
CHEBI:63581 CHEBI
CHEMBL991 ChEMBL_ID
DB00649 DRUGBANK_ID
D018119 MESH_DESCRIPTOR_UI
18283 PUBCHEM_CID
6775 INN_ID
BO9LE4QFZF UNII
203748 RXNORM
1468 MMSL
159782 MMSL
5512 MMSL
d03773 MMSL
004502 NDDF
108690008 SNOMEDCT_US
386895008 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Stavudine HUMAN PRESCRIPTION DRUG LABEL 1 31722-515 CAPSULE 15 mg ORAL ANDA 25 sections
Stavudine HUMAN PRESCRIPTION DRUG LABEL 1 31722-516 CAPSULE 20 mg ORAL ANDA 25 sections
Stavudine HUMAN PRESCRIPTION DRUG LABEL 1 31722-517 CAPSULE 30 mg ORAL ANDA 25 sections
Stavudine HUMAN PRESCRIPTION DRUG LABEL 1 31722-518 CAPSULE 40 mg ORAL ANDA 25 sections
stavudine HUMAN PRESCRIPTION DRUG LABEL 1 53104-0111 FOR SOLUTION 1 mg ORAL ANDA 26 sections
Stavudine HUMAN PRESCRIPTION DRUG LABEL 1 53808-0594 CAPSULE 40 mg ORAL ANDA 25 sections
Stavudine HUMAN PRESCRIPTION DRUG LABEL 1 53808-0595 CAPSULE 40 mg ORAL ANDA 25 sections
ZERIT HUMAN PRESCRIPTION DRUG LABEL 1 53808-0656 CAPSULE, GELATIN COATED 20 mg ORAL NDA 24 sections
ZERIT HUMAN PRESCRIPTION DRUG LABEL 1 53808-0657 CAPSULE, GELATIN COATED 30 mg ORAL NDA 24 sections
ZERIT HUMAN PRESCRIPTION DRUG LABEL 1 53808-0795 CAPSULE, GELATIN COATED 40 mg ORAL NDA 24 sections
Stavudine HUMAN PRESCRIPTION DRUG LABEL 1 53808-0852 CAPSULE 20 mg ORAL ANDA 30 sections