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Drug

D0113 | Stavudine

Molecular Formula C10H12N2O4
Molecular Weight 224.21
Structure
State solid
Clearance * Renal cl=272 mL/min [Healthy subjects receiving 80 mg PO] * 594 +/- 164 mL/min [HIV-infected adult and pediatric patients following 1-hour IV infusion] * 9.75 +/- 3.76 mL/min/kg [HIV- Exposed or -Infected Pediatric Patients(Age 5 weeks – 15 years) following 1-hour IV infusion]
Volume of distribution * 46 ± 21 L
Protein binding Negligible
Half life 0.8-1.5 hours (in adults)
Absorption Following oral administration, stavudine is rapidly absorbed (bioavailability is 68-104%).
Trade names Zerit
Description Antiretroviral; dideoxynucleoside analog; inhibits reverse transcriptase

J

J05AR07 Stavudine, lamivudine and nevirapine


[J05AR] Antivirals for treatment of HIV infections, combinations


[J05A] DIRECT ACTING ANTIVIRALS


[J05] ANTIVIRALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use

J05AF04 Stavudine


[J05AF] Nucleoside and nucleotide reverse transcriptase inhibitors


[J05A] DIRECT ACTING ANTIVIRALS


[J05] ANTIVIRALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use

Toxicity Dose Time Species Model Method Action Positive criterion Reference
MITOCHONDRIAL DNA depletion 197
MITOCHONDRIAL DNA METABOLIC PROCESS 194

Target Dose Time Species Model Method Action Positive criterion Reference
DNA polymerase gamma 194

Pictogram Signal Statements Precautionary Statement Codes
Danger

Aggregated GHS information provided by 3 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


H302 (66.67%): Harmful if swallowed [Warning Acute toxicity, oral]


H315 (33.33%): Causes skin irritation [Warning Skin corrosion/irritation]


H319 (33.33%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]


H335 (33.33%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure


Respiratory tract irritation]


H341 (33.33%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]


H361 (33.33%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]


H362 (33.33%): May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation]


H372 (33.33%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


 P201, P202, P260, P261, P263, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P314, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

Organism Test type Route Dose (normalized dose) Effect Source
mouse LD50 oral 1gm/kg (1000mg/kg) Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 40, Pg. 1944, 1998.
rat LD50 intravenous > 1200mg/kg (1200mg/kg) Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 40, Pg. 1944, 1998.
dog LD oral > 2gm/kg (2000mg/kg) gastrointestinal: nausea or vomiting Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 40, Pg. 1944, 1998.
dog LD intravenous > 1680mg/kg (1680mg/kg) gastrointestinal: nausea or vomiting Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 40, Pg. 1944, 1998.
rat LD50 oral 4gm/kg (4000mg/kg) Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 40, Pg. 1944, 1998.
mouse LD50 intravenous 1gm/kg (1000mg/kg) Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 40, Pg. 1944, 1998.

  • Immunodeficiency

  • Infection

  • Lactic acidosis

  • Pancreatitis

  • Dermatitis

  • Diarrhoea

  • Headache

  • Nausea

  • Neurological symptom

  • Neuropathy peripheral

  • Rash

  • Vomiting

    • 056S175 1-((2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 1-((2R,5S)-5-Hydroxymethyl-2,5-dihydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
    1-(2,3-Dideoxy-.beta.-D-glycero-pent-2-enofuranosyl)thymine 1-(2,3-Dideoxy-beta-D-glycero-2-pentenofuranosyl)thymine 1-(2,3-Dideoxy-beta-D-glycero-pent-2-enofuranosyl)thymine
    1-(5-Hydroxymethyl-2,5-dihydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 1-(5-Hydroxymethyl-2,5-dihydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione (ddeThd) 1-(cis-5-(Hydroxymethyl)-2,5-dihydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
    1-[(2R,5S)-2,5-Dihydro-5-(hydroxymethyl)-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione 1-[(2R,5S)-5-(HYDROXYMETHYL)-2,5-DIHYDROFURAN-2-YL]-5-METHYL-1,2,3,4-TETRAHYDROPYRIMIDINE-2,4-DIONE 1-[(2R,5S)-5-(Hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4-(1H,3H)-dione
    1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione 1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione 1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4-dione
    1-[5-(hydroxymethyl)-2,5-dihydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione & Colony-stimulating factor 2 2'',3''-didehydro-3''-deoxythymidine 2'',3''-dideoxy-2'',3''-didehydrothymidine
    2',3'-Anhydrothymidine 2',3'-Anhydrothymidine 2',3'-DIDEHYDRO-3'-DEOXYTHYMIDINE (DDI)
    2',3'-Didehydro-3'-deoxy-thymidine 2',3'-Didehydro-3'-deoxythimidine 2',3'-Didehydro-3'-deoxythymidine
    2',3'-Didehydro-3'-deoxythymidine, >=98% (TLC) 2',3'-didehydro-2',3'-dideoxythymidine 2'-Thymidinene, 3'-deoxy-
    220020-60-0 3''-deoxy-2'',3''-didehydrothymidine 3''-deoxy-2''-thymidine
    3'- Azido-3'-deoxythymidine & Granulocyte-macrophage colony-stimulating factor 3'-Deoxy-2',3'-didehydro-D-thymidine 3'-Deoxy-2',3'-didehydrothymidine
    3'-Deoxy-2',3'-didehydrothymidine, 98% 3'-Deoxy-2'-thymidinene 3'-deoxythymidin-2'-ene
    3056-17-5 A820433 AB0013374
    AB00383018_18 AB1009564 ABP000995
    AC-5263 AKOS005622554 ANW-26914
    BBL033763 BCP02952 BDBM50013111
    BIDD:GT0082 BMY 27857 BMY-27857
    BO9LE4QFZF BR-77340 BRN 0618327
    C07312 CAS-3056-17-5 CCG-100902
    CHEBI:63581 CHEMBL991 CPD000058350
    CPD000673569 CS-1872 CTK8B1419
    D 1413 D 4T D 4T (nucleoside)
    D00445 D3580 D4T & GM-CSF
    D4TMBY-27857-3 DB00649 DSSTox_CID_3819
    DSSTox_GSID_23819 DSSTox_RID_77198 DTXSID1023819
    Dideoxydidehydrothymidine EU-0100336 Estavudina
    Estavudina [INN-Spanish] FT-0082665 FT-0603625
    H940 HMS2051O20 HMS2234C10
    HMS3039O05 HMS3259L21 HMS3261C13
    HMS3428C07 HMS3714N22 HSDB 7338
    HY-B0116 J-700246 J10003
    KS-00000H34 KS-1115 LP00336
    LS-1160 Lopac0_000336 MCULE-9252477726
    MFCD00132921 MLS000028546 MLS000759504
    MLS001055348 MLS001077292 MLS001424091
    MLS006011922 NC00152 NC00684
    NCGC00023212-03 NCGC00023212-04 NCGC00023212-05
    NCGC00023212-07 NCGC00023212-08 NCGC00023212-09
    NCGC00023212-10 NCGC00023212-11 NCGC00023212-12
    NCGC00023212-13 NCGC00023212-14 NCGC00254372-01
    NCGC00258944-01 NCGC00261021-01 NSC 163661
    NSC-759897 NSC163661 NSC759897
    Opera_ID_1281 Pharmakon1600-01502339 PubChem5805
    Q-201742 Q423984 S-2155
    SAM001246729 SAM002589948 SC-03292
    SCHEMBL38661 SMR000058350 SMR000673569
    SR-01000075802 SR-01000075802-1 SR-01000075802-4
    STK801888 STV Sanilvudine (JAN)
    Stavudin Stavudine (USAN/INN) Stavudine (d4T)
    Stavudine [USAN:BAN:INN] Stavudine [USAN:INN:BAN] Stavudine [USAN:USP:INN:BAN]
    Stavudine for system suitability, European Pharmacopoeia (EP) Reference Standard Stavudine, European Pharmacopoeia (EP) Reference Standard Stavudine, United States Pharmacopeia (USP) Reference Standard
    Stavudinum Stavudinum [INN-Latin] Thymidine, 2',3'-didehydro-, 3'-deoxy-
    Thymidine, 2',3'-didehydro-3'-deoxy- Thymine, 1-(2,3-dideoxy-beta-D-glycero-pent-2-enofuranosyl)- (7CI,8CI) Tox21_110886
    Tox21_110886_1 Tox21_201393 Tox21_300583
    Tox21_500336 UNII-BO9LE4QFZF XNKLLVCARDGLGL-JGVFFNPUSA-N
    Z1695906749 ZINC137884 Zent
    Zerit Zerit (TN) Zerit Xr
    Zerit(TM) Zerut XR cid_18283
    cid_5155 d4T d4T
    ddeThd ddeTyd sanilvudine
    stavudine

    DrugBank Name Stavudine
    DrugBank DB00649
    CAS Number 220020-60-0, 3056-17-5
    PubChem Compound 18283
    KEGG Compound ID C07312
    KEGG Drug D00445
    PubChem.Substance 46506943
    ChEBI 63581
    PharmGKB PA451494
    ChemSpider 17270
    BindingDB 50013111.0
    TTD DAP000172
    Wikipedia Stavudine
    DPD 66

    1. Dykens et al. (2007)
    2. Wyatt et al., 2017
    3. Chan et al. (2005)
    4. Vuda et al. (2016)