U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C10H12N2O4
Molecular Weight 224.2133
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of STAVUDINE

SMILES

CC1=CN([C@@H]2O[C@H](CO)C=C2)C(=O)NC1=O

InChI

InChIKey=XNKLLVCARDGLGL-JGVFFNPUSA-N
InChI=1S/C10H12N2O4/c1-6-4-12(10(15)11-9(6)14)8-3-2-7(5-13)16-8/h2-4,7-8,13H,5H2,1H3,(H,11,14,15)/t7-,8+/m0/s1

HIDE SMILES / InChI

Molecular Formula C10H12N2O4
Molecular Weight 224.2133
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020412s029,020413s020lbl.pdf

Stavudine is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Stavudine is phosphorylated to active metabolites that compete for incorporation into viral DNA. They inhibit the HIV reverse transcriptase enzyme competitively and act as a chain terminator of DNA synthesis. The lack of a 3'-OH group in the incorporated nucleoside analogue prevents the formation of the 5' to 3' phosphodiester linkage essential for DNA chain elongation, and therefore, the viral DNA growth is terminated. Stavudine inhibits the activity of HIV-1 reverse transcriptase (RT) both by competing with the natural substrate dGTP and by its incorporation into viral DNA. Stavudine is used for the treatment of human immunovirus (HIV) infections. Stavudine is sold under the brand name Zerit among others.

Originator

Curator's Comment: # Bristol-Myers Squibb; Yale University; Yamasa Corporation

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Zerit

Approved Use

ZERIT (stavudine), in combination with other antiretroviral agents, is indicated for the treatment of HIV-1 infection

Launch Date

7.7232957E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
228 ng/mL
100 mg 1 times / day steady-state, oral
dose: 100 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
STAVUDINE unknown
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
536 ng/mL
40 mg 2 times / day steady-state, oral
dose: 40 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
STAVUDINE unknown
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1966 ng × h/mL
100 mg 1 times / day steady-state, oral
dose: 100 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
STAVUDINE unknown
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
2568 ng × h/mL
40 mg 2 times / day steady-state, oral
dose: 40 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
STAVUDINE unknown
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
100%
100 mg 1 times / day steady-state, oral
dose: 100 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
STAVUDINE unknown
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
100%
40 mg 2 times / day steady-state, oral
dose: 40 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
STAVUDINE unknown
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
didanosine(400 mg; 1/day)
efavirenz(600 mg; 1/day)
Sources:
unhealthy, 36.5
n = 285
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: 36.5
Sex: M+F
Population Size: 285
Sources:
Other AEs: Abdominal pain, Asthenia...
Other AEs:
Abdominal pain (19%)
Asthenia (18%)
Headache (25%)
Diarrhea (34%)
Dyspepsia (12%)
Nausea (24%)
Vomiting (12%)
Lipodystrophy (6%)
Arthralgia (6%)
Myalgia (4%)
Abnormal dreams (19%)
Depressive disorders (13%)
Dizziness (26%)
Insomnia (22%)
Neuropathy (13%)
Paresthesia (12%)
Cough increased (9%)
Rhinitis (11%)
Rash (35%)
Skin discoloration (<1%)
Sources:
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
lamivudine
indinavir
Sources:
unhealthy, adult
n = 100
Health Status: unhealthy
Condition: HIV infection
Age Group: adult
Population Size: 100
Sources:
Other AEs: Nausea, Diarrhea...
Other AEs:
Nausea (43 patients)
Diarrhea (34 patients)
Headache (25 patients)
Rash (18 patients)
Vomiting (18 patients)
Neuropathy peripheral (8 patients)
Sources:
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
didanosine
indinavir
Sources:
unhealthy, adult
n = 102
Health Status: unhealthy
Condition: HIV infection
Age Group: adult
Population Size: 102
Sources:
Other AEs: Nausea, Diarrhea...
Other AEs:
Nausea (53 patients)
Diarrhea (45 patients)
Headache (46 patients)
Rash (30 patients)
Vomiting (30 patients)
Neuropathy peripheral (21 patient)
Sources:
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Sources:
unhealthy, adult
n = 412
Health Status: unhealthy
Condition: HIV infection
Age Group: adult
Population Size: 412
Sources:
Other AEs: Headache, Diarrhea...
Other AEs:
Headache (54 patients)
Diarrhea (50 patients)
Neuropathy peripheral (52 patients)
Rash (40 patients)
Nausea and vomiting (39 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Rhinitis 11%
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
didanosine(400 mg; 1/day)
efavirenz(600 mg; 1/day)
Sources:
unhealthy, 36.5
n = 285
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: 36.5
Sex: M+F
Population Size: 285
Sources:
Dyspepsia 12%
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
didanosine(400 mg; 1/day)
efavirenz(600 mg; 1/day)
Sources:
unhealthy, 36.5
n = 285
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: 36.5
Sex: M+F
Population Size: 285
Sources:
Paresthesia 12%
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
didanosine(400 mg; 1/day)
efavirenz(600 mg; 1/day)
Sources:
unhealthy, 36.5
n = 285
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: 36.5
Sex: M+F
Population Size: 285
Sources:
Vomiting 12%
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
didanosine(400 mg; 1/day)
efavirenz(600 mg; 1/day)
Sources:
unhealthy, 36.5
n = 285
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: 36.5
Sex: M+F
Population Size: 285
Sources:
Depressive disorders 13%
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
didanosine(400 mg; 1/day)
efavirenz(600 mg; 1/day)
Sources:
unhealthy, 36.5
n = 285
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: 36.5
Sex: M+F
Population Size: 285
Sources:
Neuropathy 13%
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
didanosine(400 mg; 1/day)
efavirenz(600 mg; 1/day)
Sources:
unhealthy, 36.5
n = 285
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: 36.5
Sex: M+F
Population Size: 285
Sources:
Asthenia 18%
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
didanosine(400 mg; 1/day)
efavirenz(600 mg; 1/day)
Sources:
unhealthy, 36.5
n = 285
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: 36.5
Sex: M+F
Population Size: 285
Sources:
Abdominal pain 19%
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
didanosine(400 mg; 1/day)
efavirenz(600 mg; 1/day)
Sources:
unhealthy, 36.5
n = 285
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: 36.5
Sex: M+F
Population Size: 285
Sources:
Abnormal dreams 19%
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
didanosine(400 mg; 1/day)
efavirenz(600 mg; 1/day)
Sources:
unhealthy, 36.5
n = 285
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: 36.5
Sex: M+F
Population Size: 285
Sources:
Insomnia 22%
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
didanosine(400 mg; 1/day)
efavirenz(600 mg; 1/day)
Sources:
unhealthy, 36.5
n = 285
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: 36.5
Sex: M+F
Population Size: 285
Sources:
Nausea 24%
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
didanosine(400 mg; 1/day)
efavirenz(600 mg; 1/day)
Sources:
unhealthy, 36.5
n = 285
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: 36.5
Sex: M+F
Population Size: 285
Sources:
Headache 25%
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
didanosine(400 mg; 1/day)
efavirenz(600 mg; 1/day)
Sources:
unhealthy, 36.5
n = 285
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: 36.5
Sex: M+F
Population Size: 285
Sources:
Dizziness 26%
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
didanosine(400 mg; 1/day)
efavirenz(600 mg; 1/day)
Sources:
unhealthy, 36.5
n = 285
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: 36.5
Sex: M+F
Population Size: 285
Sources:
Diarrhea 34%
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
didanosine(400 mg; 1/day)
efavirenz(600 mg; 1/day)
Sources:
unhealthy, 36.5
n = 285
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: 36.5
Sex: M+F
Population Size: 285
Sources:
Rash 35%
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
didanosine(400 mg; 1/day)
efavirenz(600 mg; 1/day)
Sources:
unhealthy, 36.5
n = 285
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: 36.5
Sex: M+F
Population Size: 285
Sources:
Myalgia 4%
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
didanosine(400 mg; 1/day)
efavirenz(600 mg; 1/day)
Sources:
unhealthy, 36.5
n = 285
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: 36.5
Sex: M+F
Population Size: 285
Sources:
Arthralgia 6%
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
didanosine(400 mg; 1/day)
efavirenz(600 mg; 1/day)
Sources:
unhealthy, 36.5
n = 285
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: 36.5
Sex: M+F
Population Size: 285
Sources:
Lipodystrophy 6%
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
didanosine(400 mg; 1/day)
efavirenz(600 mg; 1/day)
Sources:
unhealthy, 36.5
n = 285
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: 36.5
Sex: M+F
Population Size: 285
Sources:
Cough increased 9%
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
didanosine(400 mg; 1/day)
efavirenz(600 mg; 1/day)
Sources:
unhealthy, 36.5
n = 285
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: 36.5
Sex: M+F
Population Size: 285
Sources:
Skin discoloration <1%
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
didanosine(400 mg; 1/day)
efavirenz(600 mg; 1/day)
Sources:
unhealthy, 36.5
n = 285
Health Status: unhealthy
Condition: HIV-1 infection
Age Group: 36.5
Sex: M+F
Population Size: 285
Sources:
Rash 18 patients
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
lamivudine
indinavir
Sources:
unhealthy, adult
n = 100
Health Status: unhealthy
Condition: HIV infection
Age Group: adult
Population Size: 100
Sources:
Vomiting 18 patients
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
lamivudine
indinavir
Sources:
unhealthy, adult
n = 100
Health Status: unhealthy
Condition: HIV infection
Age Group: adult
Population Size: 100
Sources:
Headache 25 patients
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
lamivudine
indinavir
Sources:
unhealthy, adult
n = 100
Health Status: unhealthy
Condition: HIV infection
Age Group: adult
Population Size: 100
Sources:
Diarrhea 34 patients
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
lamivudine
indinavir
Sources:
unhealthy, adult
n = 100
Health Status: unhealthy
Condition: HIV infection
Age Group: adult
Population Size: 100
Sources:
Nausea 43 patients
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
lamivudine
indinavir
Sources:
unhealthy, adult
n = 100
Health Status: unhealthy
Condition: HIV infection
Age Group: adult
Population Size: 100
Sources:
Neuropathy peripheral 8 patients
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
lamivudine
indinavir
Sources:
unhealthy, adult
n = 100
Health Status: unhealthy
Condition: HIV infection
Age Group: adult
Population Size: 100
Sources:
Neuropathy peripheral 21 patient
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
didanosine
indinavir
Sources:
unhealthy, adult
n = 102
Health Status: unhealthy
Condition: HIV infection
Age Group: adult
Population Size: 102
Sources:
Rash 30 patients
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
didanosine
indinavir
Sources:
unhealthy, adult
n = 102
Health Status: unhealthy
Condition: HIV infection
Age Group: adult
Population Size: 102
Sources:
Vomiting 30 patients
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
didanosine
indinavir
Sources:
unhealthy, adult
n = 102
Health Status: unhealthy
Condition: HIV infection
Age Group: adult
Population Size: 102
Sources:
Diarrhea 45 patients
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
didanosine
indinavir
Sources:
unhealthy, adult
n = 102
Health Status: unhealthy
Condition: HIV infection
Age Group: adult
Population Size: 102
Sources:
Headache 46 patients
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
didanosine
indinavir
Sources:
unhealthy, adult
n = 102
Health Status: unhealthy
Condition: HIV infection
Age Group: adult
Population Size: 102
Sources:
Nausea 53 patients
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Co-administed with::
didanosine
indinavir
Sources:
unhealthy, adult
n = 102
Health Status: unhealthy
Condition: HIV infection
Age Group: adult
Population Size: 102
Sources:
Nausea and vomiting 39 patients
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Sources:
unhealthy, adult
n = 412
Health Status: unhealthy
Condition: HIV infection
Age Group: adult
Population Size: 412
Sources:
Rash 40 patients
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Sources:
unhealthy, adult
n = 412
Health Status: unhealthy
Condition: HIV infection
Age Group: adult
Population Size: 412
Sources:
Diarrhea 50 patients
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Sources:
unhealthy, adult
n = 412
Health Status: unhealthy
Condition: HIV infection
Age Group: adult
Population Size: 412
Sources:
Neuropathy peripheral 52 patients
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Sources:
unhealthy, adult
n = 412
Health Status: unhealthy
Condition: HIV infection
Age Group: adult
Population Size: 412
Sources:
Headache 54 patients
40 mg 2 times / day multiple, oral
Recommended
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Sources:
unhealthy, adult
n = 412
Health Status: unhealthy
Condition: HIV infection
Age Group: adult
Population Size: 412
Sources:
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >133 uM]
no [IC50 >133 uM]
no [IC50 >133 uM]
no [IC50 >133 uM]
unlikely
weak
weak
Drug as victimTox targets
PubMed

PubMed

TitleDatePubMed
Tolerability of postexposure antiretroviral prophylaxis for occupational exposures to HIV.
2001
Macrocytosis in patients on stavudine.
2001
An open-label randomized trial to evaluate different therapeutic strategies of combination therapy in HIV-1 infection: design, rationale, and methods of the initio trial.
2001 Apr
ACTG (AIDS Clinical Trials Group) 384: a strategy trial comparing consecutive treatments for HIV-1.
2001 Apr
Gynecomastia associated with highly active antiretroviral therapy.
2001 Apr
Amino acid deletion at codon 67 and Thr-to-Gly change at codon 69 of human immunodeficiency virus type 1 reverse transcriptase confer novel drug resistance profiles.
2001 Apr
Treatment of hyperlipidemia in HIV-infected patients.
2001 Apr 1
Long-term safety and efficacy of nevirapine, stavudine and lamivudine in a real-world setting.
2001 Apr 13
Differing reverse transcriptase mutation patterns in individuals experiencing viral rebound on first-line regimens with stavudine/didanosine and stavudine/lamivudine.
2001 Apr 13
Chronic hyperlactatemia in HIV-infected patients taking antiretroviral therapy.
2001 Apr 13
Determination of serum levels of thirteen human immunodeficiency virus-suppressing drugs by high-performance liquid chromatography.
2001 Apr 13
R211K and L214F do not invariably confer high level phenotypic resistance to thymidine analogs in zidovudine-naive patients with M184V.
2001 Apr 15
Chemotherapy for human immunodeficiency virus-associated non-Hodgkin's lymphoma in combination with highly active antiretroviral therapy.
2001 Apr 15
Antiviral drugs: current state of the art.
2001 Aug
Genotypic correlates of a virologic response to stavudine after zidovudine monotherapy.
2001 Aug 1
Bristol-Myers warns of AIDS drugs' use.
2001 Feb
Genetic risks of antiviral nucleoside analogues--a survey.
2001 Feb
Making the most of sparse clinical data by using a predictive-model-based analysis, illustrated with a stavudine pharmacokinetic study.
2001 Feb
Indian company offers cheap anti-AIDS drugs.
2001 Feb 15
Large hepatic mitochondrial DNA deletions associated with L-lactic acidosis and highly active antiretroviral therapy.
2001 Feb 16
Gene mutations identified.
2001 Jan
Eruptive cheilitis: a new adverse effect in reactive HIV-positive patients subjected to high activity antiretroviral therapy (HAART). Presentation of six clinical cases.
2001 Jan-Feb
New developments in anti-HIV chemotherapy.
2001 Jan-Feb
Adefovir nephrotoxicity: possible role of mitochondrial DNA depletion.
2001 Jul
In vivo pharmacokinetics and metabolism of anti-human immunodeficiency virus agent D4T-5'-[p-bromophenyl methoxyalaninyl phosphate] (SAMPIDINE) in mice.
2001 Jul
Gynaecomastia in a male patient during stavudine and didanosine treatment for HIV infection.
2001 Jul
Stavudine versus zidovudine and the development of lipodystrophy.
2001 Jul 1
Effects of treatment intensification with hydroxyurea in HIV-infected patients with virologic suppression.
2001 Jul 27
Metformin in an HIV-infected patient with protease inhibitor-induced diabetic ketoacidosis.
2001 Jul-Aug
Adherence over 48 weeks in an antiretroviral clinical trial: variable within patients, affected by toxicities and independently predictive of virological response.
2001 Jun
Severe lactic acidosis and thiamine administration in an HIV-infected patient on HAART.
2001 Jun
Analysis of human immunodeficiency virus type 1 drug resistance in children receiving nucleoside analogue reverse-transcriptase inhibitors plus nevirapine, nelfinavir, or ritonavir (Pediatric AIDS Clinical Trials Group 377).
2001 Jun 15
Updated U.S. Public Health Service Guidelines for the Management of Occupational Exposures to HBV, HCV, and HIV and Recommendations for Postexposure Prophylaxis.
2001 Jun 29
Differential incorporation and removal of antiviral deoxynucleotides by human DNA polymerase gamma.
2001 Jun 29
Peripheral neuropathy and antiretroviral drugs.
2001 Mar
Resolution of microsporidial keratoconjunctivitis in an AIDS patient treated with highly active antiretroviral therapy.
2001 Mar
Incidence of pancreatitis in HIV-infected patients receiving nucleoside reverse transcriptase inhibitor drugs.
2001 Mar 30
Therapeutic effects of nucleoside analogues on psychomotor slowing in HIV infection.
2001 Mar 9
Choosing which nuke to use first.
2001 May
Effect of stavudine on mitochondrial genome and fatty acid oxidation in lean and obese mice.
2001 May
Lipodystrophy in HIV-infected children is associated with high viral load and low CD4+ -lymphocyte count and CD4+ -lymphocyte percentage at baseline and use of protease inhibitors and stavudine.
2001 May 1
An integrated system to study multiply substituted human immunodeficiency virus type 1 reverse transcriptase.
2001 May 1
Lactic acid levels in children perinatally treated with antiretroviral agents to prevent HIV transmission.
2001 May 25
Persistence of zidovudine-resistance mutations in HIV-1 isolates from patients removed from zidovudine therapy for at least 3 years and switched to a stavudine-containing regimen.
2001 May 25
Increased risk of lipodystrophy when nucleoside analogue reverse transcriptase inhibitors are included with protease inhibitors in the treatment of HIV-1 infection.
2001 May 4
HIV in body fluids during primary HIV infection: implications for pathogenesis, treatment and public health.
2001 May 4
Fatal portal hypertension, liver failure, and mitochondrial dysfunction after HIV-1 nucleoside analogue-induced hepatitis and lactic acidaemia.
2001 May 5
Warning for pregnant women on HIV therapy.
2001 May-Jun
Mismatched double-stranded RNA (polyI-polyC(12)U) is synergistic with multiple anti-HIV drugs and is active against drug-sensitive and drug-resistant HIV-1 in vitro.
2001 Sep
Novel low molecular weight spirodiketopiperazine derivatives potently inhibit R5 HIV-1 infection through their antagonistic effects on CCR5.
2001 Sep 14
Patents

Sample Use Guides

Adults: The recommended dose based on body weight is as follows: 40 mg twice daily for patients ≥60 kg. 30 mg twice daily for patients <60 kg.
Route of Administration: Oral
The concentration of Stavudine necessary to inhibit HIV-1 replication by 50% (EC50) ranged from 0.009 to 4 uM
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:04:27 UTC 2023
Edited
by admin
on Sat Dec 16 16:04:27 UTC 2023
Record UNII
BO9LE4QFZF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
STAVUDINE
EMA EPAR   EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   WHO-DD   WHO-IP  
USAN   INN  
Official Name English
STAVUDINE [WHO-IP]
Common Name English
STAVUDINE [MI]
Common Name English
STAVUDINE [USAN]
Common Name English
STAVUDINE (D4T) [VANDF]
Common Name English
Stavudine [WHO-DD]
Common Name English
ZERIT
Brand Name English
D-4T
Code English
STAVUDINE [USP MONOGRAPH]
Common Name English
NSC-163661
Code English
stavudine [INN]
Common Name English
STAVUDINE [EP MONOGRAPH]
Common Name English
SANILVUDINE
JAN  
Common Name English
THYMIDINE, 2',3'-DIDEHYDRO-3'-DEOXY-
Systematic Name English
NSC-759897
Code English
STAVUDINUM [WHO-IP LATIN]
Common Name English
STAVUDINE [EMA EPAR]
Common Name English
STAVUDINE [HSDB]
Common Name English
ZIDOVUDINE IMPURITY A [WHO-IP]
Common Name English
1-((2R,5S)-5-(HYDROXYMETHYL)-2,5-DIHYDROFURAN-2-YL)-5-METHYLPYRIMIDINE-2,4(1H,3H)-DIONE
Common Name English
STAVUDINE [EP IMPURITY]
Common Name English
STAVUDINE (DT4) [VANDF]
Common Name English
STAVUDINE [ORANGE BOOK]
Common Name English
STAVUDINE [MART.]
Common Name English
1-(2,3-DIDEOXY-.BETA.-D-GLYCERO-PENT-2-ENOFURANOSYL)THYMINE
Common Name English
ZIDOVUDINE IMPURITY A [EP IMPURITY]
Common Name English
STAVUDINE [USP-RS]
Common Name English
SANILVUDINE [JAN]
Common Name English
D4T
Code English
Classification Tree Code System Code
NDF-RT N0000175462
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
NDF-RT N0000009947
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
NDF-RT N0000175459
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 6.4.2.3 (LAM/NEV/STA)
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
NCI_THESAURUS C97452
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
WHO-VATC QJ05AF04
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
EMA ASSESSMENT REPORTS ZERIT (AUTHORIZED: HIV INFECTIONS)
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
NDF-RT N0000175459
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
WHO-VATC QJ05AR07
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
LIVERTOX NBK548694
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 6.4.2.1
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
NDF-RT N0000175459
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
WHO-ATC J05AR07
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
WHO-ATC J05AF04
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
Code System Code Type Description
NSC
759897
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
PRIMARY
NCI_THESAURUS
C1428
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
PRIMARY
RXCUI
59763
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
PRIMARY RxNorm
NSC
163661
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
PRIMARY
WIKIPEDIA
STAVUDINE
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
PRIMARY
INN
6775
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
STAVUDINE
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
PRIMARY Description: A white to almost white powder. Solubility: Soluble in water and sparingly soluble in ethanol (~750 g/l) TS. Category: Antiretroviral (Nucleoside Reverse Transcriptase Inhibitor). Storage: Stavudine should be kept in a well-closed container, protected from light. Additional information: Stavudine may exhibit polymorphism. Definition: Stavudine contains not less than 97.0% and not more than 103.0% of C10H12N2O4, calculated with reference to the dried substance.
DRUG CENTRAL
2478
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
PRIMARY
USAN
CC-53
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
PRIMARY
DAILYMED
BO9LE4QFZF
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
PRIMARY
CAS
3056-17-5
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
PRIMARY
SMS_ID
100000089694
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
PRIMARY
FDA UNII
BO9LE4QFZF
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
PRIMARY
CHEBI
63581
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
PRIMARY
LACTMED
Stavudine
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
PRIMARY
RS_ITEM_NUM
1620209
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
PRIMARY
MESH
D018119
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
PRIMARY
EPA CompTox
DTXSID1023819
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
PRIMARY
PUBCHEM
18283
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
PRIMARY
DRUG BANK
DB00649
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
PRIMARY
EVMPD
SUB10642MIG
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
PRIMARY
ChEMBL
CHEMBL991
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
PRIMARY
MERCK INDEX
m10199
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
PRIMARY Merck Index
HSDB
7338
Created by admin on Sat Dec 16 16:04:29 UTC 2023 , Edited by admin on Sat Dec 16 16:04:29 UTC 2023
PRIMARY
Related Record Type Details
EXCRETED UNCHANGED
AMOUNT EXCRETED
URINE
TARGET -> INHIBITOR
TARGET ORGANISM->INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
MINOR
URINE
METABOLITE -> PARENT
METABOLITE ACTIVE -> PARENT
The in vitro MIC (50% inhibitory concentration [IC50]) of d4T-TP against HIV-1 has been found to be between 0.009 and 6 μM, depending on the phenotypic and genotypic resistance to nucleoside reverse transcriptase inhibitors.
MAJOR
METABOLITE -> PARENT
MINOR
URINE
Related Record Type Details
IMPURITY -> PARENT
Water (2.5.12): maximum 0.5 per cent, determined on 0.500 g.
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
Amount Not Specified
INTERNATIONAL PHARMACOPEIA
IMPURITY -> PARENT
Amount Not Specified
INTERNATIONAL PHARMACOPEIA
IMPURITY -> PARENT
Amount Not Specified
INTERNATIONAL PHARMACOPEIA
IMPURITY -> PARENT
Amount Not Specified
INTERNATIONAL PHARMACOPEIA
IMPURITY -> PARENT
Amount Not Specified
INTERNATIONAL PHARMACOPEIA
IMPURITY -> PARENT
Amount Not Specified
INTERNATIONAL PHARMACOPEIA
IMPURITY -> PARENT
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC ORAL ADMINISTRATION

Biological Half-life PHARMACOKINETIC ORAL ADMINISTRATION