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

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.

CNS Activity

Originator

Bristol-Myers Squibb|Yale University|Yamasa
1
Curator's Comment: # Bristol-Myers Squibb; Yale University; Yamasa Corporation

Approval Year

1994
152
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 1.9 µM [IC50]
Inhibitor
8504
 0.0083 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
Zerit

Approved Use

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

Launch Date

1994
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
228 ng/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/21453_Zerit_lbl.pdf
100 mg 1 times / day steady-state, oral
dose: 100 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
STAVUDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
536 ng/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020412s041,020413s033lbl.pdf
40 mg 2 times / day steady-state, oral
dose: 40 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
STAVUDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1966 ng × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/21453_Zerit_lbl.pdf
100 mg 1 times / day steady-state, oral
dose: 100 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
STAVUDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
2568 ng × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020412s041,020413s033lbl.pdf
40 mg 2 times / day steady-state, oral
dose: 40 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
STAVUDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
100%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/21453_Zerit_lbl.pdf
100 mg 1 times / day steady-state, oral
dose: 100 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
STAVUDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
100%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020412s041,020413s033lbl.pdf
40 mg 2 times / day steady-state, oral
dose: 40 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
STAVUDINE plasma
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
unhealthy, 36.5
Health Status: unhealthy
Age Group: 36.5
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
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:
https://pubmed.ncbi.nlm.nih.gov/15249567/
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
unhealthy, 36.5
Health Status: unhealthy
Age Group: 36.5
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
unhealthy, 36.5
Health Status: unhealthy
Age Group: 36.5
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
unhealthy, 36.5
Health Status: unhealthy
Age Group: 36.5
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
unhealthy, 36.5
Health Status: unhealthy
Age Group: 36.5
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
unhealthy, 36.5
Health Status: unhealthy
Age Group: 36.5
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
unhealthy, 36.5
Health Status: unhealthy
Age Group: 36.5
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
unhealthy, 36.5
Health Status: unhealthy
Age Group: 36.5
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
unhealthy, 36.5
Health Status: unhealthy
Age Group: 36.5
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
unhealthy, 36.5
Health Status: unhealthy
Age Group: 36.5
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
unhealthy, 36.5
Health Status: unhealthy
Age Group: 36.5
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
unhealthy, 36.5
Health Status: unhealthy
Age Group: 36.5
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
unhealthy, 36.5
Health Status: unhealthy
Age Group: 36.5
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
unhealthy, 36.5
Health Status: unhealthy
Age Group: 36.5
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
unhealthy, 36.5
Health Status: unhealthy
Age Group: 36.5
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
unhealthy, 36.5
Health Status: unhealthy
Age Group: 36.5
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
unhealthy, 36.5
Health Status: unhealthy
Age Group: 36.5
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
unhealthy, 36.5
Health Status: unhealthy
Age Group: 36.5
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
unhealthy, 36.5
Health Status: unhealthy
Age Group: 36.5
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
unhealthy, 36.5
Health Status: unhealthy
Age Group: 36.5
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
unhealthy, 36.5
Health Status: unhealthy
Age Group: 36.5
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/15249567/
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
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
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
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
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
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
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
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
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
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
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
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
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
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
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
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
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
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
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
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
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
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
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
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
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/20412S017.pdf
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1946

inhibitor
2252
substrate
1193

inhibitor
2438
substrate
1388

inhibitor
2507
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2C8
1057

CYP2B6
926

CYP1A2
2153

CYP2A6
879

CYP2C19
2057

CYP2E1
1060

BSEP
550

MRP2
499

MRP3
246

MRP4
290
CYP1A2
1197

CYP2C19
1119

BCRP
697

P-gp
2052
P-gp
301
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
2333
 no [IC50 >10 uM]
CYP2A6
911
 no [IC50 >10 uM]
CYP2C19
2141
 no [IC50 >10 uM]
CYP2C9
2497
 no [IC50 >10 uM]
CYP2D6
2546
 no [IC50 >10 uM]
CYP2E1
1146
 no [IC50 >10 uM]
CYP3A4
2633
 no [IC50 >10 uM]
BSEP
554
 no [IC50 >133 uM]
MRP2
625
 no [IC50 >133 uM]
MRP3
326
 no [IC50 >133 uM]
MRP4
345
 no [IC50 >133 uM]
CYP2B6
1160
 unlikely
CYP2C8
1117
 weak
P-gp
1932
 weak
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
1197
 no
CYP2C19
1119
 no
CYP2C9
1193
 no
CYP2D6
1388
 no
CYP3A4
1946
 no
BCRP
697
 yes
P-gp
2052
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:63581
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63581
ChemicalBook
CB4450928
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4450928
eMolecules
536927
https://www.emolecules.com/cgi-bin/more?vid=536927
eMolecules
739264
https://www.emolecules.com/cgi-bin/more?vid=739264
MolPort
MolPort-002-507-283
https://www.molport.com/shop/molecule-link/MolPort-002-507-283
ZINC
ZINC000000137884
http://zinc15.docking.org/substances/ZINC000000137884
PubMed

PubMed

TitleDatePubMed
Novel low molecular weight spirodiketopiperazine derivatives potently inhibit R5 HIV-1 infection through their antagonistic effects on CCR5.
2001-09-14
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.
2001-09
Susceptibility of human T cell leukemia virus type 1 to reverse-transcriptase inhibitors: evidence for resistance to lamivudine.
2001-08-15
Eruptive cheilitis: a new adverse effect in reactive HIV-positive patients subjected to high activity antiretroviral therapy (HAART). Presentation of six clinical cases.
2001-08-08
Metformin in an HIV-infected patient with protease inhibitor-induced diabetic ketoacidosis.
2001-08-04
Genotypic correlates of a virologic response to stavudine after zidovudine monotherapy.
2001-08-01
Value of patient self-report and plasma human immunodeficiency virus protease inhibitor level as markers of adherence to antiretroviral therapy: relationship to virologic response.
2001-08-01
Antiviral drugs: current state of the art.
2001-08
Effects of treatment intensification with hydroxyurea in HIV-infected patients with virologic suppression.
2001-07-27
Warning for pregnant women on HIV therapy.
2001-07-19
Stavudine versus zidovudine and the development of lipodystrophy.
2001-07-01
Adefovir nephrotoxicity: possible role of mitochondrial DNA depletion.
2001-07
Predictors of protease inhibitor-associated adverse events.
2001-07
In vivo pharmacokinetics and metabolism of anti-human immunodeficiency virus agent D4T-5'-[p-bromophenyl methoxyalaninyl phosphate] (SAMPIDINE) in mice.
2001-07
Gynaecomastia in a male patient during stavudine and didanosine treatment for HIV infection.
2001-07
Updated U.S. Public Health Service Guidelines for the Management of Occupational Exposures to HBV, HCV, and HIV and Recommendations for Postexposure Prophylaxis.
2001-06-29
Differential incorporation and removal of antiviral deoxynucleotides by human DNA polymerase gamma.
2001-06-29
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).
2001-06-15
Selection by AZT and rapid replacement in the absence of drugs of HIV type 1 resistant to multiple nucleoside analogs.
2001-06-10
Adherence over 48 weeks in an antiretroviral clinical trial: variable within patients, affected by toxicities and independently predictive of virological response.
2001-06
Severe lactic acidosis and thiamine administration in an HIV-infected patient on HAART.
2001-06
Lactic acid levels in children perinatally treated with antiretroviral agents to prevent HIV transmission.
2001-05-25
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.
2001-05-25
New developments in anti-HIV chemotherapy.
2001-05-12
Fatal portal hypertension, liver failure, and mitochondrial dysfunction after HIV-1 nucleoside analogue-induced hepatitis and lactic acidaemia.
2001-05-05
Increased risk of lipodystrophy when nucleoside analogue reverse transcriptase inhibitors are included with protease inhibitors in the treatment of HIV-1 infection.
2001-05-04
HIV in body fluids during primary HIV infection: implications for pathogenesis, treatment and public health.
2001-05-04
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.
2001-05-01
An integrated system to study multiply substituted human immunodeficiency virus type 1 reverse transcriptase.
2001-05-01
Choosing which nuke to use first.
2001-05
Effect of stavudine on mitochondrial genome and fatty acid oxidation in lean and obese mice.
2001-05
R211K and L214F do not invariably confer high level phenotypic resistance to thymidine analogs in zidovudine-naive patients with M184V.
2001-04-15
Chemotherapy for human immunodeficiency virus-associated non-Hodgkin's lymphoma in combination with highly active antiretroviral therapy.
2001-04-15
Long-term safety and efficacy of nevirapine, stavudine and lamivudine in a real-world setting.
2001-04-13
Differing reverse transcriptase mutation patterns in individuals experiencing viral rebound on first-line regimens with stavudine/didanosine and stavudine/lamivudine.
2001-04-13
Chronic hyperlactatemia in HIV-infected patients taking antiretroviral therapy.
2001-04-13
Determination of serum levels of thirteen human immunodeficiency virus-suppressing drugs by high-performance liquid chromatography.
2001-04-13
Treatment of hyperlipidemia in HIV-infected patients.
2001-04-01
[A rare etiology of hepatic steatosis associated with lactic acidosis: the toxicity of antiviral nucleoside analogues].
2001-04
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.
2001-04
ACTG (AIDS Clinical Trials Group) 384: a strategy trial comparing consecutive treatments for HIV-1.
2001-04
Gynecomastia associated with highly active antiretroviral therapy.
2001-04
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.
2001-04
Incidence of pancreatitis in HIV-infected patients receiving nucleoside reverse transcriptase inhibitor drugs.
2001-03-30
Peripheral neuropathy and antiretroviral drugs.
2001-03
Large hepatic mitochondrial DNA deletions associated with L-lactic acidosis and highly active antiretroviral therapy.
2001-02-16
Bristol-Myers warns of AIDS drugs' use.
2001-02
Gene mutations identified.
2001-01
Tolerability of postexposure antiretroviral prophylaxis for occupational exposures to HIV.
2001
Macrocytosis in patients on stavudine.
2001
Patents

Patents

JP2002517465A
9
JP2002544210A
89
JP2011508747A
62
JPH09188623A
1

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
The concentration of Stavudine necessary to inhibit HIV-1 replication by 50% (EC50) ranged from 0.009 to 4 uM
Name Type Language
SANILVUDINE
JAN  
Preferred Name English
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
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 Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
NDF-RT N0000009947
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
NDF-RT N0000175459
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 6.4.2.3 (LAM/NEV/STA)
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
NCI_THESAURUS C97452
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
WHO-VATC QJ05AF04
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
EMA ASSESSMENT REPORTS ZERIT (AUTHORIZED: HIV INFECTIONS)
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
NDF-RT N0000175459
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
WHO-VATC QJ05AR07
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
LIVERTOX NBK548694
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 6.4.2.1
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
NDF-RT N0000175459
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
WHO-ATC J05AR07
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
WHO-ATC J05AF04
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
Code System Code Type Description
NSC
759897
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
PRIMARY
NCI_THESAURUS
C1428
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
PRIMARY
RXCUI
59763
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
PRIMARY RxNorm
NSC
163661
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
PRIMARY
WIKIPEDIA
STAVUDINE
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
PRIMARY
INN
6775
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
STAVUDINE
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
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 Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
PRIMARY
USAN
CC-53
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
PRIMARY
DAILYMED
BO9LE4QFZF
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
PRIMARY
CAS
3056-17-5
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
PRIMARY
SMS_ID
100000089694
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
PRIMARY
FDA UNII
BO9LE4QFZF
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
PRIMARY
CHEBI
63581
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
PRIMARY
LACTMED
Stavudine
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
PRIMARY
RS_ITEM_NUM
1620209
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
PRIMARY
MESH
D018119
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
PRIMARY
EPA CompTox
DTXSID1023819
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
PRIMARY
PUBCHEM
18283
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
PRIMARY
DRUG BANK
DB00649
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
PRIMARY
EVMPD
SUB10642MIG
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
PRIMARY
ChEMBL
CHEMBL991
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
PRIMARY
MERCK INDEX
m10199
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
PRIMARY Merck Index
HSDB
7338
Created by admin on Wed Apr 02 07:04:54 GMT 2025 , Edited by admin on Wed Apr 02 07:04:54 GMT 2025
PRIMARY
ACTIVE MOIETY
Structure of STAVUDINE
METABOLITE (PARENT)
Structure of THYMINE
METABOLITE (PARENT)
Structure of STAVUDINE GLUCURONIDE
METABOLITE ACTIVE (PARENT)
Structure of STAVUDINE TRIPHOSPHATE
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966