Stavudine

Summary

Stavudine (CHEMBL991) is an approved small-molecule EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor (ATC J05AF04); indicated across 7 conditions including hiv infectious disease and viral infectious disease.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: J05AF04
• Indications: 7 conditions
• Clinical trials: 124
• Chemistry: 224.21 Da · C10H12N2O4

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL991
Name	Stavudine
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	18283
ChEBI	CHEBI:63581
ATC	J05AF04
Molecular formula	C10H12N2O4
Molecular weight	224.21
InChIKey	XNKLLVCARDGLGL-JGVFFNPUSA-N

SMILES: CC1=CN(C(=O)NC1=O)[C@H]2C=C[C@H](O2)CO

IUPAC name: 1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4-dione

ChEBI definition: A nucleoside analogue obtained by formal dehydration across positions 2 and 3 of thymidine. An inhibitor of HIV-1 reverse transcriptase

Pharmacological roles (ChEBI): EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor, antiviral agent.

Other ChEBI roles (chemical / environmental): antimetabolite.

Also known as: BMY-27857, D-4T, D4T, Estavudina, NSC-163661, NSC-759897, Sanilvudine, Stavudine, Stavudine (d4t), Stavudine (dt4), Stavudinum, Zerit

Patent coverage: 9,333 distinct patent families (35,178 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 7 (assay-derived). Sample: Prelamin-A/C, RecQ-like DNA helicase BLM, Alpha-1A adrenergic receptor, DNA polymerase beta, Muscarinic acetylcholine receptor M1, Albumin, Aldehyde dehydrogenase 1A1.

Bioactivity

ChEMBL activities: 3 potent at pChembl ≥ 5 of 8 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
BLM	6.1	Potency	794.3	nM	CHEMBL_ACT_4745911
BLM	6.1	Potency	794.3	nM	CHEMBL_ACT_4921896
P08482	5.55	Potency	2818	nM	CHEMBL_ACT_4857754

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

2 approved indications. FDA phase 4, plus an anticancer drug’s labelled cancer uses (which ChEMBL often logs at phase 3).

Indication	Phase	MONDO	EFO
HIV infectious disease	4	MONDO:0005109	EFO:0000764
viral infectious disease	4	MONDO:0005108	EFO:0000763

4 diseases in clinical trials (phase 1–3, investigational — not approved indications). Highest ChEMBL trial phase per disease; a non-cancer approved use is occasionally logged at phase 3 here.

Disease (in trials)	Phase	MONDO	EFO
AIDS	3	MONDO:0012268	EFO:0000765
HIV-associated nephropathy	3	MONDO:0005798	EFO:0007313
AIDS dementia complex	3	MONDO:0020689	EFO:0002608
lactic acidosis	2	MONDO:0006040	EFO:1000036

1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 124.

Phase distribution

Phase	Trials
PHASE2	41
PHASE3	26
Not specified	25
PHASE4	16
PHASE1	13
PHASE1/PHASE2	2
PHASE2/PHASE3	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00002376	PHASE4	COMPLETED	The Effectiveness of HIV RNA Viral Load Testing in Determining Treatment Type in HIV-Infected Patients
NCT00002386	PHASE4	COMPLETED	Effect of Indinavir Plus Two Other Anti-HIV Drugs on Blood Clotting in HIV-Positive Males With Hemophilia
NCT00005000	PHASE4	UNKNOWN	Treatment With Nelfinavir or Efavirenz of HIV-Infected Patients Who Have Never Received Anti-HIV Drugs
NCT00005017	PHASE4	UNKNOWN	Effectiveness and Safety of Epivir/Ziagen/Zerit (3TC/ABC/d4T) Versus Epivir/Ziagen/Sustiva (3TC/ABC/EFV) Versus Epivir/Ziagen/Agenerase/Norvir (3TC/ABC/APV/RTV) in HIV Patients Who Have Never Received Treatment
NCT00005106	PHASE4	COMPLETED	A Comparison of Three Anti-HIV Drug Combinations in HIV-Infected Patients
NCT00006190	PHASE4	COMPLETED	A Study to Determine How and Why HIV-Infected Subjects on Anti-viral Treatment Develop Lipodystrophy
NCT00055120	PHASE4	COMPLETED	When to Start Anti-HIV Drugs in Patients With Opportunistic Infections
NCT00127972	PHASE4	COMPLETED	2NN & CHARM Long-Term Follow-up Study
NCT00192660	PHASE4	COMPLETED	HIV Infection And Metabolic Abnormalities Protocol 1 (HAMA001)
NCT00235222	PHASE4	UNKNOWN	Evaluation of Viral Efficacy and Safety of a Reduced Dose of Stavudine (d4T): THE PHOENIX STUDY
NCT00342355	PHASE4	COMPLETED	Antiretroviral Therapy for Advanced HIV Disease in South Africa
NCT00455585	PHASE4	COMPLETED	Comparison of Plasma Drug Levels of Triomune 40 With Those of the Originator Products
NCT00618176	PHASE4	COMPLETED	Three Generic Nevirapine-Based Antiretroviral Treatments in Chinese Patients:Multicentric Observation Cohort
NCT00986063	PHASE4	COMPLETED	Genotype Based Personalized Prescription of Nevirapine
NCT01025830	PHASE4	COMPLETED	Triomune Bioequivalence With Innovators
NCT01601899	PHASE4	TERMINATED	Differences Between Stavudine and Tenofovir Each Combined With Lamivudine and Efavirenz in SA HIV-infected Patients
NCT00000841	PHASE3	COMPLETED	A Study of Indinavir Sulfate Plus Zidovudine (AZT) Plus Lamivudine in HIV-Infected Patients Who Have Taken AZT for Six or More Months
NCT00002109	PHASE3	COMPLETED	Double-Blind Study of Timunox (Thymopentin) in Asymptomatic HIV-Infected Patients Receiving Either Mono (AZT or ddI) or Combination (AZT / ddI or AZT / ddC) Anti-Retroviral Therapy
NCT00002208	PHASE3	COMPLETED	A Multicenter, Open-Label, Randomized, 24-Week Study to Compare the Safety and Activity of Indinavir Sulfate, 800 Mg q 8 h Versus 1,200 Mg q 12 h in Combination With Zidovudine and 3TC
NCT00002224	PHASE3	COMPLETED	Comparison of Two Anti-HIV Regimens That Include One of Two Forms of Didanosine (ddI)
NCT00002230	PHASE3	COMPLETED	A Randomized, Placebo-Controlled Study of the Safety and Efficacy of Efavirenz, Didanosine, and Stavudine in Combination With or Without Hydroxyurea in Antiretroviral Naive or Experienced HIV-Infected Patients
NCT00002246	PHASE3	COMPLETED	A Study to Evaluate the Use of Stavudine (d4T) to Treat AIDS Dementia Complex
NCT00002362	PHASE3	SUSPENDED	A Comparison of Emtricitabine and Abacavir Used in a Three-Drug Combination in HIV-Infected Patients Who Have Never Taken Anti-HIV Drugs
NCT00002371	PHASE3	COMPLETED	The Safety and Effectiveness of Lamivudine Plus Stavudine or Zidovudine in HIV-Infected Patients Who Have Taken Zidovudine
NCT00002374	PHASE3	COMPLETED	A Study of Saquinavir Soft Gelatin Capsules Combined With Other Anti-HIV Drugs in HIV-1 Infected Patients
NCT00002378	PHASE3	COMPLETED	A Comparison of Three Anti-HIV Drug Combinations Containing Saquinavir Soft Gelatin Capsules Used in HIV-1 Infected Patients
NCT00002397	PHASE3	COMPLETED	A Study of Saquinavir Soft Gel Capsules (SGC) Used in Combination With Two Other Anti-HIV Drugs in Patients With HIV-Associated Kidney Disease
NCT00002429	PHASE3	COMPLETED	Evaluation of an Anti-HIV Drug Combination That Includes a Coated Form of Didanosine (ddI EC) Compared to a Typical Anti-HIV Drug Regimen
NCT00004583	PHASE3	COMPLETED	A Phase III Study Comparing Two Different Anti-HIV Drug Combinations in HIV-Positive Patients Without Previous Anti-HIV Drug Therapy
NCT00005918	PHASE3	COMPLETED	Effectiveness and Safety of Two Forms of Stavudine in HIV-Infected Patients
NCT00006154	PHASE3	COMPLETED	A Study to Evaluate the Use of a Protease Inhibitor and of Interleukin-2 (IL-2) in the Treatment of Early HIV Infection
NCT00006208	PHASE3	UNKNOWN	A Comparison of Emtricitabine and Stavudine Used With Didanosine Plus Efavirenz in HIV-Infected Patients Who Have Not Taken Anti-HIV Drugs
NCT00006397	PHASE3	UNKNOWN	Differences Between Women and Men Taking a Combination of Indinavir, Ritonavir, Enteric-Coated Didanosine, and Stavudine Who Previously Took Anti-HIV Drugs
NCT00013520	PHASE3	COMPLETED	Comparison of Three Different Initial Treatments Without Protease Inhibitors for HIV Infection
NCT00050895	PHASE3	COMPLETED	Comparing the Safety, Effectiveness, and Tolerability of Three Anti-HIV Drug Regimens for Treatment-Naive Patients
NCT00074581	PHASE3	COMPLETED	Preventing Sexual Transmission of HIV With Anti-HIV Drugs
NCT00116298	PHASE3	COMPLETED	Rollover Study for Zerit (Stavudine) ER Studies (-096, -099)
NCT00143702	PHASE2/PHASE3	COMPLETED	D4T or Abacavir Plus Vitamin Enhancement in HIV-Infected Patients (DAVE)
NCT00427297	PHASE3	TERMINATED	Optimizing Pediatric HIV-1 Treatment in Infants With Prophylactic Exposure to Nevirapine, Nairobi, Kenya
NCT00528957	PHASE3	COMPLETED	Safety and Efficacy of Switching From Stavudine or Zidovudine to Tenofovir DF in HIV-1 Infected Children
NCT00669487	PHASE3	COMPLETED	A 72-week Randomized Clinical Trial Comparing the Safety and Efficacy of Three Initial Antiretroviral Regimens -GPO-VIR S (d4T/3TC/NVP) for 24 Weeks Followed by GPO-VIR Z (AZT/3TC/NVP) vs GPO-VIR Z vs TDF/FTC/NVP
NCT01146873	PHASE3	COMPLETED	Treatment Options for Protease Inhibitor-exposed Children
NCT02670772	PHASE3	COMPLETED	Dose Optimisation of Stavudine for the Treatment of HIV Infection
NCT00000789	PHASE2	COMPLETED	A Randomized, Comparative Trial of Zidovudine (AZT) Versus 2’,3’-Didehydro-3’-Deoxythymidine (Stavudine; d4T) in Children With HIV Infection
NCT00000831	PHASE2	COMPLETED	Virologic Responses To New Nucleoside Regimens After Prolonged ZDV or ddI Monotherapy
NCT00000838	PHASE2	COMPLETED	Antiviral Activity of and Resistance to Lamivudine in Combination With Zidovudine, Stavudine, or Didanosine
NCT00000851	PHASE2	COMPLETED	Comparison of Stavudine Used Alone or in Combination With Didanosine in HIV-Infected Children
NCT00000870	PHASE2	COMPLETED	A Phase II Study of Intermittent Recombinant Human Interleukin-2 (rhIL-2) by Intravenous or Subcutaneous Administration in Subjects With HIV Infection on Highly Active Antiretroviral Therapy (HAART) Compared to HAART Alone
NCT00000872	PHASE2	COMPLETED	Treatment With Combinations of Several Antiviral Drugs in Infants and Young Children With HIV Infection
NCT00000882	PHASE2	COMPLETED	Virologic and Immunologic Activity of Continued Lamivudine (3TC) vs Delavirdine (DLV) in Combination With Indinavir (IDV) and Zidovudine (ZDV) or Stavudine (d4T) in 3TC-Experienced Subjects
NCT00000885	PHASE2	COMPLETED	Treatment Success and Failure in HIV-Infected Subjects Receiving Indinavir in Combination With Nucleoside Analogs: A Rollover Study for ACTG 320
NCT00000891	PHASE2	COMPLETED	Immunologic and Virologic Consequences of Long-Term Highly Active Antiretroviral Therapy (HAART) in Subjects With Moderately Advanced HIV-1 Disease: A Follow-Up Study to ACTG 315
NCT00000916	PHASE2	COMPLETED	A Study of the Safety and Effectiveness of Hydroxyurea in Patients on Potent Antiretroviral Therapy and Who Have Less Than 200 Copies/ml of HIV RNA in Their Blood
NCT00000918	PHASE2	COMPLETED	A Study to Compare The Ability of Different Anti-HIV Drugs to Decrease Viral Load After Nelfinavir (an Anti-HIV Drug)Treatment Failure
NCT00000924	PHASE2	COMPLETED	A Study to Compare Two Different Anti-HIV Drug Regimens
NCT00000939	PHASE2	COMPLETED	A Study to Compare the Effectiveness of Different Anti-HIV Drug Regimens in Keeping Levels of HIV in the Blood as Low as Possible
NCT00000940	PHASE2	COMPLETED	Five-Drug Anti-HIV Treatment Followed by Treatment Interruption in Patients Who Have Recently Been Infected With HIV
NCT00001063	PHASE2	COMPLETED	The Effectiveness of Three Drug Combinations in HIV-Infected Patients Who Have Taken Zidovudine for More Than 12 Weeks
NCT00001067	PHASE2	COMPLETED	The Effectiveness of Three Anti-HIV Drug Combinations in HIV-Infected Patients Who Have Never Used Anti-HIV Drugs
NCT00001083	PHASE2	COMPLETED	Comparison of New Anti-HIV Drug Combinations in HIV-Infected Children Who Have Taken Anti-HIV Drugs
NCT00001084	PHASE2	COMPLETED	A Study of Three Treatment Combinations Using Zidovudine Plus Lamivudine Plus Indinavir in HIV-Infected Patients
NCT00001087	PHASE2	COMPLETED	The Effectiveness of Nelfinavir and Efavirenz, Used Alone or Together, Combined With Other Anti-HIV Drugs in Patients Who Have Taken Anti-HIV Drugs
NCT00001095	PHASE2	COMPLETED	A Study of Three Anti-HIV Drug Combinations in Patients Who Have Taken Amprenavir
NCT00001122	PHASE2	COMPLETED	A Study of an Adherence Plan to Help HIV-Positive Patients Take Their First Anti-HIV Medications Correctly
NCT00001688	PHASE2	COMPLETED	A Pilot Study of the Immunologic Reconstitution in HIV-1 Infected Children Receiving Highly Active Antiretroviral Therapy With Combination Ritonavir, Nevirapine and Stavudine
NCT00002162	PHASE2	COMPLETED	A Randomized, Parallel Arm, Comparative, Open Label, Multicenter Study of the Activity and Safety of Two Formulations of Saquinavir in Combination With Other Antiretroviral Drugs
NCT00002184	PHASE2	COMPLETED	A Phase II, Stratified, Randomized, Double-Blind, Multi-Center Study of the Safety and Efficacy of Adefovir Dipivoxil (ADF) at Two Dose Levels in Triple Combination Therapies With Protease Inhibitors (PI) and Nucleoside Reverse Transcriptase Inhibitors (RTI) for the Treatment of HIV-Infected Patient
NCT00002225	PHASE2	COMPLETED	A Study of Efavirenz in Combination With Stavudine and Didanosine
NCT00002227	PHASE2	COMPLETED	A Study of Efavirenz in HIV-Infected Patients Who Have Never Taken Anti-HIV Drugs
NCT00002240	PHASE2	COMPLETED	Study of a New Protease Inhibitor, BMS-232632, in Combination With Other Anti-HIV Drugs
NCT00002241	PHASE2	UNKNOWN	Safety and Effectiveness of an Anti-HIV Drug Combination Taken Twice Daily
NCT00002379	PHASE2	COMPLETED	The Safety and Effectiveness of Adefovir Dipivoxil Plus Indinavir Combined With Zidovudine or Lamivudine or Stavudine in HIV-Infected Patients Who Have Not Taken Anti-HIV Drugs
NCT00002412	PHASE2	COMPLETED	A Study of MKC-442 in Combination With Other Anti-HIV Drugs
NCT00002418	PHASE2	TERMINATED	The Safety and Effectiveness of Didanosine Plus Stavudine Plus Nevirapine Combined With MKC-442 in HIV-Infected Patients Who Have Not Had Success With Protease Inhibitors
NCT00002420	PHASE2	TERMINATED	The Safety and Effectiveness of Didanosine Plus Stavudine Plus Delavirdine Mesylate Plus MKC-442 in HIV-Infected Patients Who Have Not Had Success With Protease Inhibitors
NCT00002424	PHASE2	SUSPENDED	A Study to Compare the Safety and Effectiveness of Indinavir Combined With Stavudine and Lamivudine
NCT00002442	PHASE2	COMPLETED	A Study to Compare the Safety and Effectiveness of Two Dosing Schedules of Lamivudine in Combination With Two Other Anti-HIV Drugs
NCT00002451	PHASE2	UNKNOWN	Safety and Effectiveness of Giving Indinavir, Ritonavir, Stavudine, and Lamivudine to HIV-Infected Patients Who Have Never Received Anti-HIV Drugs
NCT00004578	PHASE1/PHASE2	COMPLETED	ABT-378/Ritonavir in Combination With Reverse Transcriptase Inhibitors in Antiretroviral Naïve HIV-Infected Subjects
NCT00006144	PHASE2	COMPLETED	A Study of HIV-Disease Development in Aging
NCT00006339	PHASE2	WITHDRAWN	Safety and Effectiveness of an Anti-HIV Drug Combination With and Without Hydroxyurea in Patients With Early HIV Infection
NCT00007202	PHASE2	COMPLETED	Safety and Effectiveness of a Three-Drug Combination Treatment for Recently Infected or Converted HIV Patients
NCT00017992	PHASE2	UNKNOWN	Emtricitabine Given Once A Day With Other Anti-HIV Drugs in Children With HIV
NCT00036452	PHASE2	COMPLETED	A Study to Compare Anti-HIV Drugs Given Twice a Day or Once a Day, With or Without Direct Observation
NCT00312091	PHASE1/PHASE2	COMPLETED	Drug Levels of Tablet and Liquid Forms of Lamivudine, Nevirapine, and Stavudine in HIV Infected Thai Children
NCT02249130	PHASE2	COMPLETED	Tipranavir Dose-response Study Using a Prototype Self-emulsifying Drug Delivery System (SEDDS) Formulation in Treatment-naive HIV-1 Infected Patients Report on the Post-study Option, a Treatment of Triple Therapy With Delavirdine, ZDV and 3TC Without Tipranavir
NCT00000686	PHASE1	TERMINATED	A Study of d4T in Patients With AIDS or AIDS-Related Complex Who Cannot Take AZT
NCT00000822	PHASE1	COMPLETED	A Phase I/II Double-Blind Controlled Trial to Determine the Safety and Immunogenicity of HIV-1 MN rgp160 Immuno AG Vaccine Therapy in HIV-Infected Individuals With Greater Than or Equal to 500/mm3 CD4+ T Cells and 200-400/mm3 CD4+ T Cells
NCT00000865	PHASE1	COMPLETED	The Safety and Effects of 1592U89 Used Alone or in Combination With Other Anti-HIV Drugs in HIV-Infected Infants and Children
NCT00000878	PHASE1	COMPLETED	A Study to Evaluate the Safety and Tolerance of Stavudine (d4T) in Combination With Lamivudine (3TC) in HIV-Positive Pregnant Women and Their Infants
NCT00000899	PHASE1	COMPLETED	A Study on the Effect of Chemotherapy Combined With Anti-HIV Drugs in HIV-Positive Patients
NCT00000901	PHASE1	COMPLETED	Safety and Effectiveness of Giving Indinavir Plus Stavudine Plus Lamivudine to HIV-Infected Children
NCT00000902	PHASE1	COMPLETED	A Study on the Management of Combination Anti-HIV Drug Therapy in HIV-Positive Children With Prior Treatment
NCT00000988	PHASE1	COMPLETED	A Study of BMY-27857 in Patients With AIDS or AIDS Related Complex
NCT00001091	PHASE1	COMPLETED	Safety and Effectiveness of Four Anti-HIV Drug Combinations in HIV-Infected Children and Teens
NCT00001108	PHASE1	COMPLETED	A Study of the Safety and Effectiveness of Treating Advanced AIDS Patients Between Ages 4 and 22 With 7 Drugs, Some at Higher Than Usual Doses
NCT00002381	PHASE1	COMPLETED	The Safety and Effectiveness of Nevirapine Plus Nelfinavir in HIV-1 Infected Patients Who Have Taken Stavudine
NCT00002427	PHASE1	COMPLETED	Safety and Effectiveness of Combining Hydroxyurea (HU) With Didanosine (ddI) and Stavudine (d4T) for Treatment of HIV-Infected Adults
NCT00004736	PHASE1	COMPLETED	Effectiveness of Anti-HIV Therapy (HAART) in HIV-Infected Patients With Tuberculosis
NCT00000896	Not specified	COMPLETED	A Study to Compare the Effectiveness of a Four Drug Anti-HIV Regimen Given Alone or in Combination With GM-CSF or IL-12 to HIV-Positive Patients

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline, but PharmGKB curates 2 clinical and 12 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).