Stavudine

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trade name: Zerit; drug class: antiviral; action: inhibits replication of human immunodeficiency virus (HIV); uses: treatment of adults with advanced HIV infection who are intolerant of other therapies or who have significant deterioration while receiving other therapies.

Brand names: Zerit®Zerit® XR

Chemical formula:

Drug Forms:
• Stavudine Oral capsule (below)
• Stavudine Oral solution

Español:
• Estavudina, Cápsula oral
• Estavudina, Solución oral

Stavudine Oral capsule

What is this medicine?

STAVUDINE, d4T is an antiretroviral medicine. It is used with other medicines to treat HIV. This medicine is not a cure for HIV. It will not stop the spread of HIV to others.

This medicine may be used for other purposes; ask your health care provider or pharmacist if you have questions.

What should I tell my health care provider before I take this medicine?

They need to know if you have any of these conditions:
•diabetes
•drink alcohol daily
•gallstones
•kidney disease
•liver disease
•history of pancreatitis
•tingling, numbness in the hands, feet
•an unusual or allergic reaction to stavudine, other medicines, foods, dyes, or preservatives
•pregnant or trying to get pregnant
•breast-feeding

How should I use this medicine?

Take this medicine by mouth with a glass of water. Follow the directions on the prescription label. You may take this medicine with or without food. Take your medicine at regular intervals. Do not take your medicine more often than directed. For your anti-HIV therapy to work as well as possible, take each dose exactly as prescribed. Do not skip doses or stop your medicine even if you feel better. Skipping doses may make the HIV virus resistant to this medicine and other medicines. Do not stop taking except on your doctor's advice.

A patient information sheet for the product will be given with each prescription and refill. Read this sheet carefully each time. The sheet may change frequently.

Talk to your pediatrician regarding the use of this medicine in children. While this drug may be prescribed for children as young as newborns for selected conditions, precautions do apply.

Overdosage: If you think you have taken too much of this medicine contact a poison control center or emergency room at once.
NOTE: This medicine is only for you. Do not share this medicine with others.

What may interact with this medicine?

Do not take this medicine with any of the following medications:
•zalcitabine, ddC
•zidovudine, AZT

This medicine may also interact with the following medications:
•didanosine, ddI
•doxorubicin
•hydroxyurea
•interferon
•ribavirin

This list may not describe all possible interactions. Give your health care provider a list of all the medicines, herbs, non-prescription drugs, or dietary supplements you use. Also tell them if you smoke, drink alcohol, or use illegal drugs. Some items may interact with your medicine.

What should I watch for while using this medicine?

Visit your doctor or health care professional for regular check ups. Discuss any new symptoms with your doctor. You will need to have important blood work done while on this medicine.

HIV is spread to others through sexual or blood contact. Talk to your doctor about how to stop the spread of HIV.

Do not treat severe stomach pain, nausea or vomiting with over-the-counter medicines. Contact your doctor.

This medicine may affect blood sugar levels. If you have diabetes, check with your doctor or health care professional before you change your diet or the dose of your diabetic medicine.

What side effects may I notice from receiving this medicine?

Side effects that you should report to your doctor or health care professional as soon as possible:
•breathing problems
•increased hunger or thirst
•increased urination
•muscle weakness in arms and legs
•nausea, vomiting, unusual stomach upset or pain
•tingling, pain, burning, or numbness in the hands or feet
•unusual bleeding or bruising
•unusually weak or tired
•weight gain around waist, back, or thinning of face, arms, legs

Side effects that usually do not require medical attention (report to your doctor or health care professional if they continue or are bothersome):
•diarrhea
•difficulty sleeping
•fever, chills
•headache
•loss of appetite
•muscle pain
•weight loss

This list may not describe all possible side effects. Call your doctor for medical advice about side effects. You may report side effects to FDA at 1-800-FDA-1088.

Where should I keep my medicine?

Keep out of the reach of children and pets.

Store at room temperature between 15 and 30 degrees C (59 and 86 degrees F). Keep container tightly closed. Throw away any unused medicine after the expiration date.

You should dispose of this medicine through community take-back disposal programs when available or by placing it in an unrecognizable closed container in the household trash.

Last updated: 7/1/2002

Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.

Stavudine
Systematic (IUPAC) name
1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
Identifiers
CAS number	3056-17-5
ATC code	J05AF04
PubChem	18283
DrugBank	APRD00440
Chemical data
Formula	C10H12N2O4
Mol. mass	224.213 g/mol
Pharmacokinetic data
Bioavailability	?
Protein binding	Negligible
Metabolism	Renal elimination (ca.40%)
Half life	0.8-1.5 hours (in adults)
Excretion	?
Therapeutic considerations
Pregnancy cat.	C (USA) B3 (Aus)
Legal status
Routes	?

Stavudine (2'-3'-didehydro-2'-3'-dideoxythymidine, d4T, brand name Zerit) is a nucleoside analog reverse transcriptase inhibitor (NARTI) active against HIV.

Contents 1 History 2 Mechanism of action 3 Pharmacokinetics 4 Adverse events 5 Sources 6 References

History

d4T was first synthetized in the sixties by Jerome Horwitz.^[1][2] It was subsequently reconsidered as an anti-HIV agent by the Rega Institute for Medical Research in Belgium. Stavudine was approved by the U.S. Food and Drug Administration (FDA) in Jun 24, 1994 for adults and in Sep 6, 1996 for pediatric use and again as an extended-release version for once-a-day dosing in 2001. The fourth antiretroviral drug on the market, its patent expired in the United States on 2008-06-25.

Mechanism of action

Stavudine is an analog of thymidine. It is phosphorylated by cellular kinases into active triphosphate. Stavudine triphosphate inhibits the HIV reverse transcriptase by competing with natural substrate, thymidine triphosphate. It also causes termination of DNA synthesis by incorporating into it.

Simultaneous use of AZT is not recommended, as it can inhibit the intracellular phosphorylation of stavudine. Other anti-HIV drugs do not possess this property.

Pharmacokinetics

The oral absorption rate of stavudine is over 80%. Approximately half of stavudine is actively secreted unchanged into the urine and the other half is eliminated through endogenic pathways.

Adverse events

The main severe adverse effect is peripheral neuropathy, which can be corrected by reducing dosage. Stavudine has been shown in laboratory test to be genotoxic, but with clinical doses its carcinogenic effects are non-existent. It is also one of the most likely antiviral drugs to cause lipodystrophy, and for this reason it is no longer considered an appropriate treatment for most patients in developed countries.

It is still used as first choice in first line therapy in resource poor settings such as in India. Only in case of development of peripheral neuropathy or pregnancy is it changed to the next choice - Zidovudine.

Sources

1. ^ J.P. Horwitz et al.. J. Org. Chem. 31. 205 (1966).
2. ^ Oral account of the history of AZT, d4T and ddC by Jerome Horwitz and Hiroaki Mitsuya in the documentary film I am alive today - History of an AIDS drug.

References

• De Clercq E., Perspectives for the chemotherapy of AIDS, Chemioterapia. 1988 Dec;7(6):357-64.

v • d • e Antiviral drugs: antiretroviral drugs used against HIV (primarily J05) Entry/fusion inhibitors gp41 (Enfuvirtide) · CCR5 (Maraviroc, Vicriviroc†, PRO 140†) · CD4 (Ibalizumab†) Reverse transcriptase inhibitors (RTIs) Nucleoside & Nucleotide (NRTI) Nucleoside analogues/NARTIs: Abacavir (ABC)°§ · Emtricitabine (FTC)°§ · Lamivudine (3TC)°§ · Didanosine (ddI)§ · Zidovudine (AZT)§ · Apricitabine† · Stampidine† · Elvucitabine† · Racivir† · Amdoxovir† · Stavudine (d4T)§ · Zalcitabine (ddC)‡ Nucleotide analogues/NtRTIs: Tenofovir°§ Non-Nucleoside (NNRTI) Efavirenz°§ · Nevirapine§ · diarylpyrimidines (Etravirine, Rilpivirine†) · Loviride‡ · Delavirdine‡ · Integrase inhibitors Raltegravir · Elvitegravir† · Globoidnan A (experimental) Maturation inhibitors Bevirimat† · Vivecon† Protease Inhibitors (PI) Atazanavir° · Fosamprenavir° · Lopinavir°§ · Darunavir · Nelfinavir§ · Ritonavir§ · Saquinavir§ · Tipranavir · Amprenavir‡ · Indinavir‡§ Combined formulations Combivir · Atripla · Trizivir · Truvada · Kaletra · Epzicom Experimental agents Uncoating inhibitors TRIM5alpha (gene) Transcription inhibitors Tat antagonists Translation inhibitors Trichosanthin Other Abzyme · Calanolide A · Ceragenin · Cyanovirin-N · Diarylpyrimidines · Epigallocatechin gallate (EGCG) · Foscarnet · Griffithsin · Hydroxyurea · Miltefosine · Portmanteau inhibitors · Seliciclib† · Synergistic enhancers · Tre recombinase · Zinc finger protein transcription factor · KP-1461† Failed agents Dexelvucitabine · Capravirine · Emivirine · Lodenosine · Atevirdine · Brecanavir · Aplaviroc °DHHS preferred first-line agent. †Undergoing clinical trials, not FDA approved. ‡Formerly or rarely used agent. §WHO-EM

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