司他夫定是一种核苷逆转录酶hibitor (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.

Mechanism of action

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.

Target	Actions	Organism
AReverse transcriptase/RNaseH	inhibitor	Human immunodeficiency virus 1

Absorption

Following oral administration, stavudine is rapidly absorbed (bioavailability is 68-104%).

Volume of distribution

46 ± 21 L

Protein binding

Negligible

Metabolism

Phosphorylated intracellularly to stavudine triphosphate, the active substrate for HIV-reverse transcriptase.

Route of elimination

Not Available

Half-life

0.8-1.5 hours (in adults)

Clearance

Renal cl=272 mL/min [Healthy subjects receiving 80 mg PO]
594 +/- 164 mL/min [HIV-infected adult and pediatric patients following 1-hour IV infusion]
9.75 +/- 3.76 mL/min/kg [HIV- Exposed or -Infected Pediatric Patients(Age 5 weeks – 15 years) following 1-hour IV infusion]

Adverse Effects

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Toxicity

Side effects include peripheral neuropathy tingling, burning, numbness, or pain in the hands or feet), fatal lactic acidosis has been reported in patients treated with stavudine (ZERIT) in combination with other antiretroviral agents, severe liver enlargement, inflammation (pain and swelling) of the liver, and liver failure.

Pathways

Pathway	Category
Stavudine Action Pathway	Drug action

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Not Available

Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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Acetazolamide	The excretion of Stavudine can be decreased when combined with Acetazolamide.
Acetophenazine	Stavudine may increase the neurotoxic activities of Acetophenazine.
Acetylsalicylic acid	The excretion of Stavudine can be decreased when combined with Acetylsalicylic acid.
Acipimox	The risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Stavudine is combined with Acipimox.
Acyclovir	The excretion of Stavudine can be decreased when combined with Acyclovir.
Adefovir dipivoxil	The excretion of Stavudine can be decreased when combined with Adefovir dipivoxil.
Adenovirus type 7 vaccine live	The therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Stavudine.
Alendronic acid	The risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Alendronic acid is combined with Stavudine.
Alimemazine	Stavudine may increase the neurotoxic activities of Alimemazine.
Aminohippuric酸	The excretion of Stavudine can be decreased when combined with Aminohippuric acid.

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Food Interactions

Avoid alcohol. Ingesting alcohol while taking stavudine may increase the risk of liver damage and pancreatitis.
Take with or without food.

Products

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Product Images

International/Other Brands

Actastav (Actavis)/Ai Fu Ding (Wujing Medicine)/Avostav (Ranbaxy Laboratories)/Estavudox (Biotoscana)/Exvihr (Biogen)/Flamistav (Flamingo Pharmacueticals)/Landstav (Landsteiner)/Lion (Filaxis)/Mai Si Ting (Meijisi Pharmaceutical)/S.T.V. (Ivax)/Sazi (NEGPF)/Stadine (Stadine)/Stag (Hetero)/Stamar (LKM)/Stavex (Aurobindo)/Stavir (Cipla)/Stavubergen (Paylos)/Zerit XR (Bristol-Myers Squibb)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Zerit	Capsule, gelatin coated	30 mg/1	Oral	State of Florida DOH Central Pharmacy	2009-07-01	Not applicable
Zerit	Powder, for solution	200 mg	Oral	Bristol Myers Squibb Pharma Eeig	2016-09-08	2020-10-13
Zerit	Capsule, gelatin coated	30 mg/1	Oral	E.R. Squibb & Sons, L.L.C.	1994-06-24	2020-09-30
Zerit	Capsule	30 mg	Oral	Bristol Myers Squibb Pharma Eeig	2016-09-08	2020-10-13
Zerit	Capsule, gelatin coated	40 mg/1	Oral	Physicians Total Care, Inc.	1994-06-24	2010-06-30
Zerit	Capsule, gelatin coated	15 mg/1	Oral	Physicians Total Care, Inc.	1994-06-24	2001-06-30
Zerit	Capsule	15 mg	Oral	Bristol Myers Squibb Pharma Eeig	2016-09-08	2020-10-13
Zerit	Capsule, gelatin coated	20 mg/1	Oral	State of Florida DOH Central Pharmacy	2009-07-01	Not applicable
Zerit	Powder, for solution	1 mg/1mL	Oral	E.R. Squibb & Sons, L.L.C.	1996-06-09	2019-03-31
Zerit	Capsule	40 mg	Oral	Bristol Myers Squibb Pharma Eeig	2016-09-08	2020-10-13

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Stavudine	Capsule	15 mg/1	Oral	Rising Health, Llc	2008-12-29	2019-04-18
Stavudine	Capsule	20 mg/1	Oral	Camber Pharmaceuticals	2008-12-29	Not applicable
Stavudine	Capsule	40 mg/1	Oral	Remedy Repack	2010-03-10	2012-08-23
Stavudine	Capsule	20 mg/1	Oral	Rising Pharmaceuticals, Inc.	2008-12-29	Not applicable
Stavudine	Capsule	40 mg/1	Oral	Greenstone, Llc	2008-12-29	2013-03-31
Stavudine	Capsule	30 mg/1	Oral	Aurobindo制药有限公司	2008-12-29	Not applicable
Stavudine	Capsule	15 mg/1	Oral	Greenstone, Llc	2008-12-29	2013-03-31
Stavudine	Capsule	40 mg/1	Oral	Camber Pharmaceuticals	2008-12-29	Not applicable
Stavudine	Capsule	30 mg/1	Oral	Mylan Pharmaceuticals	2011-08-24	2019-02-28
Stavudine	Capsule	30 mg/1	Oral	Rising Health, Llc	2008-12-29	2019-04-18

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
จีพีโอเวียร์ เอส 30	Stavudine(30 MG)+Lamivudine(150 MG)+Nevirapine(200 MG)			องค์การเภสัชกรรม	2003-11-14	Not applicable

Chemical Identifiers

UNII: BO9LE4QFZF
CAS number: 3056-17-5
InChI Key: XNKLLVCARDGLGL-JGVFFNPUSA-N
InChI: 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
IUPAC Name: 1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
SMILES: CC1=CN([C@@H]2O[C@H](CO)C=C2)C(=O)NC1=O

References

Synthesis Reference

Purna Chandra Ray, Jagan Mohana Chary Tummanapalli, Seeta Ramanjaneyulu Gorantla, "Process for the Large Scale Production of Stavudine." U.S. Patent US20080312428, issued December 18, 2008.

US20080312428

General References

Not Available

External Links

Human Metabolome Database: HMDB0014787
KEGG Drug: D00445
KEGG Compound: C07312
PubChem Compound: 18283
PubChem Substance: 46506943
ChemSpider: 17270
BindingDB: 50013111
RxNav: 59763
ChEBI: 63581
ChEMBL: CHEMBL991
ZINC: ZINC000000137884
Therapeutic Targets Database: DAP000172
PharmGKB: PA451494
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
PDRhealth: PDRhealth Drug Page
Wikipedia: Stavudine

FDA label

Download (289 KB)

MSDS

Download (36.8 KB)

Clinical Trials

Clinical TrialsLearn More" title="" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Not Available	Human Immunodeficiency Virus (HIV) Infections	1
4	Completed	Diagnostic	AIDS-Related Opportunistic Infections/Human Immunodeficiency Virus (HIV) Infections	1
4	Completed	Diagnostic	Cardiovascular Disease (CVD)/HIV Lipodystrophy Syndrome	1
4	Completed	Diagnostic	Human Immunodeficiency Virus (HIV) Infections/Lipodystrophies	1
4	Completed	Treatment	Acquired Immune Deficiency Syndrome (AIDS)/Human Immunodeficiency Virus (HIV) Infections	1
4	Completed	Treatment	Acquired Immune Deficiency Syndrome (AIDS)/Human Immunodeficiency Virus (HIV) Infections/Meningitis, Cryptococcal	1
4	Completed	Treatment	Hemophilia A/Human Immunodeficiency Virus (HIV) Infections	1
4	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections	6
4	Completed	Treatment	Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)	1
4	Terminated	Treatment	Metabolic; Complications/Mitochondrial Toxicity	1

Pharmacoeconomics

Manufacturers

Bristol myers squibb co
Aurobindo pharma ltd
Hetero drugs ltd
Matrix laboratories ltd
Mylan pharmaceuticals inc
Bristol myers squibb co pharmaceutical research institute
Cipla ltd

Packagers

A-S Medication Solutions LLC
Aurobindo Pharma Ltd.
Bristol-Myers Squibb Co.
Camber Pharmaceuticals Inc.
Cipla Ltd.
DAVA Pharmaceuticals
部门健康中心药房
Dispensing Solutions
E.R. Squibb and Sons LLC
Greenstone LLC
Hetero Drugs Ltd.
Kaiser Foundation Hospital
Matrix Laboratories Ltd.
Murfreesboro Pharmaceutical Nursing Supply
Mylan
Nucare Pharmaceuticals Inc.
Physicians Total Care Inc.
Remedy Repack
Tya Pharmaceuticals

Dosage Forms

Form	Route	Strength
Capsule, coated	Oral	30 mg
Capsule, coated	Oral	40 mg
Tablet, film coated	Oral
Tablet
Capsule	Oral	15 mg/1
Capsule	Oral	20 mg/1
Capsule	Oral	30 mg/1
Capsule	Oral	40 mg/1
For solution	Oral	1 mg/1mL
Powder, for solution	Oral	1 mg/1mL
溶解tion	Oral	1 mg/1mL
Tablet	Oral
Capsule, gelatin coated	Oral	15 mg/1
Capsule, gelatin coated	Oral	20 mg/1
Capsule, gelatin coated	Oral	30 mg/1
Capsule, gelatin coated	Oral	40 mg/1
Powder, for solution	Oral	1毫克/毫升
Powder, for solution	Oral	200 MG
Capsule	Oral	15 mg
Capsule	Oral	20 mg
Capsule	Oral	40 mg
Capsule, coated	Oral	15 mg
Capsule, coated	Oral	20 mg
Powder, for solution	Oral	100 mg
Capsule	Oral	30 mg

Prices

Unit description	Cost	Unit
Zerit 1 mg/ml Solution 200ml Bottle	88.11USD	bottle
Zerit 40 mg capsule	7.75USD	capsule
Zerit 30 mg capsule	7.61USD	capsule
Zerit 20 mg capsule	7.17USD	capsule
Stavudine 40 mg capsule	6.99USD	capsule
Zerit 15 mg capsule	6.89USD	capsule
Stavudine 30 mg capsule	6.72USD	capsule
Stavudine 20 mg capsule	6.33USD	capsule
Stavudine 15 mg capsule	6.08USD	capsule

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US7135465	Yes	2006-11-14	2023-08-18

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	159-160 °C	Not Available
water solubility	5-10 g/100 mL at 21 °C	Not Available
logP	-0.72	SANGSTER (1993)

Predicted Properties

Property	Value	Source
Water Solubility	40.5 mg/mL	ALOGPS
logP	-0.73	ALOGPS
logP	-0.23	Chemaxon
logS	-0.74	ALOGPS
pKa (Strongest Acidic)	9.95	Chemaxon
pKa (Strongest Basic)	-3	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	4	Chemaxon
Hydrogen Donor Count	2	Chemaxon
Polar Surface Area	78.87 Å²	Chemaxon
Rotatable Bond Count	2	Chemaxon
Refractivity	55.32 m³·mol^-1	Chemaxon
Polarizability	21.33 Å³	Chemaxon
Number of Rings	2	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9889
Blood Brain Barrier	+	0.9381
Caco-2 permeable	-	0.8958
P-glycoprotein substrate	Non-substrate	0.7949
P-glycoprotein inhibitor I	Non-inhibitor	0.9073
P-glycoprotein inhibitor II	Non-inhibitor	0.7979
Renal organic cation transporter	Non-inhibitor	0.9226
CYP450 2C9 substrate	Non-substrate	0.6707
CYP450 2D6 substrate	Non-substrate	0.8872
CYP450 3A4 substrate	Non-substrate	0.6011
CYP450 1A2 substrate	Non-inhibitor	0.9336
CYP450 2C9 inhibitor	Non-inhibitor	0.907
CYP450 2D6 inhibitor	Non-inhibitor	0.9231
CYP450 2C19 inhibitor	Non-inhibitor	0.9026
CYP450 3A4 inhibitor	Non-inhibitor	0.9269
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9445
Ames test	Non AMES toxic	0.7275
Carcinogenicity	Non-carcinogens	0.8131
Biodegradation	Not ready biodegradable	0.6132
Rat acute toxicity	1.7802 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9413
hERG inhibition (predictor II)	Non-inhibitor	0.9375

ADMET data is predicted usingadmetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
预测气相Spectrum - GC-MS	预测气相	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Targets

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Details 1.Reverse transcriptase/RNaseH

Kind: Protein
Organism: Human immunodeficiency virus 1
Pharmacological action: Yes
Actions: Inhibitor

General Function: Rna-dna hybrid ribonuclease activity
Specific Function: Not Available
Gene Name: pol
Uniprot ID: Q72547
Uniprot Name: Reverse transcriptase/RNaseH
分子量: 65223.615哒

References

Lea AP, Faulds D: Stavudine: a review of its pharmacodynamic and pharmacokinetic properties and clinical potential in HIV infection. Drugs. 1996 May;51(5):846-64. [Article]
De Clercq E: Emerging anti-HIV drugs. Expert Opin Emerg Drugs. 2005 May;10(2):241-73. [Article]

Carriers

Details 1.Serum albumin

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Toxic substance binding
Specific Function: Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name: ALB
Uniprot ID: P02768
Uniprot Name: Serum albumin
分子量: 69365.94 Da

References

Bocedi A, Notaril S, Narciso P, Bolli A, Fasano M, Ascenzi P: Binding of anti-HIV drugs to human serum albumin. IUBMB Life. 2004 Oct;56(10):609-14. [Article]
Bocedi A, Notari S, Menegatti E, Fanali G, Fasano M, Ascenzi P: Allosteric modulation of anti-HIV drug and ferric heme binding to human serum albumin. FEBS J. 2005 Dec;272(24):6287-96. [Article]

Transporters

Details 1.溶解te carrier family 22 member 6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Sodium-independent organic anion transmembrane transporter activity
Specific Function: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name: SLC22A6
Uniprot ID: Q4U2R8
Uniprot Name: 溶解te carrier family 22 member 6
分子量: 61815.78 Da

References

Wada S, Tsuda M, Sekine T, Cha SH, Kimura M, Kanai Y, Endou H: Rat multispecific organic anion transporter 1 (rOAT1) transports zidovudine, acyclovir, and other antiviral nucleoside analogs. J Pharmacol Exp Ther. 2000 Sep;294(3):844-9. [Article]

Details 2.Sodium/nucleoside cotransporter 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Pyrimidine- and adenine-specific:sodium symporter activity
Specific Function: Sodium-dependent and pyrimidine-selective. Exhibits the transport characteristics of the nucleoside transport system cit or N2 subtype (N2/cit) (selective for pyrimidine nucleosides and adenosine)....
Gene Name: SLC28A1
Uniprot ID: O00337
Uniprot Name: Sodium/nucleoside cotransporter 1
分子量: 71583.18 Da

References

Cano-Soldado P, Lorrayoz IM, Molina-Arcas M, Casado FJ, Martinez-Picado J, Lostao MP, Pastor-Anglada M: Interaction of nucleoside inhibitors of HIV-1 reverse transcriptase with the concentrative nucleoside transporter-1 (SLC28A1). Antivir Ther. 2004 Dec;9(6):993-1002. [Article]

Drug created at June 13, 2005 13:24 / Updated at April 28, 2023 03:25

Stavudine

Identification

Structure for Stavudine (DB00649)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Targets

References

Carriers

References

Transporters

References

References