STAVUDINE

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

Structure Search

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

Approval Year

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

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

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


					BO9LE4QFZF

STAVUDINE

EXCRETED UNCHANGED

Interaction Type:

AMOUNT EXCRETED

Qualification:

URINE

Amount:


					A3Z87NSO0U

HUMAN IMMUNODEFICIENCY VIRUS TYPE 1 POLYMERASE

TARGET -> INHIBITOR

Amount:


					859A956UY8

HUMAN IMMUNODEFICIENCY VIRUS TYPE 1

TARGET ORGANISM->INHIBITOR

Amount:

Related Record Type Details


					KX2B81V402

N-ACETYL-L-CYSTEINE 2-DEOXY-3-THIO-D-ERYTHRO-PENTONIC ACID .GAMMA.-LACTONE THIOETHER

METABOLITE -> PARENT

Interaction Type:

MINOR

Qualification:

URINE

Amount:


					QR26YLT7LT

THYMINE

METABOLITE -> PARENT

Amount:


					1ZP0VJ751G

STAVUDINE TRIPHOSPHATE

METABOLITE ACTIVE -> PARENT

Comments:

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.

Interaction Type:

MAJOR

Amount:


					X4PT8NAI8E

STAVUDINE GLUCURONIDE

METABOLITE -> PARENT

Interaction Type:

MINOR

Qualification:

URINE

Amount:

Related Record Type Details


					059QF0KO0R

WATER

IMPURITY -> PARENT

Comments:

Water (2.5.12): maximum 0.5 per cent, determined on 0.500 g.

Qualification:

EP

Amount:


					E37QXU5N74

THYMIDINE, 2',3'-DIDEHYDRO-3'-DEOXY-5'-O-(1,2,5-TRIDEOXY-1-(3,4-DIHYDRO-5-METHYL-2,4-DIOXO-1(2H)-PYRIMIDINYL)-.BETA.-D-THREO-PENTOFURANOS-5-YL)-

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					5Y0U269FPI

1-(4-(HYDROXYMETHYL)-2-OXO-2,5-DIHYDROFURAN-3-YL)-5-METHYLPYRIMIDINE-2,4(1H,3H)-DIONE

IMPURITY -> PARENT

Comments:

Amount Not Specified

Qualification:

INTERNATIONAL PHARMACOPEIA

Amount:


					J69N0KNC59

STAVUDINE.ALPHA.-ANOMER

IMPURITY -> PARENT

Comments:

Amount Not Specified

Qualification:

INTERNATIONAL PHARMACOPEIA

Amount:


					19TWX5TRJ4

3',5'-ANHYDROTHYMIDINE

IMPURITY -> PARENT

Comments:

Amount Not Specified

Qualification:

INTERNATIONAL PHARMACOPEIA

Amount:


					QR26YLT7LT

THYMINE

IMPURITY -> PARENT

Comments:

Amount Not Specified

Qualification:

INTERNATIONAL PHARMACOPEIA

Amount:


					YMX6U1R2W7

THYMIDINE .ALPHA.-ANOMER

IMPURITY -> PARENT

Comments:

Amount Not Specified

Qualification:

INTERNATIONAL PHARMACOPEIA

Amount:


					VC2W18DGKR

IMPURITY -> PARENT

Comments:

Amount Not Specified

Qualification:

INTERNATIONAL PHARMACOPEIA

Amount:


					VKZ4492GHU

1-(5-O-benzoyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione

IMPURITY -> PARENT

Amount:


					4B9XT59T7S

PARENT -> IMPURITY

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					6JP2VML5TG

1-((2R)-5-OXO-2,5-DIHYDROFURAN-2-YL)-5-METHYLPYRIMIDINE-2,4(1H,3H)-DIONE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					8NWA1GEX70

1-(2'-DEOXY-.BETA.-D-THREO-PENTOFURANOSYL)THYMINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					3V868S6FA7

1-((2R,4R,5R)-4-HYDROXY-5-(ISOPROPOXYMETHYL)TETRAHYDROFURAN-2-YL)-5-METHYL-PYRIMIDINE-2,4-DIONE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					4B9XT59T7S

PARENT -> IMPURITY

Amount:

Related Record Type Details


					BO9LE4QFZF

STAVUDINE

ACTIVE MOIETY

Amount:

Name	Property Type	Amount	Referenced Substance	Defining	Parameters	References
Tmax	PHARMACOKINETIC				ORAL ADMINISTRATION

Biological Half-life	PHARMACOKINETIC				ORAL ADMINISTRATION