Stavudine

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Stavudine are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Stavudine?

The molecule Stavudine presents a molecular formula of C10H12N2O4 and its IUPAC name is 1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4-dione.

Stavudine (d4T), sold under the brand name Zerit among others, is an antiretroviral medication used to treat and prevent HIV/AIDS. It is generally recommended for use with other antiretrovirals. It is taken by mouth..

Common side effects include nausea, vomiting, headache, trouble sleeping, and rash. Serious side effects may include pancreatitis, changes in body fat, and liver problems. Use during pregnancy may result in harm to the baby. Stavudine is in the nucleoside reverse transcriptase inhibitor (NRTI) family of medications. It works by blocking the activity of reverse transcriptase, an enzyme needed by the virus to make copies of itself..

Stavudine was first described in 1984 and approved for medical use in 1994. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. In the United States the wholesale cost per month is about US$150. In 2016, it was the 208th most prescribed medication in the United States, with more than one million prescriptions..

3D structure

Cartesian coordinates

Geometry of Stavudine in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Stavudine XNKLLVCARDGLGL-JGVFFNPUSA-N chemical compound 2D structure molecule svg
Stavudine

 

Molecule descriptors

 
IUPAC name1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4-dione
InChI codeInChI=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
InChI KeyXNKLLVCARDGLGL-JGVFFNPUSA-N
SMILESCc1cn([C@H]2C=C[C@@H](CO)O2)c(=O)[nH]c1=O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • 056S175
  • 1-((2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
  • 1-((2R,5S)-5-Hydroxymethyl-2,5-dihydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
  • 1-(2,3-Dideoxy-.beta.-D-glycero-pent-2-enofuranosyl)thymine
  • 1-(2,3-Dideoxy-beta-D-glycero-2-pentenofuranosyl)thymine
  • 1-(2,3-Dideoxy-beta-D-glycero-pent-2-enofuranosyl)thymine
  • 1-(5-Hydroxymethyl-2,5-dihydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
  • 1-(5-Hydroxymethyl-2,5-dihydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione (ddeThd)
  • 1-(cis-5-(Hydroxymethyl)-2,5-dihydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
  • 1-[(2R,5S)-2,5-Dihydro-5-(hydroxymethyl)-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione
  • 1-[(2R,5S)-5-(HYDROXYMETHYL)-2,5-DIHYDROFURAN-2-YL]-5-METHYL-1,2,3,4-TETRAHYDROPYRIMIDINE-2,4-DIONE
  • 1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione
  • 1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione
  • 1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4-dione
  • 1-[5-(hydroxymethyl)-2,5-dihydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione & Colony-stimulating factor 2
  • 2'',3''-didehydro-3''-deoxythymidine
  • 2'',3''-dideoxy-2'',3''-didehydrothymidine
  • 2',3'-Anhydrothymidine; d4T
  • 2',3'-Didehydro-3'-deoxythimidine
  • 2',3'-Didehydro-3'-deoxythymidine
  • 2'-Thymidinene, 3'-deoxy-
  • 220020-60-0
  • 3''-deoxy-2'',3''-didehydrothymidine
  • 3''-deoxy-2''-thymidine
  • 3'- Azido-3'-deoxythymidine & Granulocyte-macrophage colony-stimulating factor
  • 3'-Deoxy-2',3'-didehydrothymidine
  • 3'-Deoxy-2'-thymidinene
  • 3'-deoxythymidin-2'-ene
  • 3056-17-5
  • AB00383018_18
  • AC-5263
  • BBL033763
  • BCP02952
  • BD164571
  • BDBM50013111
  • BIDD:GT0082
  • BMY 27857
  • BMY-27857
  • BO9LE4QFZF
  • BRN 0618327
  • C07312
  • CCG-100902
  • CS-1872
  • D 1413
  • D 4T
  • D 4T (nucleoside)
  • D-4T
  • D00445
  • D3580
  • D4T & GM-CSF
  • D4TMBY-27857-3
  • DB00649
  • DSSTox_CID_3819
  • DSSTox_GSID_23819
  • DSSTox_RID_77198
  • Dideoxydidehydrothymidine
  • EU-0100336
  • Estavudina
  • HMS2051O20
  • HMS2234C10
  • HMS3039O05
  • HMS3259L21
  • HMS3261C13
  • HMS3428C07
  • HMS3714N22
  • HSDB 7338
  • HY-B0116
  • J-700246
  • KS-1115
  • LP00336
  • Lopac0_000336
  • MLS000028546
  • MLS000759504
  • MLS001055348
  • MLS001077292
  • MLS001424091
  • MLS006011922
  • NC00152
  • NC00684
  • NCGC00023212-03
  • NCGC00023212-04
  • NCGC00023212-05
  • NCGC00023212-07
  • NCGC00023212-08
  • NCGC00023212-09
  • NCGC00023212-10
  • NCGC00023212-11
  • NCGC00023212-12
  • NCGC00023212-13
  • NCGC00023212-14
  • NCGC00023212-25
  • NCGC00023212-30
  • NCGC00254372-01
  • NCGC00258944-01
  • NCGC00261021-01
  • NSC 163661
  • NSC-163661
  • NSC-759897
  • NSC163661
  • NSC759897
  • Opera_ID_1281
  • Pharmakon1600-01502339
  • Q-201742
  • Q423984
  • SDCCGSBI-0050324.P002
  • SMR000058350
  • SMR000673569
  • SR-01000075802
  • SR-01000075802-1
  • SR-01000075802-4
  • STK801888
  • STV
  • Sanilvudine (JAN)
  • Stavudine
  • Stavudine (USAN/INN)
  • Stavudine (d4T)
  • Stavudine (dt4)
  • Stavudine- Bio-X
  • Stavudinum
  • Thymidine, 2',3'-didehydro-, 3'-deoxy-
  • Thymidine, 2',3'-didehydro-3'-deoxy-
  • Thymine, 1-(2,3-dideoxy-beta-D-glycero-pent-2-enofuranosyl)-
  • Z1695906749
  • Zerit
  • Zerit Xr
  • Zerit(TM)
  • Zerut XR
  • cid_18283
  • cid_5155
  • d4T
  • ddeThd
  • ddeTyd
  • sanilvudine
  • stavudine

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC137884
  • CAS-3056-17-5
  • UNII-BO9LE4QFZF
  • AKOS005622554
  • DTXSID1023819
  • CHEMBL991
  • CHEBI:63581
  • Tox21_110886
  • Tox21_201393
  • Tox21_300583
  • Tox21_500336
  • Tox21_110886_1
  • SCHEMBL38661

Physico-Chemical properties

IUPAC name1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4-dione
Molecular formulaC10H12N2O4
Molecular weight224.213
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity56.44
LogP-0.7
Topological polar surface area84.3

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.