Streptozocin

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

What is the Streptozocin?

The molecule Streptozocin presents a molecular formula of C8H15N3O7 and its IUPAC name is 1-methyl-1-nitroso-3-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]urea.

Streptozocin (STZ) is an antineoplastic antibiotic of the nitrosourea class. It is used in chemotherapy for the treatment of pancreatic cancer and other endocrine neoplasms. It is also used in research for the induction of diabetes mellitus in laboratory animals..

Chemically, streptozocin is a nitrogen mustard alkylating agent. It is thought to work by crosslinking DNA, which inhibits cell division..

STZ was first isolated in 1959 from Streptomyces achromogenes. It was approved for use in the United States in 1972..

Common side effects of streptozocin include nausea, vomiting, diarrhea, anorexia, stomatitis, and myelosuppression. More serious side effects include hepatotoxicity, renal toxicity, and pulmonary toxicity..

Streptozocin is considered a hazardous substance in the United States and must be handled with care. It is a Schedule II controlled substance..

3D structure

Cartesian coordinates

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

2D drawing

 

Streptozocin ZSJLQEPLLKMAKR-GKHCUFPYSA-N chemical compound 2D structure molecule svg
Streptozocin

 

Molecule descriptors

 
IUPAC name1-methyl-1-nitroso-3-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]urea
InChI codeInChI=1S/C8H15N3O7/c1-11(10-17)8(16)9-4-6(14)5(13)3(2-12)18-7(4)15/h3-7,12-15H,2H2,1H3,(H,9,16)/t3-,4-,5-,6-,7+/m1/s1
InChI KeyZSJLQEPLLKMAKR-GKHCUFPYSA-N
SMILESCN(N=O)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O

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.

  • .ALPHA.-D-GLUCOPYRANOSE, 2-DEOXY-2-(((METHYLNITROSOAMINO)CARBONYL)AMINO)-
  • .ALPHA.-STREPTOZOCIN
  • 1-Methyl-1-nitroso-3-((2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-3-yl)urea
  • 1-methyl-1-nitroso-3-((2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)urea
  • 1-methyl-1-nitroso-3-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]urea
  • 18883-66-4
  • 2-Deoxy-2-(((methylnitrosoamino)carbonyl)amino)-D-glucopyranose
  • 2-Deoxy-2[[(methylnitrosoamino)-carbonyl]amino]-D-glucopyranose
  • 2-Desoxy-2-(3-methyl-3-nitrosoureido)-D-glucopyranose
  • 2-deoxy-2-[[(methylnitrosoamino)carbonyl]amino]-D-glucose
  • 3-methyl-3-nitroso-1-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]urea
  • 66395-18-4
  • 883S664
  • 8H27GUR065
  • A937380
  • AB00052092-03
  • AB00052092_04
  • AB00052092_05
  • AB00513906
  • ACT03364
  • BCBcMAP01_000142
  • BPBio1_000754
  • BSPBio_000684
  • BSPBio_002734
  • C07313
  • C8H15N3O7
  • CCG-39870
  • D05932
  • DB00428
  • DSSTox_CID_1282
  • DSSTox_GSID_21282
  • DSSTox_RID_76055
  • DivK1c_000531
  • Epitope ID:134282
  • Estreptozocina
  • HMS1921A07
  • HMS2092I09
  • HMS2097C06
  • HMS3714C06
  • HMS501K13
  • IDI1_000531
  • KBio1_000531
  • KBio2_001440
  • KBio2_004008
  • KBio2_006576
  • KBio3_001954
  • KBioGR_001768
  • KBioSS_001440
  • MFCD00006607
  • MLS004774123
  • N-(METHYLNITROSOCARBAMOYL)-A-D-GLUCOSAMINE
  • N-D-Glucosyl-(2)-N'-nitrosomethylharnstoff
  • N-D-Glucosyl-(2)-N'-nitrosomethylurea
  • NCGC00016738-01
  • NCGC00178500-01
  • NCGC00178500-02
  • NCGC00178500-03
  • NCGC00178500-04
  • NCGC00178500-07
  • NCGC00256594-01
  • NCGC00259408-01
  • NINDS_000531
  • NSC-757321
  • NSC757321
  • Pharmakon1600-01500543
  • Prestwick3_000732
  • Q257331
  • SBI-0051517.P003
  • SMP1_000282
  • SMR001233317
  • SPECTRUM1500543
  • SR-01000939745
  • SR-01000939745-3
  • SR-05000001720
  • SR-05000001720-1
  • SR-05000001720-2
  • STREPTOZOTOCIN
  • STZ
  • SW199198-2
  • Streptozocin
  • Streptozocin (JAN/USAN/INN)
  • Streptozocin; Streptozotocin
  • Streptozocine
  • Streptozocinium
  • Streptozocinum
  • Streptozotocin - Zanosar
  • W-201687
  • alkylating agent
  • alpha-D-Glucopyranose, 2-deoxy-2-(((methylnitrosoamino)carbonyl)amino)-
  • alpha-Streptozocin
  • binds to DNA
  • s1312
  • streptozocin
  • streptozosin
  • streptozotocin (stz)

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3977737
  • CAS-18883-66-4
  • UNII-8H27GUR065
  • AKOS025310730
  • CHEBI:9288
  • Tox21_110585
  • Tox21_201859
  • Tox21_302974
  • Tox21_110585_1
  • SPBio_000243
  • SCHEMBL4748
  • Spectrum_000960
  • Spectrum2_000062
  • Spectrum3_001087
  • Spectrum4_001244
  • Spectrum5_001047

Physico-Chemical properties

IUPAC name1-methyl-1-nitroso-3-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]urea
Molecular formulaC8H15N3O7
Molecular weight265.221
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity55.21
LogP-2.5
Topological polar surface area151.9

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.